127-47-9

Retinyl acetate (retinol acetate, vitamin A acetate,127-47-9) is a natural form of vitamin A. It is the acetate ester of retinol. It consists of yellow crystals which are greasy or sticky. It has a mild, characteristic odor. It has potential antineoplastic and chemo-preventive activities. It can be used to fortify food with vitamin A. As vitamin A acetate can induce cell differentiation and inhibit cell proliferation, it is used in skin-conditioning agent.

Crystalline

Essential micronutrient

vitamin precursor

ChEBI: Retinyl acetate is an acetate ester. It is functionally related to an all-trans-retinol.

A method for preparing retinyl acetate the following steps:
Under alkaline conditions, 3-methyl-4-oxo-2-butene-1-yl acetate (referred to as C5 aldehyde ester) and tetraethyl methylene diphosphate undergo a condensation reaction to form an intermediate C6 phosphate (chemical name: 5-(diethyl phosphate)-3-methyl-2,4-hexadiene-1-acetate).
Under alkaline conditions, the C6 phosphate undergoes a transposition reaction. C14 aldehyde (chemical name: 2-methyl-4-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-butene-1-aldehyde) is then added to undergo a Wittig-Horner condensation reaction, yielding retinyl acetate.

Notclassified

Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as required. Retinyl acetate is used in a wide range of biological applications. It acts as a chemopreventive agent. Retinyl acetate also has antineoplastic property.

The acetate is separated from retinol by column chromatography, then crystallised from MeOH. [Kofler and Rubin Vitamins and Hormones (NY) 18 315 1960 for purification methods]. Store it in the dark, under N2 or Ar, at 0o. [Beilstein 6 IV 4135.]

[1] Volker Bühler, Vademecum for Vitamin Formulations, 2001, ISBN 3-8047-1834-5
[2] SUNATDA ARAYACHUKEAT Thapakorn T U Supason P Wanichwecharungruang. Retinyl acetate-loaded nanoparticles: Dermal penetration and release of the retinyl acetate[J]. International Journal of Pharmaceutics, 2011, 404 1: Pages 281-288. DOI:10.1016/j.ijpharm.2010.11.019.
[3] HARRISON E H. Lipases and carboxylesterases: possible roles in the hepatic metabolism of retinol.[J]. Annual review of nutrition, 1998, 18: 259-276. DOI:10.1146/annurev.nutr.18.1.259.
[4] GERSTER H. Vitamin A–functions, dietary requirements and safety in humans.[J]. International Journal for Vitamin and Nutrition Research, 1997, 67 2: 71-90.
[5] https://ods.od.nih.gov/factsheets/VitaminA-HealthProfessional/