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
• Article Data: 9

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 
• 133-03-9 sesamin 
• 1613273-67-8 (8R,8′R)-9-O-(6'-O-α-L-arabinofuranosyl)-β-D-glucopyranosyldihydrocubebin 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 120-57-0 piperonal 
• 24562-91-2 (-)-2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinic acid quinine salt 
• 24563-13-1 diethyl 2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinate 
• 24565-47-7 diethyl 2-(3,4-methylenedioxybenzylidene)succinate 
• 24563-04-0 (+/-)-2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinic acid 
• 24563-05-1 (-)-diethyl 2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinate 
• 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 
• 161745-67-1 (4S)-4-isopropyl-3-[3-(3,4-methylenedioxyphenyl)propanoyl]-2-oxazolidinone 
• 108-05-4 vinyl acetate 

Downstream Products

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

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.

Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties

Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.

Synthesis and bioactivity of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues

Full details of the total syntheses of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues are presented. The syntheses were based on a unified synthetic strategy involving the Stobbe reaction, alkylation to construct the skeleton