24563-03-9

Basic information

• Product Name: Dihydrocubebin
• Synonyms: Dihydrocubebin;(2R,3R)-2,3-Bis(1,3-benzodioxole-5-ylmethyl)-1,4-butanediol;(2R,3R)-2,3-Bis[(1,3-benzodioxole-5-yl)methyl]-1,4-butanediol;[2R,3R,(-)]-2,3-Bis(1,3-benzodioxole-5-ylmethyl)-1,4-butanediol;Dihydrocubebin, rel-
• CAS NO: 24563-03-9
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.3851
• Mol File: 24563-03-9.mol

Chemical Properties

• Boiling Point: 586.8°Cat760mmHg
• Flash Point: 308.7°C
• Appearance: /
• Density: 1.341g/cm³
• Vapor Pressure: 1.3E-14mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: Dihydrocubebin(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrocubebin(24563-03-9)
• EPA Substance Registry System: Dihydrocubebin(24563-03-9)

Safety Data

• Hazardous Substances Data: 24563-03-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H22O6/c21-9-15(5-13-1-3-17-19(7-13)25-11-23-17)16(10-22)6-14-2-4-18-20(8-14)26-12-24-18/h1-4,7-8,15-16,21-22H,5-6,9-12H2/t15-,16-/m0/s1

Upstream product

• 133-03-9 sesamin 
• 259540-41-5 (2R,3R)-1,4-bis((4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidinyl)-2,3-bis[(3,4-methylenedioxyphenyl)methyl]butane-1,4-dione 
• 161815-15-2 (1R,2R)-1,2-bis[(3,4-methylenedioxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 108-05-4 vinyl acetate 
• 161745-67-1 (4S)-4-isopropyl-3-[3-(3,4-methylenedioxyphenyl)propanoyl]-2-oxazolidinone 
• 161745-71-7 (2R,3R)-1,4-bis[(4S)-4-isopropyl-2-oxo(1,3-oxazolidin-3-yl)]-2,3-bis[(3,4-methylenedioxyphenyl)methyl]butane-1,4-dione 
• 24563-05-1 (-)-diethyl 2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinate 
• 24563-04-0 (+/-)-2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinic acid 
• 24565-47-7 diethyl 2-(3,4-methylenedioxybenzylidene)succinate 
• 24563-13-1 diethyl 2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinate 
• 24562-91-2 (-)-2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinic acid quinine salt 
• 120-57-0 piperonal 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 1613273-67-8 (8R,8′R)-9-O-(6'-O-α-L-arabinofuranosyl)-β-D-glucopyranosyldihydrocubebin 

Downstream Products

• 81410-43-7 ariensin 
• 94-53-1 Piperonylic acid 
• 26543-89-5 (-)-hinokinin 
• 81410-45-9 (8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin 

Relevant articles and documents

Two glycosides from the stem bark of Tetracentron sinense

Two glycosides, tetracentronsides A and B, were isolated from the stem bark of Tetracentron sinense Oliv., along with ten known compounds, β- sitosterol, lupeol, betulinic acid, oleanolic acid, vanillic aldehyde, vanillic acid, maslinic acid, huazhongilexin, daucosterol and catechin. On the basis of spectral and chemical evidence, tetracentronside A and B were identified as 3,4,5-trimethoxyphenyl-O-6'-O-vanilloyl-β-D-glucopyranoside and (8R, 8'R) 9-β-D-glucopyranosyl dihydrocubebin, respectively. (C) 2000 Elsevier Science Ltd.

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REDUCTION OF C-0 BONDS BY CATALYTIC TRANSFER HYDROGENOLYSIS

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Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (S,S)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (S,S)-(+)-hinokinin 9 in a high yield.

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