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FRAXIN

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FRAXIN Basic information

Product Name:
FRAXIN
Synonyms:
  • Fraxetol8-glucoside
  • 7,8-Dihydroxy-6-methoxycoumarin 8-β-D-glucopyranoside
  • Fraxetin 8-β-D-glucopyranoside
  • 8-(β-D-Glucopyranosyloxy)-7-hydroxy-6-methoxycoumarin monohydrate
  • 7,8-DIHYDROXY-6-METHOXYCOUMARIN-BETA-D-GLUCOPYRANOSIDE
  • FRAXETIN-8-GLUCOSIDE
  • FRAXETIN-8-O-GLUCOSIDE
  • FRAXIN
CAS:
524-30-1
MF:
C16H18O10
MW:
370.31
EINECS:
208-355-5
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Coumarins
Mol File:
524-30-1.mol
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FRAXIN Chemical Properties

Melting point:
205-208°C
Boiling point:
420.23°C (rough estimate)
Density 
1.4066 (rough estimate)
refractive index 
1.5376 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO : 250 mg/mL (675.11 mM; Need ultrasonic)
form 
Solid
pka
6.99±0.20(Predicted)
color 
White
Major Application
food and beverages
InChI
InChI=1/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)15(11(7)20)26-16-13(22)12(21)10(19)8(5-17)24-16/h2-4,8,10,12-13,16-17,19-22H,5H2,1H3/t8-,10-,12+,13-,16+/s3
InChIKey
CRSFLLTWRCYNNX-JAAAIXMONA-N
SMILES
C12OC(=O)C=CC=1C=C(OC)C(O)=C2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O |&1:15,16,18,19,21,r|
LogP
-1.930 (est)
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Safety Information

WGK Germany 
3
RTECS 
DJ3091000
Storage Class
11 - Combustible Solids
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FRAXIN Usage And Synthesis

Chemical Properties

Slightly soluble in cold water, soluble in hot water and hot ethanol, practically insoluble in ether. Derived from the dried bark of the ash tree of the family Mulleinaceae, the pointed leaf ash or the persistent column ash

Uses

food and beverages

Definition

ChEBI: Fraxin is a beta-D-glucoside that is fraxetin attached to a beta-D-glucopyranosyl group at position 8 via a glycosidic linkage. It is a natural product isolated from the leaves of Fraxinus excelsior and exhibits potent hepatoprotective effects in vitro and in vivo. It has a role as a plant metabolite, an anti-inflammatory agent and a hepatoprotective agent. It is a beta-D-glucoside, a hydroxycoumarin and an aromatic ether. It is functionally related to a fraxetin.

Synthesis

A method for extracting high-purity Qinpi methanin and Qinpi glucoside from Qinpi, characterized in that it comprises the steps of:

(1) using methanol or water conventional method to obtain Qinpi extract containing Qinpi methylin, Qinpi glycoside and other different mass concentrations;

(2) prepare a biphasic system and separate to obtain the upper and lower phase solutions of the biphasic phase, and dissolve the Qinpi extract repeatedly with the upper phase solution until the Qinpi extract does not contain Qinpi methylin and Qinpi glucoside;

(3) after centrifugation or filtration of the above solution containing qinpi methylin and qinpi glycoside, add 1 to 3 times the amount of the above solution to the lower phase solution, full extraction, until the proportion of solid impurities in the upper phase is no longer significantly reduced, the separation of the upper phase solution obtained, concentrated to obtain the solution containing mainly qinpi methylin and qinpi glycoside;

(4) using conventional means to remove salts and fat-soluble impurity components, concentration, crystallization to obtain high-purity Qinpi methylin and Qinpi glucoside.

in vivo

Fraxin (50 mg/kg, p.o.) significantly blocks the CCl4-induced elevation of ALT and AST. Fraxin (10 and 50 mg/kg, p.o.) significantly reduces the GSSG levels (1.7±0.3 and 1.5±0.2 nM/g liver, respectively) compared with the GSSG levels of the CCl4-treated group[1].

FRAXINSupplier

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