100903-85-3

Basic information

• Product Name: (3E)-2-(1-hydroxycyclohexyl)hexa-3,5-dienoic acid
• Synonyms: (3E)-2-(1-hydroxycyclohexyl)hexa-3,5-dienoic acid
• CAS NO: 100903-85-3
• Molecular Weight: 210.273
• Mol File: 100903-85-3.mol

Chemical Properties

• CAS DataBase Reference: (3E)-2-(1-hydroxycyclohexyl)hexa-3,5-dienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-2-(1-hydroxycyclohexyl)hexa-3,5-dienoic acid(100903-85-3)
• EPA Substance Registry System: (3E)-2-(1-hydroxycyclohexyl)hexa-3,5-dienoic acid(100903-85-3)

Safety Data

• Hazardous Substances Data: 100903-85-3(Hazardous Substances Data)

Upstream product

• 110-44-1 sorbic Acid 
• 108-94-1 cyclohexanone 
• 142252-83-3 C₆H₆O₂^(2-)*2Li⁽¹⁺⁾ 

Downstream Products

• 93531-91-0 ((E)-Penta-2,4-dienylidene)-cyclohexane 

Relevant articles and documents

LITHIUM TRIENOLATE OF SORBIC ACID AS A D6 SYNTHON. SYNTHESIS OF 7-HYDROXY 2,4-DIENOIC ACIDS.

The trienolate 2 of sorbic acid is an easily available d6 synthon.Preparation of 7-hydroxy dienoic acids 5 from ketones is here described.

New Triene Synthesis from Sorbic Acid: Two-Step Synthesis of cis- and trans-Galbanolenes

The lithium dianion of sorbic acid reacts with hexanal at the C(2)-position to afford separable anti- and syn-hydroxy carboxylic acids 3 and 4 (87percent; 3/4=59:41 or 79percent; 3/4=16:84), whose stereospecific anti-decarboxylative elimination respectively affords (3E,5Z)- and (3E,5E)-1,3,5-undecatriene (1) and (2) (cis- and trans-galbanolenes (1) and (2) (69percent).An alternative route to 1 involves conversion of 3,4 to cis-lactone 7 (45percent after chromatography) followed by thermal syn-decarboxylation (81percent).The described procedure is both new and of general applicability, as illustrated by the synthesis of trienes with different substitution pattern.Key Words: Sorbic acid; aldol reaction; triene synthesis; olefination; decarboxylative elimination.

UNSATURATED CARBOXYLIC ACID POLYENOLATES. LITHIUM TRIENOLATE OF SORBIC ACID AS d6 SYNTHON: ADDITION TO KETONES AND UNSATURATED KETONES

Deprotonation of sorbic acid by two equivalents of lithium diethylamide, and aldol-type reaction of the resulting trienolate dianion (2) with carbonylic compounds affords the pentadienyl hydroxy acids (6) or 7-hydroxyhexa-2,4-dienoic acids (7) according to the duration of the reaction.The reaction of the dianion (2) with α,β-unsaturated ketones gives 1,4-ε-adducts for di- or tri-substituted enones, but either 1,4-γ- or 1,4-α-adducts for monosubstituted enones.