CIS-9-OCTADECEN-1-OL

Cis-9-octadecen-1-ol = Oleyl alcohol

CAS Number: 143-28-2
EC Number: 205-597-3
Chemical formula: C18H36O
Molar mass: 268.485 g·mol−1

Cis-9-octadecen-1-ol /ˈoʊliˌɪl, ˈoʊliəl/, or oleyl alcohol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7−CH=CH−(CH2)8OH.
Cis-9-octadecen-1-ol is a colorless oil, mainly used in cosmetics.

Cis-9-octadecen-1-ol can be produced by the hydrogenation of oleic acid esters by Bouveault–Blanc reduction, which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation).
The required oleate esters are obtained from beef fat, fish oil, and, in particular, olive oil (from which it gains its name).
The original procedure was reported by Louis Bouveault in 1904 and subsequently refined.

Cis-9-octadecen-1-ol has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmetic products including shampoos and hair conditioners.
Cis-9-octadecen-1-ol has also been investigated as a carrier for delivering medications through the skin or mucus membranes; particularly the lungs.

Cis-9-octadecen-1-ol is a mixture of unsaturated and saturated long-chain fatty alcohols mainly made up of oleyl alcohol and elaidyl alcohol.
Being oily in nature, Cis-9-octadecen-1-ol finds good use as an emollient in topical formulations.

General description of Cis-9-octadecen-1-ol:
Cis-9-octadecen-1-ol has been reported as an effective solvent for oil/water-type tacrolimus (FK506) cream formulation, useful for atopic dermatitis treatment.
v was reported as diluting agent for Alamine 336.
Palm oil esters derived from Cis-9-octadecen-1-ol, have potential applications in the cosmetic and pharmaceutical industries due to the excellent wetting behavior of the esters without the oily feel.

Applications of Cis-9-octadecen-1-ol:
Cis-9-octadecen-1-ol may be employed as solvent during butanol production from corn stover hydrolysates (CSH) with in-situ liquid-liquid extraction.

Cis-9-octadecen-1-ol is a linear, primary alcohol that has a hydroxyl group at the end of the carbon chain.
Cis-9-octadecen-1-ol is used in the manufacture of detergents and as a food additive.
Cis-9-octadecen-1-ol has been shown to inhibit cell lysis in human leukemia HL-60 cells, and to possess anti-inflammatory properties.

The optimum concentration for Cis-9-octadecen-1-ol is between 0.01% and 1%, although it can be used up to 20%.
Cis-9-octadecen-1-ol may also be effective against bacterial enzymes when combined with metoprolol succinate, which can enhance its effects on enzyme activity by up to 3 times.
Cis-9-octadecen-1-ol is found naturally in olive oil and other plants, which makes it a safe compound for use in cosmetics or other products.

Cis-9-octadecen-1-ol is a mixture of unsaturated and saturated long-chain fatty alcohols mainly made up of oleyl alcohol and elaidyl alcohol.
Cis-9-octadecen-1-ol can form a major part of the formulation for non-aqueous bases.

IUPAC name:
(Z)-Octadec-9-en-1-ol

Other names:
Oleyl alcohol

Identifiers of Cis-9-octadecen-1-ol:
CAS Number: 143-28-2
ChEBI: CHEBI:73504
ChemSpider: 4447562
ECHA InfoCard: 100.005.089
KEGG: D05245
PubChem CID: 5284499
UNII: 172F2WN8DV
CompTox Dashboard (EPA): DTXSID0022010

Cis-9-octadecen-1-ol is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7−CH=CH−(CH2)8OH.

KEYWORDS:
143-28-2, 205-597-3, Oleyl alcohol, Crodacol-O, Conditioner 1, Loxanol M, Atalco O, Siponol OC, Sipol O, (Z)-9-Octadecen-1-ol

What Is Cis-9-octadecen-1-ol?
Stearyl Alcohol, Cis-9-octadecen-1-ol and Octyldodecanol are long chain fatty alcohols.
Stearyl Alcohol is a white, waxy solid with a faint odor, while Cis-9-octadecen-1-ol and Octyldodecanol are clear, colorless liquids.
These three ingredients are found in a wide variety of products such as hair conditioners, foundations, eye makeup, skin moisturizers, skin cleansers and other skin care products.

Why is Cis-9-octadecen-1-ol used in cosmetics and personal care products?
Stearyl Alcohol, Cis-9-octadecen-1-ol and Octyldodecanol help to form emulsions and prevent an emulsion from separating into its oil and liquid components.
Cis-9-octadecen-1-ol also reduce the tendency of finished products to generate foam when shaken.
When used in the formulation of skin care products, Stearyl Alcohol, Cis-9-octadecen-1-ol and Octyldodecanol act as a lubricants on the skin surface, which gives the skin a soft, smooth appearance.

