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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 424
실험 및 물리화학적 성질
Collision Cross Section
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
- 산도 계수 (pKa)
- 6.5 · 6.50±0.20(Predicted)
- 색상
- 미색부터 베이지까지
- 수용성
- 물(25°C에서 <1mg/ml), 클로로포름, 메탄올, DMSO(25°C에서 57mg/ml) 및 에탄올(25°C에서 9mg/ml)에 용해됩니다.
- BRN
- 278107 · 278107
- 주요 응용
- 음식 및 음료
- 화장품 원료 기능
- 보습제피부 보호피부 컨디셔닝
- InChI
- InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
- InChIKey
- WUADCCWRTIWANL-UHFFFAOYSA-N
- SMILES
- C1OC2=CC(O)=CC(O)=C2C(=O)C=1C1=CC=C(OC)C=C1
- LogP
- 3.341 · 3.341 (est)
- EPA
- 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- (491-80-5)
화학적 성질
Off-White Solid
안전 및 규제
독성 정보
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DJ3002500
- HS 번호
- 29329990
- safety_code
- 22-24/25
- F 고인화성물질
- 10
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
MeSH Pharmacological Classification
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.
용도 및 제조
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사100 곳
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