89647-87-0

Basic information

• Product Name: (3aR,4R,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one
• CAS NO: 89647-87-0
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.301
• Mol File: 89647-87-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 498.1°C at 760 mmHg
• Flash Point: 190.5°C
• Density: 1.26g/cm³
• Vapor Pressure: 5.21E-12mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: (3aR,4R,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4R,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one(89647-87-0)
• EPA Substance Registry System: (3aR,4R,6aR,8S,9aR,9bR)-4,8-dihydroxy-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one(89647-87-0)

Safety Data

• Hazardous Substances Data: 89647-87-0(Hazardous Substances Data)

Upstream product

• 68370-46-7 aguerin A 
• 35932-39-9 cynaporicrin 
• 1549718-88-8 (1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one 
• 1549718-80-0 (1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-4-yl 17-((methoxymethoxy)methyl)acrylate 
• 93395-30-3 3β-(β-D-glucopyranosyl)-oxy-8α-hydroxyguaia-4(15),10(14),11(13)-trien-5α,6β,7α-12,6-olide 
• 68370-45-6 aguerin B 
• 101153-62-2 ixerin Q 
• 101153-63-3 ixerin O 
• 101153-64-4 ixerin P 
• 101153-61-1 ixerin R 
• 101153-65-5 ixerin N 
• 101153-66-6 ixerin M 
• 100228-50-0 8-epideacylcynaropicrin-3-O-β-D-glucopyranoside 

Downstream Products

• 1007346-78-2 pulchellamine A 
• 1007346-81-7 pulchellamine D 
• 71305-80-1 8α-acetoxyzaluzanin D 

Relevant articles and documents

Cynaropicrin and inhibition of NF-κB activation: A structure activity relationship study

Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. This natural product has various biological activities including anti-inflammatory properties and antitrypanosomal activity. It was also found to suppress photoaging of the skin by inhibiting the transcription activity of nuclear factor-kappa B (NF-κB). In this paper, nine chemical derivatives of cynaropicrin were prepared, and the structure activity relationship (SAR) study for NF-κB inhibition by measuring relative light units (RLU) was conducted.

11,16 Oxetane lactones. Spectroscopic evidences and conformational analysis

Sesquiterpene lactones constitute a wide group of compounds with several biological activities, including allelopathic. The naturally occurring sesquiterpene lactones dehydrocostuslactone and cynaropicrin have been modified in three different ways: preparation of 11,13-oxetane lactones, addition of a second Michael acceptor and reduction of the α-methylene-γ-lactone in order to future structure-activity relationship (SAR) studies. We have obtained all oxetane lactones stereoisomers at C-11 and C-16 positions. This fact has allowed us to establish some correlations between experimental data, derived by NMR and X-ray analysis, and the configuration at C-11 and C-16, which could be a useful tool to establish the stereochemistry as well as to confirm the presence of an oxetane ring on similar compounds. Comparative conformational analyses as a key aspect in the biological behaviour of those compounds in future structure-activity relationship (SAR) studies are presented.

Sesquiterpene lactones from Ixeris stolonifera A. GRAY

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