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Wikipedia

Cetyl alcohol

February 15, 2024

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]
Names
Preferred IUPAC name
Hexadecan-1-ol
Other names
Cetanol, Cetyl alcohol, Ethal, Ethol, Hexadecanol, Hexadecyl alcohol, Palmityl alcohol
Identifiers
  • 36653-82-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16125 Y
ChEMBL
  • ChEMBL706 Y
ChemSpider
  • 2581 Y
ECHA InfoCard 100.048.301
EC Number
  • 253-149-0
KEGG
  • D00099 Y
  • 2682
UNII
  • 936JST6JCN Y
  • DTXSID4027991
  • InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3 Y
    Key: BXWNKGSJHAJOGX-UHFFFAOYSA-N Y
  • 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)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
Y verify (what is YN ?)

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

Occurrence and uses edit

The ether chimyl alcohol, derived from cetyl alcohol and glycerol, is a component of some lipid membranes.

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 edit

People who have 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]

Related compounds edit

References edit

  1. ^ Merck Index, 11th Edition, 2020.
  2. ^ "Hexadecan-1-ol_msds".
  3. ^ M. Raneft, D.; Eaker, H.; W. Davis, R. (2001). (PDF). Aquatic Mammals. 27 (2): 185. Archived from the original (PDF) on 2016-03-27. Retrieved 2020-04-26.
  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.

February 15, 2024
cetyl, alcohol, also, known, hexadecan, palmityl, alcohol, fatty, alcohol, with, formula, 15oh, room, temperature, cetyl, alcohol, takes, form, waxy, white, solid, flakes, name, cetyl, derives, from, whale, cetacea, from, latin, cetus, whale, from, ancient, gr. Cetyl alcohol ˈ s iː t el 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 kῆtos romanized ketos lit huge fish 3 from which it was first isolated 4 Cetyl alcohol 1 NamesPreferred IUPAC name Hexadecan 1 olOther names Cetanol Cetyl alcohol Ethal Ethol Hexadecanol Hexadecyl alcohol Palmityl alcoholIdentifiersCAS Number 36653 82 4 Y3D model JSmol Interactive imageChEBI CHEBI 16125 YChEMBL ChEMBL706 YChemSpider 2581 YECHA InfoCard 100 048 301EC Number 253 149 0KEGG D00099 YPubChem CID 2682UNII 936JST6JCN YCompTox Dashboard EPA DTXSID4027991InChI InChI 1S C16H34O c1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 h17H 2 16H2 1H3 YKey BXWNKGSJHAJOGX UHFFFAOYSA N YInChI 1 C16H34O c1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 h17H 2 16H2 1H3Key BXWNKGSJHAJOGX UHFFFAOYASSMILES OCCCCCCCCCCCCCCCCPropertiesChemical formula C 16H 34OMolar mass 242 447 g mol 1Appearance White crystals or flakesOdor Very faint waxyDensity 0 811 g cm3Melting point 49 3 C 120 7 F 322 4 K Boiling point 344 C 651 F 617 K Solubility in water InsolubleSolubility Very soluble in ether benzene and chloroform Soluble in acetone Slightly soluble in alcohol log P 7 25 2 Acidity pKa 16 20Magnetic susceptibility x 183 5 10 6 cm3 molRefractive index nD 1 4283 79 C Viscosity 53 cP 75 C HazardsNFPA 704 fire diamond 110Flash 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 verify what is Y N Infobox references Contents 1 Preparation 2 Occurrence and uses 3 Side effects 4 Related compounds 5 ReferencesPreparation editCetyl 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 Occurrence and uses editThe ether chimyl alcohol derived from cetyl alcohol and glycerol is a component of some lipid membranes 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 editPeople who have 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 Related compounds editPalmitate Palmitic acidReferences edit Merck Index 11th Edition 2020 Hexadecan 1 ol msds 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 Archived from the original PDF on 2016 03 27 Retrieved 2020 04 26 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 Philadelphia H C Baird p 429 Cetyl alcohol Encyclopedia Britannica July 20 1998 Retrieved 2023 01 28 Smolinske Susan C 1992 Handbook of Food Drug and Cosmetic Excipients CRC Press pp 75 76 ISBN 0 8493 3585 X 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 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 S2CID 19854024 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 Kato N Numata T Kanzaki T 1987 Contact dermatitis due to Japanese pharmacopeia cetyl alcohol Skin Research 29 suppl 3 258 262 Retrieved from https en wikipedia org w index php title Cetyl alcohol amp oldid 1194563920, wikipedia, wiki, book, books, library,

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