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Vitamin A


DATA No : VVA0015 INFORMANT : Hiroyuki Kagechika

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

COMMON NAME: 11-cis-retinal
SYMBOL:
FORMULA: C20H28O MOL.WT (average) : 284.436


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BIOLOGICAL ACTIVITY
Relative 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)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:63-65degC(Ref. 0013)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax=376.5 290 and254 nm (E1%1cm 878,412 and 614 respectively in ethanol)(Ref. 0013)

IR SPECTRA:

NMR SPECTRA: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)

MASS SPECTRA:

OTHER SPECTRA:X-Ray Analysis(Ref. 0022)
CHROMATOGRAM DATA

SOURCE
Retina
CHEMICAL SYNTHESIS
(Ref. 0037)
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]

[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]

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

[0033]
AUTHOR:Ablonczy, Z., Crouch, R. K., Goletz, P. W., Redmond, T. M., Knapp, D. R., Ma, J. X., and Rohrer, B.
TITLE:11-cis-retinal reduces constitutive opsin phosphorylation and improves quantum catch in retinoid-deficient mouse rod photoreceptors PubMed ID:12176991
JOURNAL:J Biol Chem.
VOL:277 PAGE : 40491-40498 (2002)
[TOP]

[0034]
AUTHOR:Kuhn, H.,et,al.
TITLE:
JOURNAL:J.Recept. Res.
VOL:7 PAGE : 283 -298 (1987)
[TOP]

[0035]
AUTHOR:Ablonczy, Z., Knapp, D. R., Darrow, R., Organisciak, D. T., and Crouch, R. K.
TITLE:Mass spectrometric analysis of rhodopsin from light damaged rats PubMed ID:10874059
JOURNAL:Mol Vis.
VOL:6 PAGE : 109-115 (2000)
[TOP]

[0036]
AUTHOR:Kennedy, M. J., Lee, K. A., Niemi, G. A., Craven, K. B., Garwin, G. G., Saari, J. C., and Hurley, J. B.
TITLE:Multiple phosphorylation of rhodopsin and the in vivo chemistry underlying rod photoreceptor dark adaptation PubMed ID:11498053
JOURNAL:Neuron.
VOL:31 PAGE : 87-101 (2001)
[TOP]

[0037]
AUTHOR:Dieterle, J. M., and Robeson, C. D.
TITLE:Crystalline neoretinene b PubMed ID:13186815
JOURNAL:Science.
VOL:120 PAGE : 219-220 (1954)
[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.