Back to HOME

Vitamin A

(total 100)


Download Data as Excel
Download All Images
Download All ChemDraw structure data
IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1
all-trans-retinol ((2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol VVA0001Vitamin AHiroyuki KagechikaROH C20H30O 286.452Download ChemDraw structure dataRelative 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>> 62-64degC<< Ref. 0013>> 120-125 at 5x10-3mm n22,D:1.6410 insol in lcohol, methanol, chloroform, ether, fats and oils 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>> 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>> m/e : M+286,268,255,241,225,213,199,185,173,159,145,133,119,105,91,81,69,55,41(70ev,270degC) Fluorescence (in ethanol at 25degC):Ex.347nm, Em. 490nm<< Ref. 0023>> Fish liver oils Animals8Liver,Lung.Kidney) by b-ionone and propargyl halide<< Ref. 0012>> by conversion of retinal<< Ref. 0015/0016/0017>> 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>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0002 >> AUTHOR: Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp568-570 Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.0005 >> AUTHOR: Gerster, H. TITLE: Vitamin A--functions, dietary requirements and safety in humans PubMed ID:9129249 JOURNAL: Int J Vitam Nutr Res. VOLUME: 67 PAGE: 71-90(1997)
<< Ref.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). VOLUME: 294 PAGE: 294-296(1987)
<< Ref.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. VOLUME: 8 PAGE: 199-203(1995)
<< Ref.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. VOLUME: 38 PAGE: 2510-2514(1979)
<< Ref.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. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0010 >> AUTHOR: Bates, C. J. TITLE: Vitamin A in pregnancy and lactation PubMed ID:6340124 JOURNAL: Proc Nutr Soc. VOLUME: 42 PAGE: 65-79(1983)
<< Ref.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. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0012 >> AUTHOR: Eiter,Truscheit, U.S.pat. 3,060,229(1962 to Bayer) TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0015 >> AUTHOR: N. L. Wendler, C. Rosenblum, M. Tishler. TITLE: The Oxidation of b-carotene . JOURNAL: VOLUME: 72 PAGE: 234 -234 (1950)
<< Ref.0016 >> AUTHOR: Klein,Kapp. U.S.pat. 1961, 2,972,634 (to Nopco) TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0017 >> AUTHOR: T.Mukaiyama, A.Ishida. TITLE: A New Synthesis of Vitamin A. JOURNAL: Chem.Lett. VOLUME: PAGE: 1201 - (1975)
<< Ref.0023 >> AUTHOR: Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp566 Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
2
All-Trans-3,4-Didehydro Retinol (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1,3-dienyl)-nona-2,4,6,8-tetraen-1-ol VVA0002Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure data40-51% of relative biological activity of all-trans-retinyl acetate as a acetate form. << Ref. 0046>> 63-65,17-19degC<< Ref. 0013>> nsol in water or glycerol. Sol in abs alcohol, methanol, chloroform, ether, fats and oils lmax=350,286,276 nm(E1%1cm 1,455, 715, 555 in ethanol)<< Ref. 0013>> 13C-NMR(d,CDCl3,22.63MHz):12.6,12.6,20.2,26.7,26.7,33.9,39.9,59.2,124.7,124.9,125.4,126.5,129.9,130.6,130.8,135.7,136.4,136.7,137.1,138.5<< Ref. 0004>> freshwater fish liver oils << Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
