66036-38-2

Basic information

• Product Name: EQUOL
• Synonyms: 3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol;3-(4-Hydroxyphenyl)-7-hydroxychroman;4-(7-Hydroxychroman-3-yl)phenol;3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
• CAS NO: 66036-38-2
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 0
• Mol File: 66036-38-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 158～160℃
• Appearance: /
• CAS DataBase Reference: EQUOL(CAS DataBase Reference)
• NIST Chemistry Reference: EQUOL(66036-38-2)
• EPA Substance Registry System: EQUOL(66036-38-2)

Safety Data

• Hazardous Substances Data: 66036-38-2(Hazardous Substances Data)

Usage

General Description

Equol is a non-steroidal estrogen that is produced by the intestinal bacterium Lactococcus garvieae when it metabolizes the soy isoflavone daidzein. It is classified as a phytoestrogen, meaning it is a plant-derived compound that has estrogen-like effects in the body. Equol has been studied for its potential health benefits, particularly in relation to its ability to alleviate menopausal symptoms such as hot flashes and bone loss. It is also believed to have anti-aging and anti-cancer properties. Equol has gained attention for its potential use in dietary supplements and functional foods, as well as for its potential role in personalized medicine based on individual differences in equol production. Further research is needed to fully understand the effects and potential applications of equol.

Upstream product

• 3682-01-7 daidzein diacetate 
• 1118431-82-5 3-(4-ethoxyphenyl)-7-methoxychroman 
• 486-66-8 daidzein 
• 17720-60-4 2,4,4'-trihydroxy deoxybenzoin 
• 156-38-7 4-hydroxyphenylacetate 
• 108-46-3 recorcinol 
• 81267-65-4 idronoxil 
• 61439-59-6 2-(4-benzyloxyphenyl)ethanol 
• 40167-10-0 2-[4-(benzyloxy)phenyl]acetaldehyde 
• 1370331-08-0 4',7-dibenzyloxy-2-morpholinoisoflav-3-ene 
• 17238-05-0 dihydrodaidzein 
• 1029608-32-9 C₂₉H₂₆O₃ 
• 13401-41-7 7-acetoxy-3-(4-acetoxy-phenyl)-chroman 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 

Downstream Products

• 104411-14-5 <6,8,3',5'-2H4>equol 
• 221054-79-1 (+)-Equol 
• 531-95-3 equol 
• 13401-41-7 7-acetoxy-3-(4-acetoxy-phenyl)-chroman 
• 4366-35-2 4',7-dimethoxyisoflavan 

Relevant articles and documents

Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities

A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.

Synthetic method for equol

The invention provides a synthetic method for equol. The synthetic method comprises the following steps: with daidzein as a raw material, subjecting daidzein to an esterification reaction to obtain a compound B; subjecting the compound B to olefinic-bond conjugation and a reduction reaction of a carbonyl group so as to obtain a compound C; subjecting the compound C to a dehydration reaction so as to obtain a compound D; and carrying out double-bond hydrogenation on the compound D so as to obtain equol. The synthetic method provided by the invention has the advantages of short synthesis steps, simple operation, economic performance, environmental protection, yield of 70% or above in each step, obviously increased overall yield and suitability for industrial mass production.

2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: Vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition

Isoflavone consumption correlates with reduced rates of cardiovascular disease. Epidemiological studies and clinical data provide evidence that isoflavone metabolites, such as the isoflavan equol, contribute to these beneficial effects. In this study we developed a new route to isoflavans and isoflavenes via 2-morpholinoisoflavenes derived from a condensation reaction of phenylacetaldehydes, salicylaldehydes and morpholine. We report the synthesis of the isoflavans equol and deoxygenated analogues, and the isoflavenes 7,4′-dihydroxyisoflav-3-ene (phenoxodiol, haganin E) and 7,4′-dihydroxyisoflav-2-ene (isophenoxodiol). Vascular pharmacology studies reveal that all oxygenated isoflavans and isoflavenes can attenuate phenylephrine-induced vasoconstriction, which was unaffected by the estrogen receptor antagonist ICI 182,780. Furthermore, the compounds inhibited U46619 (a thromboxane A2 analogue) induced vasoconstriction in endothelium-denuded rat aortae, and reduced the formation of GTP RhoA, with the effects being greatest for equol and phenoxodiol. Ligand displacement studies of rat uterine cytosol estrogen receptor revealed the compounds to be generally weak binders. These data are consistent with the vasorelaxation activity of equol and phenoxodiol deriving at least in part by inhibition of the RhoA/Rho-kinase pathway, and along with the limited estrogen receptor affinity supports a role for equol and phenoxodiol as useful agents for maintaining cardiovascular function with limited estrogenic effects.