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Vitamin A


DATA No : VVA0007 INFORMANT : Hiroyuki Kagechika

NAME : (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonatetraen-1-yl-acetate

COMMON NAME: Retinol Acetate/All-trans-retinyl Acetate
SYMBOL:
FORMULA: C22H32O2 MOL.WT (average) : 328.488


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Same as all-trans retinol
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:57-58degC(Ref. 0046)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax=325nm (E1%1cm1560 in ethanol, 1590 in hexane)(Ref. 0014)

IR SPECTRA:

NMR SPECTRA:1H-NMR(d,CDCl3,220MHz):1.03(6H,1-Me),~1.46(2H,J= n.o,2-CH2),~1.61( 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)

MASS SPECTRA: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)

OTHER SPECTRA:Fluorescence(in cyclohexane,25degC):Ex. 345 nm, Em. 495nm (Ref. 0023)
X-Ray Analysis(Ref. 0022)
CHROMATOGRAM DATA

SOURCE
Animals( mainly Liver, Lung, Kidney)
Fish liver oils
CHEMICAL SYNTHESIS

METABOLISM
same as all trans retinol:A part of all-trans-retinol is involved in diet, and stored in liver as retinyl acetate.(Ref. 0001)
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 : - ()
[TOP]

[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]

[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]

[0023]
AUTHOR:Tsukita kiyoshi, Yoshizawa Tohru, Matsumoto Hiroyuki(1975) Vitamin to Hokouso Chapter.14 Vitamin pp566 Tokyo Kagaku Dojin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0024]
AUTHOR:Tsukita Kiyoshi
TITLE:
JOURNAL:Aburakagaku.
VOL:22 PAGE : 575 - (1973)
[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.