Batyl alcohol

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 Y 6129-13-1 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,2-20H2,1H3 Key: OGBUMNBNEWYMNJ-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCCCOCC(CO)O
Properties
Chemical formula	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). Infobox references

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. 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.