INOSITOL

Inositol = Vitamin B8

CAS Number: 87-89-8 
EC Number: 201-781-2
Molecular Weight: 180.16
Molecular Formula: C6H12O6

Inositol is a vitamin-like substance. 
Inositol is found in many plants and animals. 
Inositol is also produced in the human body and can be made in a laboratory. 
Inositol can be found in many forms (called isomers). 
The most common forms are myo-inositol and D-chiro-inositol.
Inositol is used to for metabolic syndrome and polycystic ovary syndrome (PCOS). 
Inositol's also used for many other conditions, but there is no good scientific evidence to support most of these uses.

Inositol might balance certain chemicals in the body to possibly help with mental conditions such as panic disorder, depression, and obsessive-compulsive disorder. 
Inositol might also help insulin work better. 
This might help with conditions such as polycystic ovary syndrome or diabetes during pregnancy.

Inositol is a substance found naturally in cantaloupe, citrus fruit, and many fiber-rich foods (such as beans, brown rice, corn, sesame seeds, and wheat bran). 
Inositol is also sold in supplement form and used as a complementary therapy to treat a wide range of medical conditions, including metabolic and mood disorders.
Inositol is often referred to as vitamin B8, but Inositol is not actually a vitamin. 
Inositol's a type of sugar that influences the insulin response and several hormones associated with mood and cognition. 
Inositol also has antioxidant properties that fight the damaging effects of free radicals in the brain, circulatory system, and other body tissues.

D-chiro-inositol, inositol hexaphosphate (often referred to as "IP6") and the compound myo-inositol are the most widely used inositol supplements. 
They are generally considered safe if taken appropriately.

Health Benefits
Alternative health providers recommend inositol supplements for a wide range of health conditions, including:
-Anxiety
-Depression
-Diabetes
-High cholesterol
-Metabolic syndrome
-Panic disorder
-Polycystic ovary syndrome (PCOS)

Inositol, or more precisely myo-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; Inositol mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation.
Inositol is a sugar alcohol with half the sweetness of sucrose (table sugar). 
Inositol is made naturally in humans from glucose. 
A human kidney makes about two grams per day. 
Other tissues synthesize Inositol too, and the highest concentration is in the brain, where Inositol plays an important role by making other neurotransmitters and some steroid hormones bind to their receptors.
Inositol is promoted as a dietary supplement in the management of polycystic ovary syndrome (PCOS). 
However, there is only evidence of very low quality for Inositols efficacy in increasing fertility in women with PCOS.

In addition, inositol is believed by some to slow the progression of Alzheimer's disease and prevent certain cancers. 
Some people also use inositol to promote hair growth or overcome insomnia. 
Research, however, is lacking.
According to the latest research, inositol may be beneficial for some disorders, including mental health issues, PCOS, and metabolic disorders. 
Here's a closer look at the science.

Mood and Anxiety Disorders
Inositol is believed to improve depression, anxiety, and other mental disorders by stimulating the production of the "feel-good" hormones serotonin and dopamine. 
The hypothesis is largely supported by research in which myo-inositol concentrations in blood is suggested a reliable marker for clinical depression.
The benefits have mostly been seen in people with panic disorder (PD) in whom depression is common.
A small study published in the Journal of Clinical Psychopharmacology investigated the effect of myo-inositol on 20 people with PD.
After being provided a daily 18-gram dose of myo-inositol for four weeks, the participants were given a daily 150-mg dose of Luvox (fluvoxamine)—a commonly prescribed psychiatric drug—for the four weeks. 
When compared to a matched set of individuals not given myo-inositol, those who did had an average of 2.4 fewer panic attacks per week.

A number of other studies have investigated the use of inositol with selective serotonin reuptake inhibitors (SSRIs) used to treat a variety of depressive and anxiety disorders. 
The results have thus far been inconclusive.
While an earlier double-blind study found that a daily 12-gram dose of inositol improved depression scores compared to people provided a placebo, the results have not been replicated elsewhere.
In addition to panic disorder, inositol may be useful in treating obsessive-compulsive disorder (OCD), attention deficit-hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD) given its effect on serotonin and dopamine levels.

Metabolic Disorders
There is evidence to suggest inositol can correct may metabolic disorders that contribute to the development of high blood pressure, diabetes, and metabolic syndrome.
A 2016 pilot study published in the International Journal of Endocrinology reported that people with type 2 diabetes given myo-inositol and d-chiro-inositol daily along with their anti-diabetes drugs had a significant drop in their fasting blood glucose (192.6 mg/dL down to 160.9 mg/dL) and A1C (8.6 percent down to 7.7 percent) after three months.
Another small study published in the journal Menopause suggested that myo-inositol may aid in the treatment of metabolic syndrome in postmenopausal women. 
According to the research, women assigned to six months of myo-inositol supplements experienced significantly greater improvements in blood pressure and cholesterol levels than women provided a placebo.
When treated with myo-inositol, women with metabolic syndrome experienced an 11 percent drop in diastolic blood pressure, a 20 percent drop in triglycerides, and a 22 percent increase in "good" high-density lipoprotein (HDL) cholesterol.
All of these values translate to an improvement of metabolic syndrome as well as a decreased risk of cardiovascular disease.

Polycystic Ovary Syndrome (PCOS)
D-chiro-inositol may help manage PCOS, according to a small study published in Endocrine Practice. 
For this study, 20 women with PCOS were given either a placebo or 6 grams of D-chiro-inositol once daily for six to eight weeks.
The results revealed that D-chiro-inositol helped treat several abnormalities associated with PCOS, including high blood pressure and elevated levels of blood fats. 
In addition, elevated testosterone levels (consistent with PCOS-related hormone imbalances) decreased by 73 percent compared to 0 percent for those given a placebo.
Generally speaking, a normalization of hormonal balances translates to an improvement of PCOS symptoms.

Other Benefits
Inositol has also been found to reduce psoriasis symptoms in people taking lithium, a drug commonly prescribed to treat bipolar disorder, depression, schizophrenia, and eating disorders. 
Depending on the usage, lithium-induced psoriasis can affect anywhere from 3 percent to 45 percent of users.

Inositols and PCOS
While the research is promising, Inositol's important to understand the basics of inositol as Inositol applies to PCOS. 
Here’s what to know, but remember to speak to your doctor before taking any supplements.
Inositols such as myo- and d-chiro inositol (DCI) are considered members of the B-vitamin group, but are in fact carbohydrates (sugars) that also possess antioxidant properties. 
Inositol is found in healthier foods such as fruits, beans, grains, and nuts, though Inositol is also made by the body.
Myo and DCI work as secondary messengers relaying signals involved in insulin regulation.
Inositol is believed that women with PCOS may have a defect in the body’s ability to convert myo into DCI, which contributes to insulin resistance and infertility.
Supplementing with inositol is well tolerated (no gastrointestinal side effects like those associated with metformin) and has been shown to improve insulin levels and reduce intense cravings.

Inositol hexaphosphate may be useful in reducing side effects from chemotherapy.
Inositol hexaphosphate (IP6) is a carbohydrate found naturally in many plants and mammalian cells, where Inositol performs important messenger roles and affects numerous cellular processes. 
Inositol was shown to have anticancer and anti-angiogenic effects.
Small studies of breast cancer patients showed that IP6 may reduce chemotherapy-induced side effects. 
Myo-inositol may also have chemopreventive effects in some patients with chronic lung disease. 
Large-scale studies are needed to confirm these effects.

Commonly Known As
inositol
D-chiro-inositol
inositol hexaphosphate (or "IP6")
myo-inositol

Overview
myo-Inositol plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells, the various inositol phosphates. 
In addition, inositol serves as an important component of the structural lipids phosphatidylinositol (PI) and Inositols various phosphates, the phosphatidylinositol phosphate (PIP) lipids.
Inositol or Inositols phosphates and associated lipids are found in many foods, in particular fruit, especially cantaloupe and oranges.
In plants, the hexaphosphate of inositol, phytic acid or Inositols salts, the phytates, serve as phosphate stores in seed, for example in nuts and beans.

Phytic acid also occurs in cereals with high bran content. 
Phytate is, however, not directly bioavailable to humans in the diet, since Inositol is not digestible. 
Some food preparation techniques partly break down phytates to change this. 
However, inositol in the form of glycerophospholipids, as found in certain plant-derived substances such as lecithins, is well absorbed and relatively bioavailable.
myo-Inositol (free of phosphate) was once considered a member of the vitamin B complex, called Vitamin B8 in this context. 
However, because Inositol is produced by the human body from glucose, Inositol is not an essential nutrient.

Isomers and structure
The isomer myo-inositol is a meso compound, and hence optically inactive, because Inositol has a plane of symmetry. 
For this reason, meso-inositol is an obsolete name for this compound. 
Besides myo-inositol, the other naturally occurring stereoisomers are scyllo-, muco-, D-chiro-, and neo-inositol, although they occur in minimal quantities in nature. 
The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. 
As their names denote, L- and D-chiro inositol are the only pair of inositol enantiomers, but they are enantiomers of each other, not of myo-inositol.

What is inositol?
Inositol is a natural molecule found in the phospholipids of cell membranes, in the lipoproteins of the plasma and, in the form of phosphate, in the cell nucleus. 
When we talk about inositol, we actually refer to a group of nine different stereoisomers, so Inositol would be more correct to use the plural “Inositols”. 
Among these, however, the term inositol is generally used to refer to the most bioavailable type, myo-inositol.

