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Sanguinarine

HCID 5154
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2447-54-3
Standard SMILES
C[n+]1cc2c3c(ccc2c2ccc4cc5c(cc4c21)OCO5)OCO3
InChIKey
INVGWHRKADIJHF-UHFFFAOYSA-N
Molecular formula
C20H14NO4+
Average molar mass
332.3 g/mol
Monoisotopic mass
332.09228293

Overview

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

Names & identifiers

Preferred name
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
English name
SANGUINARINE
Molecular formula
C20H14NO4
Molecular weight
332.33

Names & synonyms

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
Show more names
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

Properties

Computed structural properties

XLogP
4.4
Topological polar surface area
40.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
25
Formal charge
1
Complexity
530

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
205 · 205-215°C
Boiling point
483.53 °C · 483.53°C (rough estimate)
Density
1.3463 · 1.3463 (rough estimate)
refractive index
1.518 · 1.5180 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), DMSO (Slightly)
form
Solid
color
White
LogP
-0.653 · -0.653 (est)
EWG's Food Scores
1 · 1

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

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.

Hazard information

Hazard Classes and CategoriesNot Classified

Toxicology

Toxicity Summary · 2 items

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)

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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 · 2 items

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

Uses & manufacturing

Uses · 1 item

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.

Applications · 3 items

DescriptionSanguinarine, a DNA intercalator extracted from the bloodroot plant of the poppy family, was used by Native Americans for warts and as a blood purifier. In modern use, although banned by the FDA for its association with epidemic dropsy and other toxic effects, it has shown potential as a treatment for cancer, with modes of action including inhibition of metastasis and angiogenesis, and promotion of apoptosis. It also has anti-inflammatory, anti-oxidant, and anti-microbial properties, and several applications in veterinary medicine.

Related reactions

1 records
New reaction record
HRID 2050476 reaction equation
HRID 2050476As reactantuspto-grants-1991_05

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
2447-54-3
PubChem CID
5154
DTXSID
DTXSID0045204
ChEMBL
CHEMBL417799
ChEBI
CHEBI:17183
UNII
AV9VK043SS
EC Number
219-503-3
Nikkaji
J7.576K
FDA UNII
9 VK043SS · AV9VK043SS
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
280 · P280-P305+P351+P338
Risk Statements
25 · 25
Safety Statements
13 · 13-45
RIDADR
1544 · 1544
Toxicity
50 oral · LD50 oral in rat: 1660mg/kg
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
1544
Toxicity
LD50 oral in rat: 1660mg/kg
risk_code
25
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
13-45
Hazard statements
H302
Precautionary statements
P280-P305+P351+P338

DescriptionA 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.

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

Upstream & downstream products

Upstream raw materials

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

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
山西玉宁生物科技有限公司13623677056 · [email protected]
南京济宇生物科技有限公司17712667785 18068059186 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
成都川研医工生物科技有限公司18280298385;18280298385 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
长沙上禾生物科技有限公司0731-84213302 18975842720 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
上海遐瑞医药科技有限公司+86 21 61551611
苏州润新生物科技有限公司0512-62956991 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
北京汤普森生物科技有限公司+86-13439059536 +86-15201677815 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海兴鲁化工科技有限公司02120970332 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Lifome Technologies LLC+1 347 9183313 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
BOC Sciences16314854226 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
Additional notes · 1 item

DefinitionSanguinarine 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).