120409-94-1

Basic information

• Product Name: rac Matairesinol
• Synonyms: rac Matairesinol;(3R,4R)-rel-Dihydro-3,4-bis[(4-hydroxy-3-Methoxyphenyl)Methyl]-2(3H)-furanone;trans-Dihydro-3,4-bis[(4-hydroxy-3-Methoxyphenyl)Methyl]-2(3H)-furanone
• CAS NO: 120409-94-1
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.38508
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 120409-94-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: rac Matairesinol(CAS DataBase Reference)
• NIST Chemistry Reference: rac Matairesinol(120409-94-1)
• EPA Substance Registry System: rac Matairesinol(120409-94-1)

Safety Data

• Hazardous Substances Data: 120409-94-1(Hazardous Substances Data)

Usage

Uses

Used in Dietary Applications:
rac Matairesinol is used as a dietary supplement for its potential health benefits, as it is found in various food sources such as oil seeds, whole grains, vegetables, and fruits. It contributes to a balanced diet and may help improve overall health.
Used in Pharmaceutical Applications:
rac Matairesinol is used as a precursor to enterolignans, which have potential anticancer properties. It plays a significant role in the development of pharmaceutical compounds that target cancer cells and may contribute to the reduction of cancer risk.
Used in Cardiovascular Health Applications:
As a precursor to enterolignans, rac Matairesinol is used for its potential to reduce the risk of cardiovascular diseases. It may help in the development of treatments and preventive measures for heart-related conditions.

Upstream product

• 141-78-6 ethyl acetate 
• 111798-12-0 (3RS)-3c-hydroxymethyl-3r,4ξ-divanillyl-dihydro-furan-2-one 
• 20268-71-7 (3RS)-trans-4-(4,α-dihydroxy-3-methoxy-benzyl)-3-vanillyl-dihydro-furan-2-one 
• 347359-71-1 (7RS,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 3688-23-1 (-)-secoisolariciresinol 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 33837-83-1 3-(1,1-dimethylethyl)-4-hydroxy-5-methoxybenzaldehyde 
• 2505-15-9 6-(tert-butyl)-2-methoxy-4-methylphenol 
• 93-51-6 2-Methoxy-4-methylphenol 
• 3688-23-1 2,3-Bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol 
• 111194-07-1 trans-(+/-)-dihydro-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2(3H)-furanone 
• 223801-41-0 3-(4-(benzyloxy)-3-methoxyphenyl)-prop-2-enal 

Downstream Products

• 54797-70-5 matairesinol diacetate 
• 136466-44-9 C₂₀H₂₀⁽²⁾H₂O₆ 
• 1186043-20-8 7'-hydroxymatairesinol 
• 479030-50-7 L_g-threo-4-hydroxy-2.3-bis-(4-hydroxy-3-methoxy-benzyl)-butyric acid 
• 3688-23-1 2,3-Bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol 
• 347359-71-1 7'-hydroxymatairesinol 
• 1612227-15-2 (8R,8'R)-4,4'-dihydroxy-3,3'-dimethoxy-9a,9'a-dihomolignane-9a,9'a-dinitrile 
• 1528629-84-6 diallylmatairesinol 
• 1250860-87-7 (8R,8'R)-matairesinol 4,4'-di-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 29388-33-8 (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide 
• 76543-15-2 (-)-enterolactone 
• 80704-91-2 (3R,4R)-3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 25488-59-9 dimethylmatairesinol 
• 501645-95-0 matairesinyl 4,4'-bistriflate 

Relevant articles and documents

Secoisolariciresinol dehydrogenase: Mode of catalysis and stereospecificity of hydride transfer in Podophyllum peltatum

Secoisolariciresinol dehydrogenase (SDH) catalyzes the NAD+ dependent enantiospecific conversion of secoisolariciresinol into matairesinol. In Podophyllum species, (-)-matairesinol is metabolized into the antiviral compound, podophyllotoxin, wh

Reactions of hydroxymatairesinol over supported palladium catalysts

In this work, hydroxymatairesinol (extracted from Norway spruce knots) was hydrogenolyzed to matairesinol over palladium impregnated H-Beta-300, H-Beta-150, H-Beta-25, H-Beta-11, H-Y, H-Mordenite, H-MCM-41, H-ZSM-5, SiO 2, and Al2O3. H-Beta-25 without palladium was also investigated. The hydrogenolysis was performed in 2-propanol at 70 °C under hydrogen and nitrogen atmospheres in a stirred glass reactor. The catalysts were characterized by nitrogen physisorption, direct current plasma atomic emission spectrometry, X-ray powder diffraction, CO pulse chemisorption, transmission electron microscopy, and Fourier transform infrared spectroscopy (pyridine adsorption). Palladium on H-Beta with different acidities was tested; the results showed that the reaction rate was inversely proportional to the acidity. However, Bronsted acid sites are needed for the reaction, because palladium on SiO2 and Al2O3 is not active. In addition to the acidity, a metal is needed; the H-Beta-25 support without palladium displays no activity.

Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum

Given the importance of the antitumor/antiviral lignans, podophyllotoxin and 5-methoxypodophyllotoxin, as biotechnological targets, their biosynthetic pathways were investigated in Podophyllum peltatum and Linum flavum. Entry into their pathways was established to occur via dirigent mediated coupling of E-coniferyl alcohol to afford (+)-pinoresinol; the encoding gene was cloned and the recombinant protein subsequently obtained. Radiolabeled substrate studies using partially purified enzyme preparations next revealed (+)-pinoresinol was enantiospecifically converted sequentially into (+)-lariciresinol and (-)-secoisolariciresinol via the action of an NADPH-dependent bifunctional pinoresinol/lariciresinol reductase. The resulting (-)-secoisolariciresinol was enantiospecifically dehydrogenated into (-)-matairesinol, as evidenced through the conversion of both radio- and stable isotopically labeled secoisolariciresinol into matairesinol, this being catalyzed by the NAD-dependent secoisolariciresinol dehydrogenase. (-)-Matairesinol was further hydroxylated to afford 7'-hydroxymatairesinol, this being efficiently metabolized into 5-methoxypodophyllotoxin. Thus much of the overall biosynthetic pathway to podophyllotoxin has been established, that is, from the dirigent mediated coupling of E-coniferyl alcohol to the subsequent conversions leading to 7'-hydroxymatairesinol. (C) 2000 Elsevier Science Ltd.

Regioselective oxidative coupling approach to the synthesis of (±)-matairesinol and (±)-secoisolariciresinol

An efficient method for the synthesis of (±)-matairesinol and (±)-secoisolariciresinol is presented. By using 5-(tert-butyl)ferulic acid as a precursor, a regioselective oxidative coupling step was realized, which gave the desired coupling product in much higher yield (91%) than the literature value (ca. 20%). Georg Thieme Verlag Stuttgart.

Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (?)- and (+)-niranthin against hepatitis B and influenza viruses

The asymmetric total synthesis of four lignans, dimethylmatairesinol, matairesinol, (?)-niranthin, and (+)-niranthin has been achieved using reductive ring-opening of cyclopropanes. Moreover, we performed bioassays of the synthesized (+)- and (?)-niranthins using hepatitis B and influenza viruses, which revealed the relationship between the enantiomeric structure and the anti-viral activity of niranthin.

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.

Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid

Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cel

Cytotoxic activity of dietary lignan and its derivatives: Structure-cytotoxic activity relationship of dihydroguaiaretic acid

Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cel

Synthesis of sterically hindered chiral 1,4-diols from different lignan-based backbones

Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidation, was shown to b

An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone

Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.