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]
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:
^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.
^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.
^ abTaguchi, 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.
January 01, 1970
batyl, alcohol, organic, compound, with, formula, hoch2ch, ch2oc18h37, colorless, solid, monoether, formed, condensation, stearyl, alcohol, with, primary, alcohol, sites, glycerol, together, with, selachyl, alcohol, chimyl, alcohol, batyl, alcohol, component, . 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 Batyl alcohol S enantiomer Names IUPAC name 3 octadecoxypropane 1 2 diol Other names batylic alcohol batilol 1 O octadecylglycerol stearyl monoglyceride Identifiers CAS Number 544 62 7 racemic Y6129 13 1 S enantiomer 3D model JSmol Interactive image Beilstein Reference 1725677 ChEBI CHEBI 34117 ChEMBL ChEMBL1482516 ChemSpider 3553 ECHA InfoCard 100 008 068 EC Number 208 874 7 KEGG C13858 PubChem CID 3681 UNII 39YR661C4U CompTox Dashboard EPA DTXSID0047799 InChI 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 1H3Key OGBUMNBNEWYMNJ UHFFFAOYSA N SMILES CCCCCCCCCCCCCCCCCCOCC CO O Properties Chemical formula C 21H 44O 3 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 Infobox referencesOccurrence and metabolism editIt 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 H2OReferences edit Sutter Marc Silva Eric Da Duguet Nicolas Raoul Yann Metay 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 Bordier Catherine G Sellier Nicole Foucault Alain P Le Goffic Francois 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 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 lt 43 AID MED3 gt 3 0 CO 2 S PMID 9436181 S2CID 432376 Retrieved from https en wikipedia org w index php title Batyl alcohol amp oldid 1194801360, wikipedia, wiki, book, books, library,
