3-(4-ヒドロキシフェニル)-6-メトキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン

Glycitein

HCID 5317750CAS 40957-83-3
部分構造検索類似構造を探す

基本情報

標準SMILES
COc1cc2c(=O)c(-c3ccc(O)cc3)coc2cc1O
InChIKey
DXYUAIFZCFRPTH-UHFFFAOYSA-N
分子式
C16H12O5
平均分子量
284.26 g/mol
単同位体質量
284.06847348

概要

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.

名称と識別子

優先名称
Glycitein
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
現地名
3-(4-ヒドロキシフェニル)-6-メトキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン
英語名
Glycitein
分子式
C16H12O5
分子量
284.26

名称と別名

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
名称をさらに表示
3-(4-ヒドロキシフェニル)-6-メトキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン7-ヒドロキシ-3-(4-ヒドロキシフェニル)-6-メトキシ-4H-1-ベンゾピラン-4-オングリシテイン4',7-ジヒドロキシ-6-メトキシイソフラボングリシテイン, 大豆由来3-(3,4-ジヒドロキシフェニル)-6-メトキシ-7-ヒドロキシ-4H-1-ベンゾピラン-4-オン3-(3,4-ジヒドロキシフェニル)-7-ヒドロキシ-6-メトキシ-4H-クロメン-4-オングリセテイン7-ヒドロキシ-3-(4-ヒドロキシフェニル)-6-メトキシ-4H-クロメン-4-オン4′,7-ジヒドロキシ-6-メトキシイソフラボン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

データベース識別子

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

物性

構造計算による物性

XLogP
2.4
極性表面積
76 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
2
重原子数
21

実験および物理化学的性質

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

物理化学的性質

融点
300 °C · >300°C
沸点
547.4 · 547.4±50.0 °C(Predicted)
比重(密度)
1.42 · 1.420±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
水性ベース（わずかに）、DMSO（わずかに）
酸解離定数(Pka)
7.03 · 7.03±0.20(Predicted)

化学的性質

化学的特性Pale Orange Solid

安全と法規制

危険有害性情報

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.

安全データ

wgk
3
hs_code
29329990
hazard_code
Xi
safety_code
24/25
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

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
応用分野 · 4 件

用途薬理研究用。

説明Glycitein 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.

使用Glycitein 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).

一般的な説明Glycitein is an isoflavone found in soy food products.

上流・下流製品情報

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]
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]

補足説明

定義ChEBI: 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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