Loliolide

Name: Loliolide
CAS#: 1133-03-5
Chemical Formula: C11H16O3
Exact Mass: 196.1099
Molecular Weight: 196.24
Elemental Analysis: C, 67.32; H, 8.22; O, 24.46

Description: Loliolide is a monoterpene lactone that has been found in P. urinaria and has diverse biological activities. It scavenges DPPH and peroxide radicals in cell-free assays when used at concentrations ranging from 62.5 to 250 µM and reduces peroxide-induced apoptosis in Vero cells. Loliolide (10 µg/ml) inhibits LPS-induced proliferation of isolated mouse T and B cells. It reduces hepatitis C virus (HCV) infectivity in Huh7.5 cells (EC50 = 2.48 µM) and inhibits HCV binding to Huh7.5 cells when used at concentrations of 10 and 50 µM. Loliolide also increases A. cephalotes preference for control flakes when applied to test flakes at a concentration of 6.8 mg/g of rye, indicating insect repellent activity.

IUPAC/Chemical Name: (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one

InChi Key: XEVQXKKKAVVSMW-WRWORJQWSA-N

InChi Code: InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1

SMILES Code: O[C@@H](CC1(C)C)C[C@](O2)(C)C1=CC2=O

Appearance: Solid powder