Inositol may also be effective as a supplemental treatment for the below conditions:
-Schizophrenia
-Alzheimer’s Disease
-Autism
-Depression
-Diabetic Nerve Pain
-Attention Deficit-Hyperactivity Disorder (ADHD)
-Cancer
-Hair Growth
-High Cholesterol
-Insomnia
-Fat Metabolization
-Sources of Inositol

As previously mentioned, inositol is found in naturally in certain foods but in fairly low levels. 
The highest levels of inositol are usually found in whole grains and citrus fruits.

Common Food Sources
-Oranges
-Grapefruit
-Dried prunes
-Great northern beans
-Navy beans
-Stone ground wheat
-Bran flakes
Inositol is sometimes marketed as vitamin B8 – however, so is a substance called AMP (adenosine monophosphate). 
Be sure to look for supplements specifically labeled inositol or myo-inositol.

Biosynthesis
myo-Inositol is synthesized from glucose 6-phosphate (G6P) in two steps. 
First, G6P is isomerised by an inositol-3-phosphate synthase enzyme (for example, ISYNA1) to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme (for example, IMPA1) to give free myo-inositol. 
In humans, most inositol is synthesized in the kidneys, followed by testicles, typically in amounts of a few grams per day.
at the peripheral level, myo-inositol is converted  to D-chiro-inositol by a specific epimerase. 
The activity of this epimerase is insulin dependent. 
Worthy of note, only a small quantity of myo-inositol is converted into D-chiro-inositol and the conversion is irreversible.

Inositol, phosphatidylinositol and some of their mono- and polyphosphates function as secondary messengers in a number of intracellular signal transduction pathways. 
They are involved in a number of biological processes, including:
Insulin signal transduction
Cytoskeleton assembly
Nerve guidance (epsin)
Intracellular calcium (Ca2+) concentration control
Cell membrane potential maintenance
Breakdown of fats
Gene expression

In one important family of pathways, phosphatidylinositol 4,5-bisphosphate (PIP2) is stored in cellular membranes until Inositol is released by any of a number of signalling proteins and transformed into various secondary messengers, for example diacylglycerol and inositol triphosphate.
Phytic acid in plants
2D-structure of phytic acid
Inositol hexaphosphate, also called phytic acid or IP6, is the principal storage form of phosphorus in many plant tissues, especially bran and seed.

Chemical formula: C6H12O6
Molar mass: 180.16 g/mol
Density:. 1.752 g/cm3
Melting point: 225 to 227 °C (437 to 441 °F; 498 to 500 K)

Phosphorus and inositol in phytate form are not generally bioavailable to non-ruminant animals because these animals lack the digestive enzyme phytase required to remove the phosphate groups. 
Ruminants are readily able to digest phytate because of the phytase produced by rumen microorganisms.
Moreover, phytic acid also chelates important minerals such as calcium, magnesium, iron, and zinc, making them unabsorbable, and contributing to mineral deficiencies in people whose diets rely highly on bran and seeds for their mineral intake, such as occurs in developing countries.
Inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3) are also called "phytates".

Use in explosives manufacture
At the 1936 meeting of the American Chemical Society, professor Edward Bartow of the University of Iowa presented a commercially viable means of extracting large amounts of inositol from the phytic acid naturally present in waste corn. 
As a possible use for the chemical, he suggested 'inositol nitrate' as a more stable alternative to nitroglycerin.
Today, inositol nitrate is used to gelatinize nitrocellulose, thus can be found in many modern explosives and solid rocket propellants.

Counter to road salt
When plants are exposed to increasing concentrations of road salt, the plant cells become dysfunctional and undergo apoptosis, leading to inhibited growth. 
Inositol pretreatment could reverse these effects.


CAS Number: 87-89-8 
CHEBI:17268 
ChEMBL: ChEMBL1222251 
ChemSpider: 10239179 
ECHA InfoCard: 100.027.295
IUPHAR/BPS: 4495
KEGG: D08079 
PubChem CID: 892
UNII: 4L6452S749 
CompTox Dashboard (EPA): DTXSID30110000

myo-Inositol depletion is particularly damaging to ovarian follicles because Inositol is involved in FSH signaling, which is impaired due to myo-inositol depletion.
Recent evidence reports a faster improvement of the metabolic and hormonal parameters when these two isomers are administered in their physiological ratio. 
The plasmatic ratio of myo-inositol and D-chiro-inositol in healthy subjects is 40:1 of myo- and D-chiro-inositol respectively.
The use of the 40:1 ratio shows the same efficacy of myo-inositol alone but in a shorter time. 
In addition, the physiological ratio does not impair oocyte quality.

The use of inositols in PCOS is gaining more importance, and an efficacy higher than 70% with a strong safety profile is reported. 
On the other hand, about 30% of patients could show as inositol-resistant.
New evidence regarding PCOS aetiopathogenesis describes an alteration in the species and the quantity of each strain characterizing the normal gastrointestinal flora. 
This alteration could lead to a chronic low grade of inflammation and malabsorption.

A possible solution could be represented by the combination of myo-inositol and α-lactalbumin. 
This combination shows a synergic effect in increasing myo-inositol absorption.
A recent study reported that the myo-inositol and α-lactalbumin combination is able to increase myo-inositol plasmatic content in inositol-resistant patients with a relative improvement of hormonal and metabolic parameters.
Despite its antinutrient effect, phytic acid has potential use in endodontics, adhesive, preventive, and regenerative dentistry, and in improving the characteristics and performance of dental materials.

Use as a cutting agent
Inositol has been used as an adulterant or cutting agent for many illegal drugs, such as cocaine, methamphetamine, and sometimes heroin, probably because of Inositols solubility, powdery texture, or reduced sweetness (50%) compared to more common sugars.
Inositol is also used as a stand-in film prop for cocaine in filmmaking.

Preferred IUPAC name
(1R,2S,3r,4R,5S,6s)-Cyclohexane-1,2,3,4,5,6-hexol

Difference between myo-inositol and d-chiro inositol
Myo-inositol has a chemical structure similar to glucose and is involved in cell signaling. 
In particular, Inositol is able to stimulate glucose uptake, promoting the decrease in blood levels.

Other names
cis-1,2,3,5-trans-4,6-Cyclohexanehexol
Cyclohexanehexol
Mouse antialopecia factor
Nucite
Phaseomannite
Phaseomannitol
Rat antispectacled eye factor
Scyllite (for the isomer scyllo-inositol)
Vitamin B8

Nutritional sources
myo-Inositol is naturally present in a variety of foods, although tables of food composition do not always distinguish between lecithin, the relatively bioavailable lipid form and the biounavailable phytate/phosphate form.
Foods containing the highest concentrations of myo-inositol and Inositols compounds include fruits, beans, grains, and nuts.
Fruits in particular, especially oranges and cantaloupe, contain the highest amounts of myo-inositol.
Inositol is also present in beans, nuts, and grains, however, these contain large amounts of myo-inositol in the phytate form, which is not bioavailable without transformation by phytase enzymes. 

Bacillus subtilis, the microorganism which produces the fermented food natto, produces phytase enzymes that may convert phytic acid to a more bioavailable form of inositol polyphosphate in the gut.
Additionally, Bacteroides species in the gut secrete vesicles containing an active enzyme which converts the phytate molecule into bioavailable phosphorus and inositol polyphosphate, which is an important signaling molecule in the human body.
myo-Inositol can also be found as an ingredient in energy drinks, either in conjunction with or as a substitute for glucose, ostensibly to increase serotonin levels and alertness.
In humans, myo-inositol is naturally made from glucose-6-phosphate through enzymatic dephosphorylation.

OTHER NAME(S): 
1,2,3,4,5,6-Cyclohexanehexol, 1,2,5/3,4,6-inositol, (1S)-inositol, (1S)-1,2,4/3,5,6-inositol, Antialopecia Factor
(+)-chiroinositol, cis-1,2,3,5-trans-4,6-Cyclohexanehexol, Cyclohexitol, Dambrose, D-chiro-inositol, D-Myo-Inositol
Facteur Anti-alopécique, Hexahydroxycyclohexane, Inose, Inosite, Inositol Monophosphate, Lipositol, Meso-Inositol
Méso-Inositol, Monophosphate d'Inositol, Mouse Antialopecia Factor, Myo-Inositol, Vitamin B8, Vitamine B8.

inositol
myo-inositol
Scyllo-inositol
Muco-Inositol
epi-Inositol
Allo-inositol
i-Inositol
meso-Inositol
87-89-8
Neo-inositol
1D-Chiro-inositol
1L-Chiro-inositol
cis-Inositol
D-chiro-Inositol

D-chiro inositol, myo-inositol stereoisomer, is also involved in insulin signaling: both, as inositolophosphoglycans, are “second messengers of insulin”. 
However, although their biological functions are often confused, Inositol is good to remember that they play different roles.
MYO AND D-CHIRO INOSITOL, AS INOSITOLOFOSFOGLICANS, ARE BOTH “SECOND MESSENGERS” OF THE INSULIN, BUT THEY CARRY OUT DIFFERENT FUNCTIONS.
Inositol was the scientist Larner in 1988 who intuited that myo-inositol and d-chiro inositol were part of two different insulin chemical mediators. 
Although very similar, the functions of the two isomers are different. 
In fact, myo is involved in the transporters activation and the use of glucose, while d-chiro is involved in the glycogen synthesis and storage.
MYO-INOSITOL IS INVOLVED IN THE TRANSPORTERS ACTIVATION AND THE USE OF GLUCOSE, WHILE D-CHIRO IS MAINLY INVOLVED IN THE GLYCOGEN SYNTHESIS AND STORAGE.
The differences between the two molecules were in-depth studied in the attempt to find a therapeutic response to a syndrome known as PCOS or polycystic ovary syndrome.
 
