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(±)-Equol

(±)-Equol structure

CAS No:
94105-90-5
Formula:
C15H14O3
Chemical Name:
(±)-Equol
Synonyms:
7,4'-HoMoisoflavane;NV 07α;3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol 7-Hydroxy-3-(4-hydroxyphenyl)chroman 4',7-Isoflavandiol;3,4-Dihydro-3-(4-hydroxyphenyl)-2H-chromen-7-ol, (+/-)-Equol, 4',7-Isoflavandiol, 7-Hydroxy-3-(4-hydroxyphenyl)chroman;4',7-Isoflavandiol, (+/-)-Equol;4′,7-Dihydroxyisoflavane;(+/-)-Equol (GMP);(±)-EQUOL >= 99.0% (TLC)
Categories:
Analytical Chemistry > Standard

Description

(±)-Equol is the racemate of equol. Equol is a metabolite of the soy isoflavones, daidzin and daidzein.

3-(4-Hydroxyphenyl)chroman-7-ol is a member of hydroxyisoflavans.|A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.

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.

White to Off-White Solid

ChEBI: 3-(4-Hydroxyphenyl)chroman-7-ol is a member of hydroxyisoflavans.

(±)-Equol Basic Attributes

Molecular Weight：

242.27

Exact Mass：

242.27

BRN：

87752

EC Number：

618-999-2

NSC Number：

670882

DSSTox ID：

DTXSID7058705

Color/Form：

White to Light yellow to Light red

HScode：

2932990090

Characteristics

PSA：

49.7

XLogP3：

Appearance：

solid

Density：

1.286±0.06 g/cm3(Predicted)

Melting Point：

158-160C

Boiling Point：

441.7±45.0 °C(Predicted)

Flash Point：

220.9±28.7 °C

Refractive Index：

1.645

Water Solubility：

Soluble in DMSO and methanol or 100% ethanol. Insoluble in water.

Storage Conditions：

-20°C Freezer

PKA：

9.94±0.40(Predicted)

Critical Temperature & Pressure：

Inert atmosphere,Store in freezer, under -20°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Drug Information

MeSH：

Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS. (See all compounds classified as Phytoestrogens.)

Metabolism/Metabolites：

Equol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[[3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl]oxy]oxane-2-carboxylic acid.

MeSH Entry Terms：

(+-)-isomer of equol

(±)-Equol Use and Manufacturing

Uses

A human urinary metabolite of Daidzein.It is also a natural estrogenic metabolite from soy isoflavones.

(±)-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.

Use Classification：

Polyketides [PK] -> Flavonoids [PK12] -> Isoflavans [PK1208]

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
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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