Equol

Base Information

• Chemical Name: Equol
• CAS No.: 531-95-3
• Deprecated CAS: 20879-01-0
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 2932999099
• European Community (EC) Number: 208-522-2
• UNII: 2T6D2HPX7Q
• DSSTox Substance ID: DTXSID0022309
• Nikkaji Number: J14.375H
• Wikipedia: Equol
• Wikidata: Q5384747
• NCI Thesaurus Code: C120313
• Metabolomics Workbench ID: 38078
• ChEMBL ID: CHEMBL198877
• Mol file: 531-95-3.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 Equol

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 2.05E-08mmHg at 25°C
• Melting Point: 189-190 °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
• Solubility.: DMSO (Soluble), Ethanol (Slightly), Methanol (Slightly)
• 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% up, ^*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
• Isomeric SMILES: C1[C@H](COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
• Recent ClinicalTrials: Effect of Equol Supplementation on Arterial Stiffness and Cognition in Healthy Volunteers
• Recent NIPH Clinical Trials: Efficacy of equol for endothelial function of menopausal woman
• Uses: Receptor; binding activity A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones (S)-Equol and R-Equol are metabolites of the soy isoflavones Daidzein (D103500) and Genistein. Both have significant biological actions. serine protease

Technology Process of Equol

There total 91 articles about Equol 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: 93.0%

(S)-7-(methoxymethoxy)-3-(4'-methoxymethoxy)-phenylchroman (922179-56-4) → equol (531-95-3,221054-79-1)

Guidance literature:

With hydrogenchloride; methanol; In dichloromethane; at 4.8 - 20 ℃; for 6h;

Reference yield: 91.0%

(S)-4-(3-bromo-2-(4-hydroxyphenyl)propyl)benzene-1,3-diol (1383121-33-2) → equol (531-95-3,221054-79-1)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃; for 8h;

DOI:10.1016/j.tet.2012.03.118

upstream raw materials:

ethylmagnesium iodide

(S)-7-methoxy-3-(4-methoxyphenyl)chromane

daidzein

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

Downstream raw materials:

4-hydroxysalicylic acid

4-hydroxy-benzoic acid

(+)-Equol

equol

Refernces

• 1、 Uemura, Takahito,Saito, Yusuke,Sonoda, Motohiro,Tanimori, Shinji. "A Concise Enantiodivergent Synthesis of Equol". . p. 693 - 696. Retrieved 2020/12/23.
• 2、 Umeda, Moeko,Sakamoto, Kana,Nagai, Tomotaka,Nagamoto, Midori,Ebe, Yusuke,Nishimura, Takahiro. "Rhodium-catalyzed asymmetric addition of arylboronic acids to 2: H-chromenes leading to 3-arylchromane derivatives". supporting information. p. 11876 - 11879. Retrieved 2019/10/11.