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Sanguinarine

HCID 5154
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
2447-54-3
표준 SMILES
C[n+]1cc2c3c(ccc2c2ccc4cc5c(cc4c21)OCO5)OCO3
InChIKey
INVGWHRKADIJHF-UHFFFAOYSA-N
분자식
C20H14NO4+
평균 분자량
332.3 g/mol
단동위원소 질량
332.09228293

개요

Sanguinarine is a benzophenanthridine alkaloid, an alkaloid antibiotic and a botanical anti-fungal agent.

이름 및 식별자

우선 이름
Sanguinarine
IUPAC
24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
영어명
SANGUINARINE
분자식
C20H14NO4
분자량
332.33

이름 및 동의어

SANGUINARINE2447-54-3PseudochelerythrineSanguinarinSANGUINARIUMsangvinarinSanguiritrinDimethylenedioxy benzphenanthridineDTXSID0045204AV9VK043SS24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaeneDTXCID8025204
이름 더 보기
13-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-iumC06162SangrovitsanguirineFree sanguinarineSanguinarine (8CI)SANGUINARINE, 40+% BY UV
CHEBI:17183pseudo-chelerythrine24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.0^(2,10).0^(4,8).0^(14,22).0^(17,21))tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaeneRefChem:48744219-503-324-methyl-5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium

물성

구조 계산 물성

XLogP
4.4
극성 표면적
40.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
0
무거운 원자 수
25
형식 전하
1
복잡도
530

실험 및 물리화학적 성질

Melting Point266 °C
Physical DescriptionSolid
Collision Cross Section166.87 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
205 · 205-215°C
끓는 점
483.53 °C · 483.53°C (rough estimate)
밀도
1.3463 · 1.3463 (rough estimate)
굴절률
1.518 · 1.5180 (estimate)
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
클로로포름 (약간 용해됨), DMSO (약간 용해됨)
물리적 상태
고체
색상
하얀색
LogP
-0.653 · -0.653 (est)

안전 및 규제

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

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 98.1% (52 of 53) of all reports.

Not Classified

Aggregated GHS information provided per 53 reports by companies from 2 notifications to the ECHA C&L Inventory.

유해성 정보

Hazard Classes and CategoriesNot Classified

독성 정보

Toxicity Summary · 2건

Sanguinarine [13-methyl (1,3) benzodioxolo(5,6-c)-1,3-dioxolo (4,5) phenanthridinium] kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Berberine, on the other hand, has been reported to cause cytotoxicity and adversely influence the synthesis of DNA. Studies have reported various pharmacological properties of these alkaloids, e.g., they exhibit antibacterial, antiasthma, anticancer, anti-inflammatory, and antidiabetic activities.

Sanguinarine, at micromolar concentrations, imparts cell growth inhibitory response in human squamous carcinoma (A431) cells via an induction of apoptosis. This is while sanguinarine treatment did not result in apoptosis of the normal human epidermal keratinocytes at similar dose. Sanguinarine [0.1 (M-2 (M)] treatment to HaCaT cells was found to inhibit in a dose-dependent manner the cell proliferation and induce apoptosis, as measured by 3-(4,5 dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and ELISA, respectively. Sanguinarine treatment also resulted in a significant cleavage of poly(ADP-ribose) polymerase in HaCaT cells. Sanguinarine treatment to HaCaT cells resulted in a dose-dependent (a) increase in the level of Bax with a concomitant decrease in Bcl-2 levels and (b) increase in Bax/Bcl-2 ratio. Sanguinarine also resulted in significant increases in the proapoptotic members of Bcl-2 family proteins, i.e., Bak and Bid. This was accompanied by increase in (a) protein expression of cytochrome c and apoptotic protease-activating factor-1 and (b) activity and protein expression of caspase-3, caspase-7, caspase-8, and caspase-9. This indicates the involvement of mitochondrial pathway and Bcl-2 family proteins during sanguinarine-mediated apoptosis of immortalized keratinocytes. (A15415)

화학 및 산업

약리 정보

Mechanism of Action · 1건

Sanguinarine is found in traditional herbs such as Chelidonium, Corydalis, Sanguinarum, and Borovula. This publication notes that: 1) sanguinarinehas been proven to possess broad-spectrum biological activities, such as antitumor, anti-inflammatory, antiosteoporosis, neuroprotective, and antipathogenic microorganism activities, 2) the biological activities of sanguinarine and its derivatives are related mainly to the JAK/STAT, PI3K/Akt/mTOR, NF-κB, TGF-β, MAPK and Wnt/β-catenin signaling pathways, and 3) in general, sanguinarine has many pharmacological effects but that its toxicity and safety in clinical applications need to be further studied.

MeSH Pharmacological Classification · 2건

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Cellular LocationsCytoplasm

용도 및 제조

Uses · 1건

Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of <i>Argemone mexicana</i> which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. These are organic compounds containing a benzene fused to a quinoline ring system.

응용 분야 · 2건

개요A naphthoisoquinoline alkaloid, this base occurs in the roots of Chelidonium majus L., Glaucium fimbrilligerum and Sanguinaria canadensis L. The alkaloid was stated by Schmidt, Konig and Tietz to crystallize from EtOH or AcOEt as colourless needles, m.p. 213°C but this low melting point was found to be due to the presence of chelerythrine as an impurity. Once this is removed as the pseudocyanide, the base crystallizes from Et20 and has the above melting point or 242-3°C on slow heating. Obtained from EtOH it forms the alcoholate, m.p. 195-7°C. The hydrochloride forms long, slender, bloodred needles. On distillation with Zn dust, the alkaloid furnishes a-naphthaphenanthridine and the structure given above has been further confirmed by synthesis.

관련 반응

1건
반응 기록 만들기
HRID 2050476 반응식
HRID 2050476반응물로uspto-grants-1991_05

화합물 노트

불러오는 중…

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데이터베이스 식별자

CAS
2447-54-3
PubChem CID
5154
DTXSID
DTXSID0045204
ChEMBL
CHEMBL417799
ChEBI
CHEBI:17183
UNII
AV9VK043SS
EC Number
219-503-3
Nikkaji
J7.576K
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

안전 데이터

ridadr
1544
독성
LD50 oral in rat: 1660mg/kg
risk_code
25
safety_code
13-45

용도Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.

상·하류 제품 정보

상류 원료

13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine-14(13H)-one디하이드로산귀나린

공급사100 곳

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추가 설명 · 1건

정의Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).