91739-72-9

Basic information

• Product Name: P-MENTHANE-3,8-DIOL
• Synonyms: (1R,3R,4R)-2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol;(1R,3R,4R)-p-Menthane-3,8-diol;1beta,3beta,4alpha-p-Menthane-3,8-diol;Chebi:16053
• CAS NO: 91739-72-9
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.2646
• Mol File: 91739-72-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: P-MENTHANE-3,8-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: P-MENTHANE-3,8-DIOL(91739-72-9)
• EPA Substance Registry System: P-MENTHANE-3,8-DIOL(91739-72-9)

Safety Data

• Hazardous Substances Data: 91739-72-9(Hazardous Substances Data)

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 5949-05-3 (S)-Citronellal 
• 2385-77-5 (R)-Citronellal 
• 87791-00-2 6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one 
• 470-82-6 1,8-Cineole 
• 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 
• 89-79-2 isopulegol 
• 7786-67-6 isopulegol 
• 2216-51-5 (-)-menthol 
• 1033079-99-0 C₁₃H₂₂F₃NO₂ 
• 2623-23-6 L-menthyl acetate 
• 894415-71-5 (4R,6R)-6-Hydroxy-4-methyl-cyclohex-1-enecarboxylic acid ethyl ester 
• 894415-70-4 (4R,6R)-6-Hydroxy-4-methyl-cyclohex-1-enecarboxylic acid 

Downstream Products

• 57576-09-7 (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate 
• 2623-23-6 L-menthyl acetate 
• 186038-44-8 2-((E)-2-Bromo-3-phenyl-allyl)-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-benzo[1,3]dioxin-2-ylmethyl)-malonic acid diethyl ester 
• 91667-08-2 [(1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methylcyclohexyl] acetate 

Relevant articles and documents

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.

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.

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

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.

Methods and systems for evaluating and predicting the reactivity of monooxygenase enzymes

Methods and systems for evaluating and predicting the reactivity of natural and engineered monooxygenase enzymes are provided. Methods are provided for acquiring a functional profile (fingerprint) of monooxygenases that encode information regarding the ac

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.

P450 fingerprinting method for rapid discovery of terpene hydroxylating P450 catalysts with diversified regioselectivity

Engineered P450 enzymes constitute attractive catalysts for the selective oxidation of unactivated C-H bonds in complex molecules. A current bottleneck in the use of P450 catalysis for chemical synthesis is the time and effort required to identify the P45