As regard male infertility, inositol has improved, according to several studies, motility and sperm count, while Inositol improves the oocyte and embryonic quality in women.
Again, myo-inositol induces an increase in the sensitivity of the serotonin receptor, also known as the good mood hormone, with benefits on anxiety disorders.
The benefits of inositol have been also investigated as regard the diabetes and the prevention of metabolic syndrome.

Found in many common foods, inositol (also called myo-inositol) falls into a category sometimes called pseudovitamins.
Pseudovitamins play an important role in bodily functions, but do not necessarily cause health disorders when their levels deplete. 
Inositol is sometimes referred to as vitamin B8.

Myo and D-chiro 40:1: a question of balance
Starting from the intuition on the ovarian paradox, and the different roles that myo and d-chiro play, a group of Italian scientists focused the attention on the importance of a correct myo and D-chiro inositol supplementation, taking into account the need to restore the impairment by restoring the correct myo/d-chiro ratio at ovarian level too.
But the question is: which is the optimal dosage to take advantage of the d-chiro-inositol efficacy without compromising the ovarian functionality?
To answer this question, we try to summarize some fundamental assumptions, reaffirmed in a review published recently in one of the most authoritative endocrinology journals in the world, Cell Press. 
1) The myo/d-chiro-inositol ratio is specific tissue. 
2) In healthy women, Myo and D-chiro physiological ratio in the follicular fluid is 100:1, namely a myo-inositol abundance and only a small part of d-chiro inositol. 
3) In PCOS women, at ovarian level, this ratio is dramatically altered to the detriment of myo-inositol, while there is an excess of d-chiro inositol, due to the high epimerase activity and hyperinsulinemia. 
4) Myo deficiency at ovarian level in PCOS women compromises the FSH signal, the key hormone for follicles maturation, resulting in a reduced oocyte quality, anovulation and subfertility. 
Therefore, Myo-inositol plays a crucial role in FSH signaling, oocyte maturation and embryonic development. 
5) Unlike myo-inositol, the role played by d-chiro-inositol at ovarian level remains controversial, with a worsening of the oocyte quality and ovarian response when high doses of d-chiro inositol for prolonged periods are used.

Conclusions
Finally, considering the specific Myo and D-chiro-inositol ratio (remember the 100:1 ratio in the ovary) and the different physiological roles of the two inositols, the combined oral therapy of Myo and D-chiro inositol in the 40:1 ratio (the physiological plasma ratio) has been proposed as an alternative and effective treatment for PCOS women.

What are the benefits of inositol supplementation for PCOS?
Research has shown, supplementing with inositol can: improve insulin sensitivity decrease androgens and the associated symptoms of hyperandrogenism like acne and hirsutism (facial and body hair growth) improve menstrual regularity improve egg quality promote ovulation decrease LH and improve FSH/ LH ratio reduce the risk of developing gestational diabetes improve triglyceride levels
In addition to the benefits above, my clients have reported improved mood, energy, and cravings.

How much inositol should be taken?
The therapeutic dose for inositol for PCOS is 2-4g. 
Most of my clients take around 4g/ day. 
Some start off taking a lower dose, Then, we slowly increase if they are prone to hypoglycemia (low blood sugar), are already taking an insulin sensitizer (like metformin), or have a sensitivity to sugar alcohols.

Should I take D-chiro, Myo, or Myo and D-chiro together? Which is best?
In the past, I recommended myo: d-chiro combined in a 40:1 ratio and kind of poo pooed on Myo alone. 
After taking a closer look at the research, I now recommend either myo-inositol alone or myo and d-chiro combined. 
Both have great research behind them. 
Myo-inositol alone tends to be less expensive than myo and d-chiro combined, so if budget is a major consideration for you, Inositol might be best to go with myo-inositol alone. 
On the other hand,  myo combined with d-chiro tends to be more expensive but is possibly more effective than myo alone. 
But that doesn’t mean myo alone is ineffective.
I don’t recommend taking D-chiro inositol alone because there have been some studies that showed alone, in high doses, Inositol can have negative effects on egg quality.
And just in case you were wondering where the 40:1 ratio came from, that’s the ratio we find in plasma. 
So supplementing at that ratio is simply to mimic plasma concentrations. 
Other ratios have been tried, but the results weren’t the best. 

Purported Uses of Inositol:
-To prevent and treat cancer
Lab studies have shown anticancer effects. 
Clinical data are lacking.
-To reduce chemotherapy side effects
Small studies of breast cancer patients showed that IP6 may be effective in reducing chemotherapy-associated side effects. 
Larger studies are needed.
-To treat heart disease
Evidence is lacking to support this claim.
-To treat depression
Evidence is lacking to support this claim.
-To treat kidney stones
Evidence is lacking to support this claim.

Inositol from effective nature is used for the treatment of cycle irregularities that occur due to the so-called PCO syndrome. 
But what is inositol actually about? 
Various forms of inositol occur naturally in traces in food. 
The human body also produces inositol itself, but only in small quantities. 
Two forms of inositol, Myo-inositol, and D-chiro-inositol are important messenger substances that play an important role in fat and glucose (sugar) metabolism and hormone metabolism, among other things. 
Inositol is also involved in the nervous system as an important messenger, as Inositol supports the transmission of nerve signals. 
Meanwhile, inositol is used in the treatment of PCO syndrome. 
Studies have shown a positive effect on the symptoms of PCO syndrome.

Myoinositol
643-12-9
488-59-5
Scyllitol
D-(+)-chiro-Inositol
Cyclohexane-1,2,3,4,5,6-hexaol
6917-35-7
mesoinositol
Meat sugar
cyclohexane-1,2,3,4,5,6-hexol
Myoinosite
Quercinitol
Dambose
488-58-4
Cocositol
Inositene
Inositina

Combining Myo and D-Chiro Inositols
Newer research into the effects of inositol have revealed the majority of tissues in the body have a ratio of myo to DCI of approximately 40:1.5 Taking a combination of these two supplements in this ratio rather than just taking myo or DCI alone is recommended.
When compared to myo-inositol, women with PCOS experienced more benefits relating to metabolic parameters (lowering insulin, cholesterol, and inflammatory markers) when they took a combination of myo and DCI.
When compared with metformin, a combination of myo and DCI in a 40:1 ratio showed significantly better results in regards to weight loss, ovulation, and pregnancy rates (46.7% vs.11.2%).

Myo and D-Chiro in PCOS
As anticipated, Inositol was Larner in the late 1980s who first supposed that myo-inositol and d-chiro-inositol were part of two different insulin chemical mediators. 
In the same years, in the gynecological field, PCOS (polycystic ovary syndrome) started to be correlated to the insulin resistance and hyperinsulinemia. 
Inositol was shown that the ovary has insulin receptors and that the androgens production depends on them. 

At ovarian level, myo and d-chiro inositol play different roles:
myo-inositol mediates glucose uptake and FSH signal (follicle stimulating hormone).
d-chiro-inositol is involved in the insulin-dependent synthesis of androgens and promotes glucose storage.
In the ovaries of a healthy woman, 99% of the inositol intracellular pool is made up of Myo-inositol, while the remaining part is made up of D-chiro-inositol. 
Another important difference between myo and d-chiro is the respective presence and distribution in the tissues. 
In fact, each tissues regulates the production of the two inositols myo and d-chiro in such a way to always have a specific ratio.

MYO AND D-CHIRO INOSITOL HAVE A DIFFERENT DISTRIBUTION IN THE TISSUES
In PCOS women, we observe a myo deficiency at ovarian level causing an impairment of the FSH signal. 
Research has also showed how d-chiro is synthesized from myo-inositol. 
In other words, a small amount of myo-inositol is converted into d-chiro inositol by an enzyme called epimerase which in turn is stimulated by insulin.

Therapeutic uses of myo-inositol
In 1992 Prof. Chiu, a researcher at the University of Hong Kong, was one of the first to demonstrate the efficacy of the myo-inositol treatment in women seeking pregnancy, strengthening the correlation between the presence of myo-inositol and fertility. 
Today, myo-inositol represents a safe and effective therapy that finds therapeutic application for various ailments and pathologies:
In PCOS, the administration of myo-inositol resulted in the remission of symptoms and the reduction of male hormones secretion; but also the regulation of cholesterol levels, a more efficient breakdown of fats with a consequent decrease in appetite and weight.


