Back to HOME

Vitamin A


DATA No : VVA0021 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: 9-cis-retinoic acid
SYMBOL:
FORMULA: C20H28O2 MOL.WT (average) : 300.435


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Relative physiological activity for All trans-retinyl acetate is about 10%.(Ref. 0046) Thyroid-stimulating hormone(TSH) of the anterior pituitary gland is regulated by the binding ofthe thyroid hormone-activated thyroid receptor to the TSH gene at the same time as the binding of the 9-cis-retinoic acid-activated retinoid X receptor to the same gene. Both interactions, separately or simultaneously, can suppress and thus regulate the expression fo the TSH gene. 9-cis-retinoic acid suppresses the expression of the TSH gene of the anterior pituitary gland (Ref. 0038/0039/0040/0041). 9-cis-retinoic avid induces and activates acyl-coenzyme A:cholesterol acyltransferase (ACAT) by increase in ACAT-1 messenger ribonucleic acid (mRNA) in undifferentiated human monocytotic THP-1 cells (Ref. 0042). 9-cis-retinoic avid stimulates leptin messenger ribonucleic acid (mRNA) expression and secretion in human syncytiotrophoblast (Ref. 0043).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:189-191degC(Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax=345 nm (E1%1cm 1,230 in ethanol)(Ref. 0013)

IR SPECTRA:

NMR SPECTRA:1H-NMR(d,CDCl3,220MHz):1.04(6H,1-Me),~1.48(2H,2-CH2),~1.64(2H,3- CH2),1.75(3H,5-Me),2.01(3H,9-Me),~2.04(2H,4-CH2),2.37(3H,13-Me),5.82(1H,14-H),6.09(1H,J=11.3Hz,10-H),6.27(1H,J=14.7Hz,12-H),6.31(1H,J=15.7Hz,7-H),6.67(1H,J=15.7Hz,8-H),7.15( 1H,J=11.3,14.7Hz,11-H)(Ref. 0003)
13C-NMR(d,CDCl3+DMSO-d6 1:1,22.63MHz):13.4,18.9,20.5,21.6,28.8,28.8,32.7,33.9,39.3,119.6,128.1,129.0,129.4, 129.6,129.6,134.7,137.3,137.6,151.2,167.8(CO)(Ref. 0004)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
9-cis-retinoic acid is one of the 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 : - ()
[TOP]

[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]

[0038]
AUTHOR:Sherman, S. I., Gopal, J., Haugen, B. R., Chiu, A. C., Whaley, K., Nowlakha, P., and Duvic, M.
TITLE:Central hypothyroidism associated with retinoid X receptor-selective ligands PubMed ID:10194237
JOURNAL:N Engl J Med.
VOL:340 PAGE : 1075-1079 (1999)
[TOP]

[0039]
AUTHOR:Haugen BR, Brown NS, Wood WM, Gordon DF, Ridgway EC.
TITLE:The thyrotrope-restricted isoform of the retinoid-X receptor-
JOURNAL:Mol Endocrinol.
VOL:11 PAGE : 481 -489 (1997)
[TOP]

[0040]
AUTHOR:Breen, J. J., Matsuura, T., Ross, A. C., and Gurr, J. A.
TITLE:Regulation of thyroid-stimulating hormone beta-subunit and growth hormone messenger ribonucleic acid levels in the rat: effect of vitamin A status PubMed ID:7835286
JOURNAL:Endocrinology.
VOL:136 PAGE : 543-549 (1995)
[TOP]

[0041]
AUTHOR:Wolf, G.
TITLE:The regulation of the thyroid-stimulating hormone of the anterior pituitary gland by thyroid hormone and by 9-cis-retinoic acid PubMed ID:12462521
JOURNAL:Nutr Rev.
VOL:60 PAGE : 374-377 (2002)
[TOP]

[0042]
AUTHOR:Maung, K., Miyazaki, A., Nomiyama, H., Chang, C. C., Chang, T. Y., and Horiuchi, S.
TITLE:Induction of acyl-coenzyme A:cholesterol acyltransferase-1 by 1,25-dihydroxyvitamin D(3) or 9-cis-retinoic acid in undifferentiated THP-1 cells PubMed ID:11181746
JOURNAL:J Lipid Res.
VOL:42 PAGE : 181-187 (2001)
[TOP]

[0043]
AUTHOR:Guibourdenche, J., Tarrade, A., Laurendeau, I., Rochette-Egly, C., Chambon, P., Vidaud, M., and Evain-Brion, D.
TITLE:Retinoids stimulate leptin synthesis and secretion in human syncytiotrophoblast PubMed ID:10902807
JOURNAL:J Clin Endocrinol Metab.
VOL:85 PAGE : 2550-2555 (2000)
[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.