Cyclohexane, 1-methylene-4-(1-methylethenyl)-

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  • Identifiers

    CAS number
    499-97-8

    Molecular formula
    C10H16

    SMILES
    CC(=C)C1CCC(=C)CC1

    Retention indicies (RI)

    • DB5: 1005.5
    • Carbowax: 1171.0

  • Odor profile

    Herbal 65.67%
    Citrus 63.54%
    Woody 58.39%
    Terpenic 57.26%
    Spicy 48.62%
    Sweet 47.06%
    Mint 45.75%
    Fresh 45.62%
    Lemon 42.7%
    Pine 41.88%

    Scent© AI

  • Properties

    XLogP3-AA
    3.6

    Molecular weight
    136.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    177°C

    Flash point est.
    49.62 ˚C

  • Synonyms

    • p-Mentha-1(7),8-diene
    • 499-97-8
    • 1-Methylene-4-(1-methylvinyl)cyclohexane
    • Pseudolimonene
    • Cyclohexane, 1-methylene-4-(1-methylethenyl)-
    • 1-methylene-4-(1-methylethenyl)cyclohexane
    • EINECS 207-895-9
    • Pseudolimonen
    • pseudo-limonene
    • p-Menthadien
    • 1-methylidene-4-prop-1-en-2-ylcyclohexane
    • .psi.-Limonene
    • 1(7),8-p-Menthadiene
    • 1(7), 8-p-Menthadiene
    • BM3287QA6N
    • trans-p-mentha-1(7),8-diene
    • DTXSID40198152
    • PARA-MENTA-1(7),8-DIENE
    • AKOS015906577
    • 1-Isopropenyl-4-methylenecyclohexane #
    • NS00031989
    • Q63393473

