α-TOCOPHERYL ACETATE
ATA
CAS Number: 58-95-7
Chemical formula: C31H52O3
Molar mass: 472.743 g/mol
Vitamin E Acetate has effective anti-inflammatory and antioxidant properties.
DL-Alpha tocopheryl acetate or Vitamin-E acetate is frequently preferred in cosmetic formulations for its stable structure.
Vitamin E protects cell membranes from damage by free radicals.
Therefore, it can prevent premature aging of the skin caused by UV light and lipid peroxidation.
α-Tocopheryl acetate (alpha-tocopherol acetate), also known as vitamin E acetate, is a synthetic form of vitamin E.
Vitamin E Acetate is the ester of acetic acid and α-tocopherol.
The U.S. Centers for Disease Control and Prevention says that vitamin E acetate is a very strong culprit of concern in the 2019 outbreak of vaping-associated pulmonary injury (VAPI), but there is not yet sufficient evidence to rule out contributions from other chemicals.
Vaporization of this ester produces toxic pyrolysis products.
The substance used as an additive or thickening agent in some products is also added to supplements and skin creams.
Vitamin E Acetate doesn’t seem to cause harm when swallowed or used topically in moderate amounts.
But previous research suggests that inhaling vitamin E acetate might impair people’s lung function.
Vitamin E Acetate is an active ingredient for use in cosmetic products for the skin and the hair.
As an in-vivo antioxidant, it protects the cells against free radicals and prevents the peroxidation of body fats.
Vitamin E Acetate is also an effective moisturizing agent and improves the elasticity and smoothness of the skin, and is particularly suitable for use in sun-protection products and products for daily personal care.
Vitamin E Acetate is supplied in a light yellow, viscous oil, has practically no odor, and is miscible with hydrocarbons, alcohols, fats and oils; and insoluble in water.
Alpha-tocopheryl acetate (ATA) is a specific form of vitamin E that’s often found in skin care products and dietary supplements.
Vitamin E Acetate also known as tocopheryl acetate, tocopherol acetate, or vitamin E acetate.
Vitamin E is known for its antioxidant properties.
Antioxidants help to protect your body from damaging compounds called free radicals.
Normally, free radicals form when your body converts food into energy.
However, free radicals can also come from UV light, cigarette smoke, and air pollution.
In nature, vitamin E comes in the form of tocopheryl or tocotrienol.
Both tocopheryl and tocotrienol have four forms, known as alpha, beta, gamma, and delta.
Alpha-tocopheryl (AT) is the most active form of vitamin E in humans.
ATA is more stable than AT, meaning it can better withstand environmental stresses such as heat, air, and light.
This makes it ideal for use in supplements and fortified foods because it has a longer shelf life.
ATA is a form of vitamin E that’s often included in cosmetic products and dietary supplements due to its higher stability compared to AT.
When taken orally, ATA is converted into active AT within the body.
The effectiveness of ATA in cosmetic products seems to be limited because ATA isn’t effectively broken down to AT in the upper layers of skin.
Additionally, research on the benefits of ATA supplements is limited and the results are mixed at best.
If you’re looking to get more vitamin E, try adding foods such as leafy green vegetables, nuts, and wheat germ oil to your diet.
DL-Alpha tocopheryl acetate, or Vitamin E Acetate, is the stable form of Vitamin E most often used in cosmetic formulations for its skin care benefits.
Vitamin E protects cell membranes from damage by oxygen free radicals.
Vitamin E Acetate can prevent premature aging of the skin induced by UV irradiation and lipid peroxidation.
Tocopherols and tocotrienols can rapidly scavenge lipid peroxyl free radicals by acting as chain breaking antioxidants, thus preventing them from reacting with other lipids.
This process is key to limiting the propagation of lipid peroxidation in membranes.
Vitamin E Acetate should be noted that tocopherol has the potential to act as a pro-oxidant rather than an anti-oxidant when co-antioxidants like vitamin C are not available to neutralize the tocopherol radical and when oxidative stress is mild.
Naturally occurring vitamin E can be unstable in skin care formulations.
Alpha Tocopherol is susceptible to UV irradiation, being rapidly converted to tocopheroxy radicals that use up other anitoxidants.
Use of Vitamin E Acetate, an ester of alpha tocopherol helps overcome this limitation.
Tocopheryl acetate is bioconverted to its biologically active form, vitamin E, within the skin when applied topically.
Studies show that topical use of tocopherol and alpha tocopheryl acetate are more effective than dietary supplementation in increasing the vitamin E content of the skin.
Supported by numerous studies over the past few years, Vitamin E Acetate has been shown to increase the enzyme activity in the skin, prevent free radical induced skin damage, increase epithelisation of surface wounds and increase the moisturisation of the horny layer.
Vitamin E Acetate is an active ingredient for use in cosmetic products for the skin and the hair.
