17334-50-8

Basic information

• Product Name: cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• Synonyms: cis-(1)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol;Einecs 241-357-4
• CAS NO: 17334-50-8
• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 290.27
• EINECS: 241-357-4
• Mol File: 17334-50-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 630.4°Cat760mmHg
• Flash Point: 335°C
• Appearance: /
• Density: 1.593g/cm³
• Vapor Pressure: 9.29E-17mmHg at 25°C
• Refractive Index: 1.741
• CAS DataBase Reference: cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol(17334-50-8)
• EPA Substance Registry System: cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol(17334-50-8)

Safety Data

• Hazardous Substances Data: 17334-50-8(Hazardous Substances Data)

Usage

Description

cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol, a member of the flavonoid class, is a flavonol characterized by three hydroxyl groups on its phenyl ring. It is a bioactive compound prevalent in a variety of fruits, vegetables, and teas, known for its antioxidant, anti-inflammatory, and anti-cancer properties. cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol's structure and reactivity enable it to neutralize free radicals and shield cells from oxidative stress, positioning it as a significant molecule for health and disease prevention.

Uses

Used in Health and Nutrition Industry:
cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol serves as a natural antioxidant for [application reason] its ability to scavenge free radicals and protect cells from oxidative damage, contributing to the prevention of various diseases associated with oxidative stress.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol is utilized as an anti-inflammatory agent for [application reason] its capacity to reduce inflammation, which can be beneficial in treating conditions characterized by chronic inflammation.
Used in Cancer Research and Treatment:
cis-(±)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol is employed as a potential anti-cancer agent for [application reason] its demonstrated properties in inhibiting cancer cell growth and proliferation, offering a natural alternative or supplement to conventional cancer therapies.

InChI:InChI=1/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2

Upstream product

• 7295-85-4 catechin 
• 7732-18-5 water 
• 154-23-4 catechin 
• 1392190-80-5 pentabenzylated cyanidin 
• 13157-90-9 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one 
• 1392108-91-6 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran 
• 1392108-90-5 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)-4H-1-benzopyran 
• 117-39-5 quercetol 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 528-58-5 cyanidin chloride 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 67052-53-3 4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Downstream Products

• 154-23-4 (-)-catechin 
• 7295-85-4 catechin 
• 35323-91-2 (+)-epicatechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 16198-01-9 (+/-)-epicatechol pentaacetate 
• 47299-80-9 (+/-)-5,7-O-dimethylepicatechin 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 732298-15-6 (+)-(2S,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol 
• 65350-86-9 (2R,3R)-2-(3,4-dihydroxyphenyl)-3-methoxychroman-5,7-diol 
• 20728-75-0 C₄₄H₄₀O₆ 
• 16198-01-9 (-)-epicatechin pentaacetate 
• 619-60-3 4-(N,N-dimethylamino)phenol 

Relevant articles and documents

11-β-hydroxysterols as possible endogenous stimulators of mitochondrial biogenesis as inferred from epicatechin molecular mimicry

Currently, there is great interest in identifying endogenous (i.e. physiological) stimulators of mitochondrial biogenesis (MB), in particular, those that may mediate the effects of exercise. The molecular size of the cacao flavanols (epicatechin and catechin) highly resembles that of sterols and epicatechin has been reported to activate cells surface receptors leading to the stimulation of MB in endothelial and skeletal muscle cells translating into enhanced exercise capacity. We therefore hypothesize, that epicatechin may be acting as a structural mimic of an as yet unknown sterol capable of stimulating MB. We developed a new synthetic process for obtaining enantiomerically pure preparations of (-)-epicatechin and (+)-epicatechin. Applying spatial analytics and molecular modeling, we found that the two isoforms of epicatechin, (-) and (+), have a structural resemblance to 11-β-hydroxypregnenolone, a sterol with no previously described biological activity. As reported in this proof-of-concept study performed in primary cultures of endothelial and muscle cells, 11-β-hydroxypregnenolone is one of the most potent inducers of MB as significant activity can be detected at femtomolar levels. The relative potency of (-)/(+)-epicatechin isoforms and on inducing MB correlates with their degree of spatial homology towards the 11-β-hydroxypregnenolone. On the basis of these results, the detailed in vivo characterization of the potential for these sterols to act as endogenous modulators of MB is warranted.

NOVEL APPROACH FOR SYNTHESIS OF CATECHINS

A process for synthesis of enatiomerically pure or enatiomerically enriched or racemic mixture of (+and/or?) epicatechin echm and its intermediates, comprising the steps of: (i) obtaining penta-protected quercetin; (ii) reducing the penta-protected quercetin obtained from step (i); (iii) optionally deprotecting the compound of step (ii); (iv) reducing the compound obtained from step (ii) or step (iii) in the presence of a chiral/achiral reducing agent to obtain a chiral intermediate; (v) deprotecting and/or hydrogenation of the chiral intermediate obtained from step (iv) to obtain (?)-epicatechin; (vi) optionally simultaneously deprotecting and by drogenation of the compound obtained from step (ii) to obtain racemic epicatechin.

A NOVEL PROCESS FOR SYNTHESIS OF POLYPHENOLS

The present invention provides synthetic processes for preparing racemic and/or optically pure epicatechin, epigallocatechin and related polyphenols as such or as their variously functionalized derivatives.