4159-20-0

Basic information

• Product Name: 3,4-didehydroretinoic acid
• Synonyms: 3,4-didehydroretinoic acid;3,4-DIDEHYDRO-ALL-TRANS-RETINOICACID;(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)nona-2,4,6,8-tetraenoic acid;all-trans-3,4-Didehydro Retinoic Acid;(all-E)-3,7-DiMethyl-9-(2,6,6-triMethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenoic Acid;3-Dehydroretinoic Acid
• CAS NO: 4159-20-0
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.4192
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 4159-20-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 175-177 °C
• Boiling Point: 468.2°Cat760mmHg
• Flash Point: 355.1°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 4.63E-10mmHg at 25°C
• Refractive Index: 1.568
• PKA: 4.73±0.33(Predicted)
• CAS DataBase Reference: 3,4-didehydroretinoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-didehydroretinoic acid(4159-20-0)
• EPA Substance Registry System: 3,4-didehydroretinoic acid(4159-20-0)

Safety Data

• Hazardous Substances Data: 4159-20-0(Hazardous Substances Data)

Usage

Uses

A Retinoic Acid derivative for the treatment of neuroinflammatory conditions.

Definition

ChEBI: A retinoid obtained by 3,4-desaturation of beta-ionone ring of all-trans-retinoic acid

InChI:InChI=1/C20H26O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6-12,14H,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

Upstream product

• 339-16-2 all-trans-methyl retinoate 
• 25528-86-3 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dienyl)penta-2,4-dien-1-ol 
• 6901-92-4 9-cis-Dehydro-β-jonyliden-essigsaeure 
• 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 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 25528-88-5 (2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al 
• 6901-91-3 9-trans-Dehydro-β-jonyliden-essigsaeure 
• 25528-85-2 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexa-1,3-dienyl)penta-2,4-dien-1-ol 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 25528-87-4 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1,3-cyclohexadienyl)-2,4-pentadienal 
• 24041-43-8 methyl 9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate 
• 4834-02-0 4-diethoxyphosphoryl-3-methyl-but-2-enoic acid methyl ester 

Downstream Products

• 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 
• 79-80-1 vitamin A₂ 
• 472-87-7 3,4-didehydroretinal 
• 124130-50-3 9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-[2.2.6-trimethyl-cyclohexadien-(4.6)-(yl)-nonatetraen-(1.3t.5t.7t) 
• 41553-65-5 9-cis-3-dehydroretinal 
• 90694-29-4 3.7-Dimethyl-1t-(2.2.6-trimethyl-cyclohexadien-(4.6)-yl)-nonatetraen-(1.3c.5t.7c)-ol-⁽⁹⁾ 
• 73285-25-3 3.7-Dimethyl-1t-(2.2.6-trimethyl-cyclohexadien-(4.6)-yl)-nonatetraen-(1.3c.5t.7t)-ol-(9) 
• 24041-43-8 methyl (7E,9Z,11E,13E)-9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate 
• 124130-50-3 9,13-Di-cis-vitamin-A⁽²⁾-p-phenylazobenzoat 
• 124130-50-3 9-cis-Vitamin-A⁽²⁾-p-phenylazobenzoat 
• 24041-43-8 methyl (7E,9Z,11E,13Z)-9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate 
• 25428-49-3 9-cis-Vitamin-A⁽²⁾-saeure 

Relevant articles and documents

SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS LV. SYNTHESIS OF 9,13-DIMETHYL-7-(1,1,5-DIMETHYL-3,5-CYCLOHEXADIEN-6-YL)-7E,9E,11E,13E-NONATETRAEN-15-OIC ACID (VITAMIN A2 ACID) AND ITS ESTERS

The condensation of 9-methyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11-octatrien-13-one (the C18 ketone) with isobutyl monochloroacetate under the influence of potassium isobutoxide or tert-butoxide gave the glycidic ester of the C20 acid.Opening of th