3
9-cis-retinol (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol VVA0003Vitamin AHiroyuki Kagechika C20H30O 286.452Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 22%.<< Ref. 0046>> 81-82degC<< Ref. 0013>> lmax=323,258nm (E:1477,382 respecticely in ethanol)<< Ref. 0013>> 13C-NMR(d,CDCl3,22.63MHz):12.7,19.4,20.7,21.8,29.0,29.0,33.2,34.3,39.8,124.0,128.6,128.7,129.4,130.0,130.0,134.8,135.7,136.7,137.1,138.2<< Ref. 0004>> << Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
4
11-cis-retinol (2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol VVA0004Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 23%.<< Ref. 0046>> lmax=319,233nm (E:1220,370 respecticely in ethanol)<< Ref. 0013>> 13C-NMR(d,CDCl3,22.63MHz):12.2,17.1,19.4,21.7,29.0,29.0,33.1,34.3,39.7,59.4(OCH2),125.2,126.4,127.1,129.1,130.5,132.6,136.1,137.1,138.0,138.1<<0004> << Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
5
11-cis-3,4-didehydroretinol (2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1,3-dienyl)-nona-2,4,6,8-tetraen-1-ol VVA0005Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 15%.<< Ref. 0046>> lmax=344,286,278nm (E:990,566,493 respecticely in ethanol)<< Ref. 0013>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
6
13-cis-retinol (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol VVA0006Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 70-85%.<< Ref. 0046>> 58-60degC<< Ref. 0013>> lmax=328nm (E:1686 respecticely in ethanol)<< Ref. 0013>> 1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Mex2),~1.47(2H,J= n.o,2-CH2),~1.61( 2H,J= n.o,3-CH2),1.71(3H,5-Me),~1.95(3H,13-Me),1.96(3H,9-Me),2.03(2H,J= n.o,4-Me),4.30(2H,J=7.0Hz,15-CH2),5.55(1H,J=7.0Hz,14-H),6.10(1H,J=~16Hz,8-H),6.13(1H,10-H),6.17 (1H,J=~16Hz,7-H),~6.60(1H,J=~15.0Hz,12-H),~6.65(1H,J=~15.0Hz,11-H)<< Ref. 0003>> 13C-NMR(d,CDCl3,22.63MHz CW offset 1H-decoupling):12.7,19.4,20.4,21.6,29.0,29.0,33.1,34.3,39.8,58.4,127.1,127.1,128.6,128.7,129.3,130.2,135.6,136.8,137.6,137.9,<< Ref. 0004>> << Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
7
Retinol Acetate/All-trans-retinyl Acetate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonatetraen-1-yl-acetate VVA0007Vitamin AHiroyuki Kagechika C22H32O2 328.488Download ChemDraw structure dataSame as all-trans retinol 57-58degC<< Ref. 0046>> lmax=325nm (E1%1cm1560 in ethanol, 1590 in hexane)<< Ref. 0014>> 1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Me),~1.46(2H,J= n.o,2-CH2),~1.61( 2H,J= n.o,3-CH2),1.71(3H,5-Me),1.89(3H,13-Me),1.96(3H,9-Me),2.02(2H,J= n.o,4-Me),2.05 ( 3H,J=7.0Hz,Acetyl),4.72 (2H,J=6.8Hz,15-CH2),5.61 (1H,J=6.8Hz,14-H),6.10 (1H,J=11.0Hz, 10 -H),6.10 (1H,J=~16Hz,8-H),6.19(1H,J=~16Hz,7-H),6.29(1H,J=14.8Hz,12-H),6.60 (1H,J=11.0,14.8 Hz,11-H),<< Ref. 0003>> 13C-NMR(d,CDCl3,22.63MHz):19.35,21.67,12.73,12.73,20.88(CH3),29.00,29.00,33.10,34.30,39.78,61.27(OCH2)124.60,125.82,127.00,129.26,130.22,135.89,136.46,137.66,137.95,139.02,170.66(CO)<< Ref. 0004>> M+:m/e328(100%), Fragment ion: m/e 313(4%),285(2%),268(40%),255(32%),253(5!%),145(83%),132(54%),119(63%),105(69%),95(40%),91(46%),81(51%),43(61%)<< Ref. 0024>> Fluorescence(in cyclohexane,25degC):Ex. 345 nm, Em. 495nm << Ref. 0023>> X-Ray Analysis<< Ref. 0022>> Animals( mainly Liver, Lung, Kidney) Fish liver oils same as all trans retinol:A part of all-trans-retinol is involved in diet, and stored in liver as retinyl acetate.<< Ref. 0001>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.0014 >> AUTHOR: Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman (1994) The Retinoids Biology,Chemistry, and Medicine Second Edition pp188 Raven Press New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0022 >> AUTHOR: TITLE: JOURNAL: Terpenoids Steroids. VOLUME: PAGE: 5219 - (1975)
