Isoterpinolene

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  • Identifiers

    CAS number
    586-63-0

    Molecular formula
    C10H16

    SMILES
    CC1CCC(=C(C)C)C=C1

    Retention indicies (RI)

    • DB5: 1144.0

  • Odor profile

    Woody 73.6%
    Herbal 73.49%
    Citrus 71.65%
    Spicy 66.76%
    Terpenic 64.65%
    Lemon 59.09%
    Fresh 53.46%
    Pine 48.38%
    Sweet 46.36%
    Camphoreous 40.49%

    Scent© AI

  • Properties

    XLogP3-AA
    3.5

    Molecular weight
    136.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    172°C

    Flash point est.
    51.87 ˚C

  • Synonyms

    • Isoterpinolene
    • 586-63-0
    • p-Mentha-2,4(8)-diene
    • Cyclohexene, 3-methyl-6-(1-methylethylidene)-
    • 3-Methyl-6-(1-methylethylidene)cyclohexene
    • 2,4(8)-p-Menthadiene
    • 3-methyl-6-propan-2-ylidenecyclohexene
    • VR4XVW6V2H
    • EINECS 209-579-6
    • p-2,4(8)-Menthadiene
    • para-Mentha-2,4(8)-diene
    • CHEBI:88840
    • DTXSID80862244
    • 3-Isopropylidene-6-methyl-cyclohexene
    • 3-Methyl-6-(1-methylethylidene)-cyclohexene
    • UNII-VR4XVW6V2H
    • DTXCID60811038
    • 3-methyl-6-(propan-2-ylidene)cyclohexene
    • NS00042611
    • 3-Methyl-6-(1-methylethylidene)-1-cyclohexene #
    • 3-METHYL-6-(PROPAN-2-YLIDENE)CYCLOHEX-1-ENE
    • Q24514387
    • 209-579-6

