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Vitamin A


DATA No : VVA0012 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: All-trans-Retinal
SYMBOL:
FORMULA: C20H28O MOL.WT (average) : 284.436


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Relative 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)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:61-62degC(Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Sol in ethanol,chloroform,cyclohexane,petr ether,oils .Insol in water
SPECTRAL DATA
UV SPECTRA:lmax=381 nm (E1%1cm 1,510 in ethanol), 368 nm(E1%1cm 1,690 in n-heptane)(Ref. 0014)

IR SPECTRA:

NMR SPECTRA: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)

MASS SPECTRA:

OTHER SPECTRA:Fluorescence (in ether:isopentane:ethanol =5:5:2, -196degC):Ex.420nm,Em.500nm
X-Ray Analysis(Ref. 0022)
CHROMATOGRAM DATA

SOURCE
Retina
CHEMICAL SYNTHESIS
by Vitamin A1 (Ref. 0032)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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]

[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:
VOL: PAGE : - ()
[TOP]

[0022]
AUTHOR:
TITLE:
JOURNAL:Terpenoids Steroids.
VOL: PAGE : 5219 - (1975)
[TOP]

[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:
VOL: PAGE : - ()
[TOP]

[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.
VOL:64 PAGE : 613-621 (1996)
[TOP]

[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:
VOL: PAGE : - ()
[TOP]

[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.
VOL:38 PAGE : 1471-1475 (1997)
[TOP]

[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.
VOL:7 PAGE : 500-504 (1997)
[TOP]

[0030]
AUTHOR:Surya, A., and Knox, B. E.
TITLE:Enhancement of opsin activity by all-trans-retinal PubMed ID:9628807
JOURNAL:Exp Eye Res.
VOL:66 PAGE : 599-603 (1998)
[TOP]

[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.
VOL:99 PAGE : 8372-8377 (2002)
[TOP]

[0032]
AUTHOR:G.Wald, R.Hubbard.
TITLE:The mechanism of rhodopsin synthesis.
JOURNAL:Proc. Nat. Acad. sci. USA
VOL:372 PAGE : 69 -79 (1951)
[TOP]

[0046]
AUTHOR:Seikagaku Hand Book (eds. Nihon Seikagakukai) pp.1274-1277. Tokyo Kagaku Dojin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

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