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

Description

Emodin-3-methyl ether is a dihydroxyanthraquinone derivative characterized by its chemical structure, which features hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It is a yellow solid and is known for its natural occurrence in certain plants, particularly in the roots of Chinese rhubarb (Rheum officinale).

Uses

Used in Pharmaceutical Industry:
Emodin-3-methyl ether is used as an active ingredient for its antibacterial properties, playing a crucial role in the development of new drugs to combat bacterial infections. Its ability to inhibit bacterial growth makes it a valuable component in the creation of pharmaceutical products.
Used in Traditional Medicine:
Emodin-3-methyl ether is used as a cathartic, which means it promotes bowel movements and helps relieve constipation. Its natural occurrence in plants like Chinese rhubarb has made it a popular ingredient in traditional medicine for treating digestive issues.
Used in Agricultural Industry:
Emodin-3-methyl ether is used as a natural compound to control powdery mildew, a common fungal disease that affects crops like wheat. Its presence in the ethanol extract from the roots of Chinese rhubarb contributes to the plant's ability to protect itself against Blumeria graminis, the fungus responsible for powdery mildew infection.
Used in Chemical Research:
As a dihydroxyanthraquinone derivative, Emodin-3-methyl ether is also utilized in chemical research for studying the properties and potential applications of anthraquinone compounds. Its unique chemical structure allows scientists to explore its interactions with various biological systems and develop new insights into its potential uses.

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 
• 5018-84-8 emodin-6,8-di-O-methyl ether 
• 21871-90-9 physcion-10,10'-bianthrone 
• 64-19-7 acetic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 61419-07-6 (3S)-torosachrysone 
• 106-51-4 p-benzoquinone 
• 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

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 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 
• 74-88-4 methyl iodide 
• 613-12-7 2-methylanthracene 
• 23451-01-6 physcion 8-O-β-D-glucopyranoside 
• 3571-31-1 physcion-9-anthrone 

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.