Scientific Facts about Cis-9-octadecen-1-ol:
Stearyl Alcohol and Oleyl Alcohol are mixtures of long-chain fatty alcohols.
Stearyl Alcohol consists primarily of n-octadecanol, while Oleyl Alcohol is primarily unsaturated 9-n-octadecenol.
Octyldodecanol is a branched chain fatty alcohol.

Fatty alcohols are higher molecular weight nonvolatile alcohols.
They are produced from natural fats and oils by reduction of the fatty acid (-COOH) grouping to the hydroxyl function (-OH).
Alternately, several completely synthetic routes yield fatty alcohols which may be structurally identical or similar to the naturally-derived alcohols.

Properties of Cis-9-octadecen-1-ol:
Chemical formula: C18H36O
Molar mass: 268.485 g·mol−1
Density: 0.845-0.855 g/cm3
Melting point: 13 to 19 °C (55 to 66 °F; 286 to 292 K)
Boiling point: 330 to 360 °C (626 to 680 °F; 603 to 633 K)
Solubility in water: Insoluble

Cis-9-octadecen-1-ol is an organic compound derived from the plant as well as animal sources.
Cis-9-octadecen-1-ol is a clear liquid having a unique odor.

The natural sources include soybean oil, castor oil, palm kernel oil, and rapeseed.
The synthetic sources are chemically processed by synthesis of propylene glycols and ethylene.

Cis-9-octadecen-1-ol is classified as :
-Emollient
-Emulsifying
-Opacifying
-Viscosity controlling

Origin(s): Vegetable , Synthetic
Nom INCI : OLEYL ALCOHOL
N° EINECS/ELINCS : 205-597-3 / 209-791-9
Comedogenic potential (pc): 4
Classification: Fatty alcohol

Cis-9-octadecen-1-ol's functions (INCI):
Emollient: Softens and softens the skin
Masking Agent: Reduces or inhibits base product odor or taste
Solvent: Dissolves other substances
Viscosity control agent: Increases or decreases the viscosity of cosmetics
Fragrant agent: Used for perfume and aromatic raw materials

CAS Number: 143-28-2
EINECS/ELINCS No: 205-597-3
COSING REF No: 78022
INN Name: oleyl alcohol
Chem/IUPAC Name: (Z)-Octadec-9-enol

Cis-9-octadecen-1-ol is classified under CAS No.143-28-2.
Oleyl Alcohol is also known as cis-9-octadecen-1-ol.
Cis-9-octadecen-1-ol is a non-ionic, unsaturatedfatty alcohol, a long-chain aliphatic alcohol that occurs naturally in fish oils.

Cis-9-octadecen-1-ol prepared by synthetic reduction of plant-derived oleic acid.
Cis-9-octadecen-1-ol can be used in large scale applications as the softening and lubrication of textile fabrics, and in production of carbon paper,stencil paper, and printing ink.
Cis-9-octadecen-1-ol also utilized as an antifoam agent and cutting lubricant.

Cis-9-octadecen-1-ol also known as precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents.
Cis-9-octadecen-1-ol has also been incorporated into various formulations for drug delivery.
Cis-9-octadecen-1-ol can also be used as a non-ionicsurfactant, emulsifier, emollient and thickener in skin creams, lotions and many othercosmetic products.

Cis-9-octadecen-1-ol also used as plasticizer for softening fabrics, surfactant and hair coating in shampoos and hair conditioners, and a carrier for medications.
Cis-9-octadecen-1-ol is widely demanded in the international market due to its high effectiveness, eco-friendliness and purity, and is offered in different grades to meet the varied needs of our clients.

Documentation: Certificate of Analysis
Purity: >99%
Storage: Freezer
Supplied as: Neat
Molecular formula: C18H36O
Molecular weight: 268.48
Physical state: Liquid
Lipid number: C18:1 (9(Z)

CAS Number: 143-28-2
Formula: C18-H36-O
Major Category: Other Uses

Synonyms:
9-Octadecen-1-ol; (Z)-9-Octadecen-1-ol; Oleyl alcohol; Adol 320; Adol 330; Adol 34; Adol 340; Adol 80; Adol 85; Adol 90; Atalco O; Cachalot O-1; Cachalot O-15; Cachalot O-3; Cachalot O-8; Conditioner 1; Crodacol A.10; Crodacol-O; Dermaffine; H.D. eutanol; HD oleyl alcohol 70/75; HD oleyl alcohol 80/85; HD oleyl alcohol 90/95; HD oleyl alcohol CG; HD-Ocenol 90/95; HD-Ocenol K; Lancol; Loxanol 95; Loxanol M; Novol; Ocenol; Oceol; Octadecenol; Oleic alcohol; Oleo alcohol; Oleol; Oleoyl alcohol; Olive alcohol; Satol; Sipol O; Siponol OC; Unjecol 110; Unjecol 50; Unjecol 70; Unjecol 90; Witcohol 85; Witcohol 90; cis-9-Octadecen-1-ol; cis-9-Octadecenyl alcohol; [ChemIDplus]

