521-61-9

Basic information

• Product Name: Emodin-3-methyl ether
• Synonyms: 3-methoxy-6-methyl-;1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone;EMODIN-3-METHYLETHER(RG)(CALL);1,8-Dihydroxy-3-Methoxy-6-Methyl-;Rheochrysidin (Physcione);MethyleModin;Physcic acid;Przewalskinone B
• CAS NO: 521-61-9
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 208-315-7
• Product Categories: Agro-Products;Aromatics;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Anthraquinones, Hydroquinones and Quinones;The group of Polydatin
• Mol File: 521-61-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 196-206°C
• Boiling Point: 560.5 °C at 760 mmHg
• Flash Point: 215.4 °C
• Appearance: white powder
• Density: 1.448 g/cm³
• Vapor Pressure: 3.6E-13mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Sligh
• PKA: 6.23±0.20(Predicted)
• BRN: 6770499
• CAS DataBase Reference: Emodin-3-methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Emodin-3-methyl ether(521-61-9)
• EPA Substance Registry System: Emodin-3-methyl ether(521-61-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: CB6720000
• F: 10
• Hazardous Substances Data: 521-61-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 521-61-9 differently. You can refer to the following data:
1. antibacterial, cathartic
2. 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.

Definition

ChEBI: A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6.

InChI:InChI=1/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

Upstream product

• 186581-53-3 diazomethane 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 3571-31-1 physcion-9-anthrone 
• 74-88-4 methyl iodide 
• 65120-69-6 3-chloro-5-hydroxy-7-methoxy-1,4-naphthoquinone 
• 76927-59-8 (E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane 
• 21871-90-9 physcion-10,10'-bianthrone 
• 106-51-4 p-benzoquinone 
• 61419-07-6 (3S)-torosachrysone 
• 76695-89-1 7-Methyl-5-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 
• 76695-92-6 5-Hydroxy-7-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 
• 94356-13-5 torosachrysone 8-β-D-gentiobioside 
• 139565-29-0 8-Hydroxy-1,11-dimethoxy-6-methyl-1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone 
• 139565-30-3 1,4-dihydro-1,3-dimethoxy-8-hydroxy-6-methyl-1,4-ethano-9,10-anthraquinone 

Downstream Products

• 3571-31-1 physcion-9-anthrone 
• 23451-01-6 physcion 8-O-β-D-glucopyranoside 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 613-12-7 2-methylanthracene 
• 74-88-4 methyl iodide 
• 26296-54-8 physcion-8-O-β-D-glucopyranoside 
• 2026-19-9 fragilin 
• 25672-77-9 4-chlorophyscion 
• 1332889-19-6 2,4-dichlorophyscion 
• 25672-66-6 4,5-dichlorophyscion 
• 25672-68-8 2,4,5-trichlorophyscion 

Relevant articles and documents

REVISION OF THE STRUCTURE OF PRZEWALSKINONE B

Biosynthetic considerations suggested that the recently assigned structure (1) of Przewalskinone B was incorrect.Synthetic studies support the revision of the structure of przewalskinone B to 3.

Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones

Seven hydroxyanthraquinone derivatives, 1-7, were isolated from the root of Rheum palmatum (Polygonaceae). Two propionated anthraquinone derivatives, 8 and 9, were synthesized. Four hydroxynaphthoquinone derivatives, 13, 14, 16 and 21, were isolated from the root of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) and also three naphthoquinone derivatives, 19, 22 and 23, were isolated from the root of Macrotomia euchroma (Royle) Pauls. (Boraginaceae). The cytotoxicity of the anthraquinone and naphthoquinone derivatives on P-gp-underexpressing HCT 116 cells and P-gp-overexpressing Hep G2 cells was examined by MTT assay. Among the anthraquinone derivatives, compounds 3-5 which had OH, CH2OH and COOH substituent groups on the anthraquinone skeletons, respectively, showed potent growth inhibitory activities against both types of cancer cells (IC50 values: 5.7 ± 0.9 to 13.0 ± 0.7 μM in the case of HCT 116 cells and 5.2 ± 0.7 to 12.3 ± 0.9 μM in the case of Hep G2 cells). All hydroxynaphthoquinone derivatives isolated in this study exhibited extremely potent growth inhibitory activities against both types of cancer cells (IC50 values: 0.3 ± 0.09 to 0.46 ± 1.0 μM in the case of HCT 116 cells and 0.22 ± 0.03 to 0.59 ± 0.06 μM in the case of Hep G2 cells) as well as shikonin 10 (IC50 values: 0.32 ± 0.02 μM in the case of HCT 116 cells and 0.24 ± 0.03 μM in the case of Hep G2 cells).

PHYSCION-8-O-GENTIOBIOSIDE FROM RHAMNUS VIRGATA

A new anthraquinone diglucoside isolated from rhamnus virgata has been shown to be physcion-8-O-b-gentiobioside on the basis of spectral and othe evidence.Key words: Rhamnus virgata; Rhamnaceae; physcion; physcion-8-O-gentiobioside; anthraquinone.

Modulation of ROS production in photodynamic therapy using a pH controlled photoinduced electron transfer (PET) based sensitiser

A new sensitiser (4) for use in photodynamic therapy (PDT) has been developed to enable control of ROS production as a function of pH. This pH dependent PDT behaviour was tested in HeLa cells and in SCID mice bearing human xenograft pancreatic cancer (BxPC-3) tumours.

Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS

A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C18 AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as ω-hydroxyemodin, 3-O-methyl-ω-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol.