EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

cyclohexane, 1-methyl-4-(1-methylethyl)-

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CAS Number: 99-82-1Picture of molecule3D/inchi
Other(deleted CASRN):374781-46-1
ECHA EINECS - REACH Pre-Reg:202-790-4
Nikkaji Web:J3.997G
XlogP3-AA:4.50 (est)
Molecular Weight:140.26940000
Formula:C10 H20
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 85.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: -87.60 °C. @ 760.00 mm Hg
Boiling Point: 170.00 to 171.00 °C. @ 760.00 mm Hg
Vapor Pressure:2.161000 mmHg @ 25.00 °C. (est)
Flash Point: 111.00 °F. TCC ( 43.89 °C. )
logP (o/w): 5.560
Soluble in:
 water, 0.28 mg/L @ 25 °C (exp)
Organoleptic Properties:
Odor Description:pine
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
Frinton Laboratories
For experimental / research use only.
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for para-menthane usage levels up to:
 not for fragrance use.
Recommendation for para-menthane flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):99-82-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7459
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
EPA/NOAA CAMEO:hazardous materials
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:99-82-1
Pubchem (cid):7459
Pubchem (sid):134972058
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB31455
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 juniper needle oil @ 0.10%
Data GC Search Trop Picture
 peppermint oil
Search Trop Picture
 cyclohexane, 1-methyl-4-(1-methylethyl)-
1-methyl-4-(1-methyl ethyl) cyclohexane
1-isopropyl-4-methyl cyclohexane


PubMed:Comparative analysis of three Australian finger lime (Citrus australasica) cultivars: Identification of unique citrus chemotypes and new volatile molecules.
PubMed:Acaricidal activity of five essential oils of Ocimum species on Rhipicephalus (Boophilus) microplus larvae.
PubMed:Microbial transformations of halolactones with p-menthane system.
PubMed:Assessing the efficacy of candidate mosquito repellents against the background of an attractive source that mimics a human host.
PubMed:A push-pull system to reduce house entry of malaria mosquitoes.
PubMed:Investigation of a dichlorodioxomolybdenum(VI)-pyrazolylpyridine complex and a hybrid derivative as catalysts in olefin epoxidation.
PubMed:The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. - a literature review.
PubMed:[Chemical constituents from rizomes of Homalomena occulta].
PubMed:Biotransformations of terpenes by fungi from Amazonian citrus plants.
PubMed:Two new monoterpenes from the fruits of Illicium lanceolatum.
PubMed:In silico stereo-electronic analysis of PMD (p-Menthane-3-8-Diol) and its derivatives for pharmacophore development may aid discovery of novel insect repellents.
PubMed:Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer.
PubMed:[Field efficacy of repellent formulation containing para-menthane-3,8-diol and lemongrass against Culicoides pachymerus (Diptera: Ceratopogonidae) in Colombia].
PubMed:Piperitone-derived saturated lactones: synthesis and aphid behavior-modifying activity.
PubMed:Lactones 41. Synthesis and microbial hydroxylation of unsaturated terpenoid lactones with p-menthane ring systems.
PubMed:Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves.
PubMed:Efficacy testing of several Ixodes ricinus tick repellents: different results with different assays.
PubMed:Repellents and acaricides as personal protection measures in the prevention of tick-borne diseases.
PubMed:Identification of muscadine wine sulfur volatiles: pectinase versus skin-contact maceration.
PubMed:Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
PubMed:Efficacy of DEET and non-DEET-based insect repellents against bites of Simulium damnosum vectors of onchocerciasis.
PubMed:Absorption characteristics of new solvent based on a blend of AMP and 1,8-diamino-p-menthane for CO2 absorption.
PubMed:Modulation of thermoreceptor TRPM8 by cooling compounds.
PubMed:Essential-oil diversity of three Calamintha species from Greece.
PubMed:Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.
PubMed:New monocyclic monoterpenoid glycoside from Mentha haplocalyx Briq.
PubMed:Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.
