Cetyl alcohol

Cetyl alcohol

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
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 253-149-0
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
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; 322.5 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
1.4283 (79 °C)
Viscosity 53 cP (75 °C)
Hazards
NFPA 704
1
1
0
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).
 Y  (: Y/N?)

Cetyl alcohol , also known as 1-hexadecanol 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]

Contents

  • Preparation 1
  • Uses 2
  • Side effects 3
  • Related compounds 4
  • References 5

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

  1. ^ Merck Index, 11th Edition, 2020.
  2. ^ Nordegren, Thomas (2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal Publishers. p. 165.  
  3. ^  
  4. ^ Smolinske, Susan C (1992). Handbook of Food, Drug, and Cosmetic Excipients. CRC Press. pp. 75–76.  
  5. ^ Gaul, LE (1969). "Dermatitis from cetyl and stearyl alcohols". Archives of dermatology 99 (5): 593.  
  6. ^ 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.  
  7. ^ 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.  
  8. ^ Kato N; Numata T; Kanzaki T (1987). "Contact dermatitis due to Japanese pharmacopeia cetyl alcohol". Skin Research 29 (suppl 3): 258–262.