78964-15-5

Upstream product

• 89-79-2 isopulegol 
• 78887-75-9 schizonepetozide A 
• 78916-68-4 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(E)-2-((1R,2S,4S)-2-hydroxy-4-methyl-cyclohexyl)-propenyloxy]-tetrahydro-pyran-3,4,5-triol 
• 78916-66-2 (2R,5S)-5-Methyl-2-[(R)-1-methyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-cyclohexanone 
• 78916-70-8 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(R)-2-((1R,2S,4S)-2-hydroxy-4-methyl-cyclohexyl)-propoxy]-tetrahydro-pyran-3,4,5-triol 
• 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

• 84051-31-0 (1R,5R)-2-(2-Benzyloxy-1-methyl-ethyl)-5-methyl-cyclohexanol 
• 13834-07-6 (1R,3R,4S,8R)-9-hydroxy-p-menthol 
• 167355-29-5 (+)-(1S,3S,4R,8S)-p-menthane-3,9-diol 
• 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 
• 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 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 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 
• 93913-64-5 1α,10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 93913-66-7 1α-Δ³-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 93913-65-6 1α-Δ⁴-4,10α-dimethyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalin 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 63968-64-9 arteannuin (Qinghaosu) 
• 103775-34-4 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 

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.

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).

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)