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6-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one

HCID 14334
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Basic information

CAS
1133-03-5
Standard SMILES
CC1(C)CC(O)CC2(C)OC(=O)C=C12
InChIKey
XEVQXKKKAVVSMW-UHFFFAOYSA-N
Molecular formula
C11H16O3
Average molar mass
196.24 g/mol
Monoisotopic mass
196.10994437

Overview

6-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one is a member of benzofurans.

Names & identifiers

Preferred name
6-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one
IUPAC
6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
English name
Loliolide
Molecular weight
0

Names & synonyms

1133-03-5DTXSID109210356-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-oneRefChem:1073980DTXCID0013499366-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one61927-07-92(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-LOLIOLIDE (B712568K091)Compound NP-018553MEGxp0_000165
Show more names
orb3171479SCHEMBL12939655ACon1_001265CHEBI:181628XEVQXKKKAVVSMW-UHFFFAOYSA-NNSC289632AKOS027321437NCGC00169518-01

Database identifiers

CAS
1133-03-5、5989-02-6
PubChem CID
14334
DTXSID
DTXSID10921035
ChEBI
CHEBI:181628
Nikkaji
J2.037.923E

Properties

Computed structural properties

XLogP
1
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
14
Formal charge
0
Complexity
316

Chemistry & industry

Applications · 1 item

DescriptionLoliolide 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.

Additional notes

DefinitionChEBI: 6-Hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one is a member of benzofurans.

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