1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

• ChemBase编号: 73025
• 分子式: C15H10O4
• 平均质量: 254.2375
• 单一同位素质量: 254.0579088
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(cc(c1)C)O)O
• Canonical SMILES: Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
• InChIKey: LQGUBLBATBMXHT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
• IUPAC传统名: turkey rhubarb; 1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
• 别名: Chrysophanol; NSC 37132; NSC 646567; Chrysophanic acid; Chrysophanic acid; 1,8-Dihydroxy-3-methylanthraquinone; 1,8-Dihydroxy-3-methyl-9,10-anthracenedione; 1,8-Dihydroxy-3-methylanthraquinone; 3-Methylchrysazin; Rheic acid; Archinin; Rumicin; Chrysophanol

登记号

• CAS号: 481-74-3
• EC号: 207-572-2
• MDL号: MFCD00001208
• Beilstein号: 1252300
• PubChem SID: 24853726; 162037945
• PubChem CID: 10208

理论计算性质

• Acid pKa: 7.9404755
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.1234355
• LogD (pH = 7.4): 4.0098643
• Log P: 4.1249967
• 摩尔折射率: 70.154 cm^3
• 极化性: 26.28563 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Yellow powder

安全信息

• 保存条件: -20°C
• RTECS编号: CB6725000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: EGFR(HER) / mTOR
• 相关基因信息: human ... ELA2(1991)
• 生物活性机理: Inhibitor of phosphoinositide- 3-kinase (PI3K)/AKT; Monoamine oxidase inhibitor

产品相关信息

• 纯度: 98%
• 成盐信息: Free Base
• 生物来源: Constit. of Cassia, Rumex, Rheum, Asphodelus and Muehlenbeckia spp., etc. Also isol. from Monilinia fructicola. V. widely distributed
• 应用领域: Antimicrobial; Cathartic agent
• Empirical Formula (Hill Notation): C15H10O4

详细说明

MP Biomedicals - 05203909

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2406

Research Area: Cancer
Biological Activity:
Chrysophanic acid (Chrysophanol) is a EGFR/mTOR pathway inhibitor. Chrysophanic acid (Chrysophanol) is a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid (Chrysophanol) preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid (Chrysophanol) treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µM) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. [1]References on Chrysophanic acid (Chrysophanol)[1] Phytother. Res, 2010,

Sigma Aldrich - 229075

包装
1 g in glass bottle
50 mg in glass bottle
Application
Chrysophanic acid, a natural anthraquinone, is used to study anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells 1. It is also used to study the inhibition of replication of poliovirus types 2 and 3 (Picornaviridae) in vitro 2.
Biochem/physiol Actions
Anticancer activity for chrysophanic acid is via the EGFR/mTOR mediated signaling transduction pathway 1. Chrysophanic acid has two hydrophobic positions on the molecule (C-6 and the methyl group attached to C-3) which are responsible for the compound′s activity against poliovirus 2.

Toronto Research Chemicals - C432675

A topical ointment used in the treatment of dermal conditions such as eczema and herpes.

参考文献

• Lee MS et al. Phytother Res. 2010 Nov 19. doi: 10.1002/ptr.3323.
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