(R)-Equol

Base Information

• Chemical Name: (R)-Equol
• CAS No.: 221054-79-1
• Molecular Formula: C15H14O3
• Molecular Weight: 242.27
• Hs Code.: 2932999099
• UNII: 2V8RAP1HXA
• DSSTox Substance ID: DTXSID101318590
• Nikkaji Number: J844.939B
• Wikidata: Q27255644
• ChEMBL ID: CHEMBL3127843
• Mol file: 221054-79-1.mol

Synonyms:(R)-Equol;221054-79-1;(+)-Equol;Isoequol;(R)-3-(4-hydroxyphenyl)chroman-7-ol;R-Equol;Equol, (+)-;(3R)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol;2V8RAP1HXA;2H-1-Benzopyran-7-ol, 3,4-dihydro-3-(4-hydroxyphenyl)-, (3R)-;UNII-2V8RAP1HXA;EQUOL (R)-FORM;SCHEMBL2002128;EQUOL (R)-FORM [MI];CHEMBL3127843;CHEBI:156169;DTXSID101318590;EX-A1353;BBL026747;MFCD09025608;STK801893;AKOS004120071;CS-8182;VS-08423;HY-108414;E84289;Q27255644;(3R)-3-(4-HYDROXYPHENYL)-3,4-DIHYDRO-2H-1-BENZOPYRAN-7-OL

Chemical Property of (R)-Equol

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Melting Point: 189-190 °C
• Boiling Point: 441.7 °C at 760 mmHg
• Flash Point: 220.9 °C
• PSA: 49.69000
• Density: 1.286 g/cm³
• LogP: 2.81650
• 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)-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 NIPH Clinical Trials: Efficacy of equol for endothelial function of menopausal woman
• Uses: (R)-Equol is a non-steroidal estrogen produced from the metabolism of daidzein.

Technology Process of (R)-Equol

There total 124 articles about (R)-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:

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

4',7-dimethoxyisoflavan

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

daidzein

Refernces

• 1、 Minekawa, Takayuki,Kambegawa, Akira,Shindome, Kumiko,Ohkuma, Hiroshi,Abe, Katsushi,Maekawa, Hiroaki,Arakawa, Hidetoshi. "Development of bioluminescent enzyme immunoassay for S-equol using firefly luciferase and its application to the assessment of equol-producer status". . p. 84 - 87. Retrieved 2011.
• 2、 Uemura, Takahito,Saito, Yusuke,Sonoda, Motohiro,Tanimori, Shinji. "A Concise Enantiodivergent Synthesis of Equol". . p. 693 - 696. Retrieved 2020/12/23.
• 3、 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.