Cetyl alcohol

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Cetyl alcohol[1]
Skeletal formula
Space-filling model
Names
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
Properties
C16H34O
Molar mass 242.45 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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 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).
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Infobox references

Cetyl alcohol /ˈstəl/, 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.[3]

Preparation[edit]

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.[4] Modern production is based around the reduction of palmitic acid, which is obtained from palm oil.

Uses[edit]

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.[5] 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[edit]

People who suffer from eczema can be sensitive to cetyl alcohol,[6][7] though this may be due to impurities rather than cetyl alcohol itself.[8] However, cetyl alcohol is sometimes included in medications used for the treatment of eczema.[9]

Related compounds[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 2020.
  2. ^ "Hexadecan-1-ol_msds". 
  3. ^ Nordegren, Thomas (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal Publishers. p. 165. ISBN 1-58112-404-X. 
  4. ^ Booth, James Curtis (1862). The Encyclopedia of Chemistry, Practical and Theoretical. p. 429. 
  5. ^ Smolinske, Susan C (1992). Handbook of Food, Drug, and Cosmetic Excipients. CRC Press. pp. 75–76. ISBN 0-8493-3585-X. 
  6. ^ Gaul, LE (1969). "Dermatitis from cetyl and stearyl alcohols". Archives of Dermatology. 99 (5): 593. doi:10.1001/archderm.1969.01610230085016. PMID 4238421. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ Kato N; Numata T; Kanzaki T (1987). "Contact dermatitis due to Japanese pharmacopeia cetyl alcohol". Skin Research. 29 (suppl 3): 258–262.