105015-56-3

Basic information

• Product Name: (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester
• Synonyms: (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester
• CAS NO: 105015-56-3
• Molecular Weight: 396.524
• Mol File: 105015-56-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester(105015-56-3)
• EPA Substance Registry System: (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester(105015-56-3)

Safety Data

• Hazardous Substances Data: 105015-56-3(Hazardous Substances Data)

Upstream product

• 87433-77-0 trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 

Relevant articles and documents

Stereoisomeric Flavor Substances, XII. - 3-Methyl-4-octanolide - "Quercuslactone, Whiskylactone" - Structure and Properties of the Stereoisomeres

Ethyl 3-methyl-4-oxooctanoate (2) has been synthesized by reaction of pentanal with ethyl crotonate.Reduction with NaBH4 and cyclization yields racemic cis/trans-3-methyl-4-octanolide 1 which is separated to racemic cis (1a*1a') and trans (1b*1b') isomers by liquid chromatography.From 1a*1a' and 1b*1b' the diastereomers isopropyl (3R,4R)-, (3S,4S)-, (3S,4R)-, and (3R,4S)-4--3-methyloctanoates (3-6) and the diastereomers isopropyl (3R,4R)-, (3S,4S)-, (3S,4R)-, and (3R,4S)-4--3-methyloctanoates (7-10) have been synthesized and then separated by liquid chromatography.The absolute configurations of 1a, 1a', 1b and 1b' were derived from 1H-NMR data of 3-6 and optical activity could be estimated after recyclization into the optically active lactones 1a, 1a', 1b, and 1b'.From 7-10 optically pure stereoisomers of 1 have been obtained in preparative scale.Sensory characteristics of the stereoisomers are given.