Glycitein

HCID 5317750
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Grundinformationen

CAS
40957-83-3
Standard-SMILES
COc1cc2c(=O)c(-c3ccc(O)cc3)coc2cc1O
InChIKey
DXYUAIFZCFRPTH-UHFFFAOYSA-N
Summenformel
C16H12O5
Durchschnittliche Molmasse
284,26 g/mol
Monoisotopische Masse
284,06847348

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Glycitein
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
Englischer Name
Glycitein
Summenformel
C16H12O5
Molmasse
284.26

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,4
Polarare Oberfläche (TPSA)
76 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300°C
Siedepunkt
547.4 · 547.4±50.0 °C(Predicted)
Dichte
1.42 · 1.420±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
Aqueous Base (Slightly), DMSO (Slightly)
pka
7.03 · 7.03±0.20(Predicted)

Sicherheit und Regulatorisches

Gefahrenhinweise

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.

Sicherheitsdaten

wgk
3
hs_code
29329990
hazard_code
Xi
safety_code
24/25
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

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
Anwendungen · 2 Einträge

BeschreibungGlycitein 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.

VerwendenGlycitein 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).

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

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]

Ergänzende Hinweise

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.

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