:Cetyl alcohol
{{chembox
| Watchedfields = changed
| verifiedrevid = 476992231
| Name =
| Reference = Merck Index, 11th Edition, 2020.
| ImageFile =
| ImageFile1 = cetyl alcohol structure.svg
| ImageName1 = Skeletal formula
| ImageFile2 = Cetyl-alcohol-3D-vdW.png
| ImageSize2 = 230px
| ImageName2 = Space-filling model
| PIN = Hexadecan-1-ol
| OtherNames = Cetanol, Cetyl alcohol, Ethal, Ethol, Hexadecanol, Hexadecyl alcohol, Palmityl alcohol
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2581
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 936JST6JCN
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00099
| InChI = 1/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
| InChIKey = BXWNKGSJHAJOGX-UHFFFAOYAS
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 706
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BXWNKGSJHAJOGX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 36653-82-4
| PubChem = 2682
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16125
| SMILES = OCCCCCCCCCCCCCCCC
| EINECS = 253-149-0
}}
| Section2 = {{Chembox Properties
| C=16 | H=34 | O=1
| Appearance = White crystals or flakes
| Odor = Very faint, waxy
| Density = 0.811 g/cm3
| MeltingPtC = 49.3
| BoilingPtC = 344
| Solubility = Insoluble
| SolubleOther = Very soluble in ether, benzene, and chloroform.
Soluble in acetone.
Slightly soluble in alcohol.
| pKa = 16.20
| RefractIndex = 1.4283 (79 °C)
| Viscosity = 53 cP (75 °C)
| MagSus = −183.5·10−6 cm3/mol
| LogP = 7.25{{Cite web|url=https://www.chemsrc.com/en/cas/36653-82-4_336997.html|title=Hexadecan-1-ol_msds}}
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPtC = 185
| AutoignitionPtC =
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| LD50 = 5000 mg/kg (rat, oral)
}}
| Section4 =
| Section5 =
| Section6 =
}}
Cetyl alcohol {{IPAc-en|ˈ|s|iː|t|əl}}, 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 refers to whale oil (cetacea oil, from {{langx|la|cetus|lit=whale}}, from {{langx|grc|κῆτος|translit=kētos|lit=huge fish}}){{cite journal |url=http://aquaticmammalsjournal.org/share/AquaticMammalsIssueArchives/2001/AquaticMammals_27-02/27-02_Ranneft.PDF |first1=D. |last1=M. Raneft |first2=H. |last2=Eaker |first3=R. |last3=W. Davis |year=2001 |title=A guide to the pronunciation and meaning of cetacean taxonomic names |journal=Aquatic Mammals |volume=27 |issue=2 |page=185 |access-date=2020-04-26 |archive-date=2016-03-27 |archive-url=https://web.archive.org/web/20160327235028/http://www.aquaticmammalsjournal.org/share/AquaticMammalsIssueArchives/2001/AquaticMammals_27-02/27-02_Ranneft.PDF |url-status=dead }} from which it was first isolated.{{cite book | last = Nordegren | first = Thomas | title = The A-Z Encyclopedia of Alcohol and Drug Abuse | publisher = Universal Publishers | year = 2002 | isbn = 1-58112-404-X| page = 165 }}
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.{{cite book | last = Booth | first = James Curtis | author-link = James Curtis Booth| title = The Encyclopedia of Chemistry, Practical and Theoretical | year = 1862 | url =https://archive.org/details/encyclopediache00morfgoog| page = 429 | publisher = Philadelphia, H.C. Baird }} Modern production is based around the chemical reduction of ethyl palmitate.{{Cite web |date=July 20, 1998 |title=Cetyl alcohol |url=https://www.britannica.com/science/cetyl-alcohol |access-date=2023-01-28 |website=Encyclopedia Britannica |language=en}}
Occurrence and uses
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.{{cite book | last = Smolinske | first = Susan C | title = Handbook of Food, Drug, and Cosmetic Excipients | publisher = CRC Press | year = 1992 | pages = 75–76 | isbn = 0-8493-3585-X }} 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.{{Cite journal|last1=Golemanov|first1=Konstantin|last2=Tcholakova|first2=Slavka|last3=Denkov|first3=Nikolai D.|last4=Gurkov|first4=Theodor|date=April 2006|title=Selection of surfactants for stable paraffin-in-water dispersions, undergoing solid−liquid transition of the dispersed particles|journal=Langmuir|volume=22|issue=8|pages=3560–3569|doi=10.1021/la053059y|pmid=16584227|issn=0743-7463}}
Side effects
People who have eczema can be sensitive to cetyl alcohol,{{cite journal | pmid = 4238421 | year = 1969 | last1 = Gaul | first1 = LE | title = Dermatitis from cetyl and stearyl alcohols | volume = 99 | issue = 5 | pages = 593 | journal = Archives of Dermatology | doi = 10.1001/archderm.1969.01610230085016}}{{cite journal | pmid = 15059111 | year = 2004 | last1 = Soga | first1 = F | last2 = Katoh | first2 = N | last3 = Kishimoto | first3 = S | title = Contact dermatitis due to lanoconazole, cetyl alcohol and diethyl sebacate in lanoconazole cream | volume = 50 | issue = 1 | pages = 49–50 | doi = 10.1111/j.0105-1873.2004.00271j.x | journal = Contact Dermatitis| s2cid = 19854024 }}
though this may be due to impurities rather than cetyl alcohol itself.{{cite journal | pmid = 9034687 | year = 1997 | last1 = Komamura | first1 = H | last2 = Doi | first2 = T | last3 = Inui | first3 = S | last4 = Yoshikawa | first4 = K | title = A case of contact dermatitis due to impurities of cetyl alcohol | volume = 36 | issue = 1 | pages = 44–6 | journal = Contact Dermatitis | doi = 10.1111/j.1600-0536.1997.tb00921.x| s2cid = 23444831 }} However, cetyl alcohol is sometimes included in medications used for the treatment of eczema.{{cite journal | author = Kato N|author2=Numata T |author3=Kanzaki T |title= Contact dermatitis due to Japanese pharmacopeia cetyl alcohol| journal= Skin Research | volume = 29| issue= suppl 3 | pages = 258–262|year = 1987}}