제니스테인메틸에터

Biochanin A

HCID 5280373

기본 정보

CAS
491-80-5
표준 SMILES
COc1ccc(-c2coc3cc(O)cc(O)c3c2=O)cc1
InChIKey
WUADCCWRTIWANL-UHFFFAOYSA-N
분자식
C16H12O5
평균 분자량
284.26 g/mol
단동위원소 질량
284.06847348

개요

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-).

이름 및 식별자

우선 이름
Biochanin A
IUPAC
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
현지명
제니스테인메틸에터
영어명
5,7-Dihydrox -4'-methoxyisoflavone
분자식
C16H12O5
분자량
284.26

이름 및 동의어

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
이름 더 보기
제니스테인메틸에터BIOCHANIN 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
3
극성 표면적
76 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
5
회전 가능 결합 수
2
무거운 원자 수
21

실험 및 물리화학적 성질

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
LogP4.34
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section · 4건

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]-

물리화학적 성질

녹는점
210 · 210-213 °C(lit.)
끓는 점
340 · 340-355 °C(Press: 0.5 Torr)
밀도
1.42 · 1.420±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
10 mg/mL, · 아세톤: 10mg/mL, 투명, 갈색
물리적 상태
가루

화학적 성질

Off-White Solid

안전 및 규제

독성 정보

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

안전 데이터

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

화학 및 산업

약리 정보

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

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

용도 및 제조

General Manufacturing Information4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-: INACTIVE
응용 분야 · 3건

개요Biochanin 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).

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

일반 설명Biochanin 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.

공급사100 곳

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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