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CAS No.: | 553-21-9 |
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Name: | Costunolide |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C15H20O2 |
Molecular Weight: | 232.323 |
Synonyms: | (1S,4E,8E,10S)-4,8-dimethyl-13-methylidene-11-oxabicyclo[8.3.0]trideca-4,8-dien-12-one;Cyclodeca[b]furan-2(3H)-one,3a,4,5,8,9,11ahexahydro- 6,10-dimethyl-3-methylene-,(3aS,6E,10E,11aR)-;Costunolid;(1S,10S)-4,8-dimethyl-13-methylidene-11-oxabicyclo[8.3.0]trideca-4,8-dien-12-one;Costus lactone;(E,E)-6-alpha-Hydroxygermacra-1(10),4,11(13)-trien-12-oic acid gamma-lactone; |
Density: | 1.03 g/cm3 |
Melting Point: | 106-109oC |
Boiling Point: | 385.4 °C at 760 mmHg |
Flash Point: | 162 °C |
Solubility: | Chloroform (Slightly), Ethyl Acetate (Slightly) |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-24/25 |
PSA: | 26.30000 |
LogP: | 3.55080 |
costunolide
Conditions | Yield |
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With hydrogenchloride at 20℃; for 12h; Elimination; | 100% |
costunolide
Conditions | Yield |
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With hydrogenchloride at 20℃; for 12h; Elimination; | 100% |
costunolide
Conditions | Yield |
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With hydrogenchloride at 20℃; for 12h; Elimination; | 100% |
1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol
costunolide
Conditions | Yield |
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With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Inert atmosphere; | 82% |
With manganese(IV) oxide In dichloromethane at 20℃; for 12h; | 78% |
costunolide
Conditions | Yield |
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Multi-step reaction with 5 steps 1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 3: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 4: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 5: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere 2: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 4: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 5: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
costunolide
Conditions | Yield |
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Multi-step reaction with 4 steps 1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 2: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 3: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 4: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
costunolide
Conditions | Yield |
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Multi-step reaction with 3 steps 1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 2: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 3: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
costunolide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
costunolide
Conditions | Yield |
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Multi-step reaction with 13 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere 3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere 3.2: 0.08 h / -78 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 6.2: 20 °C / Inert atmosphere 7.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 9.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 10.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 11.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 12.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 13.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 13 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium hydride / toluene; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere 3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere 3.2: 0.08 h / -78 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 6.2: 20 °C / Inert atmosphere 7.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 9.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere 10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 11.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 12.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 13.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
costunolide
Conditions | Yield |
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Multi-step reaction with 11 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere 1.2: 0.08 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere 5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 7.1: carbon tetrabromide; 2,6-dimethylpyridine; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 11 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -40 °C / Inert atmosphere 1.2: 0.08 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; ethanol; water / 0.5 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere 5.1: pyridine; hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / tert-butyl alcohol / 4 h / 0 - 20 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 7.1: triphenylphosphine; iodine; 1H-imidazole / 0 °C / Inert atmosphere 8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 9.1: magnesium / methanol; tetrahydrofuran / 20 °C / Inert atmosphere 10.1: pyridinium p-toluenesulfonate / methanol; ethylene glycol / 0.33 h / 20 °C / Inert atmosphere 11.1: manganese(IV) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme |
Molecular Structure of Costunolide (CAS NO.553-21-9):
IUPAC: (3AS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[d]furan-2-one
Molecular Formula:C15H20O2
Molecular Weight:232.32
Product Categories:Miscellaneous Natural Products;chiral
Density:1.03 g/cm3
Flash Point:162oC
Boiling Point:385.4oC at 760 mmHg
SMILES:O=C/1O[C@@H]2/C=C(/CC/C=C(/CC[C@H]2C\1=C)C)C
InChI:InChI=1/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-AHNJNIBGBA
Index of Refraction:1.519
Molar Volume:224.4 cm3
Surface Tension:35.1 dyne/cm
Molar Refractivity:68.12 cm3
Enthalpy of Vaporization:63.42 kJ/mol
Vapour Pressure:3.8E-06 mmHg at 25oC
Costunolide with cas registry number of 553-21-9 can be obtained from tree eremanthus elaegnus .
Costunolide with cas registry number of 553-21-9 is also known as (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 . Costunolide is an active sesquiterpene lactone of medicinal herbs with anti-inflammatory and potential anti-cancer activity. It affects nuclear organization and reorganized microtubule architecture. Costunolide demonstrates polymerizing ability, by inducing the formation of well organized microtubule polymers. It also used as chemoprophylactic agent in schistosomiasis.