As an in-vivo antioxidant, it protects the cells against free radicals and prevents the peroxidation of body fats.
Vitamin E Acetate is also an effective moisturizing agent and improves the elasticity and smoothness of the skin.
Vitamin E Acetate is particularly suitable for use in sun-protection products and products for daily personal care.
Tocopherol acetate is not oxidized and can penetrate through the skin to the living cells, where about 5% is converted to free tocopherol and provides beneficial antioxidant effects.
Vitamin E Acetate (Tocopherol) is the stable form of Vitamin E most often used in cosmetic formulations for its skin care benefits.
Vitamin E Acetate protects the cells against free radicals and prevents the peroxidation of body fats as an in-vivo antioxidant.
Vitamin E Acetate Care is an active ingredient for use in cosmetic products for the skin and the hair.
As an in-vivo anti-oxidant, it protects the cells against free radicals and prevent the peroxidation of body fats.
Vitamin E Acetate Care is also an effective moisturizing agent and improves the elasticity and smoothness of the skin.
Vitamin E Acetate is particularly suitable for use in sun-protection products and products for daily personal care.
DL-α-Tocopherol acetate is the ester form of α-Tocopherol.
Tocopherols are a series of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring.
Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage.
α-Tocopherol is the form of tocopherol preferentially absorbed by humans.
Because of its antioxidant characteristics and capabilities, studies have shown Vitamin E's effectiveness in treating many conditions ranging from Alzheimer's to certain blood disorders, and even decreasing menstrual cramp pain.
Vitamin E acetate doesn't necessarily cause harm when ingested as a supplement or applied to the skin via a cream, but studies have shown it can cause harm when inhaled.
The sticky oil substance can cling to lung tissue resulting in illness, though the direct correlation and affect is still being rigorously studied, tested, and analyzed.
The vitamin has been found as an additive in vaping products, especially those containing THC, either as a thickening agent or dilution to make the oil in cartridges go further.
As with most of the information regarding vaping due to its recent rise in popularity, Vitamin E acetate's role and effects are still being studied and determined.
One thing is for sure, its inclusion has been somewhat of a recent addition; for example, vape cartridges studied in Minnesota in 2018 were without Vitamin E acetate, but those from 2019 contained the additive.
Vitamin E in healthy doses is good for you.
Vitamin E Acetate a vitamin that dissolves in fat, and is naturally occurring in many of the wholesome foods you eat daily.
Vitamin E acetate isn't necessarily harmful when ingested as a supplement or applied to the skin via a cream, but studies have shown it can cause harm when inhaled.
There are many potential benefits that are claimed to be offered by tocopheryl acetate, these include:
Treating vitamin E deficiency
Promoting healthy skin (such as moisturizing and preventing wrinkles)
Helping with wound healing
Reducing inflammation
Slowing the progression of age-related macular degeneration (AMD)
Cancer prevention and cancer treatment symptoms (such as side effects of radiation therapy)
Treating heart disease
Improving cognitive decline, such as Alzheimer’s disease
Uses of Vitamin E Acetate:
Active agent suitable as anti-oxidant for cosmetic emulsions, such as sunscreen preparations, body lotions, hand and facial creams.
Use in cosmetics of Vitamin E Acetate:
α-Tocopheryl acetate is often used in dermatological products such as skin creams.
Vitamin E Acetate is not oxidized and can penetrate through the skin to the living cells, where about 5% is converted to free tocopherol.
Claims are made for beneficial antioxidant effects.
α-Tocopheryl acetate is used as an alternative to tocopherol itself because the phenolic hydroxyl group is blocked, providing a less acidic product with a longer shelf life.
Vitamin E Acetate is believed that the acetate is slowly hydrolyzed after it is absorbed into the skin, regenerating tocopherol and providing protection against the sun's ultraviolet rays.
Tocopheryl acetate was first synthesized in 1963 by workers at Hoffmann-La Roche.
Although there is widespread use of tocopheryl acetate as a topical medication, with claims for improved wound healing and reduced scar tissue, reviews have repeatedly concluded that there is insufficient evidence to support these claims.
There are reports of vitamin E-induced allergic contact dermatitis from use of vitamin E derivatives such as tocopheryl linoleate and tocopherol acetate in skin care products.
Incidence is low despite widespread use.
Cosmetics and supplements:
You’ll find ATA in a variety of skin care products.
The antioxidant properties of vitamin E can help to prevent damage to skin caused by free radicals from UV exposure.
Vitamin E may also have an anti-inflammatory effect on the skin.
Due to its higher stability, ATA is also used in vitamin E dietary supplements.
When taken orally, ATA is converted to AT within the intestine.
Vitamin E is in most multi-vitamins, so be sure to check how much is in your multi-vitamin if you take one, before adding a supplement.
