p-Menthane

Base Information

• Chemical Name: p-Menthane
• CAS No.: 99-82-1
• Deprecated CAS: 374781-46-1,25377-78-0,34448-33-4
• Molecular Formula: C₁₀H₂₀
• Molecular Weight: 140.269
• European Community (EC) Number: 202-790-4,679-820-1,679-821-7,951-486-4,951-489-0
• NSC Number: 73979,73978
• UNII: CGW5GN8TXU
• DSSTox Substance ID: DTXSID9025530,DTXSID30884219,DTXSID50883709
• Nikkaji Number: J124.993B,J130.647B,J3.997G
• Wikipedia: P-Menthane
• Wikidata: Q2043490,Q82862567,Q82862929
• Metabolomics Workbench ID: 5350
• Mol file: 99-82-1.mol

Synonyms:p-Menthane;99-82-1;6069-98-3;cis-1-isopropyl-4-methylcyclohexane;1678-82-6;trans-1-isopropyl-4-methylcyclohexane;1-ISOPROPYL-4-METHYLCYCLOHEXANE;cis-p-Menthane;trans-p-Menthane;p-Menthane, trans-;p-Menthane, cis-;1-iso-Propyl-4-methylcyclohexane;Cyclohexane, 1-methyl-4-(1-methylethyl)-, trans-;p-Menthan;Cyclohexane, 1-methyl-4-(1-methylethyl)-, cis-;1-Methyl-trans-4-isopropylcyclohexane;Cyclohexane, 1-methyl-4-(1-methylethyl)-;1-methyl-4-propan-2-ylcyclohexane;para-menthane;1-Isopropyl-cis-4-methylcyclohexane;1-Methyl-cis-4-isopropylcyclohexane;CCRIS 4664;1-Methyl-4-(1-methylethyl)-cyclohexane;HSDB 5328;CGW5GN8TXU;EINECS 202-790-4;NSC 73978;NSC 73979;1-methyl-4-(propan-2-yl)cyclohexane;AI3-24486;1-methyl-4-isopropylcyclohexane;p-Menthane, Z-;trans-1-Methyl-4-isopropylcyclohexane;menthane;(1r,4r)-1-Isopropyl-4-methylcyclohexane;EC 202-790-4;cis-1-Methyl-4-isopropylcyclohexane;p-Menthane E;1-Isopropyl-4-methyl-cyclohexane, cis;PARA-MENTHANE (2,2-D2);CIS-PARA-MENTHANE(3,3-D2);1-Methyl-4-(1-methylethyl)-cyclohexane, cis;cis-Hexahydro-p-cymene;trans-menthane;cis-menthane;Cyclohexane, cis-;UNII-CGW5GN8TXU;WOODY RIVER 10;HU0VZO1K2G;1-isopropyl-4-methylcyclohexan;DTXSID9025530;CHEBI:25826;DTXSID30884219;DTXSID50883709;NSC73978;NSC73979;MFCD00043477;MFCD00070477;NSC-73978;NSC-73979;Cis-1-isopropyl-4-methyl cyclohexane;AKOS006229182;AKOS015838428;AKOS015838431;1-methyl-4-(1-methylethyl)cyclohexane;LS-2070;Trans-1-isopropyl-4-methyl cyclohexane;1-Isopropyl-4-methyl-cyclohexane, trans;Cyclohexane, 1-methyl-4-isopropyl, trans;LS-56953;FT-0600340;FT-0695075;FT-0695076;I0284;1-ISOPROPYL-4-METHYLCYCLOHEXANE [HSDB];1-Methyl-4-(1-methylethyl)-cyclohexane, trans;4-METHYL-1-(1-METHYLETHYL)CYCLOHEXANE;(1r,4r)-1-methyl-4-(propan-2-yl)cyclohexane;(1s,4s)-1-methyl-4-(propan-2-yl)cyclohexane;(1S,4S)-1-ISOPROPYL-4-METHYLCYCLOHEXANE;J-010403;Q2043490;W-100017

Chemical Property of p-Menthane

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 3.52hPa at 25℃
• Melting Point: -87.6℃
• Refractive Index: 1.45562 (589.3 nm 22℃)
• Boiling Point: 168.2 °C at 760 mmHg
• Flash Point: 44.7 °C
• PSA: 0.00000
• Density: 0.786 g/cm³
• LogP: 3.46870
• Water Solubility.: 620μg/L at 20℃
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 140.156500638
• Heavy Atom Count: 10
• Complexity: 86.2