PubMed:Immunocytochemical localization of short-chain family reductases involved in menthol biosynthesis in peppermint.
PubMed:Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy.
PubMed:HS-SPME-GC×GC-qMS volatile metabolite profiling of Chrysolina herbacea frass and Mentha spp. leaves.
PubMed:[Studies on anti-tumor metastatic constituents from Lindera glauca].
PubMed:Characterizing the deformational isomers of bimetallic Ir2(dimen)4(2+) (dimen = 1,8-diisocyano-p-menthane) with vibrational wavepacket dynamics.
PubMed:Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes.
PubMed:Patent literature on mosquito repellent inventions which contain plant essential oils--a review.
PubMed:[Personal protection measures against blood-sucking insects and ticks].
PubMed:A new monoterpene acid from Marrubium vulgare with potential antihepatotoxic activity.
PubMed:Efficacy of four insect repellents against mosquito bites: a double-blind randomized placebo-controlled field study in Senegal.
PubMed:Efficacy and safety of catnip (Nepeta cataria) as a novel filth fly repellent.
PubMed:Dihydronepetalactones deter feeding activity by mosquitoes, stable flies, and deer ticks.
PubMed:Percutaneous absorption of an insect repellent p-menthane-3,8-DIOL: a model for human dermal absorption.
PubMed:Effective insect repellent formulation in both surfactantless and classical microemulsions with a long-lasting protection for human beings.
PubMed:Citrus essential oils and four enantiomeric pinenes against Culex pipiens (Diptera: Culicidae).
PubMed:Stereoselective synthesis of (+)-euphococcinine and (-)-adaline.
PubMed:Acaricidal effects of Corymbia citriodora oil containing para-menthane-3,8-diol against nymphs of Ixodes ricinus (Acari: Ixodidae).
PubMed:Organometallic and conjugated organic polymers held together by strong electrostatic interactions to form luminescent hybrid materials.
PubMed:Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3.
PubMed:Four new terpenoids from the roots of Ligularia narynensis.
PubMed:Metabolites from the endophytic fungus Phomopsis sp. PSU-D15.
PubMed:Cr(III), Fe(III) and Co(III) complexes of tetradentate (ONNO) Schiff base ligands: synthesis, characterization, properties and biological activity.
PubMed:Field evaluation of traditionally used plant-based insect repellents and fumigants against the malaria vector Anopheles darlingi in Riberalta, Bolivian Amazon.
PubMed:A low-cost repellent for malaria vectors in the Americas: results of two field trials in Guatemala and Peru.
PubMed:Repellency of MyggA Natural spray (para-menthane-3,8-diol) and RB86 (neem oil) against the tick Ixodes ricinus (Acari: Ixodidae) in the field in east-central Sweden.
PubMed:PMD, a registered botanical mosquito repellent with deet-like efficacy.
PubMed:[Studies on chemical constituents in spikes of Schizonepeta tenuifolia].
PubMed:Repellency of oils of lemon eucalyptus, geranium, and lavender and the mosquito repellent MyggA natural to Ixodes ricinus (Acari: Ixodidae) in the laboratory and field.
PubMed:New constituents from the heartwood of Picea morrisonicola HAYATA.
PubMed:Efficacy of repellent products against caged and free flying Anopheles stephensi mosquitoes.
PubMed:Solution and solid-state properties of luminescent M-M bond-containing coordination/organometallic polymers using the RNC-M2(dppm)2-CNR building blocks (M = Pd, Pt; R = Aryl, Alkyl).
PubMed:[Extraction and determination of volatile constituents in leaves of Eucalyptus citriodora].
PubMed:Stereocontrolled formation of amino acids and N-heterocycles bearing a quaternary chiral carbon.
PubMed:Laboratory and field tests of the effectiveness of the lemon-eucalyptus extract, Citridiol, as a repellent against land leeches of the genus Haemadipsa (Haemadipsidae).
