34258-02-1

Basic information

• Product Name: Isoneomatatabiol
• Synonyms: Isoneomatatabiol
• CAS NO: 34258-02-1
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• Mol File: 34258-02-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isoneomatatabiol(CAS DataBase Reference)
• NIST Chemistry Reference: Isoneomatatabiol(34258-02-1)
• EPA Substance Registry System: Isoneomatatabiol(34258-02-1)

Safety Data

• Hazardous Substances Data: 34258-02-1(Hazardous Substances Data)

Upstream product

• 490-09-5 (4aR,7S,7aR)-dihydronepetalactone 
• 109215-55-6 (4αS,7S,7αR)nepetalactol 
• 19479-28-8 (-)-(1R)-1-methoxymyodesert-3-ene 
• 75222-58-1 (1R)-1-methoxymyodesertan 
• 24512-63-8 geniposide 
• 26660-57-1 deoxyloganin 
• 142603-55-2 Acetic acid (1R,4aS,7S,7aR)-1-(2-ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-ylmethyl ester 
• 142603-53-0 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 142603-54-1 [(1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-yl]-methanol 
• 196509-95-2 deoxyloganin aglycone 
• 142603-56-3 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran 
• 142603-57-4 (1S,4R,4aR,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-octahydro-cyclopenta[c]pyran 

Downstream Products

• 35337-15-6 (4R,4aR,7R,7aR)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one 

Relevant articles and documents

Characterization of (1R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis

The enantiomerically pure diastereoisomers (1R,4S,4aR,7S,7aR)(1) and (1R,4R,4aR,7S,7aR)-dihydronepetalactol (2) were synthesized diastereoselectively from a renewable resource, (4aS,7S,7aR)-nepetalactone (3), isolated as the main constituent of the essent

Terpenoid Chemistry. XXIV (1R)-1-Methoxymyodesert-3-ene, an Iridoid Constituent of Myoporum deserti (Myoporaceae)

A common variety of Myoporum deserti A.Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2, (1R,4aS,7R,7aR)-1-methoxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran, b.p. 67 deg/2 mm, D - 165 deg.This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans, trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent, (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5-methylcyclopentanecarboxylic acid.Hydrogenation yields mainly (1R)-methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol.Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1',S',2'R,3'R)-2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid. (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopentapyran.Treatment of the hexahydropentapyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol,which equilibrates in solution to a mixture of α- and β-anomers.Spectral studies of these and other products establish the configuration of the natural product at C1. (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β-substituted furans characteristic of most other chemovarieties of M. deserti.