Phaseomannite
Inosital
Inosite
Iso-inositol
551-72-4
L-chiro-Inositol
Cyclohexitol
Phaseomannitol
Mesoinosit
Mesoinosite
Scyllite
Mesovit
Nucite
Mesol

Studies provide evidence that both D-chiro-inositol and Myo-inositol can significantly alleviate many symptoms of PCO syndrome.
Women who took these two substances over a period of six months had a more regular cycle and more frequent ovulations and balanced hormonal levels. 
Insulin resistance also improved significantly. 
In particular, the combination of Myo-inositol and D-chiro-inositol showed better effects in clinical trials than taking Myo-inositol alone. 
The function of the ovaries improved, the quality of the egg cells increased and ovulation occurred more regularly. 
These results should be particularly interesting for women who want to have children.

CAS Number: 87-89-8
Molecular Weight: 180.16
Beilstein/REAXYS Number: 1907329
EC Number: 201-781-2
MDL number: MFCD00077932
PubChem Substance ID: 57654297
NACRES: NA.77

Polycystic ovarian syndrome (PCO syndrome or PCOS for short) is the most common cause of unfulfilled desire for children. 
The disease belongs to hormone disorders and often affects women of childbearing age. 
In Germany alone, approximately one million women suffer from PCOS. 
Inositol causes an imbalance in the female hormone system, which leads to increased production of male hormones. 
What causes PCO syndrome has not yet been clearly explained. 
However, a connection between overweight and insulin resistance is suspected. 

Nevertheless, the disease also occurs in women who are not overweight. 
A genetic predisposition is also being discussed, as PCOS is more common in families. 
The mechanisms of PCOS are, however, clear: the pituitary gland produces increased amounts of the luteinizing hormone (LH), which actually triggers ovulation, but at the same time there is a reduction in the follicle-stimulating hormone (FSH), which is responsible for egg cell maturation. 
This leads to the increased production of the so-called androgens, the male sex hormones. 
The body in turn cannot convert these androgens into estrogens - an imbalance in favor of the male sex hormones occurs.

chiro-inositol
Cyclohexanehexol
Inositol, meso-
Inositol, myo-
Hexahydroxycyclohexane
L-Inositol
41546-34-3
D-myo-Inositol
cis-1,2,3,5-trans-4,6-Cyclohexanehexol
643-10-7
Bios I
Insitolum
Isoinositol
(-)-Inositol
L-myo-Inositol
Inositol, i-

Inositol is a word that collectively refers to molecules with a similar structure, a collection of nine stereoisomers. 
While the term 'inositol' is used commonly with dietary supplements, Inositol usually refers to a specific stereoisomer called myo-inositol. 
Inositols are pseudovitamin compounds that are falsely said to belong to the B-complex family, and are found in most foods but in highest levels in whole grains and citrus fruits.
Myo-inositol shows the most promise as a dietary supplement for promoting female fertility, restoring insulin sensitivity in instances of resistance (type II diabetes and polycystic ovarian syndrome being the most well investigated), and for reducing anxiety as well. 
Due to the mixed benefits to insulin resistance and fertility, myo-inositol is considered a good treatment for PCOS in women.
Inositol also holds some promise as an anti-depressant (although not as impressive as Inositols anxiolytic and anti-panic effects) and against some other conditions associated with anxiety such as panic disorders and binge eating. 

Inositol is relatively ineffective for schizophrenia and autism, and has failed in treating PTSD despite Inositols anti-panic effects.
In part because of Inositols benefits to fertility and PCOS, as well as the anxiolytic effects potentially helping symptoms of PMS (dysphoria and anxiety mostly), myo-inositol is sometimes referred to as a general female health supplement. 
At times, the anti-depressant effects associated with this supplement seem to only work in females with males having no benefit.
Inositol is a very safe supplement to ingest, and all side-effects associated with myo-inositol are merely mild gastrointestinal distress from high doses. 
High doses (usually in the 12-18g range) are required for any neurological effects while lower doses (2-4g) are sufficient for fertility and insulin sensitizing effects.

L-(-)-chiro-Inositol
Inositol (VAN)
488-55-1
Inositol, allo-
Inositol, muco-
1D-myo-Inositol
1L-myo-Inositol
488-54-0
1,2,3,4,5,6-Cyclohexanehexol
Rat antispectacled eye factor
(1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexaol
MFCD00077932
Levoinositol
CCRIS 6745
AZD 103
Inositol, epi-
576-63-6

myo-Inositol (inositol) is a common micronutrient. 
Inositols content is high in breast milk, especially in colostrum. 
However, Inositol is not included in parenteral nutrition of extremely preterm infants. 
On the basis of a meta-analysis of 2 trials, addition of inositol to parenteral nutrition or to enteral feeding decreased the risk of retinopathy of prematurity. 
During the presurfactant era, inositol additionally increased survival without serious pulmonary morbidity. 
Placenta is active in inositol synthesis, and the fetus reuses inositol secreted to amniotic fluid. 

As a result of loss of inositol to urine and inositol metabolism, the plasma half-life in very preterm infants shortly after birth is 5.5 hours. 
In the absence of inositol intake, 10% to 20% of total body inositol may be lost within 24 hours. 
Some preterm infants may be born with a deficient inositol pool (eg, prolonged rupture of fetal membranes). 
Mice that have a single-gene defect in inositol metabolism succumb at term birth despite apparently near-normal antenatal development. 
Pathologic features include dysfunction of the respiratory center, severe neuropathy, closure of pulmonary air spaces, defect in osteoblasts, and deformation of bones. 
All severe defects are preventable by antenatal and neonatal inositol supplementation. 

According to experimental results, inositol supplementation augments the efficacy of antenatal glucocorticoid for acceleration of lung maturity. 
The effect of inositol deficiency on the development of retina has not been studied in the experimental setting. 
Administration of inositol in small preterm infants shortly after birth appears to be safe. 
However, data are limited on the efficacy of inositol supplementation in the intensive care unit setting.
Antenatal inositol supplementation in very high-risk pregnancies remains to be studied.

Quality Level: 300
vapor density: 6.2 (vs air)
assay: ≥99%
mp: 222-227 °C (lit.)
solubility:
H2O: 50 mg/mL
SMILES string: O[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI: 1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
InChI key: CDAISMWEOUEBRE-GPIVLXJGSA-N

Inositol, scyllo-
UNII-63GQX5QW03
UNII-8LQ63P85IC
UNII-9O6Y5O4P9W
UNII-R1Y9F3N15A
1,2,3,5-trans-4,6-Cyclohexanehexol, cis-
ELND005
1,3,5/2,4,6-Hexahydroxycyclohexane
UNII-4661D3JP8D
UNII-6R79WV4R10
(1R,2R,3R,4R,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexaol
(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
1-L-chiro-Inositol
(-)-chiro-Inositol
UNII-1VS4X81277
CHEBI:17268
AI3-16111
NSC8101

Myo-inositol has been established as an important growth-promoting factor of mammalian cells and animals. 
The role of myo-inositol as a lipotropic factor has been proven, in addition to Inositols involvement as co-factors of enzymes and as messenger molecules in signal transduction. 
Myo-inositol deficiency leads to intestinal lipodystrophy in animals and “inositol-less death” in some fungi. 
Of late, diverse uses of myo-inositol and Inositols derivatives have been discovered in medicinal research. 
These compounds are used in the treatment of a variety of ailments from diabetes to cancer, and continued research in this direction promises a new future in therapeutics. 
In different diseases, inositols implement different strategies for therapeutic actions such as tissue specific increase or decrease in inositol products, production of inositol phosphoglycans (IPGs), conversion of myo-inositol (MI) to D-chiro-inositol (DCI), modulation of signal transduction, regulation of reactive oxygen species (ROS) production, etc. 
Though inositol pharmacology is a relatively lesser-known field, recent years of research has generated a critical mass of information on the subject. 

1,3,5/2,4,6-cyclohexanehexol
UNII-4L6452S749
UNII-587A93P465
1,2,3,5/4,6-Cyclohexanehexol
NSC 8101
(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexol
(1R,2R,3R,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexaol
1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE
MFCD00065455
NSC404118
Inositol, myo- (8CI)
myo-Inositol;meso-Inositol
1,2,3,4,5,6-Hexahydroxycyclohexane
NSC 404118
63GQX5QW03
8LQ63P85IC
9O6Y5O4P9W
R1Y9F3N15A
(1R,2R,3S,4R,5r,6S)-cyclohexane-1,2,3,4,5,6-hexaol

So what is Myoinositol and why is Inositol even worth talking about?
Well, Inositol turns out that this sugar alcohol (yes Inositol's actually a sugar and about half as sweet as table sugar) has some seriously beneficial side effects if used correctly. 
Myoinositol is the most common form of inositol and most of Inositols benefits come from how Inositol interacts with cellular function. 

D-chiro-inositol
The use of D-chiro-inositol alone to treat PCOS women dates back to the late 1990s by a group of American researchers. 
In a well-known study, Nestler reported innovative results on the use of d-chiro-inositol for the treatment of PCOS. 
He showed that with the use of 1.200 mg of D-chiro-inositol for 8 weeks, Inositol was possible to improve insulin sensitivity, ovarian function, reduce androgens and triglyceride levels in obese PCOS patients, and restore the menstrual cycle . 
Unfortunately, these apparently surprising results were not reconfirmed in subsequent studies. 
A crucial difference compared to the first clinical trials concerned precisely the dosages of D-chiro inositol, increased to 2.400 mg. 
These results led to an interruption of the trials.

