| Identification | More | [Name]
Costunolide | [CAS]
553-21-9 | [Synonyms]
(3AS,6E,10E,11AR)-3A,4,5,8,9,11A-HEXAHYDRO-6,10-DIMETHYL-3-METHYLENE-CYCLODECA[B]FURAN-2(3H)-ONE
COSTUNOLIDE
(e,e)-6-alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oicacidgamma-lactone
costunolid
germacra-1(10),4,11(13)-trien-12-oicacid,6-alpha-hydroxy-,gamma-lactone,(e,
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, [3aS-(3aR*,6E,10E,11aS*)]-
CUSTUNOLIDE
(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[d]furan-2-one
COSTUNDIDE
Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11a-
hexahydro-6,10-dimethyl-3-methylene-,(3aS,6E,10E,11aR)-
(3aS,6E,10E)-3-Methylene-6,10-dimethyl-2,3,3aβ,4,5,8,9,11aα-octahydrocyclodeca[b]furan-2-one
(3aS,6E,10E)-3aβ,4,5,8,9,11aβ-Hexahydro-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one | [Molecular Formula]
C15H20O2 | [MDL Number]
MFCD00210262 | [Molecular Weight]
232.32 | [MOL File]
553-21-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
106-107 °C | [Boiling point ]
385.4±42.0 °C(Predicted) | [density ]
1.03±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: soluble10mg/mL (clear solution) | [form ]
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 | [Contact allergens]
This germacranolide sesquiterpene lactone is extracted from costus oil. With alantolactone and dehydrocostunolide, it is a component of lactone mix used to elicit reactions in patients sensitive to Asteraceae-Compositae. An erythema-multiform-like occupational contact dermatitis case occurred in a chemical student after an accidental exposure to costus oil. | [InChIKey]
HRYLQFBHBWLLLL-GRFSRWIASA-N | [SMILES]
O1C(=O)C(=C)[C@]2([H])CCC(C)=CCCC(C)=C[C@@]12[H] |t:10,15| | [LogP]
4.049 (est) | [CAS DataBase Reference]
553-21-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Germacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
A sequiterpene lactone that inhibits telomerase | [Definition]
ChEBI: A germacranolide with anthelminthic, antiparasitic and antiviral activities. | [Biological Activity]
Inhibitor of human telomerase activity (IC 50 = 65 μ M in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelial cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1 β and disrupts NF κ B activation. Displays anti-inflammatory, antifungal and antiviral properties. | [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).
| [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. | [Biochem/physiol Actions]
Costunolide is a sesquiterpene lactone originally isolated from plants widely used in many herbal medicines. It has a variety of effects. Costunolide is a potent inducer of apoptosis, a potent anti-cancer agent, has anti-inflammatory, anti-viral, anti-fungal, antimycobacterial activity and has been shown to inhibit telomerase activity. | [storage]
Store at -20°C, sealed storage, away from moisture and light |
|
|