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Vitamin A


DATA No : VVA0028 INFORMANT : Hiroyuki Kagechika

NAME : (2Z,4E,6E,8E)-7-Hydroxymethyl-3-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8- tetraenoic acid

COMMON NAME: 19-Hydroxy-13-cis-retinoic acid
SYMBOL: 19-Hydroxy-13CRA
FORMULA: C20H28O3 MOL.WT (average) : 316.435


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BIOLOGICAL ACTIVITY
Differentiation-Inducing activity on human promyelocytic leukemia HL-60 cells, which is in accordance with its binding activity to nuclear reinoic acid receptors (RARs).(Ref. 0047)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:137degC(dec)(Ref. 0047)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1H-NMR(d,CD3OD):1.09(6H,s),1.52-1.55(2H,m),1.66-1.72(2H,m),1.78(3H,s),2.08(2H,t,J=6Hz),2.13(3H,d,J=1.10Hz),4.54(2H,s),5.73(s),6.12(d,J=16Hz),6.33(d,J=11.5Hz),6.57(d,J=16.5Hz),7.22(dd,J=11.5,15Hz),7.83(d,J=15Hz)(Ref. 0047)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
b-Ionone was oxidized withPb(OAC)4. The resultant acetate was hydrolyzed, and the 10-hydroxy group was protected by tert-butyldimethylsilylation. The obtained silylether ws allowed to react with triethylphosphoacetate, followed by successive reduction with DIBAL and oxidation with active MnO2. The obtained aldehyde was allowed to react with methyl-g-dimethylphosphonosenecioate to give methyl esters of 19-hydroxy-ATRA and of 19-hydroxy-13CRA in the ratio of 1.3 : 1. Separation using silica gel column chromatography, and alkaline hydrolysis followed by recrystallization gave 19-hydroxy-13CRA.(Ref. 0047)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0047]
AUTHOR:Matsushima, Y., Kawachi, E., Tanaka, H., Kagechika, H., Hashimoto, Y., and Shudo, K.
TITLE:Differentiation-inducing activity of retinoic acid isomers and their oxidized analogs on human promyelocytic leukemia HL-60 cells PubMed ID:1335240
JOURNAL:Biochem Biophys Res Commun.
VOL:189 PAGE : 1136-1142 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.