347359-71-1

Basic information

• Product Name: 7-Hydroxymatairesinol-7-allo-Hydroxymatairesinol mixture
• Synonyms: (?)-Hydroxymatairesinol, mixture of epimers;(3R,4R)-Dihydro-4-[hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone;7-Hydroxymatairesinol-7-allo-Hydroxymatairesinol mixture;(-)-Hydroxymatairesinol (2 Epimers)
• CAS NO: 347359-71-1
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.38
• Mol File: 347359-71-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Hydroxymatairesinol-7-allo-Hydroxymatairesinol mixture(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxymatairesinol-7-allo-Hydroxymatairesinol mixture(347359-71-1)
• EPA Substance Registry System: 7-Hydroxymatairesinol-7-allo-Hydroxymatairesinol mixture(347359-71-1)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 347359-71-1(Hazardous Substances Data)

Upstream product

• 689277-85-8 (7'R,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 20268-71-7 (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone 
• 689277-80-3 (-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol 
• 689277-84-7 (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 689277-79-0 (+)-4-benzyl-3-(2-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}but-3-enoyl)oxazolidin-2-one 
• 689277-82-5 (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester 
• 689277-83-6 (-)-8-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}-8'-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxybenzyl]dihydrofuran-2-one 
• 121-33-5 vanillin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 89067-58-3 (+/-)-trans-2-(3-methoxy-4-benzyloxybenzyl)-3-(3'-metyhoxy-4'-benzyloxy-α-benzoyl)butyrolactone 
• 1428741-25-6 (R)-4-((S)-(tert-butyldimethylsilyloxy)(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)methyl)dihydrofuran-2(3H)-one 
• 1428741-21-2 (S)-2-((S)-(tert-butyldimethylsilyloxy)(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)methyl)-4-methoxy-4-oxobutanoic acid 

Downstream Products

• 163634-08-0 (S)-(+)-imperanene 
• 580-72-3 matairesinol 
• 80704-91-2 (3R,4R)-3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 76543-15-2 (-)-enterolactone 
• 501645-95-0 matairesinyl 4,4'-bistriflate 
• 11041-15-9 C₂₀H₂₂O₇ 
• 518-55-8 α-conidendrin 
• 53250-61-6 7-Oxomatairesinol 
• 78178-29-7 α-conidendreic acid dimethyl ester dimethyl ether 

Relevant articles and documents

α,β-Dibenzyl-γ-butyrolactone lignan alcohols: total sytnhesis of (+/-)-7'-hydroxyenterolactone, (+/-)-7'-hydroxymatairesinol and (+/-)-8-hydroxyenterolactone

Two trans-α,β-dibenzyl-γ-butyrolactone lignans carrying a hydroxyl group at the β-benzylic carbon aton and a α-hydroxy α,β-dibenzyl-γ-butyrolactone lignan were synthesized in racemic form using the tandem conjugate addition reaction to construct the basic lignan skeleton. Subsequent reaction steps involved either a catalytic reduction of the regenerted keto group to the alcohol, or a hydrogenolysis to benzylic methylene followed by lactone enolate formation and oxidation to give the α-hydroxybutyrolactones. These procedures were applied for the synthesis of 7'-hydroxyenterolactones and 7'-hydroxymatairesinols, and 8-hydroxyenterolacotones, respectively. The diastereomeric mixtures of these compounds were separated either by HPLC techniques or column chromatography and the structures were elucidated using NMR spectroscopy.

Convenient preparation and spectroscopic characterization of 7r-hydroxymatairesinol

The preparation of 7R-HMR (allo-hydroxymatairesinol) is reported by: (a) NaBH4 kinetic reduction of 7R/7S diastereomeric mixture; and (b) epimerization of the C7 hydroxyl group by Mitsunobu reaction and subsequent ester hydrolysis. The availability of highly pure target compound (7R-HMR) made it possible to confirm the structure of the target compound and to complete the full spectroscopic characterization.

Asymmetric aldol approach to dibenzylbutyrolactone lignans: Synthesis of (-)-(7′S)-hydroxymatairesinol and (-)-(7′S)-hydroxyarctigenin

A competent and general asymmetric synthesis of 7′- hydroxydibenzylbutyrolactone lignans such as (7′S)-hydroxymatairesinol and (7′S)-hydroxyarctigenin has been reported from N-succinyl-2-oxazolidinone in six steps where diastereoselective aldol reaction and stereoselective alkylation serve as the key steps.