  • Applications

    Cyclohexane, 1-methylene-4-(1-methylethenyl)- (CAS 499-97-8) is an unsaturated monoterpene hydrocarbon occurring in certain essential oils and is used primarily as a fragrance ingredient providing fresh terpenic, citrusy, pine–herbal notes in fine fragrances, household cleaners, deodorizers, and candles; as a trace flavor modifier in foods/beverages where permitted; as a low-polarity solvent/diluent for volatile actives; and as a synthetic intermediate that can be epoxidized, hydroperoxidized, hydrogenated or hydrated to yield terpene derivatives such as epoxides, terpene alcohols (e.g., terpineol) or p-menthane, as well as a feedstock for cationic polymerization to produce terpene resins; it is also used as a GC–MS reference/standard and as a model compound in atmospheric chemistry to probe ozonolysis/OH oxidation of monoterpenes, and is being explored as a fragrance carrier/precursor in personal-care formulations, with attention to flammability, oxidative stability, and potential skin sensitization during formulation and storage.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 514.54
    methanol 252.86
    isopropanol 383.19
    water 0.05
    ethyl acetate 1064.97
    n-propanol 440.83
    acetone 501.76
    n-butanol 536.0
    acetonitrile 460.4
    DMF 249.94
    toluene 840.36
    isobutanol 257.12
    1,4-dioxane 1901.96
    methyl acetate 535.89
    THF 2984.61
    2-butanone 614.48
    n-pentanol 304.03
    sec-butanol 368.46
    n-hexane 292.41
    ethylene glycol 16.43
    NMP 273.52
    cyclohexane 591.27
    DMSO 265.21
    n-butyl acetate 1799.82
    n-octanol 251.93
    chloroform 1630.91
    n-propyl acetate 467.95
    acetic acid 191.65
    dichloromethane 1543.66
    cyclohexanone 875.37
    propylene glycol 46.88
    isopropyl acetate 684.2
    DMAc 235.51
    2-ethoxyethanol 270.58
    isopentanol 408.47
    n-heptane 718.02
    ethyl formate 372.36
    1,2-dichloroethane 870.85
    n-hexanol 939.24
    2-methoxyethanol 443.64
    isobutyl acetate 315.89
    tetrachloromethane 335.15
    n-pentyl acetate 438.63
    transcutol 1610.63
    n-heptanol 268.97
    ethylbenzene 285.39
    MIBK 411.51
    2-propoxyethanol 844.01
    tert-butanol 490.92
    MTBE 884.91
    2-butoxyethanol 319.77
    propionic acid 178.77
    o-xylene 295.03
    formic acid 26.37
    diethyl ether 1561.8
    m-xylene 399.78
    p-xylene 303.46
    chlorobenzene 568.25
    dimethyl carbonate 110.06
    n-octane 131.91
    formamide 54.12
    cyclopentanone 805.12
    2-pentanone 685.81
    anisole 423.57
    cyclopentyl methyl ether 1114.13
    gamma-butyrolactone 694.87
    1-methoxy-2-propanol 399.91
    pyridine 1294.87
    3-pentanone 457.86
    furfural 504.06
    n-dodecane 63.65
    diethylene glycol 222.24
    diisopropyl ether 442.13
    tert-amyl alcohol 368.27
    acetylacetone 554.83
    n-hexadecane 75.56
    acetophenone 272.31
    methyl propionate 435.37
    isopentyl acetate 1182.83
    trichloroethylene 1173.8
    n-nonanol 257.97
    cyclohexanol 450.97
    benzyl alcohol 189.61
    2-ethylhexanol 721.2
    isooctanol 199.77
    dipropyl ether 2004.54
    1,2-dichlorobenzene 397.43
    ethyl lactate 93.5
    propylene carbonate 479.91
    n-methylformamide 129.8
    2-pentanol 371.67
    n-pentane 313.6
    1-propoxy-2-propanol 841.23
    1-methoxy-2-propyl acetate 977.98
    2-(2-methoxypropoxy) propanol 319.11
    mesitylene 221.71
    ε-caprolactone 722.58
    p-cymene 328.93
    epichlorohydrin 1017.3
    1,1,1-trichloroethane 855.51
    2-aminoethanol 72.58
    morpholine-4-carbaldehyde 494.14
    sulfolane 403.25
    2,2,4-trimethylpentane 83.69
    2-methyltetrahydrofuran 1983.88
    n-hexyl acetate 566.76
    isooctane 93.6
    2-(2-butoxyethoxy)ethanol 505.27
    sec-butyl acetate 354.57
    tert-butyl acetate 619.15
    decalin 142.52
    glycerin 50.55
    diglyme 996.87
    acrylic acid 97.1
    isopropyl myristate 255.95
    n-butyric acid 561.78
    acetyl acetate 475.45
    di(2-ethylhexyl) phthalate 163.42
    ethyl propionate 413.83
    nitromethane 291.2
    1,2-diethoxyethane 1739.93
    benzonitrile 398.19
    trioctyl phosphate 118.76
    1-bromopropane 1008.78
    gamma-valerolactone 835.09
    n-decanol 189.14
    triethyl phosphate 230.48
    4-methyl-2-pentanol 216.33
    propionitrile 521.01
    vinylene carbonate 355.4
    1,1,2-trichlorotrifluoroethane 267.6
    DMS 253.63
    cumene 157.43
    2-octanol 168.07
    2-hexanone 456.12
    octyl acetate 302.39
    limonene 605.99
    1,2-dimethoxyethane 880.31
    ethyl orthosilicate 259.38
    tributyl phosphate 169.53
    diacetone alcohol 357.43
    N,N-dimethylaniline 224.57
    acrylonitrile 345.84
    aniline 479.85
    1,3-propanediol 191.94
    bromobenzene 702.22
    dibromomethane 1244.74
    1,1,2,2-tetrachloroethane 861.64
    2-methyl-cyclohexyl acetate 494.96
    tetrabutyl urea 207.58
    diisobutyl methanol 386.24
    2-phenylethanol 419.97
    styrene 360.51
    dioctyl adipate 277.44
    dimethyl sulfate 90.77
    ethyl butyrate 1066.48
    methyl lactate 92.64
    butyl lactate 186.46
    diethyl carbonate 483.38
    propanediol butyl ether 170.37
    triethyl orthoformate 626.1
    p-tert-butyltoluene 329.07
    methyl 4-tert-butylbenzoate 244.8
    morpholine 1868.77
    tert-butylamine 450.46
    n-dodecanol 143.52
    dimethoxymethane 502.6
    ethylene carbonate 367.92
    cyrene 150.46
    2-ethoxyethyl acetate 543.59
    2-ethylhexyl acetate 1034.97
    1,2,4-trichlorobenzene 398.7
    4-methylpyridine 1016.72
    dibutyl ether 865.09
    2,6-dimethyl-4-heptanol 386.24
    DEF 536.37
    dimethyl isosorbide 633.73
    tetrachloroethylene 567.47
    eugenol 182.07
    triacetin 302.65
    span 80 308.33
    1,4-butanediol 43.72
    1,1-dichloroethane 901.14
    2-methyl-1-pentanol 262.0
    methyl formate 99.95
    2-methyl-1-butanol 325.66
    n-decane 127.71
    butyronitrile 781.78
    3,7-dimethyl-1-octanol 311.91
    1-chlorooctane 321.65
    1-chlorotetradecane 116.05
    n-nonane 137.9
    undecane 85.04
    tert-butylcyclohexane 124.66
    cyclooctane 215.51
    cyclopentanol 358.09
    tetrahydropyran 2465.34
    tert-amyl methyl ether 531.26
    2,5,8-trioxanonane 605.06
    1-hexene 667.96
    2-isopropoxyethanol 208.94
    2,2,2-trifluoroethanol 36.82
    methyl butyrate 476.41

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Calamintha nepeta (Turkey) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.03%
Salvia cryptantha (Turkey) Salvia cryptantha Montbret et Aucher ex Benth., fam. Lamiaceae (Labiatae) 0.3%
Pistacia vera fruit hull (Turkey) Pistacia vera L., fam. Anacardiaceae 0.01%
Mentha spicata (Cuba) Chemotype Mentha spicata L., fam. Lamiaceae (Labiatae) 0.1%
Rosemary (Japan) 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Lepechinia salviaefolia (Venezuela) Lepechinia salviaefolia (Kunth) Epl., fam. Lamiaceae (Labiatae) 1.2%
Ruta chalepensis (Greece) Ruta chalepensis L., fam. Rutaceae 0.05%
Angelica (sativa) fruit 8015-64-3 Angelica archangelica L. var. sativa, fam. Apiaceae (Umbelliferae) 1.3%
Argyranthemum adauctum ssp. adauctum Argyranthemum adauctum ssp.adauctum Humphries, fam.Asteraceae (Compositae) 1.0%
Argyranthemum adauctum ssp. gracile Argyranthemum adauctum ssp.gracile Humphries, fam. Asteraceae (Compositae) 0.01%