87206-33-5

Basic information

• Product Name: (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one
• Synonyms: (3R)-dihydroarteannuin B;3H-Oxireno[7,8]naphtho[8a,1-b]furan-3-one, decahydro-4,7,9a-trimethyl-, (1aR,1bR,4R,4aS,7R,7aS,9aR)- (9CI)
• CAS NO: 87206-33-5
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.3334
• Mol File: 87206-33-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 387.1°C at 760 mmHg
• Flash Point: 163°C
• Density: 1.16g/cm³
• Vapor Pressure: 3.38E-06mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one(87206-33-5)
• EPA Substance Registry System: (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one(87206-33-5)

Safety Data

• Hazardous Substances Data: 87206-33-5(Hazardous Substances Data)

Usage

General Description

"(1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one" is a chemical compound with a complex and specific structure. It is a bicyclic triterpenoid with a molecular formula C15H24O2 and a molecular weight of 236.35 g/mol. (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one is a member of the oxirane class of compounds and has a unique carbon skeleton, making it of interest to organic chemists. The presence of multiple stereocenters and functional groups in its structure suggests potential biological activity and pharmaceutical applications. (1aR,4R,4aS,7R,7aS,9aR)-4,7,9a-trimethyldecahydro-3H-oxireno[7,8]naphtho[8a,1-b]furan-3-one may be studied for its potential medicinal properties or as a starting material for the synthesis of other organic compounds.

Upstream product

• 85031-60-3 4α-hydroperoxy-amorph-5-en-12-oic acid 
• 50906-56-4 (1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^1,5.0^12,14]tetradecan-3-one 

Downstream Products

• 63968-64-9 (+)-artemisinin 
• 141039-67-0 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 141039-66-9 2-(2-(3-(3-hydroxy-(2R)-methylpropyl)-2-methoxymethoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 126189-95-5 (+)-deoxyartemisinin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Relevant articles and documents

The mechanism of the spontaneous autoxidation of dihydroartemisinic acid

Dihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Δ4.5-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin.