Introduction：Basic information about Costunolide CAS 553-21-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Costunolide Basic information
| Product Name: | Costunolide |
| Synonyms: | Costundide 553-21-9;(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,;Costunolide (NSC-106404);Costunolide, 98%, from Saussurea costus (Falc.) Lipsch. |
| 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 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 |
| Optical Rotation | [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 | 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) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-24/25 |
| WGK Germany | 3 |
| HS Code | 29322090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Sens. 1 |
Costunolide Usage And Synthesis
| Description | Costunolide is a germacranolide sesquiterpene lactoneextracted from costus oil. With alantolactone anddehydrocostuslactone, it is a component of lactone mixused to elicit reactions in Compositae-sensitive patients.An erythema-multiform-like occupational contactdermatitis case occurred in a chemistry studentafter accidental exposure to costus oil (CJ Le Coz & JPLepoittevin, unpublished results). |
| Chemical Properties | White crystalline powder, soluble in chloroform, derived from woodsy, Inula magnifica, Kerria japonica, Malachite. |
| 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. |
| Definition | ChEBI: 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 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. |
| 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. |
| 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. |
| 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. |
Costunolide Preparation Products And Raw materials
