Cetyl alcohol
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| Names | |
|---|---|
| IUPAC name
Hexadecan-1-ol | |
| Other names
Cetanol, Cetyl alcohol, Ethal, Ethol, Hexadecanol, Hexadecyl alcohol, Palmityl alcohol | |
| Identifiers | |
36653-82-4  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:16125 |
| ChEMBL | ChEMBL706 |
| ChemSpider | 2581 |
| ECHA InfoCard | 100.048.301 |
| EC Number | 253-149-0 |
| KEGG | D00099 |
| PubChem | 2682 |
| UNII | 936JST6JCN |
| |
| |
| Properties | |
| C16H34O | |
| Molar mass | 242.45 g·mol−1 |
| Appearance | White crystals or flakes |
| Odor | very faint |
| Density | 0.811 g/cm3 |
| Melting point | 49.3 °C (120.7 °F; 322.4 K) |
| Boiling point | 344 °C (651 °F; 617 K) |
| insoluble | |
| Solubility | very soluble in ether, benzene, chloroform soluble in acetone slightly soluble in alcohol |
| Acidity (pKa) | 16.20 |
| Refractive index (nD) |
1.4283 (79 °C) |
| Viscosity | 53 cP (75 °C) |
| Hazards | |
| NFPA 704 | |
| Flash point | 185 °C (365 °F; 458 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (median dose) |
5000 mg/kg (rat, oral) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Cetyl alcohol /ˈsiːtəl/, also known as hexadecan-1-ol and palmityl alcohol, is a fatty alcohol with the formula CH3(CH2)15OH. At room temperature, cetyl alcohol takes the form of a waxy white solid or flakes. The name cetyl derives from the whale oil (Latin: cetus) from which it was first isolated.[2]
Preparation
Cetyl alcohol was discovered in 1817 by the French chemist Michel Chevreul when he heated spermaceti, a waxy substance obtained from sperm whale oil, with caustic potash (potassium hydroxide). Flakes of cetyl alcohol were left behind on cooling.[3] Modern production is based around the reduction of palmitic acid, which is obtained from palm oil.
Uses
Cetyl alcohol is used in the cosmetic industry as an opacifier in shampoos, or as an emollient, emulsifier or thickening agent in the manufacture of skin creams and lotions.[4] It is also employed as a lubricant for nuts and bolts, and is the active ingredient in some "liquid pool covers" (forming a surface layer to reduce evaporation and retain heat).
Side effects
People who suffer from eczema can be sensitive to cetyl alcohol,[5][6] though this may be due to impurities rather than cetyl alcohol itself.[7] Ironically, this ingredient is sometimes included in medications for the treatment of eczema.[8]
Related compounds
References
- ↑ Merck Index, 11th Edition, 2020.
- ↑ Nordegren, Thomas (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal Publishers. p. 165. ISBN 1-58112-404-X.
- ↑ Booth, James Curtis (1862). The Encyclopedia of Chemistry, Practical and Theoretical. p. 429.
- ↑ Smolinske, Susan C (1992). Handbook of Food, Drug, and Cosmetic Excipients. CRC Press. pp. 75–76. ISBN 0-8493-3585-X.
- ↑ Gaul, LE (1969). "Dermatitis from cetyl and stearyl alcohols". Archives of dermatology. 99 (5): 593. doi:10.1001/archderm.1969.01610230085016. PMID 4238421.
- ↑ Soga, F; Katoh, N; Kishimoto, S (2004). "Contact dermatitis due to lanoconazole, cetyl alcohol and diethyl sebacate in lanoconazole cream". Contact dermatitis. 50 (1): 49–50. doi:10.1111/j.0105-1873.2004.00271j.x. PMID 15059111.
- ↑ Komamura, H; Doi, T; Inui, S; Yoshikawa, K (1997). "A case of contact dermatitis due to impurities of cetyl alcohol". Contact dermatitis. 36 (1): 44–6. doi:10.1111/j.1600-0536.1997.tb00921.x. PMID 9034687.
- ↑ Kato N; Numata T; Kanzaki T (1987). "Contact dermatitis due to Japanese pharmacopeia cetyl alcohol". Skin Research. 29 (suppl 3): 258–262.