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7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyron

Daidzein

HCID 5281708
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Grundinformationen

CAS
486-66-8
Standard-SMILES
O=c1c(-c2ccc(O)cc2)coc2cc(O)ccc12
InChIKey
ZQSIJRDFPHDXIC-UHFFFAOYSA-N
Summenformel
C15H10O4
Durchschnittliche Molmasse
254,24 g/mol
Monoisotopische Masse
254,0579088

Überblick

Daidzein is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'. It has a role as an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor, an antineoplastic agent, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, a plant metabolite and a phytoestrogen. It is a conjugate acid of a daidzein(1-).

Namen und Bezeichner

Bevorzugter Name
Daidzein
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
Lokaler Name
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyron
Englischer Name
Daidzein
Summenformel
C15H10O4
Molmasse
254.24

Namen und Synonyme

daidzein486-66-84',7-DihydroxyisoflavoneDaidzeol7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one7,4'-Dihydroxyisoflavone7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one7-hydroxy-3-(4-hydroxyphenyl)chromen-4-oneDiadzein7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyroneDTXSID90223106287WC5J2L
Weitere Namen anzeigen
Daidzein 486-66-84’,7-dihydroxy-isoflavon4,7-Dihydroxyisoflavone(Daidzein)7-HYDROXY-3-(4-HYDROXY-PHENYL)-CHROMEN-4-ONEk251bGMP-5TatoinDaizeolK 251-6
DTXCID102310CHEBI:28197RefChem:5729207-635-44H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-Daidzein (Standard)MFCD000169544,7-Dihydroxyisoflavone

Datenbank-Bezeichner

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,5
Polarare Oberfläche (TPSA)
66,8 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
19
Formalladung
0
Komplexität
382

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point323 °C
Physical DescriptionSolid
Collision Cross Section · 3 Einträge

155.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9022310]

162.33 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

172 Ų [M+Na]+

Physikochemische Eigenschaften

Schmelzpunkt
315 · 315-323°C (dec.)
Siedepunkt
317.45 °C · 317.45°C (rough estimate)
Dichte
1.1629 · 1.1629 (rough estimate)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 3.7% (3 of 81) of reports.

Warning

H315 (95.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-: 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.
Hazard Classes and CategoriesSkin Irrit. 2 (95.1%)

Toxikologische Informationen

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
hs_code
29329990
RTECS-Nr.
DJ3100040
risk_code
36/38
hazard_code
Xi
safety_code
24-26-37/39
hazard_class
IRRITANT

Chemie und Industrie

Pharmakologische Informationen

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

Verwendung und Herstellung

Uses · 1 Eintrag

Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut.

Anwendungen · 3 Einträge

BeschreibungDaidzein mainly comes from leguminous plants, the seeds of soybean (dadou), red clover grass, or all Pueraria roots. Its medicinal value was first recorded in Shen Nong Ben Cao Jing 2838 BC.Daidzein, one of the main soy isoflavones, is also the main component of radix puerariae (Gegen) which is the dry root of kudzu leguminous plants. Radix puerariae can reduce fever, produce saliva, and relieve diarrhea. Its chemical composition is complicated, including puerarin, xyloside, soy flavonoids, soybean flavonoid glycosides, beta-sitosterol, daidzin, daidzein. The main effective components are puerarin and daidzein

HistoryDaidzein is a kind of isoflavone compound, which was first synthetized by researchers in China. It has been widely used in drugs, food supplements, and cosmetics. Because of two phenolic hydroxyl structures, Daidzein has poor water solubility, poor liposolubility, and strong first-pass effect, leading to the low bioavailability of oral absorption, which limits its widely clinical usage. Ipriflavone is a kind of isoflavone modified from Daidzein, which has been used for the treatment of osteoporosis in Japan and some European countries. The effects of a series of amino alkoxy derivatives of ipriflavones on inhibiting the bone absorption were evaluated. The researchers found that 7-amino alkoxy derivative works best. When Daidzein was alkylated or acylated at 7-hydroxyl selectively, the stability was increased, and thus the proliferation of MCF-7 cell was inhibited.

Zugehörige Reaktionen

49
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 28761
HRID 28761als Eduktuspto-grants-2008_09
Reaktionsgleichung von HRID 28763
HRID 28763als Produktuspto-grants-2008_09
Reaktionsgleichung von HRID 28764
HRID 28764als Eduktuspto-grants-2008_09
Reaktionsgleichung von HRID 227207
HRID 227207als Eduktuspto-grants-2009_07
Reaktionsgleichung von HRID 236342
HRID 236342als Eduktuspto-grants-1987_02
Reaktionsgleichung von HRID 304424
HRID 304424als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 418879
HRID 418879als Produktuspto-grants-2012_01
Reaktionsgleichung von HRID 480219
HRID 480219als Eduktuspto-grants-2003_11
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Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
CAS
486-66-8
PubChem CID
5281708
DTXSID
DTXSID9022310
ChEMBL
CHEMBL8145
ChEBI
CHEBI:28197
UNII
6287WC5J2L
EC Number
207-635-4
Nikkaji
J6.014C
Brechungsindex
1.43 · 1.4300 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
10 mg/mL · DMSO: 10 mg/mL
Aggregatzustand
Powder
pka
7.01 · 7.01±0.20(Predicted)
Farbe
White to off-white
Biologische Quelle
synthetic
Wasserlöslichkeit
insoluble
Merck
14 · 14,2801
BRN
231523 · 231523
Major Application
food and beverages
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING - MISCELLANEOUS
InChI
1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
InChIKey
ZQSIJRDFPHDXIC-UHFFFAOYSA-N
SMILES
Oc1ccc(cc1)C2=COc3cc(O)ccc3C2=O
LogP
2.632 · 2.632 (est)
CAS Datenbank
486 · 486-66-8(CAS DataBase Reference)
EPA chemische Informationen
4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)- (486-66-8)
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2

VerwendenInactive analog of Genistein (Cat. #G350000). Blocks the G1 phase of the cell cycle in Swiss 3T3 cells by inhibiting casein kinase II activity1. Daidzein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv max:250 nm (log e 4.44)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EthanolDiethyletherHydrogenchlorid

Nachgelagerte Produkte

6,7,4'-Trihydroxyisoflavone4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate

Ergänzende Hinweise

DefinitionChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.