148409-36-3

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-Matairesinol is used as a potential therapeutic agent for the prevention and treatment of chronic diseases such as cancer, cardiovascular diseases, and diabetes. Its antioxidant and anti-inflammatory properties contribute to its potential health benefits in these areas.
Used in Hormone-Related Health Conditions:
(+/-)-Matairesinol is used as a compound with estrogenic effects for the potential management of hormone-related health conditions. Its role in hormone regulation is being investigated for its potential applications in this field.
Used in Nutraceutical Industry:
(+/-)-Matairesinol is used as a nutraceutical ingredient in various plant-based foods such as sesame seeds, flaxseeds, and whole grains. Its presence in these foods may contribute to their overall health benefits and support the prevention of chronic diseases.

Upstream product

• 106647-14-7 matairesinol 4'-O-β-gentiobioside 
• 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 
• 20268-71-7 (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone 
• 81623-30-5 (-)-(7R,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylidnano-9,9'-lactone 
• 689277-84-7 (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 3688-23-1 2,3-Bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol 
• 33837-83-1 3-(1,1-dimethylethyl)-4-hydroxy-5-methoxybenzaldehyde 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 116185-11-6 benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate 
• 124988-59-6 (3S,4S)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 121-33-5 vanillin 

Downstream Products

• 54797-70-5 matairesinol diacetate 
• 501645-95-0 matairesinyl 4,4'-bistriflate 
• 1186043-20-8 7'-hydroxymatairesinol 
• 479030-50-7 L_g-threo-4-hydroxy-2.3-bis-(4-hydroxy-3-methoxy-benzyl)-butyric acid 
• 1250860-87-7 (8R,8'R)-matairesinol 4,4'-di-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 1612227-15-2 (8R,8'R)-4,4'-dihydroxy-3,3'-dimethoxy-9a,9'a-dihomolignane-9a,9'a-dinitrile 
• 73354-08-2 (2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dimethoxybenzyl)-1,4-butanediol 
• 7770-78-7 trans-2-(4''-hydroxy-3''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone 
• 119030-66-9 (+/-)-isoarctigenin 
• 10352-26-8 trans-3,4-bis(3,4,-dimethoxybenzyl)tetrahydrofuran 
• 347359-71-1 7'-hydroxymatairesinol 
• 145265-02-7 (-)-secoisolariciresinol 
• 119098-95-2 (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone 
• 3688-23-1 (-)-secoisolariciresinol 

Relevant academic research and scientific papers

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

Oxidative dehydrogenation of a biomass derived lignan - Hydroxymatairesinol over heterogeneous gold catalysts

Synthesis of the lignan oxomatairesinol via oxidative dehydrogenation of the naturally occurring lignan hydroxymatairesinol was studied over gold catalysts supported on C, TiO2, SiO2, Al2O 3, and MgO. In order to investigate the reaction performance over the gold catalyst, synthesis of lignan oxomatairesinol was carried out in different organic solvents/water mixtures under synthetic air and nitrogen atmosphere at 373 K, and using also isolated hydroxymatairesinol isomers as a starting material. The results were compared with those obtained over palladium catalysts. Synthesized supported gold catalysts as well as the corresponding supports were characterized by TEM, XRD, ICP-OES, CO2-TPD, FTIR (using pyridine as a probe molecule), and XPS. Gold catalysts were shown to display superior performance compared with palladium ones: the activity was 4 times higher, with selectivity toward oxomatairesinol being 100%, while 60-85% were obtained over palladium catalysts. In contrast to palladium, the activity of gold catalysts is high in aerobic conditions and water-propan-2-ol mixture. However, activity and selectivity of gold catalysts were shown to be dependent on the electronic state of the metal and, similar to palladium catalysts, on the support acidity.

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.

A novel approach towards dibenzylbutyrolactone lignans involving heck and radical reactions: Application to (±)-matairesinol synthesis

A highly regio- and stereoselective Heck reaction of iodoarenes with vinylated malonates, generated in situ by fluoride-induced protiodesilylation of alkenylsilanols/disiloxanes to give functionalized styrenes and 1,4-diaryl-1-butenes has been developed. The dibenzylbutyrolactone lignan skeletons have been achieved from 1,4-diaryl-1-butenes by two routes involving diastereoselective radical cyclization as the key step. This strategy has successfully been applied in the synthesis of (±)-matairesinol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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.

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