1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 73015
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: c1(cc(c2c(c1)C(=O)c1c(C2=O)c(cc(c1)OC)O)O)C
• Canonical SMILES: COc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C
• InChI: InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3
• InChIKey: FFWOKTFYGVYKIR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione
• IUPAC Systematic name: 1,8-dihydroxy-3-methoxy-6-methylanthraquinone
• IUPAC Traditional name: physcion
• Synonyms: 1,8-Dihydroxy-3-methoxy-6-methylanthraquinone; Emodin-3-methyl ether; Physcion; Physcion; Physcione; Parietin; Emodin 3-methyl ether; Rheochrysidin; 1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione; 6-Methoxychrysophanic Acid; 1,8-Dihydroxy-3-methyl-6-methoxyanthraquinone; 6-O-Methylemodin; Emodin 3-Methyl Ether; NSC 251670; Parietin; Rheochrysidin; Physcion; Physcion(e); rheochrysidi); methoxyemodin; Parietin

Database IDs

• CAS Number: 521-61-9
• EC Number: 208-315-7
• MDL Number: MFCD00017374
• Beilstein Number: 6770499
• PubChem SID: 24850704; 162037935
• PubChem CID: 10639
• Wikipedia Title: Parietin

CALCULATED PROPERTIES

• Acid pKa: 7.894089
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.9655893
• LogD (pH = 7.4): 3.8404918
• Log P: 3.9673254
• Molar Refractivity: 76.6172 cm^3
• Polarizability: 28.820513 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Orange/yellow; Yellow powder; Yellow Solid
• Melting Point: 202-204°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS: CB6720000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; R
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ELA2(1991)

Product Information

• Purity: ≥98.0% (HPLC); ≥98.0% (TLC); 99.0
• Grade: analytical standard
• Salt Data: Free Base
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C16H12O5

DETAILS

Selleck Chemicals - S2395

Research Area: Inflammation
Biological Activity:
Rheochrysidin (Physcion; physcione; parietin) is one of the major components of Da-Cheng-Qi decoction used in the treatment of inflammation. A liquid chromatography tandem mass spectrometry (LC-MS/MS) method was developed for the simultaneous determination of the 10 major components of Da-Cheng-Qi decoction (rhein, emodin, aloe-emodin, chrysophanol, rheochrysidin, naringin, naringenin, hesperidin, magnolol and honokiol) in dog plasma. Plasma samples were spiked with internal standard (ibuprofen), acidified with HCl and extracted twice by liquid-liquid extraction using ethyl acetate. The linear range of the calibration curves was 5000-19.53 ng/mL for rhein; 400-3.13 ng/mL for emodin; 800-3.13 ng/mL for aloe-emodin, chrysophanol, naringin, naringenin, hesperidin, magnolol and honokiol; 160-0.63 ng/mL for rheochrysidin. The lower limit of quantification was: 19.53 ng/mL for rhein; 3.13 ng/mL for emodin, aloe-emodin, chrysophanol, naringin, naringenin, hesperidin, magnolol and honokiol; 0.6 3 ng/mL for rheochrysidin (Physcio; physcione; parietin). [1][2]

Sigma Aldrich - 17797

Biochem/physiol Actions
Anthraquinone-derivative found in medicinal herbs.
Application
Physcion can be used to study antibiotics, antifungals, bioactive small molecules and cell biology. Physcion has been used in a study to test the cytotoxicity of juglanthraquinone C on human cancer cells. Physcion has also been used in a study that investigated the metabolic regulatory effects of Rheum undulatum in a high-fat diet model.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17797.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 93893

Biochem/physiol Actions
Anthraquinone-derivative found in medicinal herbs.

Toronto Research Chemicals - P398000

A natural anthraquinone derivative, on the infection process of Blumeria graminis on wheat. Physcion is one of the important active ingredients of ethanol extract from the roots of Chinese rhubarb (Rheum officinale) for controlling powdery mildew.

REFERENCES

• Gong HL et al. World J Gastroenterol. 2009 Dec 21;15(47):5992-9.
• Thiericke, R., et al.: Nat. Prod. Rep.,10, 265 (1993)
• Lin, C., et al.: J. Nat. Prod., 58, 1934 (1993)
• Julia, S., et al.: J. Biotechnol., 124, 690 (1993)
• Wang, W., et al.: J. Antibiot., 60, 603 (1993)