20013-34-7

Basic information

• Product Name: acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
• Synonyms: acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
• CAS NO: 20013-34-7
• Molecular Weight: 344.451
• Mol File: 20013-34-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique(CAS DataBase Reference)
• NIST Chemistry Reference: acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique(20013-34-7)
• EPA Substance Registry System: acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique(20013-34-7)

Safety Data

• Hazardous Substances Data: 20013-34-7(Hazardous Substances Data)

Upstream product

• 6802-75-1 diethyl isopropylidenemalonate 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 85458-25-9 5,5-dimethoxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-1-en-3-one 
• 180736-79-2 2-[3-(2,2-dimethoxy-ethyl)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene 
• 180736-80-5 (4E)-3-methylene-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-pentenal 
• 22035-53-6 dimethyl isopropylidenemalonate 
• 38987-91-6 5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene 
• 13830-91-6 diethyl bromoisopropylidenemalonate 
• 777916-02-6 2-[(4E,6E)-3-Benzenesulfonyl-1,5-dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienylidene]-malonic acid diethyl ester 
• 259181-78-7 2-[(2E,4E,6E)-1,5-Dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trien-(E)-ylidene]-malonic acid monomethyl ester 
• 113089-08-0 ethyl 14-carboxyretinoate 

Downstream Products

• 4759-48-2 13-cis-retinoic acid 
• 302-79-4 all-trans-retinoic-acid 
• 70244-78-9 2-((1E,3E,5E)-3,7-dimethylocta-1,3,5,7-tetraen-1-yl)-1,3,3-trimethylcyclohex-1-ene 

Relevant articles and documents

Structure-activity relationships of methylene or terminal side chain modified retinoids on the differentiation and cell death signaling in NB4 promyelocytic leukemia cells

New structure-activity relationships of a series of methylene or side chain modified retinoids on NB4 acute promyelocytic leukemia cells are investigated. The differentiation- and apoptosis-inducing potential of these compounds is analyzed on the basis of

Stereoselective and convergent syntheses of retinoic acid and its ester derivatives by the sulfone olefination reaction

An extensive study on the stereoselective and convergent syntheses of retinoic acid and its ester derivatives utilizing the Julia sulfone olefination reaction has been reported. Various C5 units of the acid 4a, the esters 4b-e from the chemically and biologically important alcohols, and the furanone 6 have been prepared and coupled with the C15 allylic sulfone 3 to give the C20 compounds 10 and 11, which provided all-(E)-retinoic acid (1a), its ester derivatives 1b-e, and the furanone analogue 12b in a highly stereoselective manner after dehydrosulfonation reaction. The Julia olefination reaction of the C5 diester 13 and the C15 allylic sulfone 3 produced the known C20 diacid 15 which underwent stereoselective mono-decarboxylation to provide either 13-(Z)-retinoic acid (2) or all-(E)-retinoic acid (1) depending on the reagent used.

Stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes as synthons

A stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes is described. In methylene-de-oxo-bisubstitution reactions (Knoevenagel, Stobbe, etc.), these new synthons produce stereoselectively E olefins. Hence, a synthesis of 13Z retinoic acids is described, via a stereospecific monodecarboxylation of carboxy-14-retinoic acids.