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Vitamin A


DATA No : VVA0001 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: all-trans-retinol
SYMBOL: ROH
FORMULA: C20H30O MOL.WT (average) : 286.452


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BIOLOGICAL ACTIVITY
Relative physiological activity for All trans-retinyl acetate is 100%.(Ref. 0046) New physiological functions of vitamin A have been identified in addition to its role in vision (Ref. 0005), namely its role in immune defence reducing morbidity of measles, (Ref. 0006) of respiratory and possibly HIV infections (Ref. 0007), in gene regulation (Ref. 0008), in cell differentiation (Ref. 0009) and morphogenesis.(Ref. 0010/0011)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:62-64degC(Ref. 0013)

BOILING POINT:120-125 at 5x10-3mm

REFRACTIVE INDEX:n22,D:1.6410

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:insol in lcohol, methanol, chloroform, ether, fats and oils
SPECTRAL DATA
UV SPECTRA:lmax=324-325 nm(E1%1cm 1832 in Ethanol, 1830 in Petro. ether, 1835 in Isopropanol ),326.5 nm(E1%1cm 1745 in Cyclohexane)(Ref. 0013)

IR SPECTRA:

NMR SPECTRA:1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Me),~1.47(2H,J= n.o,2-CH2), ~1.61( 2H,J= n.o,3-CH2),1.72(3H,5-Me),1.85(3H,13-Me),1.97(3H,9-Me),2.02(2H, J= n.o,4-Me),4.29 ( 2H,J=6.8Hz,15-CH2),5.67 (1H,J=6.8 Hz,14-H),6.08(1H,J=11.0Hz, 10-H),6.09(1H,J=~16Hz,8-H ), 6.14(1H,J=~16Hz,7-H),6.27(1H,J=14.8Hz,12-H),6.60(1H, J=11.0,14.8Hz,11-H)(Ref. 0003)
13C-NMR(d,CDCl3,22.63MHz):12.5,12.6,19.4,21.7,29.0,29.0,33.1,34.2,39.8,59.1,124.8,126.5,128.9, 130.2,130.6,135.6,136.2,136.5,137.7,137.9,(Ref. 0004)

MASS SPECTRA:m/e : M+286,268,255,241,225,213,199,185,173,159,145,133,119,105,91,81,69,55,41(70ev,270degC)

OTHER SPECTRA:Fluorescence (in ethanol at 25degC):Ex.347nm, Em. 490nm(Ref. 0023)
CHROMATOGRAM DATA

SOURCE
Fish liver oils
Animals8Liver,Lung.Kidney)
CHEMICAL SYNTHESIS
by b-ionone and propargyl halide(Ref. 0012)
by conversion of retinal(Ref. 0015/0016/0017)
METABOLISM
The dietary preformed retinoids are mainly converted to all-trans-retinol by retinyl-ester hyrdolase, and uptaken from intesitine.The absorbed all-trans-retinol is packaged as retinyl esters(palmitate,stearate,linolate) in chylomicrons. Chylomicrons are secreted into the lymphatic system, and the bulk of the chylomicron retinoids are taken up by the liver,where the majority of the body's retinoids are stored mainly in the parenchymal cells and the stellate cells in the form of complex with protein. During hepatic storage and metabolism,Retinyl esters are hydrolyzed to retinol by bile-salt-independent or bile-salt-dependent retinyl ester hydrolase, which in turn is esterified by ARAT or LRAT.Hydrolyzed retinol is released to the bloodstream binding to RBP,controlling the supply of retinol to target tissues.Other tissues except liver can store retinols,part of which is oxidized to retinal or retinoic acid. (Ref. 0001)(Ref. 0002)
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
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[0002]
AUTHOR:Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp568-570 Tokyo Kagaku Dojin
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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)
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[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]

[0005]
AUTHOR:Gerster, H.
TITLE:Vitamin A--functions, dietary requirements and safety in humans PubMed ID:9129249
JOURNAL:Int J Vitam Nutr Res.
VOL:67 PAGE : 71-90 (1997)
[TOP]

[0006]
AUTHOR:Barclay, A. J., Foster, A., and Sommer, A.
TITLE:Vitamin A supplements and mortality related to measles: a randomised clinical trial PubMed ID:3101849
JOURNAL:Br Med J (Clin Res Ed).
VOL:294 PAGE : 294-296 (1987)
[TOP]

[0007]
AUTHOR:Karter, D. L., Karter, A. J., Yarrish, R., Patterson, C., Kass, P. H., Nord, J., and Kislak, J. W.
TITLE:Vitamin A deficiency in non-vitamin-supplemented patients with AIDS: a cross-sectional study PubMed ID:7834403
JOURNAL:J Acquir Immune Defic Syndr Hum Retrovirol.
VOL:8 PAGE : 199-203 (1995)
[TOP]

[0008]
AUTHOR:Chytil, F., and Ong, D. E.
TITLE:Cellular retinol- and retinoic acid-binding proteins in vitamin A action PubMed ID:573703
JOURNAL:Fed Proc.
VOL:38 PAGE : 2510-2514 (1979)
[TOP]

[0009]
AUTHOR:Norum KR. Retinoids and acute myeloid leukemia. In: Vitamin A in Health and Disease (Blomhoff, R., ed), pp.485-501, Marcel Dekker Inc., New York.
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[0010]
AUTHOR:Bates, C. J.
TITLE:Vitamin A in pregnancy and lactation PubMed ID:6340124
JOURNAL:Proc Nutr Soc.
VOL:42 PAGE : 65-79 (1983)
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[0011]
AUTHOR:Maden M. Role of retionids in embryonic development. Vitamin A in Health and Disease (Blomhoff, R., ed.), pp.289-322, Marcel Dekker Inc., New York.
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[0012]
AUTHOR:Eiter,Truscheit, U.S.pat. 3,060,229(1962 to Bayer)
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[0013]
AUTHOR:Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso (eds Nihon Seikagakukai) Chapter.14 Vitamin A pp.549 Tokyo Kagaku Dojin
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[0015]
AUTHOR:N. L. Wendler, C. Rosenblum, M. Tishler.
TITLE:The Oxidation of b-carotene .
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[0016]
AUTHOR:Klein,Kapp. U.S.pat. 1961, 2,972,634 (to Nopco)
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[0017]
AUTHOR:T.Mukaiyama, A.Ishida.
TITLE:A New Synthesis of Vitamin A.
JOURNAL:Chem.Lett.
VOL: PAGE : 1201 - (1975)
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[0023]
AUTHOR:Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp566 Tokyo Kagaku Dojin
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[0046]
AUTHOR:Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.