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塩化サングイナリウム

Sanguinarine chloride

HCID 68635
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1099738-80-3
標準SMILES
C[n+]1cc2c3c(ccc2c2ccc4cc5c(cc4c21)OCO5)OCO3.[Cl-]
InChIKey
GIZKAXHWLRYMLE-UHFFFAOYSA-M
分子式
C20H14NO4.Cl
平均分子量
367.8 g/mol
単同位体質量
367.0611356

概要

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. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. 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. Epidemic dropsy is a disease that results from ingesting sanguinarine. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (A3208, A3209, A3208, A3208, A3208).

名称と識別子

優先名称
Sanguinarine chloride
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 chloride
現地名
塩化サングイナリウム
英語名
SANGUINARINE CHLORIDE
分子式
C20H14ClNO4
分子量
367.78

名称と別名

SANGUINARINE CHLORIDERefChem:884540621-641-85578-73-4Sanguinarium ChlorideSanguinarine hydrochlorideViadentSanguinarine chloride hydrateSanguinarine (chloride)MFCD0001212613-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)
名称をさらに表示
塩化サングイナリウムサンギナリンクロリド塩化サングイナリンサングイナリウムクロリドサンギナリン・クロリド13-メチル[1,3]ベンゾジオキソロ[5,6-c]-1,3-ジオキソロ[4,5-i]フェナントリジン-13-イウム・クロリドサンギナリウムクロリド塩化サンギナリンSanguinariumSANGUINARINE HCLSANGUINARINE(SH)PSEUDOCHELERYTHRINESPECIOCILIATINE(SH)sanguinariumchlorideSANGUINARINE HCl hplcSanguinarine Choloride
CHEMBL490129B8Z8J4400HPseudochelerythrine chloride;Sanguinarium chloride(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-, chloride13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i] phenanthridinium chloride24-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;chlorideSanguinarine, chlorideSanguinarium chloride [USAN:INN]

物性

構造計算による物性

極性表面積
40.8 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
0
重原子数
26
形式電荷
0
複雑度
530

物理化学的性質

融点
281 · 281-285°C
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
20 mg/mL、透明、オレンジ · メタノール: 20 mg/mL、透明、オレンジ
外見
オレンジ色の固体。
色
オレンジからダークオレンジ
水溶解度
2 O: · H2O: slightly soluble methanol: 3.8mg/mL
安定性
吸湿性、光感受性
InChI
InChI=1S/C20H14NO4.ClH/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21;/h2-8H,9-10H2,1H3;1H/q+1;/p-1
InChIKey
GIZKAXHWLRYMLE-UHFFFAOYSA-M
SMILES
C12[N+](C)=CC3=C4OCOC4=CC=C3C1=CC=C1C=C3OCOC3=CC=21.[Cl-]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory InformationChemical: [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-, chloride
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and Categories · 2 件

Acute Tox. 4 (97.6%)

Acute Tox. 4 (100%)

毒性情報

Toxicity Summary · 1 件

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)

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

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).

用途と製造

Uses · 1 件

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.

応用分野 · 2 件

使用Sanguinarine chloride hydrate was tested for anti-schistosomal activities against Schistosoma mansoni.9 It was tested for anti-lipase activity against Candida rugosa lipase.10

一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

上流・下流製品情報

下流製品

13-メチル[1,3]ベンゾジオキソロ[5,6-c]-1,3-ジオキソロ[4,5-i]フェナントリジン-14(13H)-オン

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
1099738-80-3、5578-73-4
PubChem CID
68635
DTXSID
DTXSID30971158
ChEMBL
CHEMBL490129
UNII
B8Z8J4400H
EC Number
621-641-8、835-522-5
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
10
wgk
3
rtecs
VP5220000
hs_code
29399990
risk_code
22
hazard_code
Xn
safety_code
36-26
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids

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