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아이소람네틴

3-Methylquercetin

HCID 5281654
노트반응

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기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
480-19-3
표준 SMILES
COc1cc(-c2oc3cc(O)cc(O)c3c(=O)c2O)ccc1O
InChIKey
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
분자식
C16H12O7
평균 분자량
316.265 g/mol
단동위원소 질량
316.05830272

이름 및 식별자

우선 이름
3-Methylquercetin
IUPAC
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
현지명
아이소람네틴
영어명
Isorhamnetin
분자식
C16H12O7
분자량
316.26

이름 및 동의어

아이소람네틴QUERCETIN-3-METHYLETHERsorhamnetin3-METHYLQUERCETINISOHAMNETINisorhamnetol3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-onec.i.75680IsorhanetinISORHAMNETIN

데이터베이스 식별자

CAS
480-19-3
PubChem CID
5281654
DTXSID
DTXSID10197379
ChEMBL
CHEMBL379064
ChEBI
CHEBI:6052
UNII
07X3IB4R4Z
EC Number
207-545-5
Nikkaji
J1.543A

물성

물리화학적 성질

녹는점
307 °C · 307°C
끓는 점
599.4 · 599.4±50.0 °C(Predicted)
밀도
1.634 · 1.634±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
10 mg/ml; · DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
산도 계수 (pKa)
6.31 · 6.31±0.40(Predicted)
물리적 상태
Solid
색상
Light yellow to Amber to Dark green
BRN
44723 · 44723
안정성
흡습성
주요 응용
대사체학비타민, 기능성 식품 및 천연 제품
화장품 원료 기능
피부 보호
InChI
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChIKey
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
SMILES
C1(C2=CC=C(O)C(OC)=C2)OC2=CC(O)=CC(O)=C2C(=O)C=1O
LogP
1.76 · 1.760 (est)

화학적 성질

Beige to lighet yellow powder

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
rtecs
LK9275450
HS 번호
29329990
risk_code
36/37/38-40
hazard_code
Xi,Xn
safety_code
22-36-26-36/37
스토리지 클래스
11 - Combustible Solids

화학 및 산업

응용 분야 · 2건

용도Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.

일반 설명Isorhamnetin is one of the important flavanols found in G.biloba leaf extracts. Isorhamnetin is also found in parsley, and thereby it is a common dietary flavonoid as the metabolite of quercetin.Generally, it is well known as antagonist of peroxisome proliferator-activated receptor Y (PPARy), which inhibits adipocyte differentiation induced by the PPARy agonist rosiglitazone. Isorhamnetin is a naturally occurring compound in fruits and vegetables; recent study showed that isorhamnetin could significantly inhibit the invasion of MDA-MB-231 cells by downregulating matrix metalloproteinases(MMP-2 and MMP-9) through inhibiting p38 MAPK and STAT3. Similar results were also obtained in another study, which showed that isorhamnetin inhibited cell proliferation and led to apoptosis. In addition, isorhamnetin was found effective on Akt/mTOR/MAPKs signaling axis. It was established that isorhamnetin-induced autophagy can be reversed by the co-treatment of 3-methyl-adenine in lung cancer cells. The results indicated that isorhamnetin exerts antitumor effect in breast cancer through targeting multiple molecular targets.

상·하류 제품 정보

상류 원료

2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-, (2E)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethanone바닐린

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추가 설명 · 1건

정의ChEBI: Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It derives from a quercetin. It is a conjugate acid of an isorhamnetin(1-).