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Acylglycerol


DATA No : NAG5053 INFORMANT : Nobuo Ueta

NAME : Glycerol 1-(9-octadecenoate)(pm)-(Z)-form / 9-Octadecenoic acid 2,3-dihydroxypropyl ester

COMMON NAME: a-Monoolein / 1-Monoolein/1-Monooleate
SYMBOL:
FORMULA: C21H40O4 MOL.WT (average) : 356.540


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BIOLOGICAL ACTIVITY
Is a competitive inhibitor of dansylsacrosine binding to human serum albumin.(Ref. 5071)
Inactivates African swine fever virus and inhibits its replication in Vero cells.(Ref. 5059)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:Cryst. 35deg. Exhibits polymrphism. (Ref. 5162)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:
Parent ion(P) 1.5
P-[H2O] 1.2
P-[CH2OH] 1.9
Acyl CH3(CH2)nCO 20
CH2(CH2)nCO 39
Acid CH3(CH2)nCOOH 1.4
Acid+H 0.5
Monoacetin 3.8
C3H7 56
-CH2CH2CH=CH2 100
-CH2CHCH=CHCH=CH2 4.3
-CH=CHCH=CHCH=CH2 8.4
m/e=98 46(Ref. 5086)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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 9-octadecenoic 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 at -25degC.(Ref. 5093)/(Ref. 5065)
Can also be prepared using glycidol.(Ref. 5112)
METABOLISM

GENETIC INFORMATION

NOTE

FATTY ACID COMPOSITION
REFERENCES
[5059]
AUTHOR:Sola, A., Rodriguez, S., Garcia Gancedo, A., Vilas, P., and Gil-Fernandez, C.
TITLE:Inactivation and inhibition of African swine fever virus by monoolein, monolinolein, and gamma-linolenyl alcohol. Brief report PubMed ID:3707358
JOURNAL:Arch Virol.
VOL:88 PAGE : 285-292 (1986)
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[5065]
AUTHOR:Anfinsen,J,R. and Perkins,E.G.
TITLE:Preparation of a-monoglycerides
JOURNAL:J. Am. Oil Chem. Soc.
VOL:4111 PAGE : 779 -780 (1964)
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[5071]
AUTHOR:Thumser, A. E., Buckland, A. G., and Wilton, D. C.
TITLE:Monoacylglycerol binding to human serum albumin: evidence that monooleoylglycerol binds at the dansylsarcosine site PubMed ID:9610770
JOURNAL:J Lipid Res.
VOL:39 PAGE : 1033-1038 (1998)
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[5086]
AUTHOR:Johnson,C.B., Holman,R.T.
TITLE:Mass spectrometry of lipids. II. Monoglycerides, their diactetyl derivatives and their trimethylsilyl esters.
JOURNAL:Lipids
VOL:1 PAGE : 371 -380 (1966)
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[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
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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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[5162]
AUTHOR:Gunstone, F.D., Harwood, J.L. and Padley, F.B.(1994) The Lipid Handbook second edition (Gunstone, F.D., Harwood, J.L. and Padley, F.B.), Dictionary section pp151, Chapman & Hall, London
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.