THE FIRST POSITIVE RESULTS ON D-CHIRO INOSITOL WERE NOT RECONFIRMED IN THE FOLLOWING STUDIES, SO MUCH THAT THE RESEARCH WAS STOPPED. WHY?
As anticipated, d-chiro-inositol is partially converted by Myo through epimerase, an insulin-sensitive enzyme.
Myo-inositol is instead the most abundant. 
But, in compromised health conditions such as PCOS, the situation changes. 
In fact, in PCOS women the activity of the epimerase enzyme is increased: this induces a substantial reduction of Myo and D-chiro ratio at intraovarian level, because there is an enhanced conversion of myo to d-chiro due to the excessive levels of circulating insulin.

This phenomenon, better known as the ovarian paradox, arises from an intuition, subsequently demonstrated through experimental data: since the ovary is never insulin resistant and that the activity of epimerase (mediated by insulin) was more understood in women PCOS, causing a myo-inositol deficiency and therefore a reduced oocyte quality.
THE INTUITION ON OVARIAN PARADOX, SUPPORTED BY CLINICAL EVIDENCE SHOWING THE EFFECTIVENESS OF MYO-INOSITOL-BASED TREATMENTS OF PCOS AND FOR FERTILITY, OFFER AN ANSWER TO THE CONTRADICTIVE RESULTS ON THERAPIES WITH HIGH DOSAGE OF D-CHIRO-INOSITOL ALONE FOR PROLONGED PERIODS.
However, the role of d-chiro in reducing insulin levels remains irrefutable.


MI
CHEBI:10642
CHEBI:23927
CHEBI:27372
CHEBI:27987
4661D3JP8D
6R79WV4R10
Inositol (VAN8C
NSC-8101
NSC45517
NSC55551
NSC55552
NSC-25142
NSC-55551
UNII-M94176HJ2F
1VS4X81277
NSC-404118
INS

Do I Need A Inositol Supplement?
Inositol is a psuedovitamin and not critical for human function. 
However, as seen in long-term lithium therapy, inositol depletion can result in psoriasis. 
Given the promising results of clinical trials for conditions ranging from fertility problems and metabolic disorders to behavioral and neurological conditions, inositol supplementation should be given strong consideration for anyone struggling with these conditions.

Inositol, 98+%
(1s,2s,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol
NCGC00159409-02
(1R,2R,3R,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
(1r,2R,3S,4r,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol
(1R,2R,3S,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexaol
(1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol
(1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
4L6452S749
587A93P465
DSSTox_CID_3146
D-chiro Inositol
DSSTox_RID_76890
DSSTox_GSID_23146
1,3,4,5,6-Cyclohexanehexol
1,3,5/4,6-Cyclohexanehexol
alloinositol
neoinositol

How Much Inositol Do I Need?
To experience maximum benefits from inositol, the dosage will vary depending on both the goals of supplementation and the type of inositol taken. 
The below-recommended amounts are for powdered inositol supplements.

INOSITOL is a sugar that is used as a messenger within the brain cells. 
[Inositol is constituent of the intracellular phosphatidyl (PI)) secondary messenger system.] 
This sugar is found in some fruit that we eat. 
The body also makes inositol itself. 
When you take in large amounts of Inositol, some of it goes into brain cells. 
When you raise levels of Inositol Inositol seems to help depression, anxiety, and and OCD in some people.

(1r,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
1,2,4/3,5,6-cyclohexanehexol
rel-(1r,2r,3r,4r,5r,6r)-Cyclohexane-1,2,3,4,5,6-hexaol
rel-(1R,2r,3S,4R,5s,6S)-Cyclohexane-1,2,3,4,5,6-hexaol
Mouse antialopecia factor
1,2,3,4,5,6-Cyclohexanehexol #
cis-1,2,3,4,5,6-cyclohexanehexol
Inositol, cis-
Inositol, neo-
CAS-87-89-8
cis-1,3,5-trans-4,6-Cyclohexanehexol
SMR000857145
SMR000857319
SMR000857320
M94176HJ2F
(+)-Inositol
Inositol NF 12
SR-05000001655
Chiro-inositol, (-)-
EINECS 201-781-2
inositols
Matezodambose
an inositol
Inositol [Nonspecific isomer]
Muscle sugar
ELND 005

The aim of this paper is to critically analyze the composition of many inositol-based products currently used to treat Polycystic Ovary Syndrome (PCOS). 
Several different combinations of myo-inositol and D-chiro-inositol, with and without additional compounds such as micro- and macroelements, vitamins, and alpha-lipoic acid, have been formulated over the years. 
Such therapeutic proposals do not take various features of inositol stereoisomers into consideration. 
As an example, Inositol is important to know that D-chiro-inositol treatment may be beneficial when administered in low doses, yet the progressive increase of its dosage results in the loss of Inositols advantageous effects on the reproductive performance of women and a deterioration in the quality of blastocysts created via in vitro fertilization (IVF). 
In addition, we have to consider that the intestinal absorption of myo-inositol is reduced by the simultaneous administration of D-chiro-inositol since the two stereoisomers compete with each other for the same transporter that has similar affinity for each of them. 
A decrease in myo-inositol absorption is also found when Inositol is coadministered with inhibitors of sugar intestinal absorption and/or types of sugars such as sorbitol, maltodextrin, and sucralose. 

The combination of these may require higher amounts of myo-inositol in order to reach a therapeutic dosage compared to inositol administration alone, a particularly important fact when physicians strive to obtain a specific plasma level of the stereoisomer. 
Finally, we must point out that D-chiro-inositol was found to be an aromatase inhibitor which increases androgens and may have harmful consequences for women. 
Therefore, the inositol supplements used in PCOS treatment must be carefully defined. 
Clinical evidence has demonstrated that the 40 : 1 ratio between myo-inositol and D-chiro-inositol is the optimal combination to restore ovulation in PCOS women. 
Therefore, Inositol is quite surprising to find that inositol-based treatments for PCOS seem to be randomly chosen and are often combined with useless or even counterproductive molecules, all of which can weaken myo-inositol’s efficacy. 
Such treatments clearly lack therapeutic rationale.

inositol myo-D-muco-Inositol
Inositol FCC
4irx
Inositol, chiro-
rac-chiro-inositol
Inosital (TN)
Inositol (NF)
CBU
EINECS 207-681-5
EINECS 207-682-0
EINECS 209-000-7
EINECS 211-393-5
EINECS 211-394-0
EINECS 230-024-9
NSC 25142
EPIINOSITOL
(+)-Epi-Inositol
(+)-Chiro-Inositol
Epi-inositol, 98%
allo-Inositol, 97%
Inositol [USAN:NF]
INOSITOL, MESO
Spectrum_001595
2os9

Inositol is a type of sugar molecule, similar to glucose, but with several substantially different biological functions. 
Inositol is produced by the body and is found naturally in foods.  
Inositol has been studied extensively for use as a dietary supplement due to Inositols many potential health benefits.  
Fertility specialists worldwide are keenly interested in inositol because research indicates Inositol can encourage PCOS patients to ovulate regularly and improve their chances of achieving pregnancy.  
This article will explore the relationship between inositol, PCOS, and insulin to explain why fertility specialists are so excited about this natural, low-intervention, and low-cost treatment.  
We will also review how inositol improves ovulation and pregnancy rates, the ideal inositol dosage for PCOS, and the different types of inositol. 

myo-Inositol-C-[d6]
orthorhombic myo-inositol
D-(+)-Chiro Inositol
J101.890F
J101.891D
Chiro-inositol, (+)-
INOSITOL (D)
INOSITOL (L)
Spectrum3_001053
Spectrum4_001193
Spectrum5_000961
myo-Inositol, >=99%
bmse000102
bmse000103
bmse000113
bmse000901
bmse000922
Epitope ID:144993
scyllo-Inositol, >=98%

Myoinositol is one of nine isomeric forms of inositol. 
This polyol is present in animal and plant cells, either in Inositols free form or as a bound component of phospholipids or inositol phosphate derivatives. 
Inositol plays an important role in various cellular processes as the structural basis for secondary messengers in eukaryotic cells, and in particular as inositol triphosphates (IP3), phosphatidyl inositol phosphate lipids (PIP2/PIP3), and possibly inositol glycans. 
For this reason, myoinositol is important or even essential for the smooth running of a wide range of cell functions, including cell growth and survival, development and functioning of peripheral nerves, osteogenesis, and reproduction. 

Myoinositol was once considered to belong to the vitamin B family; however, because Inositol is produced in sufficient amounts by the human body from d-glucose, it is no longer regarded as an essential nutrient. 
The human diet from animal and plant sources may contain myoinositol in Inositols free form, as inositol containing phospholipid (phosphoinositides), or as phytic acid (inositol hexaphosphate or IP6). 
Indeed, all living cells (animal, plant, bacteria, fungi) contain inositol phospholipids in their membranes, and phytic acid is the principal storage form of phosphorus in many plant tissues, especially bran and seed. 
Hence, the greatest amounts of myoinositol in common foods are found in fresh fruits and vegetables, and in all foods containing seeds (beans, grains, and nuts). 

