Basic information
- CAS
553-21-9- Standard SMILES
C=C1C(=O)OC2/C=C(/C)CC/C=C(/C)CCC12- InChIKey
HRYLQFBHBWLLLL-GYIATTAWSA-N- Molecular formula
- C15H20O2
- Average molar mass
- 232.32 g/mol
- Monoisotopic mass
- 232.14632988
Names & identifiers
- Preferred name
- (6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
- IUPAC
- (6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
- English name
- Costunolide
- Molecular formula
- C15H20O2
- Molecular weight
- 232.32
Names & synonyms
NSC 106404(6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-oneHRYLQFBHBWLLLL-GYIATTAWSA-NCyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, [3aS-(3aR*,6E,10E,11aS*)]-BRD-A49888826-001-01-8(E,E)-6-.alpha.-Hydroxygermacra-1(10),4,11(13)-trien-12-oic acid .gamma.-lactoneGermacra-1(10),4,11(13)-trien-12-oic acid, 6.alpha.-hydroxy-, .gamma.-lactone, (E,E)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one-, (3aS,6E,10E,11aR)-COSTUNDIDEcostunolidCostunlideCUSTUNOLIDE
Show more names
(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-oneCostulidecostunoideCOSTUNOLIDECosinolactone
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 401
Experimental & physicochemical properties
Boiling Point205.00 to 211.00 °C. @ 13.00 mm Hg
Melting Point106 - 107 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 106 · 106-107 °C
- Boiling point
- 385.4 · 385.4±42.0 °C(Predicted)
- Density
- 1.03 · 1.03±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL · DMSO: soluble10mg/mL (clear solution)
- form
- powder
- color
- white to beige
- optical activity
- 110 to · [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
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
- 3
- hs_code
- 29322090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P280-P302+P352
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionCostunolide 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).
UsesCostunolide 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 DescriptionCostunolide 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.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Related reactions
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Compound notes
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