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AVICULARIN

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AVICULARIN Basic information

Product Name:
AVICULARIN
Synonyms:
  • AVICULARIN
  • QUERCETIN-3-ARABINOSIDE
  • Avicularoside
  • Fenicularin
  • 3-(α-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • Quercetin 3-α-L-arabinofuranoside
  • Avicularin(Quercetin 3-alpha-L-arabinofuranoside)
  • QUERCETIN-3-ARABINOSIDE hplc
CAS:
572-30-5
MF:
C20H18O11
MW:
434.35
Product Categories:
  • Flavanols
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
572-30-5.mol
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AVICULARIN Chemical Properties

Melting point:
207-208 °C
Boiling point:
855.4±65.0 °C(Predicted)
Density 
1.86±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated), Methanol (Slightly, Sonicated)
form 
Solid
pka
6.17±0.40(Predicted)
color 
Pale Yellow to Light Yellow
Stability:
Hygroscopic
InChI
InChI=1/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20?/s3
InChIKey
PZZRDJXEMZMZFD-TTYPJOBMNA-N
SMILES
C1(OC2=C(C(O)=CC(O)=C2)C(=O)C=1OC1OC[C@H](O)[C@H](O)[C@H]1O)C1C=CC(O)=C(O)C=1 |&1:17,19,21,r|
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Safety Information

WGK Germany 
3
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AVICULARIN Usage And Synthesis

Chemical Properties

Pale yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from Saururus chinensis (Lour.) Baill.

Uses

Quercetin-3-arabinoside can be used to prevent or treat degenerative brain disease.

Definition

ChEBI: A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and ital Foeniculum vulgare.

in vivo

Avicularin (injected in articular cavity of the knee, 0.5-2 mg/kg, twice a week for 4 weeks) attenuates the development of OA (osteoarthritis) in ACLT-induced rats[4].
? Avicularin (oral administration, 50 and 100 mg/kg, for 21 days) attenuates memory Impairment in rats with amyloid Beta-induced Alzheimer's disease[5].

Animal Model:ACLT (anterior cruciate ligament transection)-induced rats[4]
Dosage:0.5, 1, 2 mg/kg
Administration:Injected into the articular cavity of the right knee, twice a week for 4 weeks.
Result:Alleviated the tibial subchondral osteolysis, reduces bone loss, and increases the bone mass of tibial subchondral bone.
Attenuated ECM degradation, the loss of Aggrecan and Collagen II in ACLT-induced rats.
Decreased the MMP3 and MMP13 protein level.
Animal Model:Rats with amyloid Beta-induced Alzheimer's disease[5]
Dosage:25, 50, and 100 mg/kg
Administration:Oral administration, for 21 days
Result:Enhanced cognition activity, and reversed the effects of amyloid beta-induced inflammatory response and excessive oxidative stress.

IC 50

GLUT4; PPARγ; COX-2

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