EPOXIDATION OF RETINOL AND THE STRUCTURE OF "CHROMOGEN 574"

DOI: 10.1016/0040-4020(80)87015-3

Source and publish data:

Tetrahedron p. 1179 - 1182 (1980)

Update date:2022-08-03

Topics:

Authors:

Welch, Steven C.

Gruber, John M.

Rao, Prakasa A. S. C.

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Article abstract of DOI:10.1016/0040-4020(80)87015-3

Epoxidation of retinol (vitamin A alcohol, 1) with freshly prepared and standardized mono-perphtalic acid in ether affords a product which Karrer named "chromogen 574" in 1945.Repetition of this peracid oxidation of retinol (1) with several peracids (m-PPA, m-CPBA, or CH3CO3H) with or without a buffer (NaHCO3 or Na2HPO4) produces dihydropyran alcohol 4 as characterised by spectroscopy and subsequent chemical transformations.Thus the structures proposed for "chromogen 574" by Karrer in 1945-47 and Troitskii in 1948 are now revised to correspond to cyclic alkohol 4.

Full text of DOI:10.1016/0040-4020(80)87015-3

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