LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Retinol Acetate/All-trans-retinyl Acetate

Systematic Name

Retinyl acetate

Synonyms

LM ID

LMPR01090012

Formula

C₂₂H₃₂O₂

Exact Mass

Calculate m/z

328.24023

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Retinyl acetate is a natural form of vitamin A .¹ It inhibits ascorbic acid- or ferrous sulfate-induced increases in malondialdehyde (MDA) levels in rat brain mitochondria when used at a concentration of 100 µM.² Retinyl acetate binds to retinol-binding protein (Kd = 220 nM for the human protein) and inhibits organic anion transporting polypeptide 1B1 (OATP1B1) and OATP1B3 in CHO cells expressing the human transporters (Kis = 1.22 and 3.89, respectively).^3,4 It inhibits the formation of mammary adenocarcinomas induced by the polycyclic aromatic hydrocarbon 7,12-dimethylbenz[a]anthracene (DMBA) in rats when administered at a dose of 2.5 mg/animal.⁵ Retinyl acetate (352 µmol/kg) is teratogenic to rat fetuses when administered to pregnant dams.⁶ Formulations containing retinyl acetate have been used as skin-conditioning agents in cosmetics.

This information has been provided by Cayman Chemical

References

1. De Bruyn, T., van Westen, G.J.P., Ijzerman, A.P., et al. Structure-based identification of OATP1B1/3 inhibitors. Mol. Pharmacol. 83(6), 1257-1267 (2013).

2. Gomis, D.B., Fernández, M.P., and Alvarez, M.D.G. Simultaneous determination of fat-soluble vitamins and provitamins in milk by microcolumn liquid chromatography. J. Chromatogr. A 891(1), 109-114 (2000).

3. Das, N.P. Effects of vitamin A and its analogs on nonenzymatic lipid peroxidation in rat brain mitochondria. J. Neurochem. 52(2), 585-588 (1989).

4. Cogan, U., Kopelman, M., Mokady, S., et al. Binding affinities of retinol and related compounds to retinol binding proteins. Eur. J. Biochem. 65(1), 71-78 (1976).

5. Duitsman, P.K., and Olson, J.A. Comparative embryolethality and teratogenicity of the all-trans isomers of retinoic acid, 3,4-didehydroretinyl acetate, and retinyl acetate in pregnant rats. Teratology 53(4), 237-244 (1996).

6. Moon, R.C., Grubbs, C.J., and Sporn, M.B. Inhibition of 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis by retinyl acetate. Cancer Res. 36(7 PT 2), 2626-2630 (1976).