4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

• ChemBase编号: 73020
• 分子式: C15H8O6
• 平均质量: 284.22042
• 单一同位素质量: 284.03208798
• SMILES: c1ccc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)C(=O)O
• Canonical SMILES: Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1O)C(=O)O
• InChI: InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
• InChIKey: FCDLCPWAQCPTKC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC传统名: 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid; rhein; monorhein
• 别名: 1,8-二羟基-3-羧基蒽醌; 4,5-二羟基蒽醌-2-羧酸; 9,10-二氢-4,5-二羟基-9,10-二氧代-2-蒽羧酸; 大黄酸; 大黄酸; 4,5-Dihydroxy-2-anthraquinonecarboxylic Acid; Rhein; Monorhein; NSC 38629; Rheic acid; Rheinic acid; Rhubarb yellow; Rhein(Monorhein); 4,5-Dihydroxyanthraquinone-2-carboxylic acid; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid; 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid; Cassic acid; Chrysazin-3-carboxylic acid; Rhein (molecule); Rhein; 1,8-dihydroxy-3-carboxyanthraquinone; Rhein; 4,5-Dihydroxyanthraquinone-2-carboxylic acid

登记号

• CAS号: 478-43-3
• EC号: 207-521-4
• MDL号: MFCD00009618
• Beilstein号: 2222155
• PubChem SID: 24856659; 162037940; 24899390
• PubChem CID: 10168
• CHEMBL: 418068
• 医学主题词(MeSH): Rhein
• 维基百科标题: Rhein_(molecule)

理论计算性质

• 质子供体: 3
• LogD (pH = 5.5): 1.1787103
• LogD (pH = 7.4): -0.26175544
• Log P: 3.2691584
• 摩尔折射率: 72.369 cm^3
• 极化性: 26.928041 Å^3
• 极化表面积: 111.9 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true
• Acid pKa: 3.398774
• 质子受体: 6

分子性质

理化性质

• 溶解度: DMSO; Insoluble in water
• 外观: Orange crystals; Yellowish Brown Solid
• 熔点: >280°C (dec.); >300°C; ≥300 °C(lit.); 350–352 °C
• 沸点: 597.8°C at 760 mmHg
• 闪点: 329.4°C
• 密度: 1.687 g/cm^3

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: CA9516000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38; R36/R37/R38
• 安全公开号: 26-37/39; 26-37-60; S26-37/S39
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• 主要危害: Irritant
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Inhibits interleukin-1 activity

产品相关信息

• 纯度: ~85%; 98%
• 级别: technical; technical grade
• 成盐信息: Free Base
• 生物来源: Obt. from various Cassia spp. such as senna. Also isol. from Scrophularia nodosa, Kniphofia uvaria and other plants
• 应用领域: Used in treatment of arthritis
• Empirical Formula (Hill Notation): C15H8O6

详细说明

Selleck Chemicals - S2400

Research Area: Immunology
Biological Activity:
Rhein(Monorhein; NSC 38629; Rheic acid; Rheinic acid) is a constituent of rhubarb which was isolated from the fresh rhizome of Rheum coreanum Nakai. The WTK1 cells were treated by rhein of different concentrations (20, 40, 80, 120 μg/ml) and then the comet assay, in vitro micronucleus test and TK gene mutation assay were conducted simultaneously. The solvent control and positive control (mthylmethane sulfonate, MMS) groups were included in the study. Positive results were found at the concentrations of 120 μg/ml and 80 μg/ml of emodin in comet assay and tk gene mutation analysis. High dose of rhein (120 μg/ml) also showed weak mutagenicity in TK gene mutation analysis. In a study, compared with the db/db control group, the fasting glucose concentration was significantly decreased in the rhein treatment group. The first-phase insulin secretory function was impaired significantly in db/db mice, while the first-phase insulin secretory peak was obvious in the rhein treatment mice. Rhein treatment significantly improved glucose tolerance, restored the first-phase insulin secretion and protected the islets function. [1]

Sigma Aldrich - R7269

Biochem/physiol Actions
Constituent that is enriched in rhubarb with anti-inflammatory, anti-osteoarthritic, and anti-cancer activity. It reduces IL-1β production and secretion, caspase-3 activity, inducible nitric oxide synthase activity, and phosphorylation of c-Jun and c-Jun NH2-terminal kinase (JNK).

Sigma Aldrich - 275611

包装
50, 250 mg in glass bottle

Toronto Research Chemicals - R318500

Found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb) and in Senna leaves.A potential antioxidant resource: endophytic fungi from medicinal plants.

参考文献

• Du H et al. Zhongguo Zhong Yao Za Zhi. 2010 Oct;35(20):2764-7.
• Wanitschke, Pharmacology, 20, Suppl. 1, 21 (1980)
• Raimondi, L., et al.: Pharmacol. Res. Commun., 14, 103 (1980)
• Franchi-Micheli, S., et al.: J. Pharm. Pharmacol., 35, 262 (1980)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 34