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

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

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

• 3571-31-1 physcion-9-anthrone 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 21871-90-9 physcion-10,10'-bianthrone 
• 62993-89-9 2-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione 
• 90857-62-8 ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane 
• 107953-76-4 1,3,4-trimethoxy-1-trimethylsilyloxy-1,3-butadiene 
• 14787-38-3 7-methyljuglone 
• 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 
• 64-19-7 acetic acid 
• 84268-38-2 physcion 8-β-D-gentiobioside 

Downstream Products

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 74-88-4 methyl iodide 
• 1332889-19-6 2,4-dichlorophyscion 
• 2026-19-9 fragilin 
• 25672-77-9 4-chlorophyscion 
• 25672-66-6 4,5-dichlorophyscion 
• 25672-68-8 2,4,5-trichlorophyscion 
• 26296-54-8 physcion-8-O-β-D-glucopyranoside 
• 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.

Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents

Twenty-six emodin derivatives (17 novel) which attach quaternary ammonium salt were synthesized and evaluated for their anticancer activities in vitro and in vivo. Compounds 11g + 12g and 11h + 12h had more significant antiproliferative ability against three cancer cell lines and low cytotoxicity to HELF. 11g + 12g and 11h + 12h induced AGS cell apoptosis and arrested cell cycle at the G0/G1 phase in a dose-dependent manner. Furthermore, the activities of the caspase-3, -9 enzymes were increased in the treated cells. In vivo studies revealed that compounds 11g + 12g and 11h + 12h showed significant anti-tumor activity compared with controlled group.

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.

4-AMINOPHYSCION, AN ANTHRAQUINONE DERIVATIVE FROM DERMOCYBE (AGARICALES)

The anthraquinones physcion, erythroglaucin and 4-aminophyscion (4-amino-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone) have been isolated from the fungal species Dermocybe canaria Horak (ined.). 4-Aminophyscion is reported for the first time as a natural product and represents the first fungal anthraquinone with an amino group. - Key Word Index: Dermocybe; Cortinariaceae; anthraquinones; erythroglaucin; physcion; 4-aminophyscion (4-amino-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone).

Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cells were evaluated. A structure-activity relationship (SAR) study indicated that the hydroxyl groups and the methyl group in the emodin skeleton were crucial for anti-MRSA activity. Furthermore, the presence of an iodine atom or ethylamino group on the aromatic ring enhanced the anti-MRSA activity with higher selectivity indices, while derivatives containing bromine, chlorine atoms or quaternary ammonium salt were as active as emodin. The quaternary ammonium group on the aromatic ring also led to non-cytotoxicity against Vero cells.

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.

In vitro formation of the anthranoid scaffold by cell-free extracts from yeast-extract-treated Cassia bicapsularis cell cultures

The anthranoid skeleton is believed to be formed by octaketide synthase (OKS), a member of the type III polyketide synthase (PKS) superfamily. Recombinant OKSs catalyze stepwise condensation of eight acetyl units to form a linear octaketide intermediate which, however, is incorrectly folded and cyclized to give the shunt products SEK4 and SEK4b. Here we report in vitro formation of the anthranoid scaffold by cell-free extracts from yeast-extract-treated Cassia bicapsularis cell cultures. Unlike field- and in vitro-grown shoots which accumulate anthraquinones, cell cultures mainly contained tetrahydroanthracenes, formation of which was increased 2.5-fold by the addition of yeast extract. The elicitor-stimulated accumulation of tetrahydroanthracenes was preceded by an approx. 35-fold increase in OKS activity. Incubation of cell-free extracts from yeast-extract-treated cell cultures with acetyl-CoA and [2-14C]malonyl-CoA led to formation of torosachrysone (tetrahydroanthracene) and emodin anthrone, beside two yet unidentified products. No product formation occurred in the absence of acetyl-CoA as starter substrate. To confirm the identities of the enzymatic products, cell-free extracts were incubated with acetyl-CoA and [U- 13C3]malonyl-CoA and 13C incorporation was analyzed by ESI-MS/MS. Detection of anthranoid biosynthesis in cell-free extracts indicates in vitro cooperation of OKS with a yet unidentified factor or enzyme for octaketide cyclization.

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.

A new anthraquinone glycoside from the roots of plumbago zeylanica

Isolation of a new anthraquinone, 1-hydroxy-3-methyl-6-methoxyanthraquinone-8-O-β-D-xylopyrano side 1 along with naphthoquinones, droserone 2 and zeylanone 3 is reported from roots of the Plumbago zeylanica. Structures of the compounds have been elucidated by spectroscopic and chemical studies.