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Vitamin A


DATA No : VVA0018 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: Tretinoin/All-Trans Retinoic Acid
SYMBOL: ATRA
FORMULA: C20H28O2 MOL.WT (average) : 300.435


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BIOLOGICAL ACTIVITY
A pleiotropic biological activities of vitamin A except visual function result from the binding and activating of retinoid nuclear receptors by all-trans-retinoic acid. (Ref. 0067) All-trans-retinoic acid is effective to acute promyelocytic leukemia (APL).(Ref. 0068)Relative physiological activity for All trans-retinyl acetate is 100%.(Ref. 0046)Differentiation-inducing activity,proliferation-inhibitory activity(Ref. 0018)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:179-180degC(Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:ether 1.56 acetone 1.09 ethanol 0.33 water 0.01 (W/V%)
SPECTRAL DATA
UV SPECTRA:lmax=350nm (E1%1cm 1,510 in Ethanol)(Ref. 0013)

IR SPECTRA:1685,1601,1570,1251,1184,962cm-1(Ref. 0018)

NMR SPECTRA:1H-NMR(d,CDCl3,220MHz):1.02(6H,1-Me),~1.47(2H,2-CH2),~1.62(2H,3-CH2),1.72(3H,5-Me),2.01(3H,9-Me),~2.02(2H,CH2),2.37(3H,13-Me),5.79(1H,14-H),6.14(1H,J=16.0Hz,8-H),6.15(1H,J=11.5Hz,10-H),6.29(1H,J=16.0Hz,7-H),6.31(1H,J=15.0Hz,12-H), 7.03 (1H,J=11.5,15.0Hz,11-H)(Ref. 0003)
13C-NMR(d,CDCl3,22.63MHz):12.9,13.9,19.5,21.6,29.0,29.0,33.3,34.5,40.0,118.5,128.7,129.8,129.8,131.1,135.5,137.6,138.0,139.3,153.2,168.6(CO)(Ref. 0004)

MASS SPECTRA:Fragment(m/e):M +300,285,255,105,91,77,55,41(Ref. 0018)

OTHER SPECTRA:Fluorescence (in Ethanol 25degC):Ex.334 nm, Em.484 nm
X-ray analysis(Ref. 0018/0022)
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
by oxidation of retinal (Ref. 0019)
Single-step process for all-trans nad 13-cis isomers (Ref. 0020/0021)
METABOLISM
All-trans-retinoic acid is metabolized to 13-cis-RA, 9-cis-RA, retunoyl b-glucuronide, 5,6-epoxyretinoic acid, 4-hydroxyretinoic acid, 4-oxoretinoic acid, and 3,4-didehydroretinoic acid. The 4-oxidization or 4-hydroxylation occurs in liver.(Ref. 0001)
GENETIC INFORMATION
Teratogenecity
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 : - ()
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[0018]
AUTHOR:Japan Roche Shiryou
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0019]
AUTHOR:Lakshmanan, M. R., Vaidyanathan, C. S., and Cama, H. R.
TITLE:Oxidation of vitamin A1 aldehyde and vitamin A2 aldehyde to the corresponding acids by aldehyde oxidase from different species PubMed ID:4953590
JOURNAL:Biochem J.
VOL:90 PAGE : 569-573 (1964)
[TOP]

[0020]
AUTHOR:R.Marbet, Ger. pat. 1971, 2,061,507 (to Hoffmann-La Roche)
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0021]
AUTHOR:R.Marbet, U.S. pat. 1973, 3,746,730 (to Hoffmann-La Roche)
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0022]
AUTHOR:
TITLE:
JOURNAL:Terpenoids Steroids.
VOL: PAGE : 5219 - (1975)
[TOP]

[0046]
AUTHOR:Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0067]
AUTHOR:Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman (1994) The Retinoids Biology,Chemistry, and Medicine Second Edition pp443-520 Raven Press New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0068]
AUTHOR:Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman (1994) The Retinoids Biology,Chemistry, and Medicine Second Edition pp597-630 Raven Press New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

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