Especially high phytic acid contents are found in almonds, walnuts, and Brazil nuts, and oats and bran contain more myoinositol than cereals derived from other grains. 
Among the vegetables, the highest contents are observed in beans and peas, while leafy vegetables are the poorest vegetable sources. 
Among the fruits, cantaloupe and citrus fruits (with the exception of lemons) have extraordinarily high contents of myoinositol. 
Cells normally derive inositol from three sources: de novo biosynthesis from glucose-6-phosphate by the 1-d-myoinositol-phosphate synthase (MIPS) and inositol monophosphatase (IMPase) pathways; dephosphorylation of inositol phosphates derived from the breakdown of inositol-containing membrane phospholipids; and uptake from the extracellular fluid via specialized myoinositol transporters.

SCHEMBL5831
SCHEMBL5832
SCHEMBL5969
NCIOpen2_008191
BSPBio_002606
KBioGR_001885
KBioSS_002075
38876-99-2
MLS001332377
MLS001332378
MLS001335965
MLS001335966
MLS001335967
MLS001335968
SCHEMBL187278
SCHEMBL187397
SCHEMBL187796
SCHEMBL188106
SCHEMBL188237
SCHEMBL491333
SCHEMBL959404
SCHEMBL959405
AZD103

Inositol hexanicotinate (also known as inositol hexaniacinate or inositol nicotinate) is the hexanicotinic acid ester of meso-inositol. 
This chemical compound consists of six molecules of nicotinic acid (niacin) with an inositol molecule in the center of the structure.
Inositol is a popular form of food supplement where Inositol acts as a source of niacin (vitamin B3), one of the essential human nutrients. 
Although the inositol hexanicotinate complex does not represent an essential nutrient, niacin is pivotal to cellular metabolism, playing the important role in coenzyme function and oxidation-reduction reactions.

Research and clinical applications
Large doses of inositol have been studied for treatment of depression, but further study is needed to determine whether this is an effective treatment.
Inositol has been found to have modest effects in patients with panic disorder or obsessive-compulsive disorder.

Inositol should not be routinely implemented for the management of preterm babies who have or are at a risk of infant respiratory distress syndrome (RDS).
Noteworthily, myo-inositol helps prevent neural tube defects with particular efficacy in combination with folic acid.
Inositol is considered a safe and effective treatment for polycystic ovary syndrome (PCOS). 
Inositol works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism.
Inositol is also shown to reduce the risk of metabolic disease in people with PCOS.
In addition, thanks to Inositols role as FSH second messenger, myo-inositol is effective in restoring FSH/LH ratio and menstrual cycle regularization.

myo-Inositol's role as FSH second messenger leads to a correct ovarian follicle maturation and consequently to a higher oocyte quality. 
Improving the oocyte quality in both women with or without PCOS, myo-inositol can be considered as a possible approach for increasing the chance of success in assisted reproductive technologies.
In contrast, D-chiro-inositol can impair oocyte quality in a dose-dependent manner.
The high level of DCI seems to be related to elevated insulin levels retrieved in about 70% of PCOS women.
In this regard, insulin stimulates the irreversible conversion of myo-inositol to D-chiro-inositol causing a drastic reduction of myo-inositol. 


CHEMBL278373
CHEMBL468154
ELND-005
GTPL4495
GTPL4645
GTPL4648
GTPL4649
MEGxp0_001817
SCHEMBL1055883
SCHEMBL4748543
SCHEMBL6378921
SCHEMBL6468882
SCHEMBL6791918
CHEMBL1222251
CHEMBL1231671
CHEMBL1950780
CHEMBL3976780
DTXSID7023146

Inositol is also a component of phospholipids and, similar to choline, results in a fatty liver, if insufficient in supply. 
Inositol is synthesized from glucose-6-phosphate after cyclization. 
In some animals, particularly gerbils and hamsters, there is a nutritional need for inositol when they are given diets containing coconut oil. 
Myoinositol is plentiful in foodstuffs. 
The estimated daily intake for large animals can be as high as 1 or 2 g per day. 
Inositol is particularly important in cellular signal transduction and phospholipid assembly. 

Plasma levels of inositol are increased during renal disease and nephrectomy. 
The presence of myoinositol hexabisphosphate (InsP6) in biological fluids (blood, urine, saliva, interstitial fluid) of animals has been clearly demonstrated. 
The existence of intracellular InsP6 in mammalian cells has also been established. 
A relationship between InsP6 ingestion and the InsP6 distribution in various tissues exists. 
Whereas intracellular inositol depends on endogenous synthesis, depletion of extracellular InsP6 occurs at high rates when InsP6-poor diets are consumed. 

Consequently, there are probably health benefits that are linked to dietary inositol and InsP6 intake. 
The suggestion that inositol is important in young animals came from studies carried out throughout the 1970s and 1980s. 
In particular, Inositol was noted that female gerbils fed a diet containing high coconut oil (relatively saturated) develop an intestinal lipodystrophy that is not seen in animals fed a diet containing 20% safflower oil (relatively unsaturated) or a diet of 20% coconut oil supplemented with 0.1% inositol. 
The level of inositol in the intestinal tissue of animals fed the coconut oil diet not supplemented with inositol has been shown to decrease. 
Clearance of lipid (i.e., resolution of the lipodystrophy) was dependent on inositol.

SCHEMBL12371461
SCHEMBL12377889
SCHEMBL12411898
SCHEMBL12711208
SCHEMBL12735687
SCHEMBL13058696
SCHEMBL13114115
SCHEMBL13114116
SCHEMBL13114128
SCHEMBL13207905
SCHEMBL13580047
SCHEMBL14542470
SCHEMBL21388397
ACon1_002457
CHEBI:22357
CHEBI:23311
CHEBI:24848
CHEBI:25492
CHEBI:27374
D-(+)-chiro-Inositol, 95%
KBio2_002075
KBio2_004643
KBio2_007211
KBio3_001826
L-(-)-chiro-Inositol, 95%
AZD-103
DTXSID30110000
DTXSID50905091
DTXSID60903982
myo-Inositol, p.a., 98.0%
1,2,3,4,5/6-cyclohexanehexol
1,2,3,4/5,6-cyclohexanehexol
1,2,3/4,5,6-cyclohexanehexol
1,2,4,5/3,6-cyclohexanehexol
HMS2091N13
HMS2230N03
HMS2235H05
HMS2235M23
HMS3369B06
HMS3369F20
HMS3373E05

Metabolism of the inositol hexanicotinate
Inositol hexanicotinate is (at least partially) absorbed intact and subsequently hydrolyzed in the body, resulting in a free nicotinic acid and inositol. 
Although gastrointestinal absorption of inositol hexanicotinate can vary significantly, approximately 70% of an orally ingested dose absorbs into the bloodstream.
Oral administration of inositol hexanicotinate results in a steady increase in the level of free nicotinic acid in blood and plasma. 
The compound appears to be metabolized slowly, with serum levels of nicotinic acid peaking roughly 6-10 hours after ingestion, compared to the intake of free nicotinic acid when plasma levels can peak after merely half an hour.
The extent of hydrolysis of inositol hexanicotinate appears to be very low; therefore, differences in plasma levels of free nicotinic acid after administering similar oral doses of inositol hexanicotinate and free nicotinic acid may be responsible for different effects observed in clinical studies. 
In fact, the observed effects for inositol hexanicotinate may not be related to Inositols total nicotinic acid content, but rather to a direct effect of the compound on the organism.
The beneficial effects of free nicotinic acid and extended-release nicotinic acid in lowering the concentration of lipids are well established, but the beneficial effects of inositol hexanicotinate on serum lipids depends on the uptake and subsequent release of the nicotinic acid moieties from the inositol hexanicotinate molecule. 
Considering the aforementioned low extent of hydrolysis, this mechanism is not sufficient to significantly alter plasma lipid profiles.

Pharmakon1600-01500352
1,2,3,4,5,6-Cyclohexanehexaol
BCP25172
HY-B1411
HY-N3021
NSC25142
NSC55558
ZINC1530357
D-myo-Inositol, Cell Culture Grade
Tox21_111642
Tox21_302035
6643AB
ANW-43204
CCG-36096
cis-Inositol, >=98.0% (TLC)
KM0846
MFCD00003863
MFCD00272608
MFCD00799555
MFCD00799556
MFCD01321249
NSC 55552
NSC 55558
NSC-45517
NSC-55552
NSC-55558
NSC103959
NSC127230
NSC757076
s4530
STL453612

About inositol
Inositol is a substance found in many foods, including beans, fruits, and vegetables. 
Though similar in structure to a glucose molecule — sugar — inositol is more like a vitamin than a sugar. 
In fact, Inositol’s sometimes referred to as vitamin B8. 
However, inositol isn’t considered an essential nutrient because your body produces Inositol. 
This means there are no recommended amounts you need to consume every day to make sure your body is getting the amount Inositol needs.
Despite your body’s ability to produce Inositols own supply of inositol, most of what your body needs comes from the food you eat.
When in your cells, inositol serves as a signaling agent for insulin, which is a hormone produced in your pancreas that regulates blood sugar. 
The vitamin-like substance also triggers the release of other hormones, including follicle-stimulating hormone and thyroid-stimulating hormone (TSH), which regulates your body’s metabolism.

Benefits of inositol
Though researchers are still learning about inositol what Inositol does in your body, Inositol’s used as a complementary therapy for health conditions such as metabolic syndrome and polycystic ovary syndrome (PCOS). 
People with metabolic syndrome and PCOS struggle with hormone imbalance, as well as weight loss. 
Supplementing with inositol may improve hormone balance, including insulin and TSH.
Inositol supplements may also benefit mental health conditions like depression and anxiety. 
Though the research is limited, Inositol’s theorized that inositol influences the brain chemicals that alter your mood, including serotonin and dopamine. 

