19956-48-0

Basic information

• Product Name: (1S,3R,4S)-p-menthane-3,8-diol
• Synonyms: (1S,3R,4S)-p-menthane-3,8-diol
• CAS NO: 19956-48-0
• Molecular Weight: 172.268
• Mol File: 19956-48-0.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (1S,3R,4S)-p-menthane-3,8-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R,4S)-p-menthane-3,8-diol(19956-48-0)
• EPA Substance Registry System: (1S,3R,4S)-p-menthane-3,8-diol(19956-48-0)

Safety Data

• Hazardous Substances Data: 19956-48-0(Hazardous Substances Data)

Upstream product

• 106-23-0 3,7-dimethyl-oct-6-enal 
• 470-82-6 1,8-Cineole 
• 76735-22-3 (1RS,4SR,5RS)-1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-ol 
• 87791-00-2 6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one 
• 2385-77-5 (R)-Citronellal 
• 89-79-2 isopulegol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 5949-05-3 (S)-Citronellal 
• 20747-49-3 (-)-neomenthol 

Relevant articles and documents

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.

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.

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