3-(p-メトキシフェニル)-5,7-ジヒドロキシクロモン

Biochanin A

HCID 5280373
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基本情報

CAS
491-80-5
標準SMILES
COc1ccc(-c2coc3cc(O)cc(O)c3c2=O)cc1
InChIKey
WUADCCWRTIWANL-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

Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a plant metabolite and a phytoestrogen. It is a member of 4'-methoxyisoflavones and a member of 7-hydroxyisoflavones. It is a conjugate acid of a biochanin A(1-).

名称と識別子

優先名称
Biochanin A
IUPAC
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
現地名
3-(p-メトキシフェニル)-5,7-ジヒドロキシクロモン
英語名
5,7-Dihydrox -4'-methoxyisoflavone
分子式
C16H12O5
分子量
284.26

名称と別名

biochanin A491-80-5Biochanin5,7-Dihydroxy-4'-methoxyisoflavone4'-Methylgenistein5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-oneolmelin5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-onePratensolBiochanine AGenistein 4-methyl etherBiochanin-A
名称をさらに表示
3-(4-メトキシフェニル)-5,7-ジヒドロキシ-4H-1-ベンゾピラン-4-オンビオカニンA4'-メチルゲニステイン4'-メトキシ-5,7-ジヒドロキシイソフラボン5,7-ジヒドロキシ-3-(4-メトキシフェニル)-4H-1-ベンゾピラン-4-オン5,7-ジヒドロキシ-4'-メトキシイソフラボン3-(p-メトキシフェニル)-5,7-ジヒドロキシクロモンゲニステイン4'-メチルエーテル5,7-ジヒドロキシ-4′-メトキシイソフラボン5，7-ジヒドロキシ-3-（4-メトキシフェニル）-4H-クロメン-4-オンバイオカニンAビオカニン AバイオカニンA (AHP VERIFIED)4′-メチルゲニステイン4′-メトキシ-5,7-ジヒドロキシイソフラボンビオカニンゲニステイン4′-メチルエーテルゲニステインメチルエーテルBIOCHANIN A (AHP)Bilchanin ABiochani,Olmelin
DTXSID10223945,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-oneNSC123538NSC-123538CHEBI:17574U13J6U390T5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-oneDTXCID102394

データベース識別子

CAS
491-80-5
PubChem CID
5280373
DTXSID
DTXSID1022394
ChEMBL
CHEMBL131921
ChEBI
CHEBI:17574
UNII
U13J6U390T
EC Number
207-744-7
Nikkaji
J11.761G

物性

構造計算による物性

XLogP
3
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]
LogP4.34
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section · 4 件

168.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1022394]

160.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

169.8 Ų [M-H]-

物理化学的性質

融点
210 · 210-213 °C(lit.)
沸点
340 · 340-355 °C(Press: 0.5 Torr)
比重(密度)
1.42 · 1.420±0.06 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
10 mg/mL、透明、茶色 · アセトン: 10 mg/mL、透明、茶色
外見
粉

化学的性質

化学的特性Off-White Solid

安全と法規制

毒性情報

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

安全データ

F
10
wgk
3
tsca
TSCA listed
rtecs
DJ3002500
hs_code
29329990
safety_code
22-24/25

化学と産業

薬理情報

Metabolism/MetabolitesBiochanin a has known human metabolites that include Genistein.
MeSH Pharmacological Classification · 2 件

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.

Cellular LocationsMembrane

用途と製造

General Manufacturing Information4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-: INACTIVE
応用分野 · 3 件

説明Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 μM).

使用An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

一般的な説明Biochanin A (BCA) is synthesized in vitro from phloroglucinol. A series of steps involving FriedelCrafts reaction results in an intermediate product 1-(2,4,6-trihydroxyphenyl)-2-(4 methoxyphenyl) ethanone, which post cyclization leads to BCA. It is catabolized to isoflavone genistein post ingestion.

上流・下流製品情報

サプライヤー100 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

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