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(-)-Arctigenin

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(-)-Arctigenin Basic information

Product Name:
(-)-Arctigenin
Synonyms:
  • (3R,4R)-4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-2(3H)-FURANONE
  • 2(3H)-FURANONE,4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-,(3R,4R)
  • 2(3H)-FURANONE,4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]
  • ARCTIGENIN:2(3H)-FURANONE,4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-,(3R,4R)
  • 2(3H)-Furanone,4-[(3,4-dimethoxyphenyl) methyl]
  • dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-,(3R,4R)-
  • ARCTIGENIN
  • ARCTIGENIN(P)
CAS:
7770-78-7
MF:
C21H24O6
MW:
372.41
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Inhibitors
  • Miscellaneous Natural Products
  • Protein Kinase
Mol File:
7770-78-7.mol
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(-)-Arctigenin Chemical Properties

Melting point:
98.0 to 102.0 °C
Boiling point:
567.0±45.0 °C(Predicted)
Density 
1.227±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO: 34 mg/mL with heating and sonicating, soluble
form 
solid
pka
10.03±0.20(Predicted)
color 
White to Light yellow
λmax
280nm(EtOH)(lit.)
InChI
InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
InChIKey
NQWVSMVXKMHKTF-JKSUJKDBSA-N
SMILES
O1C[C@H](CC2=CC=C(OC)C(OC)=C2)[C@@H](CC2=CC=C(O)C(OC)=C2)C1=O
LogP
2.470 (est)
CAS DataBase Reference
7770-78-7(CAS DataBase Reference)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
LY9247000
HS Code 
2932.20.4500

MSDS

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(-)-Arctigenin Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Arctium lappa, Trachelospermi chinensis, Rhizoma Cynanchum, Saussurea jellyfish and Forsythia suspensa.

Uses

Arctigenin is a plant ligan associated with anticancer and antioxidant properties.

Definition

ChEBI: (-)-Arctigenin is a lignan.

Biological Activity

Antioxidant, anti-inflammatory, antiproliferative and antiviral agent. Inhibits LPS-induced iNOS expression via inhibition of I κ B α phosphorylation and p65 nuclear translocation (IC 50 = 10 nM). Inhibits HIV-1 replication in vitro . Also potently inhibits MKK1 (IC 50 = 0.5 nM) and provides neuroprotection by binding to kainate receptors.

storage

-20°C (desiccate)

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