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553-21-9

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Basic Information
CAS No.: 553-21-9
Name: Costunolide
Article Data: 4
Molecular Structure:
Molecular Structure of 553-21-9 (Costunolide)
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
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553-21-9

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Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%

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553-21-9

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Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%

(S)-2-[((6E,10E)-(3R,3aS,11aS)-6,10-Dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid

553-21-9

costunolide

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h; Elimination;100%
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1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol

553-21-9

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Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Inert atmosphere;82%
With manganese(IV) oxide In dichloromethane at 20℃; for 12h;78%

(2E,6E)-7-((4R,5S)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepan-4-yl)-2,6-dimethylhepta-2,6-dien-1-ol

553-21-9

costunolide

Conditions
ConditionsYield
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

(4R,5S)-4-((1E,5E)-7-bromo-2,6-dimethylhepta-1,5-dien-1-yl)-2,2-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)-1,3-dioxepane

553-21-9

costunolide

Conditions
ConditionsYield
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

(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-6-(phenylsulfonyl)-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

553-21-9

costunolide

Conditions
ConditionsYield
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

(5aS,8E,12E,13aR)-2,2,8,12-tetramethyl-5-methylene-4,5,5a,6,7,10,11,13a-octahydrocyclodeca[d][1,3]dioxepine

553-21-9

costunolide

Conditions
ConditionsYield
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

(E)-4-((tert-butyldimethylsilyl)oxy)-3-methylbut-2-enoic acid

553-21-9

costunolide

Conditions
ConditionsYield
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

(E)-4-((tert-butyldimethylsilyl)oxy)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-methylbut-2-en-1-one

553-21-9

costunolide

Conditions
ConditionsYield
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
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Chemistry

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

Production

 Costunolide with cas registry number of 553-21-9 can be obtained from tree eremanthus elaegnus .

Specification

 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.