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Vitamin A


DATA No : VVA0020 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: 13-cis-retinoic acid,Isotretinoin
SYMBOL:
FORMULA: C20H28O2 MOL.WT (average) : 300.435


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BIOLOGICAL ACTIVITY
Relative physiological Activity for all-trans-retinyl acetate is 24%.(Ref. 0046)Keratolytic 13-cis-retinoic acid so dramatically reduces sebaceous gland size and sebum excretion (Ref. 0044), presumably due to the inhibition on lipogenesis in human sebaceous gland (Ref. 0045).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:174-175degC(Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax=354 nm(E1%1cm 1,325 in ethanol)(Ref. 0013)

IR SPECTRA:

NMR SPECTRA:1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Me),~1.46(2H,2-CH2),~1.63(2H,3-CH2),1.72(3H,5-Me),2.00(3H,9-Me),~2.0(2H,4-Me),2.10(3H,13-Me),5.69(1H,14-H),6.17(1H,J=16.0Hz,8-H),6.29(1H,J=11.5Hz,10-H),6.29(1H,J=16.0Hz,7-H),7.03 (1H,J=11.5,15.0Hz,11-H),7. 77(1H,J=15.0Hz,12-H),~9.9(1H,COOH)(Ref. 0003)
13C-NMR(d,CDCl3,22.63MHz):12.9,19.4,21.1,21.6,29.0,29.0,33.3,34.4,40.0,115.9,128.9,129.4,130.1,130.3,132.9,137.4,137.9,140.3,153.3,171.4(CO)(Ref. 0004)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
Single step process(Ref. 0020/0021)
METABOLISM
13-cis retinoic acid is one of metabolites from all-trans-retinoic acid.(Ref. 0001)
GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman,The Retinoids Biology,Chemistry, and Medicine Second Edition, pp229-256, Raven Press, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0003]
AUTHOR:Schwieter, U., Englert, G., Rigassi, N., and Vetter, W.
TITLE:Physical organic methods in carotenoid research PubMed ID:5377333
JOURNAL:Pure Appl Chem.
VOL:20 PAGE : 365-420 (1969)
[TOP]

[0004]
AUTHOR:Englert, G.
TITLE:A 13C-NMR. Study of cis-trans isomeric vitamins A, carotenoids and related compounds PubMed ID:1194053
JOURNAL:Helv Chim Acta.
VOL:58 PAGE : 2367-2390 (1975)
[TOP]

[0013]
AUTHOR:Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso (eds Nihon Seikagakukai) Chapter.14 Vitamin A pp.549 Tokyo Kagaku Dojin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0020]
AUTHOR:R.Marbet, Ger. pat. 1971, 2,061,507 (to Hoffmann-La Roche)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0021]
AUTHOR:R.Marbet, U.S. pat. 1973, 3,746,730 (to Hoffmann-La Roche)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0044]
AUTHOR:Landthaler, M., Kummermehr, J., Wagner, A., and Plewig, G.
TITLE:Inhibitory effects of 13-cis-retinoic acid on human sebaceous glands PubMed ID:6453562
JOURNAL:Arch Dermatol Res.
VOL:269 PAGE : 297-309 (1980)
[TOP]

[0045]
AUTHOR:Guy, R., Ridden, C., and Kealey, T.
TITLE:The improved organ maintenance of the human sebaceous gland: modeling in vitro the effects of epidermal growth factor, androgens, estrogens, 13-cis retinoic acid, and phenol red PubMed ID:8648176
JOURNAL:J Invest Dermatol.
VOL:106 PAGE : 454-460 (1996)
[TOP]

[0046]
AUTHOR:Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.