472-87-7

Usage

Chemical Properties

Dark-Brown Oil

Uses

An oxidized derivative of the visual pigment carotenoid.

InChI:InChI=1/C20H26O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,15H,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13-

Upstream product

• 4159-20-0 3,4-didehydroretinoic acid 
• 6248-59-5 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile 
• 6901-91-3 9-trans-Dehydro-β-jonyliden-essigsaeure 
• 25528-87-4 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1,3-cyclohexadienyl)-2,4-pentadienal 
• 25528-85-2 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dienyl)penta-2,4-dien-1-ol 
• 24041-43-8 methyl (7E,9E,11E,13E)-9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate 
• 14538-58-0 3-methyl-5t-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2t,4-dienoic acid methyl ester 
• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 26918-26-3 ethyl 3,4-didehydroretinoate 
• 817203-14-8 1-[(trifluoromethanesulfonyl)oxy]-2,6,6-trimethylcyclohexa-1,3-diene 
• 79-80-1 vitamin A₂ 

Downstream Products

• 79-80-1 vitamin A₂ 
• 6248-59-5 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenenitrile 
• 564-87-4 (11Z)-retinal 

Relevant academic research and scientific papers

A convenient and stereoselective synthesis of 11Z-3,4-didehydroretinal by Horner-Emmons reaction using diphenyl phosphonate

A convenient synthesis of 3,4-didehydroretinal was developed. The Horner-Emmons reaction between 3,4-didehydro-β-ionone and diphenyl phosphonate in the presence of crown ether gave the retinonitrile as an isomeric mixture, in which the newly produced double bond was predominantly 11Z-form. After separation of the 11Z-form retinonitrile, it was converted into the corresponding retinal in good yield without isomerization of the double bonds.

Synthesis of ring-oxidized retinoids as substrates of mouse class I alcohol dehydrogenase (ADH1)

Ring-oxidized retinoids have been synthesized stereoselectively using the Stille cross-coupling reaction. Kinetic constants of mouse class I alcohol dehydrogenase (ADH1) with these retinoids were determined.