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	:	63-65C(Ref. 0013)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	l_m_a_x=376.5 290 and254 nm (E¹^%₁_c_m 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)

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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
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

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[0022]

AUTHOR	:
TITLE	:
JOURNAL	:	Terpenoids Steroids.
VOL	:	PAGE : 5219 - (1975)

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[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)

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[0034]

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

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[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)

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[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)

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[0037]

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

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[0046]

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

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