<< Ref.0023 >> AUTHOR: Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp566 Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0024 >> AUTHOR: Tsukita Kiyoshi TITLE: JOURNAL: Aburakagaku. VOLUME: 22 PAGE: 575 - (1973)
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
8
all-trans-retinyl Palmitate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-palmitate / (2E,4E,6E,8E)-Hexadecanoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester VVA0008Vitamin AHiroyuki Kagechika C36H60O2 524.860Download ChemDraw structure dataSame as all-trans-retinol lmax=325nm (E1%1cm 940 in ethanol)<< Ref. 0014>> Fluorescence (in ethanol 25degC):Ex.325 nm Em.470 nm Animals(mainly Liver, Lung and Kidney) Fish liver oils All-trans-retinyl palmitate is hydrolyzed and converted to all-trans-retinol by retinyl-ester hydrolase in intestine and pancreas.<< Ref. 0001>> << Ref.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: VOLUME: PAGE: - ()
<< Ref.0014 >> AUTHOR: Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman (1994) The Retinoids Biology,Chemistry, and Medicine Second Edition pp188 Raven Press New York TITLE: JOURNAL: VOLUME: PAGE: - ()
9
all-trans-retinyl stearate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-stearate/(2E,4E,6E,8E)-Octadecanoic acid3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester VVA0009Vitamin AHiroyuki Kagechika C38H64O2 552.914Download ChemDraw structure data All-trans-retinyl stearate is hydrolyzed and converted to all-trans-retinol by retinyl-ester hydrolase in intestine and pancreas, and a part of retinol is stored as all-trans-retinyl acetate.<< Ref. 0001>> << Ref.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: VOLUME: PAGE: - ()
10
all-trans-retinyl oleate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-oleate/(2E,4E,6E,8E)-Octadec-9-enoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester VVA0010Vitamin AHiroyuki Kagechika C38H62O2 550.898Download ChemDraw structure data All-trans-retinyl oleate is hydrolyzed and converted to all-trans-retinol by retinyl-ester hydrolase in intestine and pancreas, and a part of retinol is stored as all-trans-retinyl oleate.<< Ref. 0001>> << Ref.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: VOLUME: PAGE: - ()
11
all-trans-retinyl linolate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-linolate/(2E,4E,6E,8E)-Octadeca-9,12,15-enoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)- nona-2, 4,6,8,tetraenyl ester VVA0011Vitamin AHiroyuki Kagechika C38H58O2 546.866Download ChemDraw structure data All-trans-retinyl linolate is hydrolyzed and converted to all-trans-retinol by retinyl-ester hydrolase in intestine and pancreas, and a part of retinol is stored as all-trans-retinyl linolate.<< Ref. 0001>> << Ref.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: VOLUME: PAGE: - ()
12
