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

• ChemBase ID: 73020
• Molecular Formular: C15H8O6
• Molecular Mass: 284.22042
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid; rhein; monorhein
• Synonyms: 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; 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

Database IDs

• CAS Number: 478-43-3
• EC Number: 207-521-4
• MDL Number: MFCD00009618
• Beilstein Number: 2222155
• PubChem SID: 24856659; 162037940; 24899390
• PubChem CID: 10168
• CHEMBL: 418068
• MeSH Name: Rhein
• Wikipedia Title: Rhein_(molecule)

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): 1.1787103
• LogD (pH = 7.4): -0.26175544
• Log P: 3.2691584
• Molar Refractivity: 72.369 cm^3
• Polarizability: 26.928041 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 3.398774
• H Acceptors: 6

PROPERTIES

Physical Property

• Solubility: DMSO; Insoluble in water
• Apperance: Orange crystals; Yellowish Brown Solid
• Melting Point: >280°C (dec.); >300°C; ≥300 °C(lit.); 350–352 °C
• Boiling Point: 597.8°C at 760 mmHg
• Flash Point: 329.4°C
• Density: 1.687 g/cm^3

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: CA9516000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38; R36/R37/R38
• Safety Statements: 26-37/39; 26-37-60; S26-37/S39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: Irritant
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Inhibits interleukin-1 activity

Product Information

• Purity: ~85%; 98%
• Grade: technical; technical grade
• Salt Data: Free Base
• Biological Source: Obt. from various Cassia spp. such as senna. Also isol. from Scrophularia nodosa, Kniphofia uvaria and other plants
• Application(s): Used in treatment of arthritis
• Empirical Formula (Hill Notation): C15H8O6

DETAILS

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

Packaging
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.

REFERENCES

• 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