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]
 S-enantiomer
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| Names | |
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| IUPAC name
3-octadecoxypropane-1,2-diol
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| Other names
batylic alcohol, batilol, 1-O-octadecylglycerol, stearyl monoglyceride
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| Identifiers | |
3D model (JSmol)
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| 1725677 | |
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| ECHA InfoCard | 100.008.068 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence 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 + H2O
References
edit- ^ 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.
- ^ 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.