All-trans-Retinal (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetranal VVA0012Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 91%.<< Ref. 0046>>all-trans-retinal directly and markedly inhibits cloned rod CNG channels in excised patches. 11-cis-retinal and all-trans-retinol also inhibited the channels, but at somewhat higher concentrations. Single-channel analysis suggests that all-trans-retinal reduces average open probability of rod CNG channels by inactivating channels for seconds at a time. At physiological cGMP levels, all-trans-retinal inhibited in the nanomolar range. Our results suggest that all-trans-retinal may be a potent regulator of the channel in rods during the response to bright light, when there is a large surge in the concentration of all-trans-retinal.<< Ref. 0025/0026/0027/0028/0029/0030/0031>> 61-62degC<< Ref. 0013>> Sol in ethanol,chloroform,cyclohexane,petr ether,oils .Insol in water lmax=381 nm (E1%1cm 1,510 in ethanol), 368 nm(E1%1cm 1,690 in n-heptane)<< Ref. 0014>> 1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Me),~1.46(2H,J= n.o,2-CH2),~1.62( 2H,J= n.o,3-CH2),1.72(3H,5-Me),~2.0(2H,J= n.o,4-Me),2.03(3H,9-Me),2.32(3H,13-Me),5.97( 1H,J=8.3Hz,14-H),6.17(1H,J=16.0Hz,8-H),6.19(1H,J=11.3Hz,10-H),6.35(1H,J=16.0Hz,7-H),7.15(1H,J=11.3,15.0Hz,11-H),6.37 (1 H,J=15.0Hz,12-H),10.09(1H,J=8.3Hz,CHO)<< Ref. 0003>> 13C-NMR(d,CDCl3,22.63MHz):13.0,13.0,19.3,21.7,29.0,29.0,33.2,34.1,39.6,128.9,129.4,129.6,130.3,132.4,134.5,137.1,137.6,141.1,154.5,190.7(CO)<< Ref. 0004>> Fluorescence (in ether:isopentane:ethanol =5:5:2, -196degC):Ex.420nm,Em.500nm X-Ray Analysis<< Ref. 0022>> Retina by Vitamin A1 << Ref. 0032>> << Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0014 >> AUTHOR: Michael B. Sporn, Anita B. Roberts, DeWitt S. Goodman (1994) The Retinoids Biology,Chemistry, and Medicine Second Edition pp188 Raven Press New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0022 >> AUTHOR: TITLE: JOURNAL: Terpenoids Steroids. VOLUME: PAGE: 5219 - (1975)
<< Ref.0025 >> AUTHOR: Saari, J. C.(1999) in Retinoids:The Biochemical and Molecular Basis of Vitamin A and Retinod Action. (eds. Nau, H. & Blaner, W.S.) Vol.139, pp.563-588. Springer New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0026 >> AUTHOR: Crouch, R. K., Chader, G. J., Wiggert, B., and Pepperberg, D. R. TITLE: Retinoids and the visual process PubMed ID:8863467 JOURNAL: Photochem Photobiol. VOLUME: 64 PAGE: 613-621(1996)
<< Ref.0027 >> AUTHOR: Mangelsdorf, D., Umesono, K. & Evans, R. M. (1994) in The Retinoids: Biology, Chemistry and Medicine. (eds. Sporn, M. B., Roberts, A. B. & Goodman, D. S. (2nd Ed.)) pp.319-350. Raven, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0028 >> AUTHOR: Hyatt, G. A., and Dowling, J. E. TITLE: Retinoic acid. A key molecule for eye and photoreceptor development PubMed ID:9224274 JOURNAL: Invest Ophthalmol Vis Sci. VOLUME: 38 PAGE: 1471-1475(1997)
<< Ref.0029 >> AUTHOR: Palczewski, K., and Saari, J. C. TITLE: Activation and inactivation steps in the visual transduction pathway PubMed ID:9287193 JOURNAL: Curr Opin Neurobiol. VOLUME: 7 PAGE: 500-504(1997)
<< Ref.0030 >> AUTHOR: Surya, A., and Knox, B. E. TITLE: Enhancement of opsin activity by all-trans-retinal PubMed ID:9628807 JOURNAL: Exp Eye Res. VOLUME: 66 PAGE: 599-603(1998)
