Chimyl alcohol

Chimyl alcohol is an organic compound with the formula HOCH₂CH(OH)CH₂OC₁₆H₃₃. It is a colorless solid. Chimyl alcohol is a monoether formed by condensation of cetyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-selachyl alcohol and S-batyl alcohol, S-chimyl alcohol is a component of some lipid membranes.^[1] It is found in the liver of the shark Centrophorus squamosus.^[2] The name chimyl is derived from a classification of ratfish, order Chimaeriformes. Like other glyceryl ethers, those derived from chimyl alcohol are not saponifiable.^[3]

Chimyl alcohol

Names
IUPAC name 3-hexadecoxypropane-1,2-diol
Other names chimylic alcohol, 1-O-hexadecyl glycerol
Identifiers
CAS Number	6145-69-3 racemic Y 506-03-6 S-enantiomer (see image)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76061
ChEMBL	ChEMBL142186
ChemSpider	65572
ECHA InfoCard	100.025.591
EC Number	228-149-9
KEGG	C13859
PubChem CID	72733
UNII	P9FNL3D0MN
CompTox Dashboard (EPA)	DTXSID80862067
InChI InChI=1S/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3 Key: OOWQBDFWEXAXPB-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCOCC(CO)O
Properties
Chemical formula	C19H40O3
Molar mass	316.526 g·mol−1
Appearance	colorless solid
Melting point	62.5–63.5 °C (144.5–146.3 °F; 335.6–336.6 K)
Boiling point	445 °C (833 °F; 718 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015). "Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies" (PDF). Chemical Reviews. 115 (16): 8609–8651. doi:10.1021/cr5004002. PMID 26196761.
2. Bordier, Catherine G.; Sellier, Nicole; Foucault, Alain P.; Le Goffic, François (1996). "Purification and characterization of deep sea shark Centrophorus squamosus liver oil 1- O -aklylglycerol ether lipids". Lipids. 31 (5): 521–528. doi:10.1007/bf02522646. PMID 8727645. S2CID 39937991.
3. Taguchi, Hiroyasu; Armarego, Wilfred L. F. (1998). "Glyceryl-Ether Monooxygenase [EC 1.14.16.5]. A Microsomal Enzyme of Ether Lipid Metabolism". Medicinal Research Reviews. 18 (1): 43–89. doi:10.1002/(SICI)1098-1128(199801)18:1<43::AID-MED3>3.0.CO;2-S. PMID 9436181. S2CID 432376.