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

Download ChemDraw structure data

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	:	62-64C(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	:	l_m_a_x=324-325 nm(E¹^%₁_c_m 1832 in Ethanol, 1830 in Petro. ether, 1835 in Isopropanol ),326.5 nm(E¹^%₁_c_m 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,270C)

OTHER SPECTRA	:	Fluorescence (in ethanol at 25C):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
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

AUTHOR	:	Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp568-570 Tokyo Kagaku Dojin
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

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)

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)

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)

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)

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)

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)

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.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

AUTHOR	:	Bates, C. J.
TITLE	:	Vitamin A in pregnancy and lactation PubMed ID:6340124
JOURNAL	:	Proc Nutr Soc.
VOL	:	42 PAGE : 65-79 (1983)

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.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

AUTHOR	:	N. L. Wendler, C. Rosenblum, M. Tishler.
TITLE	:	The Oxidation of b-carotene .
JOURNAL	:
VOL	:	72 PAGE : 234 -234 (1950)

AUTHOR	:	Klein,Kapp. U.S.pat. 1961, 2,972,634 (to Nopco)
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

AUTHOR	:	Eiter,Truscheit, U.S.pat. 3,060,229(1962 to Bayer)
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

AUTHOR	:	T.Mukaiyama, A.Ishida.
TITLE	:	A New Synthesis of Vitamin A.
JOURNAL	:	Chem.Lett.
VOL	:	PAGE : 1201 - (1975)

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