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Acylglycerol


DATA No : NAG5254 INFORMANT : Nobuo Ueta

NAME : Glycerol 1-eicosanoate /Eicosanoic acid 2,3-dihydroxypropyl ester

COMMON NAME: 1-Monoarachin
SYMBOL:
FORMULA: C23H46O4 MOL.WT (average) : 386.609


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:bform 84degC.

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CHEMICAL SYNTHESIS
Glycerol is reacted with acetone in the presence of p-toluensulphonic acid to yield 1,2-isopropylidene glycerol, which can be acylated with eicosanoic acid under refluxing conditions in the presence of the acid catalyst. Acid catalyst and excess isopropylidene glycerol are removed with sodium acetate solution, and the extent of the acetonation and acylation reactions can be determined by quantification of the amount of water released. The isopropylidene ester is then cleaved with boric acid and the product is purified by crystallization and other methods.(Ref. 5093)
Can also be prepared using glycidol.(Ref. 5112)
METABOLISM

GENETIC INFORMATION

NOTE

FATTY ACID COMPOSITION
REFERENCES
[5093]
AUTHOR:Jensen,R.G. and Pitas,R.E.(1976)Synthesis of Some Acylglycerols and Phosphoglycerides, in Advances in LIPID RESEARCH, vol.14(Paoletti,R. and Kritchevsky,D.,eds), pp224-226, Academic Press, New York,San Francisco,London
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[5112]
AUTHOR:Burgos,C.E.,Ayer,D.E. and Johnson,R.A.
TITLE:
JOURNAL:J.Org.Chem.
VOL:52 PAGE : 4973 - (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.