Foods:
In addition to dietary supplements and cosmetic products, you can find vitamin E in the following foods:
Green leafy vegetables, such as broccoli and spinach
Oils, such as sunflower oil, wheat germ oil, and corn oil
Sunflower seeds
Nuts, such as almonds and peanuts
Whole grains
Fruits, such as kiwi and mango
Vitamin E is also added to fortified foods, such as cereals, fruit juices, and many spreads.
You can check food labels to see if vitamin E has been added.
If you want to increase your vitamin E intake, you should start by first increasing your intake of these foods.
Applications of Vitamin E Acetate:
After Sun
Baby Care and Cleansing
Body Care
Color Care
Conditioning
Face Care
Face Cleansing
Personal Care Wipes
Self Tanning
Sun Protection
Toothpaste/Mouthwash
α-Tocopheryl acetate (alpha-tocopherol acetate), also known as vitamin E acetate, is a synthetic form of vitamin E.
KEYWORDS:
58-95-7, α-TOCOPHERYL ACETATE, ATA, 2H-1-BENZOPYRAN-6-OL, TRIMETHYLTRIDECYL]-, ACETATE (2R)-, ACETATE 2H-1-BENZOPYRAN-6-OL, D-A-TOCOPHERYL ACETATE, D-ALPHA-TOCOPHERYL ACETATE, DL-A -TOCOPHERYL ACETATE
Potential benefits of Vitamin E Acetate:
Using AT on the skin, especially with vitamin C, helps to prevent UV damage to the skin.
However, AT is less stable in the environment than ATA, which makes it harder to store.
While ATA is less sensitive to heat and light than AT is, there’s less conversion of ATA to the active AT form within the skin.
This is because the cells in the upper layer of your skin are much less metabolically active.
As a result, using cosmetic products containing ATA on your skin may not be very effective.
While there are many studies on the potential benefits of AT, studies on the benefits of ATA are limited.
The results of these studies on ATA are mixed.
ATA usually needs to be used with other vitamins and minerals to have a beneficial effect.
A 2013 study of over 4,000 participants with age-related macular degeneration (AMD) from the Age-Related Eye Disease Study found that their combination of high dose antioxidants C, E, and beta-carotene, along with zinc, worked to delay progression to advanced AMD.
Regarding the benefits of vitamin E supplements overall, study results have been mixed Trusted Source on whether they’re beneficial for the following conditions:
Coronary heart disease
Cancer
Cognitive decline, such as Alzheimer’s disease
Chemistry of Vitamin E Acetate:
At room temperature, α-tocopheryl acetate is a fat-soluble liquid.
Vitamin E Acetate has 3 chiral centers and thus 8 stereoisomers.
Vitamin E Acetate is made by esterifying α-tocopherol with acetic acid.
2R,4R,8R-isomer, also known as RRR-α-tocopheryl acetate, is the most common isomer used for various purposes.
This is because α-tocopherol occurs in nature primarily as RRR-α-tocopherol.
α-Tocopherol acetate does not boil at atmospheric pressure and begins to degrade at 240 °C.
Vitamin E Acetate can be vacuum distilled: it boils at 184 °C at 0.01 mmHg, at 194 °C (0.025 mmHg) and at 224 °C (0.3 mmHg).
In practice, it is not degraded notably by air, visible light or UV-radiation.
Vitamin E Acetate has a refractive index of 1.4950–1.4972 at 20 °C.
α-Tocopherol acetate is hydrolyzed to α-tocopherol and acetic acid under suitable conditions or when ingested by people.
Misuse of Vitamin E Acetate:
Ingredient in vape liquids:
On September 5, 2019, the United States Food and Drug Administration (US FDA) announced that 10 out of 18, or 56% of the samples of vape liquids sent in by states, linked to the recent vaping-related lung disease outbreak in the United States, tested positive for vitamin E acetate which had been used as a thickening agent by illicit THC vape cartridge manufacturers.
On November 8, 2019, the Centers for Disease Control and Prevention (CDC) identified vitamin E acetate as a very strong culprit of concern in the vaping-related illnesses, but has not ruled out other chemicals or toxicants as possible causes.
The CDC's findings were based on fluid samples from the lungs of 29 patients with vaping-associated pulmonary injury, which provided direct evidence of vitamin E acetate at the primary site of injury in all the 29 lung fluid samples tested.
Research suggests when vitamin E acetate is inhaled, it may interfere with normal lung functioning.
A 2020 study found that vaporizing vitamin E acetate produced carcinogenic alkenes and benzene, but also exceptionally toxic ketene gas, which may be a contributing factor to the pulmonary injuries.
Handling and storage of Vitamin E Acetate:
Conditions for safe storage, including any incompatibilities:
Storage conditions
Tightly closed.
Storage class:
Storage class (TRGS 510): 10: Combustible liquids
First aid measures of Vitamin E Acetate:
After inhalation:
fresh air.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Remove contact lenses.
