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Emodin-3-methyl ether

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Emodin-3-methyl ether 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:
521-61-9
MF:
C16H12O5
MW:
284.26
EINECS:
208-315-7
Product Categories:
  • Agro-Products
  • Aromatics
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • The group of Polydatin
  • Anthraquinones, Hydroquinones and Quinones
Mol File:
521-61-9.mol
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Emodin-3-methyl ether Chemical Properties

Melting point:
196-206°C
Boiling point:
560.5±50.0 °C(Predicted)
Density 
1.448±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under Inert Atmosphere
solubility 
Chloroform (Slightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
form 
Solid
pka
6.23±0.20(Predicted)
color 
Yellow to Dark Yellow to Dark Orange
BRN 
6770499
Stability:
Hygroscopic
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
SMILES
C1(O)=C2C(C(=O)C3=C(C2=O)C(O)=CC(C)=C3)=CC(OC)=C1
LogP
5.078 (est)
CAS DataBase Reference
521-61-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
CB6720000
10
HS Code 
29146990

MSDS

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Emodin-3-methyl ether Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

antibacterial, cathartic

Uses

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.

Biological Activity

Anthraquinone-derivative found in medicinal herbs.

in vivo

Physcion (20 or 40 mg/kg, p.o., once daily for 7 days) exerts neuroprotective effects by inhibiting the TLR4/NF-κB signaling pathway in an ischemia-reperfusion-induced SD rat model[3]. Physcion (4 or 9 mg/kg, p.o., once daily for 6 days) effectively alleviates infection symptoms caused by Chlamydia psittaci 6 BCE in SPF chickens[4].

Animal Model:Ischemia-reperfusion (I/R)-induced focal cerebral ischemia model in SD rats[3]
Dosage:20 or 40 mg/kg
Administration:Oral gavage (p.o.), once daily for 7 days
Result:Significantly reduced the brain water content and the NSS (Neurological Severity Score) in I/R rats, compared to I/R group. Obviously decreased areas of infarction compared to I/R group.
Animal Model:SPF chickens (21 days old) infected intra-laryngeally with Chlamydia psittaci 6 BCE[4]
Dosage:4 or 9 mg/kg
Administration:Oral gavage (p.o.), once daily for 6 days
Result:Dose-dependently alleviated respiratory distress, air sac and lung lesions, and bacterial load in the spleen in infected chickens.

IC 50

TLR4

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