Inositol and weight loss
So, how can inositol help you lose weight? 
By improving hormone balance, namely insulin and TSH levels, inositol may support your weight-loss efforts by regulating your blood sugar and boosting your metabolism. 
Though beneficial to your weight loss, inositol alone won’t help you lose the weight and keep Inositol off. 
Our inositol supplements are part of our lipotropic shots, which also include other metabolism-boosting nutrients: methionine, choline, and vitamin B12.
But even the fat-burning injection isn’t enough to help you lose the weight and keep Inositol off. 
Our lipotropic shots serve as a complementary therapy for our 10-week program. 
Our 10-week weight-loss program includes personalized dietary counseling, behavioral therapy, medical monitoring and management, and other weight-loss treatments like prescription appetite suppressants and vibra therapy. 
Inositol supports your weight-loss efforts, but Inositol’s not a magical fat-burning supplement. 
Inositol works best when combined with a comprehensive weight-loss program.

epi-Inositol, >=98.0% (HPLC)
1,2,3,4,5,6/0-cyclohexanetetrol
AKOS006240678
AKOS006332036
AKOS015895894
AKOS015912905
AKOS015912934
AKOS015960429
AKOS015960633
AKOS015994742
AKOS024318869
Tox21_111642_1
ZINC100018867
ZINC100019018
ZINC100024490
ZINC100032893
ZINC100035580
ZINC100037751
ZINC100055570
ZINC100073149
ZINC100513675
ZINC101185827
ZINC102201844
ZINC103574430
ZINC103574467
ZINC103574475
ZINC250615063
ZINC253837650
ZINC306121118
CS-4782
CS-W010757
DB03106
DB13178
DB15350
HY-W010041
KS-1284
KS-1420
MCULE-2727773046
NSC 103959
NSC 127230
NSC-103959
NSC-127230
NSC-757076
VC30505

Applications
Myo-Inositol is a growth factor for animals and microorganisms. 
Inositol is the most abundant form of polyols that serves as a structural element of secondary messengers in eukaryotic cells. 
Inositol is used as an adulterant in many illegal drugs like cocaine and methamphetamine. 
Further, Inositol is used as a stand-in for cocaine on television and film.

Solubility
Soluble in water. 
Slightly soluble in ethanol, dimethyl sulfoxide and alcohol. Insoluble in ether.    

Notes about Inositol
Incompatible with strong oxidizing agents.    

D-chiro-Inositol, >=98.0% (HPLC)
NCGC00159409-03
NCGC00159409-04
NCGC00169828-01
NCGC00178580-01
NCGC00178580-03
NCGC00255362-01
AC-11070
AK546883
AS-10616
AS-68396
AS-68424
cyclohexane-1R,2R,3S,4S,5R,6S-hexol
K572
LS-13189
NCI60_041778
SY060836
myo-Inositol, purum, >=98.0% (HPLC)
rac-chiro-1,2,3,4,5,6-cyclohexanehexol
SBI-0051369.P003
AB0014290
cis-1,2,4-trans-3,5,6-Cyclohexanehexol
DB-051583
DB-051584
DB-054642
HY-121962
myo-Inositol, for microbiology, >=99.0%
CS-0023004
CS-0083766
FT-0627237
FT-0632208
FT-0632209
FT-0632730
FT-0652045
FT-0670351
FT-0670357
FT-0693444
FT-0693614

Inositol and Heart health
Inositol also has free radical fighting properties that can help prevent various types of chronic diseases.
Free radicals are created when oxygen splits into individual atoms but has unpaired electrons. 
Electrons need to be coupled, so the atoms (free radicals) in your body look for other electrons to form a pair. 
This leads to damage to cells, proteins and DNA.
Combined with better blood sugar control, inositol can play an even bigger role in preventing high blood pressure, cholesterol, and heart disease.

Myo-inositol is one of nine possible structural forms of inositol. 
Inositol is the most stable form and is widely used as a supplement by manufacturers.
Inositol plays a structural role in the membranes around our cells, helping to control which substances and enzymes can enter or leave the body or act in the body.
One example is inositol's involvement in “feel good hormones” such as serotonin, dopamine and glutamine - which leads to Inositols effects on the brain and mental health. 
Myo-inositol is the most commonly tested form for this purpose.

Melting Point: 224°C to 227°C
Density: 1.75
Quantity: 100g
Assay Percent Range: 98%
Beilstein: 1907329
Merck Index: 14,4978
Solubility Information: 
Soluble in water. 
Slightly soluble in ethanol,dimethyl sulfoxide and alcohol. 
Insoluble in ether.
Formula Weight: 180.16
Percent Purity: ≥98%
Chemical Name or Material: Inositol

Polycystic ovary syndrome is a common cause of anovulation and infertility, and a risk factor for development of metabolic syndrome and endometrial cancer. 
Systematic review and meta-analysis of randomised controlled trials (RCT) that evaluated the effects of inositol as an ovulation induction agent.
We searched MEDLINE, EMBASE, Cochrane and ISI conference proceedings, Register and Meta-register for RCT and WHO trials’ search portal. 
We included studies that compared inositol with placebo or other ovulation induction agents. 
Quality of studies was assessed for risk of bias. 
Results were pooled using random effects meta-analysis and findings were reported as relative risk or standardised mean differences. 
We included ten randomised trials. 

A total of 362 women were on inositol (257 on myo-inositol; 105 on di-chiro-inositol), 179 were on placebo and 60 were on metformin. 
Inositol was associated with significantly improved ovulation rate (RR 2.3; 95% CI 1.1–4.7; I2 = 75%) and increased frequency of menstrual cycles (RR 6.8; 95% CI 2.8–16.6; I2 = 0%) compared with placebo. 
One study reported on clinical pregnancy rate with inositol compared with placebo (RR 3.3; 95% CI 0.4–27.1), and one study compared with metformin (RR 1.5; 95% CI 0.7–3.1). 
No studies evaluated live birth and miscarriage rates. 
Inositol appears to regulate menstrual cycles, improve ovulation and induce metabolic changes in polycystic ovary syndrome; however, evidence is lacking for pregnancy, miscarriage or live birth. 
A further, well-designed multicentre trial to address this issue to provide robust evidence of benefit is warranted.

I0040
I0628
I0629
I0630
I0631
I0632
I0633
S6176
ST50406013
myo-Inositol, BioUltra, >=99.5% (HPLC)
myo-Inositol, SAJ special grade, >=99.0%
myo-Inositol, Vetec(TM) reagent grade, 99%
3635-EP2275412A1
3635-EP2280282A1
3635-EP2289886A1
3635-EP2292088A1
3635-EP2295417A1
3635-EP2295437A1
3635-EP2298312A1
3635-EP2298775A1
3635-EP2305636A1
3635-EP2305677A1
3635-EP2305682A1
3635-EP2308879A1
C00137
C06151
C06152
C06153
C19891
D08079
I-6500
K-9876
M01914

myo-Inositol is an inositol isoform. 
Inositol is a derivative of cyclohexane with six hydroxyl groups, making Inositol a polyol. 
Inositol also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. 
Inositol exists in nine possible stereoisomers, of which cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol is the most widely occurring form in nature. 
The other known inositols include scyllo-inositol, muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol.
myo-Inositol is found naturally in many foods (particularly in cereals with high bran content) and can be used as a sweetner as Inositol has half the sweetness of sucrose (table sugar). 
myo-Inositol was once considered a member of the vitamin B complex and given the name: vitamin B8. 
However, because Inositol is produced by the human body from glucose, Inositol is not an essential nutrient, and therefore cannot be called a vitamin. 

myo-Inositol is a precursor molecule for a number of secondary messengers including various inositol phosphates. 
In addition, inositol/myo-inositol is an important component of the lipids known as phosphatidylinositol (PI) phosphatidylinositol phosphate (PIP). 
myo-Inositol is synthesized from glucose, via glucose-6-phosphate (G-6-P) in two steps. 
First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme to give free myo-inositol. 
In humans, myo-inositol is primarily synthesized in the kidneys at a rate of a few grams per day. 
myo-Inositol can be used in the management of preterm babies who have or are at a risk of infant respiratory distress syndrome. 
Inositol is also used as a treatment for polycystic ovary syndrome (PCOS). 
Inositol works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism. 
Reduced levels of myo-inositol have been found in the spinal fluid of depressed patients and levels are significantly reduced in brain samples of suicide victims.