PubMed:Sterically biased 3,3-sigmatropic rearrangement of azides: efficient preparation of nonracemic alpha-amino acids and heterocycles.
PubMed:Validation of quantitative NMR.
PubMed:Stereoselective synthesis of cis-p-menth-8-ene-1,7-diol, cis-p-menthane-1,7-diol, and cis-p-menthane-1,7,8-triol.
PubMed:Monoterpene metabolism. Cloning, expression, and characterization of (-)-isopiperitenol/(-)-carveol dehydrogenase of peppermint and spearmint.
PubMed:Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase.
PubMed:p-Menthane-3-carboxaldehyde: a useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity.
PubMed:A very large Rh-Rh bond shortening on excitation of the [Rh2(1,8-diisocyano-p-menthane)4]2+ ion by time-resolved synchrotron X-ray diffraction.
PubMed:Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochierotatus triseriatus (Diptera: Culicidae).
PubMed:Mixed-ligand organometallic polymers containing the "Pd(2)(dmb)2(2+)" fragment: properties of the [Pd2(dmb)2(diphos)2+](n) polymers/oligomers in solution and in the solid state.
PubMed:Enhancement effect of p-menthane-3,8-diol on in vitro permeation of antipyrine and indomethacin through Yucatan micropig skin.
PubMed:Preparation and solid-state characterization of mixed-ligand coordination/organometallic oligomers and polymers of copper(I) and silver(I) using diphosphine and mono- and diisocyanide ligands.
PubMed:Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.
PubMed:Organometallic oligomers based on 1,8-Diisocyano-p-menthane (dmb): syntheses and characterization of the [[M(diphos)(dmb)]BF4]n and [[Pd2(diphos)2(dmb)](ClO4)2]n materials (M = Cu, Ag; diphos = dppe, dppp).
PubMed:Polyoxygenated eudesmanes and trans-chrysanthemanes from the aerial parts of Santolina insularis.
PubMed:Molecular evaluation of a spearmint mutant altered in the expression of limonene hydroxylases that direct essential oil monoterpene biosynthesis.
PubMed:Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations.
PubMed:Use of repellents as prophylactic agents.
PubMed:Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and deet to black salt marsh mosquitoes (Diptera: Culicidae) in the Everglades National Park.
PubMed:Trypanocidal terpenoids from Laurus nobilis L.
PubMed:Repellent activities of stereoisomers of p-menthane-3,8-diols against Anopheles gambiae (Diptera: Culicidae).
PubMed:Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.
PubMed:Characterization of the [Ag(dmb)(2)(+)](n) oligomers (dmb = 1,8-diisocyano-p-menthane) in solution.
PubMed:Preparation, Spectroscopic Characterization, and Frontier MO Study of the Heteronuclear Luminescent [Pt(2)Au(2)(dmb)(2)(PPh(3))(4)](PF(6))(2) Cluster (dmb = 1,8-Diisocyano-p-menthane). A Cluster with a Formal Au(0)-Au(0) Bond Encapsulated inside a "Pt(2)(dmb)(2)(2+) " Fragment.
PubMed:Preparation, Spectroscopic Characterization, and Theoretical Study of the [Pd(4)(dmb)(4)(PPh(3))(2)]Cl(2) Complex (dmb = 1,8-Diisocyano-p-menthane) and Its Organometallic Polymer {[Pd(4)(dmb)(5)](CH(3)CO(2))(2)}(n)(): The First Examples of 58-Electron Linear Pd(4) Clusters.
PubMed:Chemistry of the Ag(2)(dmb)(2)(2+) Template (dmb = 1,8-Diisocyano-p-menthane). Preparation, Characterization, and X-ray Structures of the Ag(2)(dmb)(2)Y(2) Dimers (Y = NO(3)(-), ClO(4)(-), CH(3)CO(2)(-)) and the Paramagnetic [Ag(4)(dmb)(4)(TCNQ)(3)]TCNQ Complex (TCNQ = 7,7,8,8-Tetracyanoquinodimethane).
