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

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

Uses

Used in Pharmaceutical Industry:
Bigelovin is used as an antineoplastic agent for its ability to inhibit the growth and progression of cancer cells. It targets various oncological signaling pathways, making it a promising candidate for the development of novel cancer treatments.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of bigelovin, researchers are exploring the use of different drug delivery systems, such as organic and metallic nanoparticles, to improve its delivery to cancer cells and enhance its therapeutic outcomes. This approach aims to overcome potential limitations associated with the direct use of bigelovin and maximize its potential as an anticancer agent.

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 
• 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 
• 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 

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.

Helenanolides: Stereocontrolled Total Synthesis of dl-Bigelovin, dl-Mexicanin I, and dl-Linifolin A

Stereocontrolled total syntheses of the sesquiterpene lactones dl-bigelovin (11), dl-mexicanin I (12), and dl-linifolin A (13) are described.The syntheses start with the hydroazulenone 4 and proceed via the key epoxy alkohol 9.Elaboration of 9 into the tricyclic γ-lactone 14 dl-bigelovin. α-methylenation.Subsequent oxidation at C(4) completes the synthesis of dl-bigelovin.Epoxide opening of 9 with dilithioacetate provides access to tricyclic lactone 23 which gives way to 24 via reduction of ketone 25.Cleavage of the benzyl ether in 24 followed by α-methylenationand oxidation generates dl-mexicanin I.Acetylation of 12 affords dl-linifolin A.