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521-61-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:73015 http://www.chembase.cn/molecule-73015.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem
Acid pKa 7.894089  H Acceptors
H Donor LogD (pH = 5.5) 3.9655893 
LogD (pH = 7.4) 3.8404918  Log P 3.9673254 
Molar Refractivity 76.6172 cm3 Polarizability 28.820513 Å3
Polar Surface Area 83.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Apperance
Orange/yellow expand Show data source
Yellow powder expand Show data source
Yellow Solid expand Show data source
Melting Point
202-204°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
CB6720000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
R expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... ELA2(1991) expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
≥98.0% (TLC) expand Show data source
99.0 expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C16H12O5 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2395 external link
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 external link
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 external link
Biochem/physiol Actions
Anthraquinone-derivative found in medicinal herbs.
Toronto Research Chemicals - P398000 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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