3668-14-2

Basic information

• Product Name: bigelovin
• Synonyms: bigelovin
• CAS NO: 3668-14-2
• Molecular Formula: C17H20O5
• Molecular Weight: 304.3377
• Mol File: 3668-14-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 466.6°Cat760mmHg
• Flash Point: 207.1°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 6.95E-09mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: bigelovin(CAS DataBase Reference)
• NIST Chemistry Reference: bigelovin(3668-14-2)
• EPA Substance Registry System: bigelovin(3668-14-2)

Safety Data

• Hazardous Substances Data: 3668-14-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupe ensis, it exhibits antineoplastic activity.

InChI:InChI=1/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1

Upstream product

• 73407-89-3 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-4,5-bis<(tetrahydro-2H-pyran-2-yl)oxy>-azuleno<6.5-b>furan-2(3H)-one 
• 68241-56-5 (3aR,4R,4aS,5S,7aR,8R,9aS)-4a,8-Dimethyl-4,5-bis-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 
• 71686-37-8 (3aα,4α,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 
• 71686-37-8 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 
• 68241-57-6 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4,5-dihydroxy-3-methylene-4a,8-dimethylazuleno<6,5-b>-furan-2(3H)-one 
• 108-24-7 acetic anhydride 
• 5945-41-5 dl-Mexicanin I 
• 20483-26-5 2α,6α-diacetoxy-4β-hydroxy-pseudoguaia-11(13)-en-12,8α-olide 
• 73407-87-1 (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 
• 73407-84-8 (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione 
• 73407-88-2 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-8-hydroxy-4a,8-dimethyl-4-<(tetrahydro-2H-pyran-2-yl)oxy>-azyleno<6,5-b>furan-2(3H)-one 

Relevant articles and documents

Chemical modification of Britanin and of inuchenolide C

Analogs of helenalin possessing a broad spectrum of biological activity have been synthesized from the readily available sesquiterpene lactones britanin and inuchenolide C. Conditions for the hydrolysis, oxidative transformations, and skeletal rearrangements of the pseudoguaianolides that are characteristic for plants of the genus Inula have been studied.

Antitumor agents. I. Augustibalin, a new cytotoxic sesquiterpene lactone from Balduina angustifolia (Pursh.) Robins.

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