ダイゼイン

Daidzein

HCID 5281708CAS 486-66-8

基本情報

標準SMILES
O=c1c(-c2ccc(O)cc2)coc2cc(O)ccc12
InChIKey
ZQSIJRDFPHDXIC-UHFFFAOYSA-N
分子式
C15H10O4
平均分子量
254.24 g/mol
単同位体質量
254.0579088

概要

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-).

名称と識別子

優先名称
Daidzein
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
現地名
ダイゼイン
英語名
Daidzein
分子式
C15H10O4
分子量
254.24

名称と別名

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
名称をさらに表示
ダイゼインダイジェイン3-(p-ヒドロキシフェニル)-7-ヒドロキシクロモンジメチルビオカニンB4',7-ジヒドロキシイソフラボン3-(4-ヒドロキシフェニル)-7-ヒドロキシ-4H-1-ベンゾピラン-4-オンダイゼオール7-ヒドロキシ-3-(4-ヒドロキシフェニル)-4H-1-ベンゾピラン-4-オンダイドゼインdiadzein (ジアゾゼイン)7-ヒドロキシ-3-(4-ヒドロキシフェニル)-4H-クロメン-4-オン4′,7-ジヒドロキシイソフラボン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

データベース識別子

CAS
486-66-8
PubChem CID
5281708
DTXSID
DTXSID9022310
ChEMBL
CHEMBL8145
ChEBI
CHEBI:28197
UNII
6287WC5J2L
EC Number
207-635-4
Nikkaji
J6.014C

物性

構造計算による物性

XLogP
2.5
極性表面積
66.8 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
1
重原子数
19

実験および物理化学的性質

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

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]+

物理化学的性質

融点
315 · 315-323°C (dec.)
沸点
317.45 °C · 317.45°C (rough estimate)
比重(密度)
1.1629 · 1.1629 (rough estimate)
屈折率
1.43 · 1.4300 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
10 mg/mL · DMSO: 10 mg/mL

化学的性質

化学的特性Off-White Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

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%)

毒性情報

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

安全データ

wgk
3
rtecs
DJ3100040
hs_code
29329990
risk_code
36/38
hazard_code
Xi
safety_code
24-26-37/39

化学と産業

薬理情報

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

用途と製造

Uses · 1 件

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.

応用分野 · 5 件

解説ダイゼイン,イソフラボン類の一つ.マメ科Pueraria thunbergiana Benth.の根に含まれ,またGlycine hispida L.の種子では配糖体ダイジンとして存在する植物エストロゲンの一種.マメ科の植物に存在し、大豆や豆腐などの食品にも含まれる。体内で雌性ホルモンと似たはたらきをするファイトエストロゲンの一つとして知られる。無色の柱状晶.融点315~320 ℃(300 ℃ より黒変する).λmax 250 nm(log ε 4.44).水に不溶,アルコール類,アセトンに可溶.アルカリに溶けて,溶液は紫外線下で蛍光を発する.塩化鉄(Ⅲ)溶液で呈色しない.

説明Daidzein 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

来歴Daidzein 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.

使用Inactive 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)

一般的な説明Daidzein is an endocrine-active estrogenic isoflavone. This phytoestrogen is capable to bind to estrogen to exert estrogenic effects in vivo. It can naturally be found in soybean seed and flour.

サプライヤー50 社

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]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山西玉宁生物科技有限公司13623677056

補足説明

定義本品は、次の化学式で表される有機化合物である。

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

関連反応

49 件

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