Batyl alcohol

Last updated
Batyl alcohol
S-batylic alcohol.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-874-7
KEGG
PubChem CID
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
Appearancecolorless 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).

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

Related Research Articles

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In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver and are a major component of human skin oils.

Acetaldehyde is an organic chemical compound with the formula CH3CH=O, sometimes abbreviated as MeCH=O. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

<span class="mw-page-title-main">Xanthine oxidase</span> Class of enzymes

Xanthine oxidase is a form of xanthine oxidoreductase, a type of enzyme that generates reactive oxygen species. These enzymes catalyze the oxidation of hypoxanthine to xanthine and can further catalyze the oxidation of xanthine to uric acid. These enzymes play an important role in the catabolism of purines in some species, including humans.

<span class="mw-page-title-main">Glycerol</span> Chemical compound widely used in food and pharmaceuticals

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<span class="mw-page-title-main">Shark liver oil</span> Oil obtained from the livers of sharks

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<span class="mw-page-title-main">Ether lipid</span>

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<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

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<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

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<span class="mw-page-title-main">Glycerol-3-phosphate dehydrogenase</span> Class of enzymes

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<span class="mw-page-title-main">Flavin-containing monooxygenase 3</span> Protein-coding gene in the species Homo sapiens

Flavin-containing monooxygenase 3 (FMO3), also known as dimethylaniline monooxygenase [N-oxide-forming] 3 and trimethylamine monooxygenase, is a flavoprotein enzyme (EC 1.14.13.148) that in humans is encoded by the FMO3 gene. This enzyme catalyzes the following chemical reaction, among others:

Alkylglycerol monooxygenase (AGMO) is an enzyme that catalyzes the hydroxylation of alkylglycerols, a specific subclass of ether lipids. This enzyme was first described in 1964 as a pteridine-dependent ether lipid cleaving enzyme. In 2010 finally, the gene coding for alkylglycerol monooxygenase was discovered as transmembrane protein 195 (TMEM195) on chromosome 7. In analogy to the enzymes phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase and nitric oxide synthase, alkylglycerol monooxygenase critically depends on the cofactor tetrahydrobiopterin and iron.

<span class="mw-page-title-main">2-Arachidonyl glyceryl ether</span> Chemical compound

2-Arachidonyl glyceryl ether is a putative endocannabinoid discovered by Lumír Hanuš and colleagues at the Hebrew University of Jerusalem, Israel. It is an ether formed from the alcohol analog of arachidonic acid and glycerol. Its isolation from porcine brain and its structural elucidation and synthesis were described in 2001.

<span class="mw-page-title-main">Glyceric acid</span> Chemical compound

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<span class="mw-page-title-main">Chimyl alcohol</span> Chemical compound

Chimyl alcohol is an organic compound with the formula HOCH2CH(OH)CH2OC16H33. It is a colorless solid. Chimyl alcohol is a monoether formed by condensation of cetyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-selachyl alcohol and S-batyl alcohol, S-chimyl alcohol is a component of some lipid membranes. It is found in the liver of the shark Centrophorus squamosus. The name chimyl is derived from a classification of ratfish, order Chimaeriformes. Like other glyceryl ethers, those derived from chimyl alcohol are not saponifiable.

Selachyl alcohol is an organic compound with the formula HOCH2CH(OH)CH2OC18H35. It is a colorless oil. Selachyl alcohol is a monoether formed by condensation of oleyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-batyl alcohol and S-chimyl alcohol, S-selachyl alcohol is a component of some lipid membranes. It is found in the liver of the shark Centrophorus squamosus. The name selachyl is derived from a classification of sharks, the neoselachii. Like other glyceryl ethers, those derived from selachyl alcohol are not saponifiable.

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. 1 2 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.