Batyl alcohol

From WikiProjectMed
Jump to navigation Jump to search
Batyl alcohol

S-enantiomer
Names
IUPAC name
3-octadecoxypropane-1,2-diol
Other names
batylic alcohol, batilol, 1-O-octadecylglycerol, stearyl monoglyceride
Identifiers
3D model (JSmol)
1725677
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.068 Edit this at Wikidata
EC Number
  • 208-874-7
KEGG
UNII
  • InChI=1S/C21H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-20-21(23)19-22/h21-23H,2-20H2,1H3
    Key: OGBUMNBNEWYMNJ-UHFFFAOYSA-N
  • CCCCCCCCCCCCCCCCCCOCC(CO)O
Properties
C21H44O3
Molar mass 344.580 g·mol−1
Appearance colorless solid
Melting point 70.5 °C (158.9 °F; 343.6 K)
Boiling point 215–220 °C (419–428 °F; 488–493 K) 2 mm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Batyl alcohol is an organic compound with the formula HOCH2CH(OH)CH2OC18H37. It is a colorless solid. Batyl alcohol is a monoether formed by condensation of stearyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-selachyl alcohol and S-chimyl alcohol, S-batyl alcohol is a component of some lipid membranes.[1]

Occurrence and metabolism

It is found in the liver of the shark Centrophorus squamosus.[2] The name batyl is derived from a classification of rays, order Batoidea. Like other glyceryl ethers, those derived from batyl alcohol are not saponifiable.[3]

Batyl alcohol and related glycyl ethers are susceptible to oxidation catalyzed by glyceryl-ether monooxygenases. The net oxidation gives glycerol and the carboxylic acid:

HOCH2CH(OH)CH2OC18H37 + 1.5 O2 → HOCH2CH(OH)CH2OH + HO2CHC17H35 + H2O

Batyl alcohol and related glycyl ethers are also susceptible to dehydrogenation catalyzed unsaturases to give the vinyl ethers called plasmalogens:[3]

HOCH2CH(OH)CH2OC18H37 + [O] → HOCH2CH(OH)CH2OCH=CHC16H35 + H2O

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. ^ a b 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.
Retrieved from "https://mdwiki.org/wiki/Batyl_alcohol"