13834-16-7

Upstream product

• 89-79-2 isopulegol 
• 20549-46-6 (+)-neoisopulegol 
• 345898-37-5 (1R,3S,4S)-3-methoxymethyl-p-menthane 
• 7786-67-6 isopulegol 
• 17882-43-8 (?)-trans-isopulegone 
• 345898-38-6 2-(1-hydroxyprop-2-yl)-5-methylcyclohexan-1-ol methoxymethyl ether 
• 181960-76-9 (1S,2R,5R)-2-[(R)-1-methyl-1,2-epoxyethyl]-5-methylcyclohexan-1-ol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 85503-26-0 (+/-)-2(R)-<2'(R)-acetoxy-4'(R)-methylcyclohex-(1'S)-yl>propionic acid 

Downstream Products

• 103775-34-4 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 63968-64-9 arteannuin (Qinghaosu) 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 93913-65-6 1α-Δ⁴-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 93913-66-7 1α-Δ³-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 93913-64-5 1α,10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 87322-20-1 (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 106623-24-9 (R)-2-{(1R,2S,3S,4R)-2-Formyl-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 
• 87322-21-2 (R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 
• 647035-12-9 (+)-(1R,3S,4S,8S)-9-benzyloxy-p-menthan-3-ol 
• 252289-19-3 (1S,1'S,2S,5R)-2-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-5-methylcyclohexanol 
• 181960-78-1 (2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-5-methylcyclohexan-1-one 

Relevant academic research and scientific papers

Hydroxylation of (+)-menthol by Macrophomina phaseolina

Biotransformation of (+)-menthol with Macrophomina phaseolina led to hydroxylations at C-1, C-2, C-6, C-7, C-8 and C-9, with the C-8 position being preferentially oxidized. The resulting metabolites were identified as 8-hydroxymenthol (2), 6R-hydroxymenthol (3), 1R-hydroxymenthol (4), 9-hydroxymenthol (5), 2R,8-dihydroxymenthol (6), 8S,9-dihydroxymenthol (7), 6R,8-dihydroxymenthol (8), 1R,8-dihydroxymenthol (9) and 7,8-dihydroxymenthol (10). Metabolites 6-10 are described here for the first time. Their structures were characterized by spectroscopic analysis.

Enantioselective synthesis of three stereoisomers of 5,9- dimethylpentadecane, sex pheromone component of Leucoptera coffeella, from (-)-isopulegol

The coffee leaf miner, Leucoptera coffeella, is an economically important pest of coffee trees in Brazil. It has been demonstrated that the main sex pheromone component of this species is 5,9-dimethylpentadecane, however the stereochemistry of the natural

Enzyme-mediated preparation of enantiomerically pure p-menthan-3,9-diols and their use for the synthesis of natural p-menthane lactones and ethers

The diastereoselective preparation of the p-menthane-3,9-diols (±)-12, (±)-13a, (±)-13b, and (±)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

Calculated and experimental NMR chemical shifts of p-menthane-3,9-diols. A combination of molecular dynamics and quantum mechanics to determine the structure and the solvent effects

NMR chemical shifts have been experimentally measured and theoretically estimated for all the carbon atoms of (1R,3S,4S,8S)-p-menthane-3,9-diol in chloroform solution. Theoretical estimations were performed using a combination of molecular dynamics simula

Enantiospecific syntheses of pseudopterosin aglycones. Part 2. Synthesis of pseudopterosin K-L aglycone and pseudopterosin A-F aglycone via a B→BA→BAC annulation strategy

The enantiomeric aglycones of pseudopterosins K-L and A-F are synthesised from (-)- and (+)-isopulegol respectively. Key features are (a) the construction of the C3 stereogenic centre by a directed epoxidation-reduction sequence (K-L); (b) the creation of

Synthesis and organoleptic properties of p-menthane lactones

The stereoselective synthesis and organoleptic properties of p-menthane lactones 7a-h are described. Apart from correcting the published data concerning these compounds, this work has also allowed an unambiguous identification of 7a, 7b and 7g in Italo Mi

A synthetic approach to the pseudopterosins

Three Lewis acid catalysed reactions used in a synthesis of the tricyclic core of the marine anti-inflammatory pseudopterosins are reported; the reductive cleavage of an oxirane with inversion, the cyclisation of an α-hydroxy ketenedithioacetal to an aren

Pheromone syntheses: A tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate

The enantioselective syntheses of two stereoisomers, (2R,6S,10S) and (2S,6S,10S), of methyl 2,6,10-trimethyldodecanoate, out of eight possible isomers, are described, employing the stereoselective hydroboration of (-)-isopulegol (2) and (+)-neo-isopulegol

Synthesis and Transformations of (+/-)-trans-4aβ(H),8aα(H)-Octahydro-4α,7β-dimethyl-2H-1-benzopyran-2-one

Hydrogenation of 4,7-dimethylcoumarin (1) in alkaline medium has been shown to furnish a mixture of (+/-)-trans-4aβ(H),8aα(H)-octahydro-4α,7β-dimethyl-2H-1-benzopyran-2-one (2), (+/-)-trans-4aβ(H),8aα(H)-octahydro-4α,7α-dimethyl-2H-1-benzopyran-2-one (3)