Glycitein

HCID 5317750CAS 40957-83-3

Basic information

Standard SMILES
COc1cc2c(=O)c(-c3ccc(O)cc3)coc2cc1O
InChIKey
DXYUAIFZCFRPTH-UHFFFAOYSA-N
Molecular formula
C16H12O5
Average molar mass
284.26 g/mol
Monoisotopic mass
284.06847348

Overview

Glycitein is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis. It has a role as a plant metabolite, a fungal metabolite and a phytoestrogen. It is a 7-hydroxyisoflavone and a methoxyisoflavone. It is functionally related to an isoflavone.

Names & identifiers

Preferred name
Glycitein
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
English name
Glycitein
Molecular formula
C16H12O5
Molecular weight
284.26

Names & synonyms

Glycitein40957-83-37,4'-Dihydroxy-6-methoxyisoflavone4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one92M5F28TVFDTXSID40193960CHEBI:34778RefChem:143895DTXCID801164516-methoxy-7,4'-dihydroxyisoflavone
Show more names
GLYCETEINGliceteinGlycitein-RMGlycitein(SH)Glycitein, >=98%Glycitein (15 mg)Glycitein USP/EP/BP
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one4',7-Dihydroxy-6-methoxyisoflavoneMFCD00016679GyciteinUNII-92M5F28TVFGlycitein (Standard)CHEMBL513024s9107

Database identifiers

CAS
40957-83-3
PubChem CID
5317750
DTXSID
DTXSID40193960
ChEMBL
CHEMBL513024
ChEBI
CHEBI:34778
UNII
92M5F28TVF
Nikkaji
J17.583H

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
76 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
21

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
LogP2.57
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physicochemical properties

Melting point
300 °C · >300°C
Boiling point
547.4 · 547.4±50.0 °C(Predicted)
Density
1.42 · 1.420±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
Aqueous Base (Slightly), DMSO (Slightly)
pka
7.03 · 7.03±0.20(Predicted)

Safety & regulation

Hazard information

Regulatory Information4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29329990
Signal word
Danger
Symbol(GHS)
GHS05,GHS06
hazard_code
Xi

Chemistry & industry

Pharmacology

Metabolism/MetabolitesGlycitein has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid.
MeSH Pharmacological ClassificationCompounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.
Cellular LocationsMembrane
Applications · 5 items

DescriptionGlycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM. It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor. It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.

UsesGlycitein may be used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC).

UsesGlycitein has been used as standard for the analysis of soy isoflavones and metabolites in urine. It has also been used to bind to recombinant estrogen and progesterone receptors to know the relative binding affinity (RBA) for detection of potential endocrine disruptors.

UsesThe compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss

General DescriptionGlycitein is an isoflavone found in soy food products.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]

Additional notes

DefinitionChEBI: A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.

Related reactions

2 records

Linked notes

Loading…