Purity/Quality:

99.9% ^*data from raw suppliers

p-Menthane ^*data from reagent suppliers

Safty Information:

• Statements: 11
• Safety Statements: 9-16-26-33

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Aliphatics, Saturated (
• Canonical SMILES: CC1CCC(CC1)C(C)C

Technology Process of p-Menthane

There total 148 articles about p-Menthane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

cis epoxyde du carvomenthene (3626-19-5,4680-25-5,4959-34-6,5034-17-3,5034-18-4,51424-68-1) → Menthane (99-82-1,1678-82-6,6069-98-3,129939-70-4,129939-71-5) + carvomenthone (499-70-7) + cis p-menthanol (3901-95-9) + 5-isoprpyl-2-methylcyclohexan-1-ol (499-69-4,1126-39-2,1126-40-5,1126-41-6,1845-59-6,3127-80-8,3858-43-3,3858-45-5,3858-47-7,3858-49-9,5563-78-0,42846-32-2,60320-28-7,116783-34-7) + 5-isopropyl-2-methylcyclohexan-1-ol (499-69-4,1126-39-2,1126-40-5,1126-41-6,1845-59-6,3127-80-8,3858-43-3,3858-45-5,3858-47-7,3858-49-9,5563-78-0,42846-32-2,60320-28-7,116783-34-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In cyclohexane; at 20 ℃; under 760 Torr; Rate constant;

DOI:10.1016/S0040-4020(01)98846-5

Reference yield: 43.0%

trans epoxyde du carvomenthene (3626-19-5,4680-25-5,4959-34-6,5034-17-3,5034-18-4,51424-68-1) → Menthane (99-82-1,1678-82-6,6069-98-3,129939-70-4,129939-71-5) + carvomenthone (499-70-7) + 5-isopropyl-2-methylcyclohexan-1-ol (499-69-4,1126-39-2,1126-40-5,1126-41-6,1845-59-6,3127-80-8,3858-43-3,3858-45-5,3858-47-7,3858-49-9,5563-78-0,42846-32-2,60320-28-7,116783-34-7) + 5-isopropyl-2-methylcyclohexan-1-ol (499-69-4,1126-39-2,1126-40-5,1126-41-6,1845-59-6,3127-80-8,3858-43-3,3858-45-5,3858-47-7,3858-49-9,5563-78-0,42846-32-2,60320-28-7,116783-34-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In cyclohexane; at 20 ℃; under 760 Torr;

DOI:10.1016/S0040-4020(01)98846-5

Reference yield: 35.0%

2-isopropyl-5-methylcyclohexyl acetate (89-48-5,2230-87-7,2552-91-2,2623-23-6,5157-89-1,16409-45-3,20777-36-0,20777-45-1,29066-34-0,42241-42-9,50539-17-8,55058-46-3,79199-84-1,146502-80-9) → Menthane (99-82-1,1678-82-6,6069-98-3,129939-70-4,129939-71-5) + menthol (89-78-1)

Guidance literature:

With sodium; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; tert-butyl alcohol;

upstream raw materials:

pulegone

p-menth-1-ene

8-bromo-p-menthane

Terpinolene

Downstream raw materials:

1,8-dinitro-p-menthane

4-methylisopropylbenzene

4-chloro-p-menthane

1-ethyl-4-methyl-cyclohexane

Refernces

Synthesis and organoleptic properties of p-menthane lactones

10.1016/S0040-4020(00)00397-5

The study focuses on the stereoselective synthesis and organoleptic properties of p-menthane lactones (7a-h), a class of compounds with significant interest to the perfume industry due to their exceptional odor intensity and typical coumarin-like note. The research corrects published data concerning these compounds and identifies 7a, 7b, and 7g as trace components in Italo Mitcham black peppermint oil (Mentha piperita). Various chemicals were used in the study, including (-)-isopulegol, (+)-neoisopulegol, m-chloroperbenzoic acid, lithium diisopropylamide (LDA), potassium permanganate, Raney nickel, and several others, serving as starting materials, reagents, and catalysts in the synthesis of the lactones. The purpose of these chemicals was to facilitate the synthesis of the p-menthane lactones, allowing for their characterization and evaluation of their sensory properties, which are crucial for their potential use in the perfume and flavoring industries.

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