If swallowed:
After swallowing:
Make victim drink water (two glasses at most).
Consult doctor if feeling unwell.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting measures of Vitamin E Acetate:
Suitable extinguishing media:
Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture:
Carbon oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
In the event of fire, wear self-contained breathing apparatus.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental release measures of Vitamin E Acetate:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel: Do not breathe vapors, aerosols.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions:
Take up with liquid-absorbent material (e.g. Chemizorb).
Dispose of properly.
Clean up affected area.
Identifiers of Vitamin E Acetate:
CAS Number: 58-95-7 RRR-α-isomer
ChEMBL: ChEMBL1047
ChemSpider: 77987
DrugBank: DB14003
ECHA InfoCard: 100.000.369
PubChem CID: 86472
UNII: A7E6112E4N
CompTox Dashboard (EPA): DTXSID1031096
InChI:
InChI=1S/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1 check
Key: ZAKOWWREFLAJOT-CEFNRUSXSA-N check
InChI=1/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1
Key: ZAKOWWREFLAJOT-CEFNRUSXBQ
SMILES: O=C(Oc2c(c(c1O[C@](CCc1c2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C)C
Properties of Vitamin E Acetate:
Chemical formula: C31H52O3
Molar mass: 472.743 g/mol
Appearance: pale yellow, viscous liquid
Melting point: –27.5 °C
Boiling point: 240 °C decays without boiling
Solubility in water: insoluble
Solubility: soluble in acetone, chloroform, diethyl ether; poorly soluble in ethanol
Specifications of Vitamin E Acetate:
all-rac-α-Tocopheryl acetate content (GC, Ph Eur): 50.0 - 57.5 %
all-rac-α-Tocopheryl acetate content (GC, USP): 49.0 - 57.5 %
Identity (TLC): conforms
Identity (GC): conforms
Optical rotation α 20/D (all-rac-α-Tocopheryl acetate): -0.01 - 0.01 °
Acetic acid (HS-GC): ≤ 5000 ppm
Heptane (HS-GC): ≤ 5000 ppm
Methanol (HS-GC): ≤ 3000 ppm
Pyridine (HS-GC): ≤ 200 ppm
Toluene (HS-GC): ≤ 890 ppm
Other residual solvents (ICH Q3C): excluded by production process
Loss on drying (130 °C, vacuum, 4 h): ≤ 5.0 %
Total aerobic microbial count (TAMC): ≤ 100 CFU/g
Total combined yeasts/moulds count (TYMC): ≤ 100 CFU/g
Bile-tolerant gram-negative bacteria (absent in 1 g): passes test
Candida albicans (absent in 1 g): passes test
Escherichia coli (absent in 1 g): passes test
Pseudomonas aeruginosa (absent in 1 g): passes test
Salmonella (absent in 10 g): passes test
Staphylococcus aureus (absent in 1 g): passes test
INCI Name: Tocophery acetate
Other names: DL-Alpha Tocopheryl Acetate, Vitamin E
Cosmetic Applications: In all kinds of skin care products, sun care products and make-up products.
Recommended Usage: 0.5 – 5%
Appearance: Transparent yellow viscous oil
Names of Vitamin E Acetate:
Preferred IUPAC name of Vitamin E Acetate:
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate
Other names of Vitamin E Acetate:
α-Tocopherol acetate
Vitamin E acetate
Synonyms of Vitamin E Acetate:
2H-1-BENZOPYRAN-6-OL
3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]-
ACETATE, (2R)-
2H1BENZOPYRAN6OL
3,4DIHYDRO2,5,7,8TETRAMETHYL2(4,8,12TRIMETHYLTRIDECYL),
ACETATE
[2R*(4R*,8R*)](+/)
2H1BENZOPYRAN6OL
3,4DIHYDRO2,5,7,8TETRAMETHYL2(4,8,12TRIMETHYLTRIDECYL)
[2R[2R*(4R*,8R*)]]
3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)- ACETATE 2H-1-BENZOPYRAN-6-OL
3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-2H-BENZOPYRAN-6-YL ACETATE
3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL-2H-BENZOPYRAN-6-OL,
ACETATE 2H-1-BENZOPYRAN-6-OL
3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-
ACETATE 3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL-2H-BENZOPYRAN-6-OL
ALPHA-TOCOPHERYL ACETATE
D-A-TOCOPHERYL ACETATE
D-ALPHA-TOCOPHERYL ACETATE
DL-A -TOCOPHERYL ACETATE
DL-ALPHA TOCOPHERYL ACETATE
DL-ALPHA-TOCOPHERYL ACETATE
TOCOPHERYL ACETATE
DL-ALPHA
VITAMIN E ACETATE
[2R*(4R*,8R*)]-(±)-3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-2H-BENZOPYRAN-6-YL ACETATE