Category: Emulsifiers/Surfactants

Description of Cis-9-octadecen-1-ol:
Liquid (usually pale yellow)
mp = 13-19 deg C
Pale yellow liquid

Sources/Uses of Cis-9-octadecen-1-ol:
Cis-9-octadecen-1-ol is present in fish oils.
Cis-9-octadecen-1-ol is used to make its sulfuric esters (detergents and wetting agents) and in carbon paper, stencil paper, printing inks, and bath oils.
Cis-9-octadecen-1-ol is used as metal cutting lubricant, plasticizer, softener and lubricant for textiles, carrier for medicaments, thickener in hair colorants, solvent for fragrances, and emulsifying, opacifying, antifoam, and viscosity increasing agent.

Synonym(s):
Z-9-Dodecen-1-ol, cis-9-Octadecen-1-ol

Linear Formula:
CH3(CH2)7CH=CH(CH2)7CH2OH

CAS Number:
143-28-2

Molecular Weight:
268.48

Beilstein:
1723962

EC Number:
205-597-3

MDL number:
MFCD00002993

PubChem Substance ID:
24862955

Application Notes of Cis-9-octadecen-1-ol:
Cis-9-octadecen-1-ol is used in largescale applications as the softening and lubrication of textile fabrics, and the production of carbon paper, stencil paper, and printing ink.
Cis-9-octadecen-1-ol is also utilized as an antifoam agent and cutting lubricant.
Cis-9-octadecen-1-ol also is a precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents.
Cis-9-octadecen-1-ol has also been incorporated into various formulations for drug delivery.

Usage Statement of Cis-9-octadecen-1-ol:
Unless specified otherwise, MP Biomedical's products are for research or further manufacturing use only, not for direct human use.

Application Insights of Cis-9-octadecen-1-ol:
The cosmetics and personal care segment dominated the market with a revenue share of over 25.0% in 2021.
Cis-9-octadecen-1-ol's high share is attributed to the increasing consumer awareness regarding personal hygiene, along with the growing demand for anti-aging products at a global level.
Cis-9-octadecen-1-ol is found in various products such as eye cream, foundation, hair conditioner, and skin cleansers.
The moisturizing and emollient properties of Cis-9-octadecen-1-ol also drive its demand in personal care and cosmetic applications.

Specifications of Cis-9-octadecen-1-ol:
SKU: 02155996-CF
Alternate Names: Z-9-Dodecen-1-ol;cis-9-Octadecen-1-ol;ocenol

Base Catalog Number: 155996
Beilstein Registry Number: 1723962
Boiling Point: 195 deg C at 8 mm Hg; 182-184 deg C at 1.5 mm Hg (Distilling range at 760 mm Hg: 305-370 deg C)
CAS #: 143-28-2
Density: 0.8489 at 20 deg C/4 deg C
EC Number: 205-597-3
Format: Liquid
Hazard Statements: H315
Melting Point: 13-19 deg C
Molecular Formula: C18H36O
Molecular Weight: 268.485 g/mol
Personal Protective Equipment: Eyeshields, full-face respirator , Gloves, multi-purpose combination respirator cartridge
Purity: ≥99%
Refractive Index: n20/D 1.46(lit.)
RTECS Number: RG4120000
Safety Symbol: GHS07
Usage Statement: Unless specified otherwise, MP Biomedical's products are for research or further manufacturing use only, not for direct human use.
Vapor Pressure: 9.3X10-5 mm Hg at 25 deg C (est)

Molecular Weight: 268.5
XLogP3: 7.4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 15
Exact Mass: 268.276615768
Monoisotopic Mass: 268.276615768
Topological Polar Surface Area: 20.2 Å²
Heavy Atom Count: 19
Formal Charge: 0
Complexity: 175
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count   : 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Description of Cis-9-octadecen-1-ol:
Cis-9-octadecen-1-ol is an emulsifier, lubricant and foam controlling agent.
Cis-9-octadecen-1-ol is a type of unsaturated fatty alcohol.
Cis-9-octadecen-1-ol shows lower melting point compared to saturated long chain fatty alcohols.
Cis-9-octadecen-1-ol is used in oil and other personal care products

Additional Information about Cis-9-octadecen-1-ol:
CAS#:
143-28-2

Formula:
‎C18H36O

grade:
technical grade

Quality Level:
200

assay:
85%

form:
liquid

refractive index:
n20/D 1.46 (lit.)

bp:
207 °C/13 mmHg (lit.)

mp:
0-5.0 °C (lit.)

density:
0.849 g/mL at 25 °C (lit.)

