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Costunolide

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Name

Costunolide

EINECS N/A
CAS No. 553-21-9 Density 1.03 g/cm3
PSA 26.30000 LogP 3.55080
Solubility Chloroform (Slightly), Ethyl Acetate (Slightly) Melting Point 106-109oC
Formula C15H20O2 Boiling Point 385.4 °C at 760 mmHg
Molecular Weight 232.323 Flash Point 162 °C
Transport Information N/A Appearance N/A
Safety 26-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 553-21-9 (Costunolide) Hazard Symbols Xi
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;

Article Data 4

Costunolide Synthetic route

saussureamine A

553-21-9

costunolide

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

(R)-2-Amino-3-((6E,10E)-(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethylsulfanyl)-propionic acid

553-21-9

costunolide

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%
97317-60-7, 104486-16-0

1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol

553-21-9

costunolide

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

Costunolide Chemical Properties

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 Production

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

Costunolide 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.

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