기본 정보
- CAS
22888-70-6- 표준 SMILES
COc1cc([C@H]2Oc3cc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)ccc3O[C@@H]2CO)ccc1O- InChIKey
SEBFKMXJBCUCAI-HKTJVKLFSA-N- 분자식
- C25H22O10
- 평균 분자량
- 482.4 g/mol
- 단동위원소 질량
- 482.12129689
개요
Silibinin is a flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent and a plant metabolite. It is a secondary alpha-hydroxy ketone, a polyphenol, an aromatic ether, a benzodioxine and a flavonolignan.
이름 및 식별자
- 우선 이름
- Silibinin
- IUPAC
- (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
- 현지명
- 실리빈
- 영어명
- Silybin
- 분자식
- C25H22O10
- 분자량
- 482.44
이름 및 동의어
silibininSilymarin IFlavobinSilybineSilibininaSilibinineSilliverSilymarine ISilibininumLegalon(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-oneCHEBI:9144
이름 더 보기
실리빈SILYBINSILYBIN ASILYBININSilybin(Silibinin)Sylibinybin7c3mtMepasilRealsil
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-oneSilibinin a-silibinin b mixt.(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydro-4H-chromen-4-one(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-oneRefChem:1830594RKY41TBTF245-302-5(2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one
데이터베이스 식별자
물성
구조 계산 물성
- XLogP
- 2.4
- 극성 표면적
- 155 Ų
- 수소 결합 공여자 수
- 5
- 수소 결합 수용자 수
- 10
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 35
- 형식 전하
- 0
- 복잡도
- 750
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
208.16 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
213.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 164 · 164-174°C
- 끓는 점
- 793 · 793.0±60.0 °C(Predicted)
- 밀도
- 1.527 · 1.527±0.06 g/cm3(Predicted)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 아세톤(약간 용해됨), DMSO, 메타노(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 6.42 · pKa 6.42±0.04 (Uncertain)
- 색상
- 옅은 노랑
- 수용성
- 54 mg/L · 54mg/L(24.99ºC)
- Merck
- 13 · 13,8607
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 9.6% (5 of 52) of reports.
Warning
H315 (82.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory InformationChemical: 4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
Hazard Classes and CategoriesSkin Irrit. 2 (82.7%)
안전 데이터
- wgk
- 3
- rtecs
- DJ2981770
- ridadr
- 3172
- 독성
- LD50 intravenous in mouse: 1056mg/kg
- HS 번호
- 29329990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-37/39-24/25-22-36
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Metabolism/MetabolitesSilybin has known human metabolites that include O-demethylated-silybin.
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Synthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
응용 분야
개요Silybin, also known as silibinin, is the principal biologically active constituent of the silymarin complex (about 70–80%) and is a mixture of silybin A and silybin B. Pharmacological research demonstrated that silybin has shown pleiotropic biological properties, including potent antioxidant, anti-inflammatory, anticancer, antidiabetic, hepatoprotective, neuroprotective, antiviral, antimicrobial and immunosuppressive activities. Silibinin demonstrates promising anticancer effects in vitro and in vivo[1].
용도Silibinin has been used:to study its effect on gene expression levels of various proteins involved in chromatin regulations of prostate cancer, by real time polymerase chain reaction (RT-PCR)to study its effect on cell proliferation in platelet-derived growth factor (PDGF)-treated human tenon′s fibroblasts (HTFs) by investigating the expression of proliferating cell nuclear antigen (PCNA) and by water-soluble tetrazolium salt (WST-1) assayto examine its effect on gene expression levels of stromelysine 1 (STM1), acetyl hexoseamines and collagen production during skin wound healingto study its inhibitory effect on Escherichia coli ATP synthase
일반 설명Silibinin, a principal component of silymarin, is a flavonolignan and an orally active flavonoid. It is isolated from the seeds of milk thistle (Sylibum marianum L).
상·하류 제품 정보
상류 원료
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