19906-72-0

Basic information

• Product Name: bakkenolide A
• Synonyms: bakkenolide A;(3R)-1',3',3'a,4,4',5,5',6',7',7'aβ-Decahydro-3'aβ,4'β-dimethyl-4-methylenespiro[furan-3(2H),2'-[2H]inden]-2-one;(3R,3'aR,7'aβ)-3'aβ,4'β-Dimethyl-4-methylenespiro[oxolane-3,2'-hydrindane]-2-one;Bakkenolid a;Fukinanolid;Nsc 292655;Spiro(furan-3(2H),2'-(2H)inden)-2-one, decahydro-3'A,4'-dimethyl-4-methylene-, (2'R-(2'alpha,3'aalpha,4'alpha,7'aalpha))- (9ci);Spiro(furan-3(2H),2'-indan)-2-one, 3'A,4,4',5,5',6',7',7'abeta-octahydro-3'abeta,4'beta-dimethyl-4-methylene-, (2'R)- (8ci)
• CAS NO: 19906-72-0
• Molecular Formula: C15H22O2
• Molecular Weight: 234.337
• Mol File: 19906-72-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 80-81℃
• Boiling Point: 360.7°Cat760mmHg
• Flash Point: 150.7°C
• Appearance: /
• Density: 1.06
• Vapor Pressure: 2.18E-05mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: bakkenolide A(CAS DataBase Reference)
• NIST Chemistry Reference: bakkenolide A(19906-72-0)
• EPA Substance Registry System: bakkenolide A(19906-72-0)

Safety Data

• Hazardous Substances Data: 19906-72-0(Hazardous Substances Data)

Usage

General Description

Bakkenolide A is a natural product derived from the plant Petasites tricholobus and belongs to the class of sesquiterpene lactones. It is characterized by its unique chemical structure and has shown various biological activities, including anti-inflammatory and anti-tumor properties. Bakkenolide A has been found to inhibit the production of inflammatory mediators, such as nitric oxide and prostaglandins, and has also demonstrated potent cytotoxic effects against cancer cells. Its potential therapeutic applications make it a promising candidate for the development of novel pharmaceutical agents. Additionally, the discovery of bakkenolide A highlights the importance of natural products in drug discovery and development.

InChI:InChI=1/C15H22O2/c1-10-5-4-6-12-7-15(9-14(10,12)3)11(2)8-17-13(15)16/h10,12H,2,4-9H2,1,3H3/t10-,12+,14+,15+/m0/s1

Upstream product

• 488857-09-6 (3aR,4S,7aR)-2-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-3a,4-dimethyl-octahydro-indene-2-carboxylic acid methyl ester 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 6610-16-8 (R)-(+)-2-methyl-2-cyclohexen-1-ol 
• 122518-93-8 (1R,2S,6S)-1,2-bis-iodomethyl-1,6-dimethylcyclohexane 
• 122518-92-7 (1S,2R,3S)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol 
• 122518-90-5 (1R,2S,6S)-8,8-Dichloro-1,2-dimethyl-bicyclo[4.2.0]octan-7-one 
• 122564-88-9 (1R,2S,6S)-1,6-dimethylcyclohexane-1,2-dicarboxylic acid 
• 122452-76-0 Phenyl-carbamic acid (R)-2-methyl-cyclohex-2-enyl ester 
• 122518-91-6 (S)-1,6-dimethyl-1-cyclohexene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 98540-08-0 (3aR,4S,7aR)-2-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-3a,4-dimethyl-octahydro-indene-2-carboxylic acid methyl ester 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 245724-20-3 ethy 4-benzyloxy-2-[2-methyl-2(E)-butenyl]-2-[2(Z)-4-pentadienyl]malonate 
• 350229-13-9 ethy 4-benzyloxy-2-[2-methyl-2(E)-butenyl]-2-[2(E)-4-pentadienyl]malonate 

Relevant articles and documents

Conversion of optically active hydrindanone to (+)-bakkenolide-A

A total synthesis of (+)-bakkenolide-A was carried out via the key intermediate 4, which was prepared based on an asymmetric cyclization- carbonylation reaction established in our laboratory. Diastereoselective construction of the spirolactone moiety was achieved using Mitsuhashi's protocol as a key step.

Synthesis of bakkenolide A

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Core structure of eremophilanes and bakkanes through niobium catalyzed Diels-Alder reaction: Synthesis of (±)-bakkenolide A

A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermed