3-(4-Hydroxyphenyl)chroman-7-ol

Base Information

• Chemical Name: 3-(4-Hydroxyphenyl)chroman-7-ol
• CAS No.: 94105-90-5
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.274
• Hs Code.: 2932990090
• European Community (EC) Number: 618-999-2
• NSC Number: 670882
• UNII: 2RZ8A7D0E8
• DSSTox Substance ID: DTXSID7058705
• Nikkaji Number: J254.135A
• Wikipedia: Equol
• Wikidata: Q27255516
• ChEMBL ID: CHEMBL1957037
• Mol file: 94105-90-5.mol

Synonyms:(+-)-isomer of equol;3' Hydroxy Equol;3'-hydroxy-equol;4' methoxy 7 isoflavanol;4' O Methyl Equol;4'-methoxy-7-isoflavanol;4'-O-methyl equol;6' Hydroxy Equol;6'-hydroxy-equol;equol;Equol, 4'-O-Methyl

Chemical Property of 3-(4-Hydroxyphenyl)chroman-7-ol

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 2.05E-08mmHg at 25°C
• Melting Point: 158-160?C
• Refractive Index: 1.644
• Boiling Point: 441.7 °C at 760 mmHg
• PKA: 9.94±0.40(Predicted)
• Flash Point: 220.9 °C
• PSA: 49.69000
• Density: 1.286 g/cm³
• LogP: 2.81650
• Storage Temp.: -20°C Freezer
• Sensitive.: Hygroscopic
• Solubility.: soluble in Ethanol
• Water Solubility.: Soluble in DMSO and methanol or 100% ethanol. Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

(R,S)-Equol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
• Recent ClinicalTrials: Equol Supplementation on Blood Pressure and Vascular Function
• Recent NIPH Clinical Trials: Efficacy of equol for endothelial function of menopausal woman
• Description: Equol is a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora. The estrogen receptor (ER) binding activity of the naturally occurring (S)-enantiomer demonstrates greater affinity toward ERβ while the (R)-enantiomer demonstrates greater affinity towards ERα. Synthesized as a racemic mixture, (±)-equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM.
• Uses: (R,S)-Equol is a human urinary metabolite of the soy isoflavones Daidzein (D103500). (+/-)-Equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM. It is a weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. It inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. It functions as a DHT blocker. A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones.

Technology Process of 3-(4-Hydroxyphenyl)chroman-7-ol

There total 18 articles about 3-(4-Hydroxyphenyl)chroman-7-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3,4-dihydro-7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran (10499-17-9,61514-94-1) → equol (531-95-3,66036-38-2,94105-90-5,221054-79-1)

Guidance literature:

With tertamethylammonium iodide; boron trichloride; In dichloromethane; at -78 - 0 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.02.159

Reference yield: 83.2%

daidzein diacetate (3682-01-7) → acetamide (60-35-5) + equol (531-95-3,66036-38-2,94105-90-5,221054-79-1)

Guidance literature:

With ammonium formate; acetic acid; palladium hydroxide on carbon; for 1.4h; Product distribution / selectivity; Heating / reflux;

Reference yield: 83.0%

C29H26O3 (1029608-32-9) → equol (531-95-3,66036-38-2,94105-90-5,221054-79-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h;

DOI:10.1016/j.tetlet.2008.03.003

upstream raw materials:

daidzein

3,4-dihydro-7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

7-acetoxy-3-(4-acetoxy-phenyl)-chroman

Downstream raw materials:

(+)-Equol

equol

<6,8,3',5'-2H4>equol

7-acetoxy-3-(4-acetoxy-phenyl)-chroman

Refernces

• 1、 -. "Method for preparing equol". . . Retrieved 2020/01/08.
• 2、 Xiao, Zhu-Ping,Peng, Zhi-Yun,Dong, Jing-Jun,He, Juan,Ouyang, Hui,Feng, Yu-Ting,Lu, Chun-Lei,Lin, Wan-Qiang,Wang, Jin-Xiang,Xiang, Yin-Ping,Zhu, Hai-Liang. "Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors". . p. 685 - 695. Retrieved 2013/07/25.