Batyl alcohol
Chemical compound
From Wikipedia, the free encyclopedia
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 | |
| Names | |
|---|---|
| IUPAC name
3-octadecoxypropane-1,2-diol | |
| Other names
batylic alcohol, batilol, 1-O-octadecylglycerol, stearyl monoglyceride | |
| Identifiers | |
3D model (JSmol) |
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| 1725677 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| 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
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