68370-47-8

Basic information

• Product Name: (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
• Synonyms: (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one;Micheliolide;[3aS-(3aalpha,9alpha,9aalpha,9bbeta)]-3a,4,5,7,8,9,9a,9b-Octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one
• CAS NO: 68370-47-8
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• Mol File: 68370-47-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 131-133 °C
• Boiling Point: 426.1°C at 760 mmHg
• Flash Point: 181.8°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 4.78E-09mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.65±0.40(Predicted)
• CAS DataBase Reference: (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one(68370-47-8)
• EPA Substance Registry System: (3aS)-3aβ,4,5,7,8,9,9aβ,9bα-Octahydro-9β-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one(68370-47-8)

Safety Data

• Hazardous Substances Data: 68370-47-8(Hazardous Substances Data)

Usage

Uses

Micheliolide, a sesquiterpene lactone is used in the inhibition of resistant acute leukemic cells. Selectively targets cancer stem and progenitor cells.

InChI:InChI=1/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1

Upstream product

• 503551-53-9 parthenolide 
• 1403357-81-2 11βH,13-dihydro-13-dimethylaminomicheliolide 
• 1403357-80-1 11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride 
• 67-56-1 methanol 

Relevant articles and documents

Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids

We describe the synthesis and biological evaluation of a new natural product-inspired compound class obtained by combining the conceptually complementary pseudo-natural product (pseudo-NP) design strategy and a formal adaptation of the complexity-to-diversity ring distortion approach. Fragment-sized α-methylene-sesquiterpene lactones, whose scaffolds can formally be viewed as related to each other or are obtained by ring distortion, were combined with alkaloid-derived pyrrolidine fragments by means of highly selective stereocomplementary 1,3-dipolar cycloaddition reactions. The resulting pseudo-sesquiterpenoid alkaloids were found to be both chemically and biologically diverse, and their biological performance distinctly depends on both the structure of the sesquiterpene lactone-derived scaffolds and the stereochemistry of the pyrrolidine fragment. Biological investigation of the compound collection led to the discovery of a novel chemotype inhibiting Hedgehog-dependent osteoblast differentiation.

Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome

Parthenolide (PTL) can target NLRP3 inflammasome to treat inflammation and its related disease, but its cytotoxicity limits further development as an anti-inflammatory drug. A series of PTL analogs and their Michael-type adducts were designed and synthesi

Micheliolide derivative, pharmaceutical composition as well as preparation method and application thereof

The invention discloses a new type micheliolide derivative (the formulas of the derivative are shown as formula I and II, and the formulas are shown in the description) or salt, a preparation method,a pharmaceutical composition and application thereof, pa