CAS Number553-21-9
SynonymsCostunlide; (3aS,6Z,10Z,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; costunolid; Costulide; MFCD00210262; Costunolide; COSTUNDIDE; (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; CUSTUNOLIDE; (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; (3aS,6Z,10Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
Molecular FormulaC15H20O2
Molecular Weight232.32
Purity≥97 (HPLC)%
Density1.0±0.1 g/cm3
Boiling Point385.4±42.0 °C at 760 mmHg
Melting Point106 °C
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 553-21-9 |
| Catalog No. | 2A-9022847 |
| Chinese Name | 木香烃内酯 |
| Synonyms | Costunlide; (3aS,6Z,10Z,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; costunolid; Costulide; MFCD00210262; Costunolide; COSTUNDIDE; (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; CUSTUNOLIDE; (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one; (3aS,6Z,10Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one |
| Molecular Formula | C15H20O2 |
| Molecular Weight | 232.32 |
| Purity | ≥97 (HPLC) |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 385.4±42.0 °C at 760 mmHg |
| Melting Point | 106 °C |
| Appearance | powder |
| Storage Condition | Store at -20°C |
| Packaging | III |
| Application | Costunolide has anti-inflammatory and antioxidant activities and can mediate apoptosis. |
| PubChem ID | 329825412 |
| MDL Number | MFCD00210262 |
| SMILES | C\C1=C/CC\C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]2CC1 |
| 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 |
| InChI Key | HRYLQFBHBWLLLL-AHNJNIBGSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | 6.1 |
| MSDS | msds/22847_1_553_21_9.pdf |
| Bioactivity | Costunolide, a sesquiterpene lactone, exhibits anti-inflammatory and anti-oxidant properties and mediates apoptosis.IC50 Value: 6.2 - 9.8 ug/mL(sarcoma cells viability)[3]Target: Apoptosis inducerin vitro: Costunolide significantly inhibited RANKL-induced BMM differentiation into osteoclasts in a dose-dependent manner without affecting cytotoxicity. Costunolide did not regulate the early signaling pathways of RANKL, including the mitogen-activated protein kinase and NF-κB pathways. However, costunolide suppressed nuclear factor of activated T-cells, cytoplasmic 1 (NFATc1) expression via inhibition of c-Fos transcriptional activity without affecting RANKL-induced c-Fos expression. The inhibitory effects ofcostunolide were rescued by overexpression of constitutively active (CA)-NFATc1 [1]. Exposure of T24 cells to costunolide was also associated with increased expression of Bax, down-regulation of Bcl-2, survivin and significant activation of caspase-3, and its downstream target PARP [2]. Both costunolide and dehydrocostus lactone inhibited cell viability dose- and time-dependently. IC50 values ranged from 6.2 ug/mL to 9.8 ug/mL. Cells treated with costunolide showed no changes in cell cycle, little in caspase 3/7 activity, and low levels of cleaved caspase-3 after 24 and 48 h [3].in vivo: Neither costunolide nor alpha-MGBL affected the blood-ethanol elevation in pylorus-ligated rats or that induced by intraperitoneal and intraduodenal ethanol administration [4]. Costunolide and alpha-MGBL suppressed gastric emptying in rats given 20% ethanol and 1% sodium carboxymethyl cellulose.Clinical trial: Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides References [1]. Cheon YH, Song MJ, Kim JY, Costunolide Inhibits Osteoclast Differentiation by Suppressing c-Fos Transcriptional Activity. Phytother Res. 2013 Jul 6. [2]. Rasul A, Bao R, Malhi M, Induction of apoptosis by costunolide in bladder cancer cells is mediated through ROS generation and mitochondrial dysfunction. Molecules. 2013 Jan 24;18(2):1418-33. [3]. Kretschmer N, Rinner B, Stuendl N, Effect of costunolide and dehydrocostus lactone on cell cycle, apoptosis, and ABC transporter expression in human soft tissue sarcoma cells. Planta Med. 2012 Nov;78(16):1749-56. [4]. Matsuda H, Shimoda H, Ninomiya K, Inhibitory mechanism of costunolide, a sesquiterpene lactone isolated from Laurus nobilis, on blood-ethanol elevation in rats: involvement of inhibition of gastric emptying and increase in gastric juice secretion. Alcohol Alcohol. 2002 Mar-Apr;37(2):121-7. Chemical & Physical Properties Density 1.0±0.1 g/cm3 Boiling Point 385.4±42.0 °C at 760 mmHg Melting Point 106 °C Molecular Formula C15H20O2 Molecular Weight 232.318 Flash Point 162.0±25.3 °C Exact Mass 232.146332 PSA 26.30000 LogP 4.05 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.519 InChIKey HRYLQFBHBWLLLL-BOHUOVHSSA-N SMILES C=C1C(=O)OC2C=C(C)CCC=C(C)CCC12 Storage condition Store at -20°C |
| Use of | Properties Articles34 Name costunolide Synonym More Synonyms Costunolide Biological Activity Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides References [1]. Cheon YH, Song MJ, Kim JY, Costunolide Inhibits Osteoclast Differentiation by Suppressing c-Fos Transcriptional Activity. Phytother Res. 2013 Jul 6. [2]. Rasul A, Bao R, Malhi M, Induction of apoptosis by costunolide in bladder cancer cells is mediated through ROS generation and mitochondrial dysfunction. Molecules. 2013 Jan 24;18(2):1418-33. [3]. Kretschmer N, Rinner B, Stuendl N, Effect of costunolide and dehydrocostus lactone on cell cycle, apoptosis, and ABC transporter expression in human soft tissue sarcoma cells. Planta Med. 2012 Nov;78(16):1749-56. [4]. Matsuda H, Shimoda H, Ninomiya K, Inhibitory mechanism of costunolide, a sesquiterpene lactone isolated from Laurus nobilis, on blood-ethanol elevation in rats: involvement of inhibition of gastric emptying and increase in gastric juice secretion. Alcohol Alcohol. 2002 Mar-Apr;37(2):121-7. Chemical & Physical Properties Molecular Formula C15H20O2 Exact Mass 232.146332 PSA 26.30000 Index of Refraction 1.519 InChIKey HRYLQFBHBWLLLL-BOHUOVHSSA-N |
| Transport Info | Product name: Purity: 95.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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