SMILES string:
CCCCCCCC\C=C/CCCCCCCCO

InChI:
1S/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9-

InChI key:
ALSTYHKOOCGGFT-KTKRTIGZSA-N

OLEYL ALCOHOL
(Z)-octadec-9-en-1-ol
143-28-2
cis-9-Octadecen-1-ol
Ocenol
Dermaffine
Lancol
Novol
Oceol
Oleol
Satol
Oleic alcohol
Oleo alcohol
Crodacol-O
Conditioner 1
Loxanol M
Atalco O
Siponol OC
Sipol O
(Z)-9-Octadecen-1-ol
Cachalot O-1
Cachalot O-3
Cachalot O-8
H.D. eutanol
HD-Ocenol K
Loxanol 95
Unjecol 50
Unjecol 70
Unjecol 90
Oleoyl alcohol
Olive alcohol
Cachalot O-15
Crodacol A.10
Unjecol 110
HD oleyl alcohol CG
cis-9-Octadecenyl alcohol
Adol 34
Adol 80
Adol 85
Adol 90
HD-Ocenol 90/95
HD oleyl alcohol 70/75
HD oleyl alcohol 80/85
HD oleyl alcohol 90/95
(Z)-Octadec-9-enol
Witcohol 85
Witcohol 90
9-Octadecen-1-ol, (Z)-
Adol 320
Adol 330
Adol 340
Z-9-Dodecen-1-ol
(9Z)-octadec-9-en-1-ol
cis-octadecen-1-ol
9-Octadecen-1-ol
(Z)-9-octadecenol
Oleylalcohol
Polyoxyl 10 oleyl ether
HD-Eutanol
Octadec-9Z-enol
cis-9-octadecenol
UNII-172F2WN8DV
(9Z)-9-Octadecen-1-ol
9Z-Octadecen-1-ol
Oleyl alcohol (NF)
Oleyl alcohol [NF]
( Z)-9-octadecenol
Witcohol 85 (TN)
9-Octadecen-1-ol, (9Z)-
9-Octadecen-1-ol, cis-
172F2WN8DV
CHEBI:73504
MFCD00002993
NSC-10999
0leyl alcohol
9-Octadecenol
Poly(oxy-1,2-ethanediyl), alpha-((Z)-9-octadecenyl)-omega-hydroxy-
HSDB 6484
EINECS 205-597-3
NSC 10999
AI3-07620
Genapol O
Lipocol O
cis-Oleyl alcohol
C18H36O
Anjecol 90N
Unjecol 90N
(Z)-oleyl alcohol
Anjecol 90NR
Unjecol 90NR
Francol OA-95
Fancol OA-95
cis 9 octadecen-1-ol
cis-9-0ctadecen-1-ol
9(Z)-Octadecen-1-ol
HD-Echelon 90/95
cis-octadec-9-en-1-ol
DSSTox_CID_2010
Octadeca-9-cis-en-1-ol
EC 205-597-3
cis-.DELTA.9-Octadecenol
HD-Ocenol 90/95 V
SCHEMBL5668
(Z)-octadeca-9-en-1-ol
DSSTox_RID_76459
DSSTox_GSID_22010
(9Z)-9-Octadecen-1-ol #
Octadec-9-en-1-ol, (Z)-
CHEMBL2105350
DTXSID0022010
FEMA NO. 4363
Oleyl alcohol, >=99% (GC)
Oleyl alcohol, analytical standard
cis-Laquo deltaRaquo 9-Octadecenol
NSC10999
ZINC8214634
Tox21_200111
(9Z)-9-Octadecen-1-ol, 85%
7025AA
LMFA05000213
Oleyl alcohol, technical grade, 85%
AKOS004910411
(9Z)-9-Octadecen-1-ol, 85per cent
Oleyl alcohol, technical, ~60% (GC)
NCGC00164365-01
NCGC00164365-02
NCGC00257665-01
BS-42539
CAS-143-28-2
DB-007794
O0058
D05245
A884989
Q7086489
W-109512
UNII-13F4MW8Y9K component ALSTYHKOOCGGFT-KTKRTIGZSA-N
UNII-CH428W5O62 component ALSTYHKOOCGGFT-KTKRTIGZSA-N
UNII-UDR641JW8W component ALSTYHKOOCGGFT-KTKRTIGZSA-N
3164D881-7E14-4979-9E60-58DDC0468323
Oleyl alcohol, United States Pharmacopeia (USP) Reference Standard