<< Ref.0031 >> AUTHOR: Dean, D. M., Nguitragool, W., Miri, A., McCabe, S. L., and Zimmerman, A. L. TITLE: All-trans-retinal shuts down rod cyclic nucleotide-gated ion channels: a novel role for photoreceptor retinoids in the response to bright light? PubMed ID:12034887 JOURNAL: Proc Natl Acad Sci U S A. VOLUME: 99 PAGE: 8372-8377(2002)
<< Ref.0032 >> AUTHOR: G.Wald, R.Hubbard. TITLE: The mechanism of rhodopsin synthesis. JOURNAL: Proc. Nat. Acad. sci. USA VOLUME: 372 PAGE: 69 -79 (1951)
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
13
All-Trans-3,4-Didehydro Retinal (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1,3-dienyl)-nona-2,4,6,8-tetraenal VVA0013Vitamin AHiroyuki Kagechika C20H26O 282.420Download ChemDraw structure data57% of relative biological activity of all-trans-retinyl acetate.<< Ref. 0046>> 78-79,66-68degC<< Ref. 0013>> lmax=401,314nm (E:1470, 395 respectively in ethanol)<< Ref. 0013>> 13C-NMR(d,CDCl3,22.63MHz):12.9,13.1,20.3,26.8,26.8,34.0,40.0,125.0,127.7,128.3,129.0,130.0,130.0,132.3,134.8,136.4,138.2,140.9,154.3,190.5<< Ref. 0004>> Freshwater fish retina << Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
14
9-cis-retinal (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenal VVA0014Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 19%.<< Ref. 0046>> 64degC<< Ref. 0013>> lmax=373nm (E:1270 respecticely in ethanol)<< Ref. 0013>> 1H-NMR(d,CDCl3,220MHz):1.05(6H,1-Me),1.75(3H,5-Me),2.00(3H,9-Me),2.30 (3H,13-Me),5.94(1H,J=8.2Hz,14-H),6.06(1H,J=11.8Hz,10-H),6.27(1H,J=15.4Hz,12-H),6.31(1H,J=15.9Hz,7-H),6.64(1H,J=15.9Hz,8-H),7.20(1H,J=11.8,15.4Hz,11-H),10.07(1H,J=8.2Hz,CHO)<< Ref. 0003>> 13C-NMR(d,CDCl3,22.63MHz):13.2,19.3,20.9,21.8,29.0,29.0,33.2,34.1,39.7,127.9,128.9,129.4,130.4,131.1,131.2,133.8,138.1,140.0,154.3,167.8(CO)<< Ref. 0004>> << Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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. VOLUME: 58 PAGE: 2367-2390(1975)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin TITLE: JOURNAL: VOLUME: PAGE: - ()
15
11-cis-retinal (2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenal VVA0015Vitamin AHiroyuki Kagechika C20H28O 284.436Download ChemDraw structure dataRelative physiological activity for All trans-retinyl acetate is 48%.<< Ref. 0046>>Application(intraperitoneal injection)of 11-cis-retinal to Rpe65 -/- mice increased the rod ERG signal, increased levels of rhodopsin, and decreased opsin phosphorylation. Therefore, exogenous 11-cis-retinal improves photoreceptor function by regenerating rhodopsin and removes constitutive opsin phosphorylation. Our results indicate that opsin, which has not been exposed to 11-cis-retinal, does not generate the activity generally associated with the bleached apoprotein.<< Ref. 0033/0034/0035/0036>> 63-65degC<< Ref. 0013>> lmax=376.5 290 and254 nm (E1%1cm 878,412 and 614 respectively in ethanol)<< Ref. 0013>> 1H-NMR(d,CDCl3,220MHz):1.02(6H,1-Me),1.71(3H,5-Me),1.99(3H,9-Me),2.36 (3H,13-Me),5.92 (1H,J=13.0Hz,12-H),6.07(1H,J=8.0Hz,14-H),6.14(1H,J=16.0Hz,8-H),6.32(1H,J=16.0Hz,7-H)6.54(1H,J=11.5Hz,10-H),6.69(1H,J=11.5,13.0Hz,11-H),10.10(1H,J=8.0Hz,CHO)<< Ref. 0003>> X-Ray Analysis<< Ref. 0022>> Retina << Ref. 0037>> << Ref.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. VOLUME: 20 PAGE: 365-420(1969)
<< Ref.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: VOLUME: PAGE: - ()
<< Ref.0022 >> AUTHOR: TITLE: