85443-49-8

Basic information

• Product Name: (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran
• Synonyms: (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran;(2R)-2α-[3,4-Bis(benzyloxy)phenyl]-3β,5,7-tris(benzyloxy)-3,4-dihydro-2H-1-benzopyran;(2R,3S)-2-[3,4-Bis(benzyloxy)phenyl]-3,5,7-tris(benzyloxy)-3,4-dihydro-2H-1-benzopyran;(2R,3S)-2-[3,4-Bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran;2α-[3,4-Bis(benzyloxy)phenyl]-3β,5,7-tris(benzyloxy)-3,4-dihydro-2H-1-benzopyran;3,5,7,3',4'-Pentabenzyl-(+)-catechin;Einecs 287-241-7;(+)-3',4',3,5,7-Penta-O-benzylcatechin
• CAS NO: 85443-49-8
• Molecular Formula: C₅₀H₄₄O₆
• Molecular Weight: 740.88076
• EINECS: 287-241-7
• Mol File: 85443-49-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 856.2°C at 760 mmHg
• Flash Point: 306.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 1.6E-28mmHg at 25°C
• Refractive Index: 1.671
• Solubility: Chloroform, DCM, Ethyl Acetate
• CAS DataBase Reference: (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran(85443-49-8)
• EPA Substance Registry System: (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran(85443-49-8)

Safety Data

• Hazardous Substances Data: 85443-49-8(Hazardous Substances Data)

Usage

Description

(2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran is a complex organic compound with a unique molecular structure. It is characterized by its 3,4-dihydro-2H-1-benzopyran core, which is substituted with three phenylmethoxy groups at positions 3, 4, and 5, and a 3,4-bis(phenylmethoxy)phenyl group at position 2. (2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran exhibits a trans configuration at the 2R stereocenter, which is crucial for its properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
(2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran is also used in chemical research as a model compound to study the synthesis, reactivity, and properties of complex organic molecules. Its unique structure and functional groups provide opportunities for exploring new synthetic routes and understanding the fundamental principles of organic chemistry.
Used in Synthesis of (+)-trans Taxifolin:
(2R-trans)-2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran serves as an intermediate in the synthesis of (+)-trans Taxifolin (T010005), an antioxidant flavenoid. Its role in the synthesis process highlights its potential use in the development of natural antioxidants and other health-promoting compounds.

InChI:InChI=1/C50H44O6/c1-6-16-37(17-7-1)32-51-43-29-46(53-34-39-20-10-3-11-21-39)44-31-49(55-36-41-24-14-5-15-25-41)50(56-47(44)30-43)42-26-27-45(52-33-38-18-8-2-9-19-38)48(28-42)54-35-40-22-12-4-13-23-40/h1-30,49-50H,31-36H2/t49-,50+/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 154-23-4 catechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 574749-29-4 (+)-3',4',3,5,7-penta-O-benzyl-(4S)-hydroxycatechine 
• 478241-14-4 (+)-(4S)-acetoxy-3',4',3,5,7-penta-O-benzylcatechine 
• 89385-18-2 3,5,7,3',4'-penta-O-benzyl-8-formylcatechin 
• 89386-27-6 (2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-(2,2,2-trifluoroacetyl)flavan 
• 848047-63-2 (2R,3S)-3,5,7,3',4'-penta-O-benzyl-6-hydroxyflavan 
• 89385-96-6 3,5,7,3',4'-penta-O-benzyl-8-carboxycatechin 
• 69256-15-1 (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan 
• 480-18-2 taxifolin 
• 574749-31-8 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one 
• 1352123-19-3 3,5,7,3',4'-penta-O-benzyl-catechin-8-boronic acid 
• 89385-19-3 8-bromo-3,5,7,3',4'-penta-O-benzyl-(+)-catechin 
• 89385-62-6 C₅₅H₅₀O₈ 
• 1312298-15-9 C₂₀H₂₂O₈ 

Relevant articles and documents

COMPOSITION FOR ENHANCING SKIN ELASTICITY OR IMPROVING SKIN WRINKLES COMPRISING HEPTAHYDROXYFLAVAN AS AN EFFECTIVE INGREDIENT

Heptahydroxyflavan or a salt, isomer, hydrate or solvate thereof, which is an active ingredient of the present disclosure, can enhance skin elasticity and improve skin wrinkles by inhibiting the activity of MMP-1. In addition, the heptahydroxyflavan or a salt, isomer, hydrate or solvate thereof, which is an active ingredient of the present disclosure, can be used in various compositions such as cosmetics, health functional foods, etc. because it is safe with no cytotoxicity.

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.

Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy

Interest in the synthesis of procyanidin (catechin or epicatechin) oligomers that contain the 4→8 interflavan linkage remains high, principally due to research into their health effects. A novel coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 (i.e., 3,4-trans-(+)-catechin-4α→8-(+)- catechin dimer). The key interflavan bond was forged using a novel Lewis acid-promoted coupling of C4-ether 6 with C8-boronic acid 16 to provide the α-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the new coupling procedure was extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2.