eupatolide
(3aR,4S,6Z,10Z,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Identification
| Name | eupatolide |
| IUPAC | (3aR,4S,6Z,10Z,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one |
| CAS Number | 6750-25-0 |
| FDA UNII | Search |
| Molecular Formula | C15 H20 O3 |
| Molecular Weight | 248.32200000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 438.70 °C. @ 760.00 mm Hg (est) |
| Flash Point | 368.00 °F. TCC ( 186.70 °C. ) (est) |
| logP (o/w) | 2.820 (est) |
| Soluble in | water, 510.7 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for eupatolide usage levels up to | not for fragrance use. |
| Recommendation for eupatolide flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(3aR,4S,6Z,10Z,11aR)-4-
hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
PubMed:
Eupatolide inhibits PDGF-induced proliferation and migration of aortic smooth muscle cells through ROS-dependent heme oxygenase-1 induction.
PubMed:
Eupatolide inhibits lipopolysaccharide-induced COX-2 and iNOS expression in RAW264.7 cells by inducing proteasomal degradation of TRAF6.
PubMed:
The sesquiterpene lactone eupatolide sensitizes breast cancer cells to TRAIL through down-regulation of c-FLIP expression.
PubMed:
New sesquiterpene dimers from Inula britannica inhibit NF-kappaB activation and NO and TNF-alpha production in LPS-stimulated RAW264.7 cells.
PubMed:
Eupatoriopicrin 19-O-Linolenoate and Other Constituents from Eupatorium cannabium.
PubMed:
Sesquiterpene lactones. Part XIII. Cytotoxic activity of eupatolide and eupatoriopicrin on human and animal malignant cells in tissue culture in vitro.
PubMed:
Antitumor agents. II. Eupatolide, a new cytotoxic principle from Eupatorium formosanum HAY.