Equol
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Equol
structure -
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CAS No:
531-95-3
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Formula:
C15H14O3
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Chemical Name:
Equol
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Synonyms:
2H-1-Benzopyran-7-ol,3,4-dihydro-3-(4-hydroxyphenyl)-,(3S)-;4′,7-Isoflavandiol;2H-1-Benzopyran-7-ol,3,4-dihydro-3-(4-hydroxyphenyl)-,(S)-;(3S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol;4′,7-Dihydroxyisoflavan;Equol;(S)-(-)-4′,7-Isoflavandiol;Equol,(-)-;(-)-Equol;(-)-(S)-Equol;(S)-Equol;(3S)-Equol;SE 5OH;S-equol;AUS 131;(S)-(-)-Equol;(3S)-3-(4-Hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol;(S)-3-(4-Hydroxyphenyl)chroman-7-ol;20879-01-0
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CAS No:
Description
(-)-(S)-Equol is a high affinity ligand for estrogen receptor β with a Ki of 0.73 nM.
Solid
Equol is a member of hydroxyisoflavans.|Equol has been used in trials studying the treatment of Breast Cancer.|S-equol is an orally bioavailable, non-steroidal estrogen naturally produced by the metabolism of the isoflavonoid daidzein by human intestinal microflora, with potential chemoprotective and estrogen receptor (ER) modulating activities. S-equol preferentially binds to and activates the beta isoform of ER in certain target tissues, while having an antagonistic effect in other tissues. This modulates the expression of ER-responsive genes in a tissue-specific manner. This agent may increase bone mineral density, affect vasomotor symptoms, and may decrease the proliferation rate of susceptible cancer cells. In addition, this agent interferes with the activity of enzymes involved in steroid biosynthesis. S-equol inhibits dihydrotestosterone (DHT) production and may inhibit the proliferation of androgen-driven prostate cancer. S-equol is the biologically active enantiomer while R-equol is essentially inactive and has a weak affinity for alpha-ER.|A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.
Characteristics
49.7
3
Solid
1.3±0.1 g/cm3
189.5 °C
441.7°C at 760 mmHg
220.9±28.7 °C
1.645
72.3 mg/L @ 25 °C (est)
-20°C Freezer
D -21.5°
Drug Information
Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS. (See all compounds classified as Phytoestrogens.)
(+-)-isomer of equol
Equol Use and Manufacturing
Deprotecting the bis-MOM-S-equol to S-Equol ((S)-3-(4-hydroxyphenyl)-chroman-7-ol); A solution of 42.17 g (0.128 mol) of (S)-bis-MOM-equol in 200 mL of 1:1 mixture of CHA mixture of phenol 6 (259 mg, 0.8 mmol) and KThe dimethoxy chromane (−)-23 (18g, 66.7mmol) was dissolved in pyridine hydrochloride (192g, 148mL, 1.67mol), heated overnight at 150°C and cooled to room temperature. After neutralizing with excessive NaHCOTo a suspension Of LiAlHTo a mixture of alcohol of formula (9) (50 g) and triphenyl phosphine (151 g) in THF (2.5 L) diisopropyl azodicarboxylate (1 16.5 g) in THF (500 mL) was added at 15-20 °C and maintained at that temperature for 1 -2 hours. About 5percent lithium hydroxide solution (1000 mL) was added into the reaction mass and extracted with MTBE (3 x 750 mL) to remove the organic impurities. The pH of the aqueous layer was adjusted to 1 -4 by dilute hydrochloric acid (250 mL). The reaction mass was maintained at RT for 5-6 hours and the product was filtered off. The crude product was taken with I PA (7.5 vol) and added water (22.5 vol). The reaction mass was then maintained at RT for 12-14 hours. The solid was filtered and dried at 50-55 for 10-12 hours to afford the title compound. Yield: 36 g Chemical purity (by HPLC): 98.9percent. Chiral purity (by HPLC): 99.7percent e.e. To a mixture of alcohol of formula (9) (50 g) and triphenyl phosphine (151 g) in THF (2.5 L) diisopropyl azodicarboxylate (116.5 g) in THF (500 mL) was added at 15-20° C. and maintained at that temperature for 1-2 hours.
serine protease
Computed Properties
Molecular Weight:242.27
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:49.7
Heavy Atom Count:18
Complexity:273
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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