131235-62-6

Basic information

• Product Name: (2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid
• CAS NO: 131235-62-6
• Molecular Weight: 318.456
• Mol File: 131235-62-6.mol

Chemical Properties

• CAS DataBase Reference: (2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid(131235-62-6)
• EPA Substance Registry System: (2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid(131235-62-6)

Safety Data

• Hazardous Substances Data: 131235-62-6(Hazardous Substances Data)

Upstream product

• 63797-82-0 (2E,4E)-3-methyl-2,4-hexadienoic acid 
• 79-77-6 (E)-β-ionone 
• 22936-96-5 4,6-Dimethyl-3,6-dihydro-2H-pyran-2-one 

Downstream Products

• 302-79-4 all-trans-retinoic-acid 
• 302-79-4 (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 

Relevant articles and documents

Polyenolates of unsaturated carboxylic acids in synthesis. A straightforward synthesis of retinoic acids

Retinoic acids are prepared in a two step procedure by addition of lithium trienediolates of sorbic acid and 3-methyl-sorbic acid to β-ionone.

Trienediolates of hexadienoic acids in synthesis. Addition to unsaturated ketones. A convergent approach to the synthesis of retinoic acids

The regioselectivity of the addition of the lithium trienediolates generated from hexa-2,4-dienoic acids 1 and 2 or the dihydropyran-2-ones 4 and 5 to unsaturated ketones 6 is studied. Equilibration conditions favour reaction of the trienediolates through their ω carbon, and the ketones according to 1,2- and 1,4-additions. β-Ionone 6a and the aryl-butenone 6b lead to the 1,2-ω-adducts 8, which undergo a facile acid catalyzed dehydration to retinoic acids 11. On reaction with the unsaturated ketone 6b or with the aryl ketones 21, the trimethyldihydropyran-2-one 5 leads to γ'-adducts derived from deprotonation of the chain methyl substituent along with the 1,4-ω-adducts.