ISOBAVACHALCONE Chemical Properties

Melting point:

156.8-157.8 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))

Boiling point:

549.0±50.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in DMSO

pka

7.99±0.40(Predicted)

form 

Yellow oil.

color 

Yellow-orange

InChI

InChI=1S/C20H20O4/c1-13(2)3-9-16-19(23)12-10-17(20(16)24)18(22)11-6-14-4-7-15(21)8-5-14/h3-8,10-12,21,23-24H,9H2,1-2H3/b11-6+

InChIKey

DUWPGRAKHMEPCM-IZZDOVSWSA-N

SMILES

C(C1=CC=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1

ISOBAVACHALCONE Usage And Synthesis

Chemical Properties

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Psoralea corylifolia Linn.

Uses

Isobavachalcone is an inhibitor of platelet aggregation.

Definition

ChEBI: A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.

Biological Activity

Isobavachalcone is a chalcone isolated from multipurpose medical plant Psoralea corylifolia th at inhibits LPS-induced ICAM-1 expression and leukocyte adhesion to brain endothelial cells. It appears th at isobavachalcone modulates both MyD88-dependent and TRIF-dependent signaling of toll-like receptor 4 (TLR4). Isobavachalcone significantly inhibits both oligomerization and fibrillization of Aβ42. Isobavachalcone exhibits a wide spectrum of biological activities including antioxidative, antiplatelet, antimicrobial, anti-inflammatory, antitumor, and neuroprotective.

Synthesis

The general procedure for the synthesis of 1-(2,4-dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one from the compound (CAS: 1449202-18-9) is as follows: General method: 1. Compound 13 (100 mg, 0.22 mmol) was dissolved in methanol (2 mL) at 0 °C and 1N aqueous hydrochloric acid solution (1 mL) was slowly added. 2. The reaction mixture was heated to 50 °C and maintained at this temperature for 6 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature and the methanol was subsequently removed under vacuum. 4. The organic and aqueous layers were separated by adding ethyl acetate (10 mL) for extraction. 5. The aqueous layer was further extracted with ethyl acetate (2 x 10 mL) and all organic layers were combined. 6. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated in vacuum to obtain the crude product. 7. The crude product was purified by rapid chromatography on silica gel, the eluent was n-hexane/ethyl acetate (15:1), and the target product, bavarone (53 mg, yield 75%), was obtained as a yellow solid. Note: This method is also applicable to the preparation of Compound 1 using Compound 22 (100 mg, 0.22 mmol) as substrate under the same reaction conditions as above, resulting in Compound 1 (53 mg, 75% yield) as a yellow solid.

in vivo

References

[1] Tetrahedron Letters, 2014, vol. 55, # 4, p. 897 - 899
[2] Tetrahedron Letters, 2014, vol. 55, # 4, p. 897 - 899
[3] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 439 - 448

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