10499-17-9

Basic information

• Product Name: 3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
• CAS NO: 10499-17-9
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• Mol File: 10499-17-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 418°C at 760 mmHg
• Flash Point: 206.6°C
• Density: 1.198g/cm³
• Vapor Pressure: 1.4E-07mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol(10499-17-9)
• EPA Substance Registry System: 3-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol(10499-17-9)

Safety Data

• Hazardous Substances Data: 10499-17-9(Hazardous Substances Data)

Upstream product

• 10499-16-8 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran 
• 108-46-3 recorcinol 
• 95307-71-4 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-2-(4-methoxyphenyl)ethanone 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 104-01-8 4-Methoxyphenylacetic acid 
• 10499-15-7 7-benzyloxy-3-(4-methoxyphenyl)-3H-benzopyran-4-one 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 

Downstream Products

• 955950-58-0 4-[3-(4-methoxyphenyl)-chroman-7-yloxy]butyric acid ethyl ester 
• 531-95-3 equol 
• 221054-79-1 (+)-Equol 
• 531-95-3 equol 
• 4626-22-6 Dihydroformononetin 

Relevant articles and documents

Equol, a natural estrogenic metabolite from soy isoflavones: Convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta

Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of gut microflora. It is known to be estrogenic, so human exposure to equol could have significant biological effects. Equol is a chiral molecule that can exist as the enantiomers R-equol and S-equol. To study the biological activity of racemic (±)-equol, as well as that of its pure enantiomers, we developed an efficient and convenient method to prepare (±)-equol from available isoflavanoid precursors. Furthermore, we optimized a method to separate the enantiomers of equol by chiral HPLC, and we studied for the first time, the activities of the enantiomers on the two estrogen receptors, ERα and ERβ. In binding assays, S-equol has a high binding affinity, preferential for ERβ (Ki[ERβ]=16 nM; β/α=13 fold), that is comparable to that of genistein (K i[ERβ]=6.7 nM; β/α=16), whereas R-equol binds more weakly and with a preference for ERα (Ki[ERα]=50 nM; β/α=0.29). All equol isomers have higher affinity for both ERs than does the biosynthetic precursor daidzein. The availability and the in vitro characterization of the equol enantiomers should enable their biological effects to be studied in detail.

Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D3 mimics as osteogenic agents

3-Arylbenzopyran based non-steroidal osteogenic agents have been explored as structural templates of estrogen and vitamin-D3. The target molecules 18a-c, 19a-c, 26a-c, 27a-c and intermediates 17a-c and 25a-c were studied for their osteogenic activity in an osteoblast differentiation assay in vitro using mouse calvarial osteoblast cells. Compounds 25c, 26b, 27b and 27c effectively increased ALP activity at 1 pM concentration compared to the untreated cells. The active compounds were devoid of inherent toxicity at 1 pM concentration in osteoblast cells. The most active compound, 27b, was studied for mineralization of osteoblast cells and expression of marker genes, viz. BMP-2, RUNX-2 & Osx, involved in osteogenesis. Molecular docking analysis performed for 27b showed its possible interactions with estrogen receptor-α and -β (ER-α and ER-β) as well as the vitamin-D receptor (VDR).

Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material

Disclosed herein are processes for the preparation of isoflavonoids, in particular haginin E, equol, daidzein, formononetin and the like, in which 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran is used as a common starting material.