1195-31-9

Basic information

• Product Name: (+)-P-MENTH-1-ENE
• Synonyms: (R)-(+)-4-Isopropyl-1-methylcyclohexene, Carvomenthene;(4R)-1-methyl-4-propan-2-ylcyclohexene;(4R)-1-methyl-4-propan-2-yl-cyclohexene;(4R)-4-isopropyl-1-methyl-cyclohexene;R(+)-4-ISOPROPYL-1-METHYLCYCLOHEXENE;(+)-P-MENTH-1-ENE;(+)-1-Menthene;(+)-1-p-menthene
• CAS NO: 1195-31-9
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 214-794-3
• Mol File: 1195-31-9.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 175-177 °C(lit.)
• Flash Point: 35 °C
• Appearance: /
• Density: 0.823 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.5mmHg at 25°C
• Refractive Index: n20/D 1.457
• CAS DataBase Reference: (+)-P-MENTH-1-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-P-MENTH-1-ENE(1195-31-9)
• EPA Substance Registry System: (+)-P-MENTH-1-ENE(1195-31-9)

Safety Data

• Statements: 10
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1195-31-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 1014, 1979 DOI: 10.1021/jo01320a033

InChI:InChI=1/C10H18/c1-8(2)10-6-4-9(3)5-7-10/h4,8,10H,5-7H2,1-3H3/t10-/m0/s1

Upstream product

• 2492-22-0 dihydromyrcene 
• 5989-27-5 D-limonene 
• 138-86-3 limonene. 
• 5989-54-8 (-)-(S)-limonene 
• 201230-82-2 carbon monoxide 
• 5432-85-9 4-isopropyl-cyclohexanone 
• 1124-24-9 1-methylene-4-isopropylcyclohexane 
• 85719-15-9 (+)-endo-3,9-dibromocamphor 
• 64474-56-2 (+)-9-bromocamphor 
• 10293-06-8 (1R)-3-endo-bromocamphor 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 5718-75-2 (1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane 

Downstream Products

• 125627-55-6 (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol 
• 61585-35-1 p-menth-1-ene 
• 1678-82-6 trans-1,4-menthane 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 6153-16-8 (+)-β-phellandrene 
• 99-83-2 (S)-2-methyl-5-(1-methylethyl)-1,3-cyclohexadiene 
• 51795-53-0 (2S,5R)-(+)-2-chloro-2-methyl-5-isopropylcyclohexanone 
• 84098-59-9 5-(2,2-Dichloro-ethyl)-6-methyl-heptan-2-one 
• 80324-58-9 3-Chloro-5-(2-chloro-ethyl)-6-methyl-heptan-2-one 
• 80845-81-4 (R)-(+)-3-isopropyl-6-oxoheptanoic acid 
• 5729-92-0 (1S,2R,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol 
• 1975-33-3 (1S,4R)-1-hydroxy-p-menthan-2-one 
• 72808-14-1 (1Ξ,2Ξ,5R)-5-isopropyl-2-methyl-cyclohexanecarbaldehyde 

Relevant articles and documents

Identification of an Asexual Reproduction Inducer of Phytopathogenic and Toxigenic Fusarium

Asexual and sexual reproduction are the most important biological events in the life cycle of phytopathogenic and toxigenic Fusarium and are responsible for disease epidemics. However, the signaling molecules which induce the asexual reproduction of Fusarium are unknown. Herein we describe the structure elucidation, including the absolute configuration, of Fusarium asexual reproduction inducer (FARI), a new sesquiterpene derivative, by spectroscopic analysis, total synthesis, and conidium-inducing assays of synthetic isomers. We have also uncovered the universality of FARI among Fusarium species. Moreover, a mechanism-of-action study suggested that the Gpmk1 and LaeA signaling pathways are required for conidium formation induced by FARI; conversely, the Mgv1 of mitogen-activated protein kinase is not involved in conidium formation. FARI exhibited conidium-inducing activity at an extremely low dose and high stereoselectivity, which may suggest the presence of a stereospecific target.

Convenient one-pot synthesis of 4,8-dimethyl-bicyclo[3.3.1)non-7-en-2-ol via platinum/tin catalyzed hydroformylation/cyclization of limonene

Limonene (1) was converted in one step into two diastereoisomers of 4,8-dimethyl-bicyclo[3.3.1]non-7-en-2-ol (2), useful as perfumes, employing PtCl2(PPh3)2/PPh3/SnCl2 and PtCl2(diphosphine)/PPh3/SnCl2 systems as bifunctional catalysts whose diphosphines were 1,3-bis(diphenylphosphino)propane (dppp) and 1,4-bis(diphenylphosphino)butane (dppb). In the presence of the PtCl2(dppb)/PPh3/SnCl2 system, which was found to be the most promising combination, the selectivity for 2 reached the value of 82% at 95% conversion of 1.

Synthesis of puleganic amides via a catalytically efficient two-step approach

Puleganic amides display interesting insect-repellent properties. A new synthetic route to this type of amide was developed involving an organocatalytic cyclization and metal-catalyzed hydrogenation in a one-pot protocol. An eco-friendly oxidative amination provided the puleganic amides with only one purification step and acceptable yields.

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.

Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

With the aim of preparing bio-sourced supports with enhanced properties in catalysis, we devised an original strategy allowing the immobilization of metal nanoparticles. Thus, size-controlled hydrochars with a high degree of hydroxyl functionalities, from both neat sucrose or modified with acrylic acid (10 wt.%), were derivatized with ether linkers containing ammonium groups. These non-porous carbon-based materials were used as suitable supports for the immobilization of palladium nanoparticles. The catalytic materials were synthesized by reduction of Pd(OAc)2 to Pd(0) under H2 atmosphere in the presence of the corresponding hydrochar, and fully characterized by standard methods. Among the different hydrochar-supported palladium materials, those functionalized with tetraalkylammonium groups afforded heterogeneous catalysts, exhibiting high activity in hydrogenations of different types of substrates (alkynes, alkenes, and carbonyl and nitro derivatives). The most efficient catalyst was recycled up to ten runs without loss of catalytic behavior, in agreement with the unchanged composite materials after catalysis (Transmission Electron Microscopy (TEM) analyses) and the lack of metal leaching in the extracted organic products (no palladium detected by Inductively Coupled Plasma-Atomic Emission Spectrometry (ICP-AES)); these systems exhibited enhanced recyclability properties as compared to commercial Pd/C catalyst.