(6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
COSTUNDIDE · costunolid · Costunlide · CUSTUNOLIDE · (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one · Costulide · NSC 106404 · costunoide
![(6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one molecular structure](/img/chemical/5367559.png)
Identifiers & Physical Properties
| CAS No. | 553-21-9 |
|---|---|
| Molecular formula | C15H20O2 |
| Average molar mass | 232.32 g/mol |
| Monoisotopic mass | 232.14632988 g/mol |
| SMILES | C=C1C(=O)OC2/C=C(/C)CC/C=C(/C)CCC12 |
| InChIKey | HRYLQFBHBWLLLL-GYIATTAWSA-N |
| PubChem CID | 5367559 |
Chemical & Physical Properties
| XLogP | 2.1 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 17 |
| Formal charge | 0 |
| Complexity | 401 |
| Boiling point | 205.00 to 211.00 °C. @ 13.00 mm Hg385.4±42.0 °C(Predicted) |
| Melting point | 106 - 107 °C106-107 °C |
| Physical Description | Solid |
| Density | 1.03±0.1 g/cm3(Predicted) |
| Storage conditions | -20°C |
| Solubility | DMSO: soluble10mg/mL (clear solution) |
| Physical state | powder |
| Color | white to beige |
| optical activity | [α]/D +110.0 to +130.0°, c =0.5 in chloroform-d |
| InChI | InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1 |
| InChIKey | HRYLQFBHBWLLLL-GRFSRWIASA-N |
| SMILES | O1C(=O)C(=C)[C@]2([H])CCC(C)=CCCC(C)=C[C@@]12[H] |t:10,15| |
| LogP (partition coefficient) | 4.049 (est) |
| CAS DataBase Reference | 553-21-9(CAS DataBase Reference) |
| FDA UNII | 4IK578SA7Z |
| NIST Chemistry Reference | Germacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9) |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H317 |
| GHS precautionary statements | P280-P302+P352 |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-24/25 |
| Water hazard class (WGK) | 3 |
| Customs code | 29322090 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Skin Sens. 1 |
Safety & Regulations
| Water hazard class (WGK) | 3 |
|---|---|
| Customs code | 29322090 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317 |
| Hazard class | Skin Sens. 1 |
| GHS precautionary statements | P280-P302+P352 |
Applications & Uses
Description
Costunolide is a germacranolide sesquiterpene lactone extracted from costus oil. With alantolactone and dehydrocostuslactone, it is a component of lactone mix used to elicit reactions in Compositae-sensitive patients. An erythema-multiform-like occupational contact dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).
Uses
Costunolide is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.
Uses
(+)-Costunolide is an inhibitor of osteoclast differentiation, acting as an anti-inflammatory and anti-oxidant agent. It is a sesquiterpene lactone which mediates apoptosis.
General Description
Costunolide has anti-ulcer and antipyretic properties. It inhibits the cellular proliferation of melanin, human lamin-B by farnesyl-protein transferase (FPTase) and protein tyrosine phosphatase 1B (hPTP1B). Costunolide has strong larvicidal activity against A.albopictus. It inhibits the expression of inducible nitric oxide synthase and DNA-binding activity of nuclear factor kappa B subunit (NF-κB). It might function as a natural herbicide.