12513-EP2277880A1
12513-EP2277881A1
12513-EP2292597A1
12513-EP2292610A1
12513-EP2298744A2
12513-EP2298768A1
12513-EP2305825A1
12513-EP2316831A1
12513-EP2374790A1
13719-EP2269977A2
13719-EP2280010A2
13719-EP2289891A2
13719-EP2295437A1
13719-EP2298734A2
13719-EP2298775A1
13719-EP2308875A1
13719-EP2311831A1
13719-EP2316836A1

Pharmacodynamics
Inositol can stimulate glucose uptake in skeletal muscle cells which allows the decrease in blood sugar levels. 
This effect of Inositol is later seen as a reduction in urine glucose concentration and indicates a decrease in high blood sugar levels.
In PCOS, the administration of inositol has produced the remission of symptoms as well as a reduction in male hormone secretion, a regulation of the cholesterol level, and a more efficient fat breakdown which allow to a significant reduction on body mass and appetite.
In the cases of infertility, inositol has been proven to increase sperm count and motility, as well as increase the overall quality of oocytes and embryos.
In the brain, inositol has been shown to produce an increase in serotonin receptor sensitivity. 
This activity produces an increase in GABA release.
Some of the effects observed in the brain produced a relief in symptoms of anxiety and obsessive-compulsive disorders.
In high doses, Inositol has been shown to even reduce panic attacks.
In cancer research, inositol has gained interest as Inositol can act as an antioxidant, anti-inflammatory and Inositol seems to enhance immune properties.

Inositol Mechanism of action
The mechanism of action of inositol in brain disorders is not fully understood but Inositol is thought that Inositol may be involved in neurotransmitter synthesis and Inositol is a precursor to the phosphatidylinositol cycle. 
The change that occurs in the cycle simulates when the postsynaptic receptor is activated but without activating the receptor. 
This activity provokes a fake activation which regulated the activity of monoamines and other neurotransmitters.

Reports have shown that insulin resistance plays a key role in the clinical development of PCOS. 
The presence of hyperinsulinemia can induce an excess in androgen production by stimulating ovaries to produce androgens and by reducing the sex hormone binding globulin serum levels. 
One of the mechanisms of insulin deficiency is thought to be related to a deficiency in inositol in the inositolphosphoglycans. 
The administration of inositol allows Inositol to act as a direct messenger of the insulin signaling and improves glucose tissue uptake.
This mechanism is extrapolated to Inositols functions in diabetes treatment, metabolic syndrome, and weight loss.

In cancer, the mechanism of action of inositol is not fully understood. 
Inositol is hypothesized that the administration of inositol increases the level of lower-phosphate inositol phosphates why can affect cycle regulation, growth, and differentiation of malignant cells. 
On the other hand, the formation of inositol hexaphosphate after administration of inositol presents antioxidant characteristics by the chelation of ferric ions and suppression of hydroxyl radicals.

Inositol Absorption
Inositol is absorbed from the small intestine.
In patients with inositol deficiency, the maximal plasma concentration after oral administration of inositol is registered to be of 4 hours.
Inositol is taken up by the tissues via sodium-dependent inositol co-transporter which also mediates glucose uptake.
Oral ingestion of inositol is registered to generate a maximal plasma concentration of 36-45 mcg.

Inositol and Volume of distribution
The pharmacokinetic profile of inositol was studied in preterm infants and the estimated volume of distribution was reported to be 0.5115 L/kg.18

Inositol and Protein binding
Inositol is thought that inositol can be found bound to plasma proteins.

Inositol and Metabolism
Inositol is thought that inositol is metabolized to phosphoinositol and then converted to phosphatylinositol-4,5-biphosphate which is a precursor of the second-messenger molecules.
Inositol can be transformed to D-chiro-inositol via the actions of an epimerase. 
The normal modifications to inositol structure seem to be between all the different isomers.

Inositol may be used in food without any limitation. 
As a drug, inositol is used as a nutrient supplement in special dietary foods and infant formula.
As Inositol presents a relevant role in ensuring oocyte fertility, inositol has been studied for Inositols use in the management of polycystic ovaries.
Inositol is also being researched for the treatment of diabetes, prevention of metabolic syndrome, aid agent for weight loss, treatment of depression, psychiatric disorder and anxiety disorder6 and for prevention of cancer.

2-Cyano-N-(2,4,6-trimethyl-phenyl)-acetamide
40032-EP2298312A1
40032-EP2311830A1
AB00051982_13
643C129
A834712
A836375
Q407997
Q743661
Q-201583
Q2838375
Q2974313
Q3011024
Q3023527
Q3205874
Q3331426
Q3347078
Q3589114

What is the issue?
This review aimed to investigate if myo-inositol is an effective antenatal dietary supplement for preventing gestational diabetes in pregnant women. 
Women who develop gestational diabetes have a higher risk of experiencing complications during pregnancy and birth, as well as developing diabetes later on in life. 
The babies of mothers who have gestational diabetes can be larger than they should be potentially causing injuries to the babies at birth. 
These babies are at risk of diabetes even as young children or young adults.

Why is Inositol important?
The number of women being diagnosed with gestational diabetes is increasing around the world so finding simple and cost-effective ways to prevent women developing gestational diabetes is important. 
Myo-inositol is a naturally occurring sugar found in cereals, corn, green vegetables and meat that has a role in the body's sensitivity to insulin.

What evidence did we find?
We searched for studies on 2 November 2015 and included four small randomised controlled trials involving a total of 567 women who were less than 11 weeks' to 24 weeks' pregnant at the start of the trials. 
The quality of the evidence was assessed as low or very low and the overall risk of bias was unclear.
Myo-inositol was associated with a reduction in the rate of gestational diabetes (low quality evidence), reducing the incidence from 28% in women who did not take the supplement, to between 8% and 18% in the women who took Inositol. 
There was no difference between groups in terms of the number of women who had hypertensive disorders of pregnancy (including pre-eclampsia, eclampsia and abnormally high blood pressure during pregnancy) (very low quality evidence). 
The trials did not provide any information about the number of babies that died (either before being born or shortly afterwards) or babies that were large-for-gestational age. 
There were no maternal adverse effects of therapy in the two trials that reported on this outcome (the other two trials did not mention this).
This review did not find any impact on other outcomes such as the risk of having a caesarean section (low quality evidence), a large baby, obstructed labour when the baby's shoulder becomes stuck (shoulder dystocia) or a baby with low blood glucose levels. 
This may be due to the trials being too small to detect differences in these outcomes and the outcomes not being reported by all trials. 
All four trials were from Italy.
The included trials did not report on a large number of other mother and baby outcomes listed in this review and nor were there any data relating to longer-term outcomes for the mother or the infant, or the cost of health services.

What does this mean?
Myo-inositol as a dietary supplement during pregnancy shows promise in preventing gestational diabetes but there is not enough evidence at this stage to support Inositols routine use. 
Further large, well-designed, randomised controlled trials are required to assess the effectiveness of myo-inositol in preventing gestational diabetes and improving other health outcomes for mothers and their babies.
Ideally, future studies should consider involving women from different ethnicities and with differing risk factors for gestational diabetes. 
Inositol would be useful for future studies to consider the ways that myo-inositol can be used (different doses, frequency and when to take Inositol) and compare the intervention with a placebo control, diet and exercise or pharmacological interventions. 
We recommend that future studies utilise the outcomes listed in this review and that potential harms, including adverse effects are included.

Authors' conclusions: 
Evidence from four trials of antenatal dietary supplementation with myo-inositol during pregnancy shows a potential benefit for reducing the incidence of gestational diabetes. 
No data were reported for any of this review's primary neonatal outcomes. 
There were very little outcome data for the majority of this review's secondary outcomes. 
There is no clear evidence of a difference for macrosomia when compared with control.
The current evidence is based on small trials that are not powered to detect differences in outcomes including perinatal mortality and serious infant morbidity. 
All of the included studies were conducted in Italy which raises concerns about the lack of generalisability of the evidence to other settings. 
There is evidence of inconsistency and indirectness and as a result, many of the judgements on the quality of the evidence were downgraded to low or very low quality (GRADEpro Guideline Development Tool).
Further trials for this promising antenatal intervention for preventing gestational diabetes are encouraged and should include pregnant women of different ethnicities and varying risk factors and use of myo-inositol (different doses, frequency and timing of administration) in comparison with placebo, diet and exercise or pharmacological interventions. 
Outcomes should include potential harms including adverse effects.

SR-05000001655-1
SR-05000001655-5
W-202861
W-202862
W-203081
W-203168
W-203392
1,2,4/3,5,6-Cyclohexane-1,2,3,4,5,6-hexol
7B0CEF84-D9CE-4A88-AA7D-EC50C89387A5
1D7A27BF-6060-4FA9-AC46-3BD18DBA406E
220128F1-89BF-442D-AD6D-E6D1EA7BA625
(1r,2r,3r,4r,5r,6r)-cyclohexane-1,2,3,4,5,6-hexaol
(1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
D-MYO-INOSITOL-1,2,5,6-TETRAPHOSPHATE SODIUM SALT
UNII-M94176HJ2F component CDAISMWEOUEBRE-LKPKBOIGSA-N
UNII-M94176HJ2F component CDAISMWEOUEBRE-SHFUYGGZSA-N
(1R,2R,3S,4R,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
Inositol, United States Pharmacopeia (USP) Reference Standard
myo-Inositol, European Pharmacopoeia (EP) Reference Standard
(1R,2R,3S,4S,5S,6R)-CYCLOHEXANE-1,2,3,4,5,6-HEXOL
1,2,3,4,5,6-Cyclohexanehexol, (cis,cis,cis,trans,cis,trans)- #
1,2,3,4,5,6-cyclohexanehexol, (1alpha,2alpha,3alpha,4beta,5alpha,6beta)
Inositol, Pharmaceutical Secondary Standard; Certified Reference Material
2H3
myo-Inositol, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture
myo-Inositol, PharmaGrade, meets FCC testing specifications, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production.

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