92471-23-3

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 5949-05-3 (S)-Citronellal 
• 2385-77-5 (R)-Citronellal 
• 2216-52-6 Neomenthol 
• 89-79-2 isopulegol 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 76735-22-3 (1RS,4SR,5RS)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-ol 
• 470-82-6 1,8-Cineole 
• 87791-00-2 6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one 
• 17882-43-8 (?)-trans-isopulegone 
• 7786-67-6 isopulegol 
• 98-01-1 furfural 

Relevant academic research and scientific papers

Effect of the Stereoselectivity of para-Menthane-3,8-diol Isomers on Repulsion toward Aedes albopictus

Vector-borne diseases cause around 700,000 deaths every year. Insect repellents are one of the strategies to limit them. Para-menthane-3,8-diol (PMD), a natural compound, is one of the most promising alternatives to conventional synthetic repellents. This work describes a diastereodivergent method to synthesize each diastereoisomer of PMD from enantiopure citronellal and studies their repellence activity against Aedes albopictus. We found that cis-PMD is the kinetic control product of the cyclization of citronellal, while trans-PMD is the thermodynamic control product. X-ray diffraction analysis of crystals highlighted some differences in hydrogen-bond patterns between cis or trans isomers. The present paper demonstrates that (1R)-(+)-cis-PMD has the highest repellency index using a new evaluation system for 24 h. (1S)-(-)-cis-PMD has somewhat lower and (1S)-(+)-trans-PMD and (1R)-(-)-trans-PMD have a slight effect. Volunteer tests show that (1R)-(+)-cis-PMD is the most efficient. This effect could be ascribed to the interaction of PMD/insect odorant receptors and their physical properties, that is, the evaporation rate.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Synthesis of: P-menthane-3,8-diol from citronellal over lignin-derived carbon acid catalysts

p-Menthane-3,8-diol (PMD) is receiving growing attention as a natural mosquito repellent with lower toxicity compared to the widely-used N,N-diethyl m-toluamide (DEET). In this study, sustainable carbon acid catalysts derived from alkaline lignin (AL) were prepared for synthesizing PMD from a popular chemical (±)-citronellal in an environmentally friendly solvent of water. The catalytic performances of the AL-derived carbon acid catalysts prepared at different pyrolysis temperatures were better than those of other catalysts such as carbon black and H-USY. In particular, when the AL pyrolyzed at 500 °C was used as the carbon acid catalyst, the conversion of (±)-citronellal was as high as 97% with a high PMD yield of 86%, indicating that waste alkaline lignin from pulp and paper industries can be used as a source of acid catalysts. It is found that the formation of PMD is preferred over catalysts with weaker acid sites, whereas isopulegol was more easily formed over stronger acid sites. Moreover, the reaction route of the citronellal cyclization-hydration reaction was more dominant via the carbocation-hydration pathway rather than the isopulegol hydration route on the weaker carbon acid catalyst. This journal is

Selective C-H bond hydroxylation of cyclohexanes in water by supramolecular control

A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using β-CD and γ-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3-and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with β-CD and γ-CD in water.

Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol

A large set of chiral heterocyclic compounds with the octahydro-2H-chromene scaffold was first obtained by a reaction of (?)-isopulegol and (+)-neoisopulegol with furan-2-carbaldehyde, thiophene-2-carbaldehyde and their derivatives and isomers in the pres

P-MENTHANE-3,8-DIOL ISOMER MIXTURE, COOLING SENSATION COMPOSITION COMPRISING THE SAME, AND PRODUCT COMPRISING THE COOLING SENSATION COMPOSITION

The present invention relates to a p-menthane-3,8-diol isomer mixture 50% by mass or more of which is constituted of (1S)-isomers and a cooling sensation composition containing this mixture. The present invention also relates to a flavor and/or fragrance composition, food, beverage, cosmetic, daily use product, oral cavity composition, or pharmaceutical containing the p-menthane-3,8-diol isomer mixture in an amount of 0.0001 to 90% by mass.

Biotransformations of terpenes by fungi from amazonian Citrus plants

The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The

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.

A practical and efficient synthesis of p-menthane-3,8-diols

The diastereomeric repellents of p-menthane-3,8-diol were produced from citronellal by treatment with 0.25% sulfuric acid at 50°C for 11 h to give 97.9% conversion and 92.3% selectivity and citronellal acetal by-products with only 2.7%. The crude products were crystallized from n-heptane at -50°C for 20 h to give p-menthane-3,8-diols in 80% yield and high purity. The stereochemistry of the citronellal acetal by-products was determined by 2D NMR and NOE.

New Lewis-acidic molybdenum(II) and tungsten(II) catalysts for intramolecular carbonyl erie and prins reactions. Reversal of the stereoselectivity of cyclization of citronellal

New Mo(II) complexes BnEt3N+[Mo(CO)4ClBr2]- (A) and Mo(CO)5(OTf)2 (B) and their W(II) congeners D and E have been developed as catalysts for the title reactions. Unlike other Lewis acids, the latter catalysts exhibit cis-stereoselectivity in the cyclization of citronellal (1 → 3 with A and 1 → 5 with B). Isotopic labeling allowed formulation of the reaction mechanism, according to which these complexes act as bulky Lewis acids, η1- coordinated to the carbonyl oxygen. The stereochemistry appears to be controlled by the protruding ligand L(p), which dictates the boatlike transition state III. The kinetically formed cis-alkenol 3 can be equilibrated by [Mo(CO)4Br2]2 (C) or ZnCl2 to its trans-epimer 2 via a retro-ene reaction.