Loliolide

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Basic information

CAS: 5989-02-6
Standard SMILES: CC1(C)C[C@H](O)C[C@@]2(C)OC(=O)C=C12
InChIKey: XEVQXKKKAVVSMW-WRWORJQWSA-N
Molecular formula: C11H16O3
Average molar mass: 196.24 g/mol
Monoisotopic mass: 196.10994437

Overview

Loliolide is a member of benzofurans. It has a role as a metabolite.

Names & identifiers

Preferred name: Loliolide
IUPAC: (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
English name: loliolide
Molecular formula: C11H16O3
Molecular weight: 196.24

Names & synonyms

LOLIOLIDE5989-02-6calendinU3BB4IM281DTXSID501019112(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactoneNSC-2896322(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-RefChem:41679DTXCID801477117Loliolid

Show more names

CaulilideDiruprideNSC 289632loliolide (calendin)1,3-dihydroxy-3,5,5-trimethylcyclohexylidene-4-aceticacidlactone5,6,7,7a-Tetrahydro-6α-hydroxy-4,4,7aα-trimethylbenzofuran-2(4H)-one5,6,7,7a-Tetrahydro-4,4,7aα-trimethyl-6α-hydroxybenzofuran-2(4H)-one

(-)-loliolideCHEBI:69774(6S,7aR)-5,6,7,7a-Tetrahydro-6-hydroxy-4,4,7a-trimethyl-2(4H)-benzofuranoneDigiprolactone(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one(3S,5R)-LoliolideLOLIOLIDE (B712568K091)XEVQXKKKAVVSMW-WRWORJQWSA-N

Database identifiers

CAS: 5989-02-6
PubChem CID: 100332
DTXSID: DTXSID501019112
ChEMBL: CHEMBL227113
ChEBI: CHEBI:69774
UNII: U3BB4IM281
Nikkaji: J16.007E

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 316

Physicochemical properties

Melting point: 151 · 151-153℃
Boiling point: 352.7 · 352.7±42.0 °C(Predicted)
Density: 1.16 · 1.16±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: DMSO: soluble
form: Powder
pka: 14.39 · 14.39±0.60(Predicted)
color: White to off-white
biological source: plant
Water Solubility: water: soluble
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
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
InChIKey: XEVQXKKKAVVSMW-WRWORJQWSA-N
SMILES: O1[C@@]2(C[C@H](CC(C2=CC1=O)(C)C)O)C
LogP: 0.61 · 0.610 (est)
FDA UNII: 3 BB4IM281 · U3BB4IM281

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk: WGK 3
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications

UsesLoliolide is a natural product derived from plant source th at finds application in compound screening libraries, metabolomics, phytochemical, and drug discovery research.

Additional notes

DefinitionChEBI: A natural product found in Brachystemma calycinum.

Related reactions

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Compound notes

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