Costunolide

Costunolide Basic information
Product Name:Costunolide
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;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;Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11a-;hexahydro-6,10-dimethyl-3-methylene-,(3aS,6E,10E,11aR)-
CAS:553-21-9
MF:C15H20O2
MW:232.32
EINECS:
Product Categories:Sesquiterpenoids;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chiral;Miscellaneous Natural Products
Mol File:553-21-9.mol
Costunolide Structure
Costunolide Chemical Properties
Melting point 106-107 °C
Boiling point 385.4±42.0 °C(Predicted)
density 1.03±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility DMSO: soluble10mg/mL (clear solution)
form powder
color white to beige
InChIKeyHRYLQFBHBWLLLL-GRFSRWIASA-N
LogP4.049 (est)
CAS DataBase Reference553-21-9(CAS DataBase Reference)
NIST Chemistry ReferenceGermacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-24/25
WGK Germany 3
HS Code 29322090
MSDS Information
Costunolide Usage And Synthesis
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dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).
Chemical PropertiesWhite crystalline powder, soluble in chloroform, derived from woodsy, Inula magnifica, Kerria japonica, Malachite.
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.
DefinitionChEBI: Costunolide is a germacranolide with anthelminthic, antiparasitic and antiviral activities. It has a role as an anthelminthic drug, an antiinfective agent, an antineoplastic agent, an antiparasitic agent, an antiviral drug and a metabolite. It is a germacranolide and a heterobicyclic compound.
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.
Biological ActivityInhibitor 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.
Biochem/physiol ActionsCostunolide 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.
Contact allergensThis 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.
Costunolide Preparation Products And Raw materials
(3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one TRANS-2-HEXENYL VALERATE Tulipalin A Costunolide std.,COSTUNOLIDE(SH) Dacthal TRANS-2-HEXENYL HEXANOATE Costunolide PRENYL CAPROATE 5-METHYL-3-METHYLENE-DIHYDRO-FURAN-2-ONE ETHYL 6-METHYL-6-HEPTENOATE TRANS-2-HEXENYL BUTYRATE (E)-5-DECEN-1-YL ACETATE Dimethyl sebacate 6-decenoic acid Costuslactone 2-hydroxyeupatolide 3-methylbuten-2-yl methacrylate Spironolactone

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