Cetyl alcohol

Cetyl alcohol /ˈsiːtəl/, also known as hexadecan-1-ol and palmityl alcohol, is a C-16 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 (cetacea oil, from Latin: cetus, lit. 'whale', from Ancient Greek: κῆτος, romanized: kētos, lit. 'huge fish')[3] from which it was first isolated.[4]

Cetyl alcohol[1]
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Hexadecan-1-ol
Other names
Cetanol, Cetyl alcohol, Ethal, Ethol, Hexadecanol, Hexadecyl alcohol, Palmityl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.048.301
EC Number
  • 253-149-0
KEGG
UNII
  • InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3 checkY
    Key: BXWNKGSJHAJOGX-UHFFFAOYSA-N checkY
  • InChI=1/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
    Key: BXWNKGSJHAJOGX-UHFFFAOYAS
  • OCCCCCCCCCCCCCCCC
Properties
C16H34O
Molar mass 242.447 g·mol−1
Appearance White crystals or flakes
Odor Very faint, waxy
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, and chloroform.
Soluble in acetone.
Slightly soluble in alcohol.
log P 7.25[2]
Acidity (pKa) 16.20
−183.5·10−6 cm3/mol
1.4283 (79 °C)
Viscosity 53 cP (75 °C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
1
0
Flash point 185 °C (365 °F; 458 K)
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.[5] Modern production is based around the chemical reduction of ethyl palmitate.[6]

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.[7] It is also employed as a lubricant for nuts and bolts, and is the active ingredient in some "liquid pool covers" (forming a non-volatile surface layer to reduce water evaporation, related latent vaporization heat loss, and thus to retain heat in the pool). Moreover, it can also be used as a non-ionic co-surfactant in emulsion applications.[8]

Side effects

People who suffer from eczema can be sensitive to cetyl alcohol,[9][10] though this may be due to impurities rather than cetyl alcohol itself.[11] However, cetyl alcohol is sometimes included in medications used for the treatment of eczema.[12]

References
  1. Merck Index, 11th Edition, 2020.
  2. "Hexadecan-1-ol_msds".
  3. M. Raneft, D.; Eaker, H.; W. Davis, R. (2001). "A guide to the pronunciation and meaning of cetacean taxonomic names" (PDF). Aquatic Mammals. 27 (2): 185.
  4. Nordegren, Thomas (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal Publishers. p. 165. ISBN 1-58112-404-X.
  5. Booth, James Curtis (1862). The Encyclopedia of Chemistry, Practical and Theoretical. Philadelphia, H.C. Baird. p. 429.
  6. "Cetyl alcohol". Encyclopedia Britannica. July 20, 1998. Retrieved 2023-01-28.
  7. Smolinske, Susan C (1992). Handbook of Food, Drug, and Cosmetic Excipients. CRC Press. pp. 75–76. ISBN 0-8493-3585-X.
  8. Golemanov, Konstantin; Tcholakova, Slavka; Denkov, Nikolai D.; Gurkov, Theodor (April 2006). "Selection of surfactants for stable paraffin-in-water dispersions, undergoing solid−liquid transition of the dispersed particles". Langmuir. 22 (8): 3560–3569. doi:10.1021/la053059y. ISSN 0743-7463. PMID 16584227.
  9. Gaul, LE (1969). "Dermatitis from cetyl and stearyl alcohols". Archives of Dermatology. 99 (5): 593. doi:10.1001/archderm.1969.01610230085016. PMID 4238421.
  10. 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. S2CID 19854024.
  11. 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. S2CID 23444831.
  12. Kato N; Numata T; Kanzaki T (1987). "Contact dermatitis due to Japanese pharmacopeia cetyl alcohol". Skin Research. 29 (suppl 3): 258–262.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.