PubMed:Preparation, Characterization, and Luminescence Properties of a 58-Electron Linear Pt(4) Cluster, [Pt(4)(dmb)(4)(PPh(3))(2)](2+) (dmb = 1,8-Diisocyano-p-menthane), and Its Diphosphine Polymers.
PubMed:Calculated and experimental NMR chemical shifts of p-menthane-3,9-diols. A combination of molecular dynamics and quantum mechanics to determine the structure and the solvent effects.
PubMed:Preparation and characterization of [[M(dmb)2]TCNQ.xTCNQo]n polymers (M=Cu,Ag; dmb = 1,8-diisocyano-p-menthane; x = 0, 0.5, 1.0, 1.5; TCNQ = 7,7,8,8-tetracyano-p-quinodimethane) and design of new semi- and photoconducting organometallic materials.
PubMed:Efficacy of three insect repellents against the malaria vector Anopheles arabiensis.
PubMed:Suppression of the furylfuramide-induced SOS response by monoterpenoids with a p-menthane skeleton using the Salmonella typhimurium TA1535/pSK1002 Umu test.
PubMed:A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase.
PubMed:Induction of hepatic CYP2B1/2 by a teratogenic compound cis-1-[-4-(p-menthane-8-yloxy)phenyl]piperadine (YM9429) in rats.
PubMed:Flavonoids and terpenoids from Luma gayana (Barn.) Burret.
PubMed:Chemoenzymatic synthesis of homochiral (R)- and (S)-karahanaenol from (R)-limonene.
PubMed:Percutaneous absorption of disopyramide, lidocaine and trimecaine.
PubMed:Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase.
PubMed:Plant compounds that induce polychlorinated biphenyl biodegradation by Arthrobacter sp. strain B1B.
PubMed:Inhibition of insulin-induced chondrogenic differentiation of embryonic carcinoma cells by a teratogenic compound YM9429.
PubMed:Evaluation of a eucalyptus-based repellent against Anopheles spp. in Tanzania.
PubMed:In vitro assessment of teratogenic potential of cis-1-[4-(p-menthane-8-yloxy) phenyl]piperidine [corrected].
PubMed:Effects of pindobind 5-hydroxytryptamine1A (5-HT1A), a novel and potent 5-HT1A antagonist, on social and agonistic behaviour in male albino mice.
PubMed:A new potent teratogen in CD rats inducing cleft palate.
PubMed:Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene.
PubMed:beta(1)-Adrenergic and D(1) Dopaminergic Receptors in Human Neurotumor Cells: Differences in Spare Receptors and Desensitization of Adenylyl Cyclase.
PubMed:Characterization and mechanism of (4S)-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita).
PubMed:Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita) and spearmint (Mentha spicata).
PubMed:[New monoterpenoids from Cynanchum hancockianum].
PubMed:Metabolism of monoterpenes in mint (mentha) species.
PubMed:Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content.
PubMed:Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes.
PubMed:Effect of limonene and related compounds on the percutaneous absorption of indomethacin.
PubMed:Persistent beta-adrenoceptor blockade with alkylating pindolol (BIM) in guinea-pig left atria and trachea.
PubMed:Studies on the metabolism of l-menthol in rats.
PubMed:Characterization of a bromoacetylated derivative of pindolol as a high affinity, irreversible beta adrenergic antagonist in cultured cells.
PubMed:Synthesis of p-menthane derivatives with potential biological activity.
PubMed:A bromoacetylated analogue of cyanopindolol: an irreversible antagonist at rat beta-adrenoceptors.
PubMed:Affinity labels for beta-adrenoceptors: preparation and properties of alkylating beta-blockers derived from indole.
PubMed:Alkylating beta-blockers: activity of isomeric bromoacetyl alprenolol menthanes.
PubMed:Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.
PubMed:Purification and characterization of selenium-glutathione peroxidase from hamster liver.
PubMed:Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species.
PubMed:Synthesis of glycols by microbial transformation of some monocyclic terpenes.
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