  • Applications

    Isoterpinolene (CAS 586-63-0) is a fragrant monoterpene hydrocarbon with a fresh woody–pine, slightly citrusy and herbal odor, used to brighten and boost top notes and control evaporation in fine fragrances, soaps, shampoos, detergents, air-care sprays and candles; employed at trace levels as a flavor modifier for citrus, apple, herbal and spice profiles (use in foods depends on local regulations); leveraged as a natural-origin odorant in outdoor repellant/masking blends; used as a chemical intermediate en route to terpineols, carveol/carvone, epoxides and other p-menthane derivatives, and in R&D for essential-oil fingerprinting; sometimes considered a pleasant bio-based solvent/diluent for specialty cleaning and adhesive-removal systems; in formulations it is typically stabilized against oxidation to minimize peroxide formation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 157.85
    methanol 56.92
    isopropanol 148.1
    water 0.03
    ethyl acetate 359.59
    n-propanol 154.47
    acetone 200.71
    n-butanol 212.13
    acetonitrile 172.43
    DMF 102.19
    toluene 485.63
    isobutanol 118.63
    1,4-dioxane 634.97
    methyl acetate 214.84
    THF 1004.67
    2-butanone 302.17
    n-pentanol 145.29
    sec-butanol 168.8
    n-hexane 288.91
    ethylene glycol 6.68
    NMP 154.38
    cyclohexane 413.17
    DMSO 111.17
    n-butyl acetate 818.57
    n-octanol 194.56
    chloroform 713.34
    n-propyl acetate 204.78
    acetic acid 63.64
    dichloromethane 617.52
    cyclohexanone 436.8
    propylene glycol 20.26
    isopropyl acetate 254.41
    DMAc 137.85
    2-ethoxyethanol 100.48
    isopentanol 191.63
    n-heptane 554.79
    ethyl formate 116.42
    1,2-dichloroethane 348.71
    n-hexanol 527.68
    2-methoxyethanol 126.98
    isobutyl acetate 169.09
    tetrachloromethane 196.23
    n-pentyl acetate 259.43
    transcutol 662.5
    n-heptanol 178.97
    ethylbenzene 223.45
    MIBK 227.57
    2-propoxyethanol 333.38
    tert-butanol 216.65
    MTBE 450.66
    2-butoxyethanol 171.18
    propionic acid 71.22
    o-xylene 232.55
    formic acid 6.72
    diethyl ether 627.19
    m-xylene 290.83
    p-xylene 246.79
    chlorobenzene 318.65
    dimethyl carbonate 47.97
    n-octane 125.33
    formamide 13.5
    cyclopentanone 374.3
    2-pentanone 314.35
    anisole 272.41
    cyclopentyl methyl ether 514.94
    gamma-butyrolactone 264.82
    1-methoxy-2-propanol 146.95
    pyridine 525.57
    3-pentanone 249.21
    furfural 191.57
    n-dodecane 70.37
    diethylene glycol 86.52
    diisopropyl ether 239.6
    tert-amyl alcohol 209.05
    acetylacetone 219.47
    n-hexadecane 81.64
    acetophenone 179.77
    methyl propionate 180.77
    isopentyl acetate 575.78
    trichloroethylene 497.41
    n-nonanol 188.19
    cyclohexanol 235.06
    benzyl alcohol 109.9
    2-ethylhexanol 447.8
    isooctanol 146.29
    dipropyl ether 914.57
    1,2-dichlorobenzene 245.33
    ethyl lactate 52.64
    propylene carbonate 188.1
    n-methylformamide 37.21
    2-pentanol 187.45
    n-pentane 241.15
    1-propoxy-2-propanol 352.54
    1-methoxy-2-propyl acetate 378.54
    2-(2-methoxypropoxy) propanol 221.59
    mesitylene 181.44
    ε-caprolactone 348.07
    p-cymene 262.72
    epichlorohydrin 371.41
    1,1,1-trichloroethane 452.83
    2-aminoethanol 24.17
    morpholine-4-carbaldehyde 202.46
    sulfolane 210.63
    2,2,4-trimethylpentane 81.99
    2-methyltetrahydrofuran 827.2
    n-hexyl acetate 382.39
    isooctane 83.29
    2-(2-butoxyethoxy)ethanol 282.12
    sec-butyl acetate 180.96
    tert-butyl acetate 280.19
    decalin 139.43
    glycerin 21.71
    diglyme 473.89
    acrylic acid 40.26
    isopropyl myristate 189.41
    n-butyric acid 187.53
    acetyl acetate 179.64
    di(2-ethylhexyl) phthalate 129.18
    ethyl propionate 190.72
    nitromethane 91.71
    1,2-diethoxyethane 648.27
    benzonitrile 211.79
    trioctyl phosphate 92.01
    1-bromopropane 586.11
    gamma-valerolactone 328.99
    n-decanol 149.46
    triethyl phosphate 136.15
    4-methyl-2-pentanol 129.32
    propionitrile 213.57
    vinylene carbonate 140.21
    1,1,2-trichlorotrifluoroethane 118.98
    DMS 153.23
    cumene 152.21
    2-octanol 134.23
    2-hexanone 262.73
    octyl acetate 221.57
    limonene 443.09
    1,2-dimethoxyethane 331.15
    ethyl orthosilicate 161.69
    tributyl phosphate 115.21
    diacetone alcohol 172.36
    N,N-dimethylaniline 183.57
    acrylonitrile 138.35
    aniline 222.14
    1,3-propanediol 55.51
    bromobenzene 421.48
    dibromomethane 572.76
    1,1,2,2-tetrachloroethane 391.42
    2-methyl-cyclohexyl acetate 303.94
    tetrabutyl urea 149.98
    diisobutyl methanol 235.15
    2-phenylethanol 243.33
    styrene 258.26
    dioctyl adipate 204.47
    dimethyl sulfate 50.76
    ethyl butyrate 480.75
    methyl lactate 42.31
    butyl lactate 112.16
    diethyl carbonate 225.65
    propanediol butyl ether 104.19
    triethyl orthoformate 302.28
    p-tert-butyltoluene 259.54
    methyl 4-tert-butylbenzoate 202.52
    morpholine 598.44
    tert-butylamine 222.28
    n-dodecanol 123.86
    dimethoxymethane 176.22
    ethylene carbonate 137.49
    cyrene 111.08
    2-ethoxyethyl acetate 280.34
    2-ethylhexyl acetate 564.46
    1,2,4-trichlorobenzene 266.17
    4-methylpyridine 479.43
    dibutyl ether 526.8
    2,6-dimethyl-4-heptanol 235.15
    DEF 232.35
    dimethyl isosorbide 387.61
    tetrachloroethylene 244.14
    eugenol 139.75
    triacetin 201.82
    span 80 214.31
    1,4-butanediol 19.33
    1,1-dichloroethane 396.22
    2-methyl-1-pentanol 159.0
    methyl formate 29.15
    2-methyl-1-butanol 170.45
    n-decane 126.03
    butyronitrile 315.2
    3,7-dimethyl-1-octanol 219.97
    1-chlorooctane 272.58
    1-chlorotetradecane 114.63
    n-nonane 140.61
    undecane 89.54
    tert-butylcyclohexane 125.61
    cyclooctane 196.6
    cyclopentanol 170.94
    tetrahydropyran 1001.67
    tert-amyl methyl ether 328.16
    2,5,8-trioxanonane 349.99
    1-hexene 524.43
    2-isopropoxyethanol 99.75
    2,2,2-trifluoroethanol 14.15
    methyl butyrate 215.12

    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
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.04%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 1.5%
Parsley herb (Egypt) 1 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.6%
Sequoia leaf 1 Sequoiadendron giganteum Buchh., fam. Taxodiaceae 0.01%
Santolina chamaecyparisus (France) 2 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.04%
Parsley leaf (Korea) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (C. sativum Hoffm.), fam. Apiaceae 0.06%
Celery plant 8015-90-5 Apium graveolens L. var. dulce, fam. Apiaceae (Umbelliferae) 0.01%
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 2.9%
Gingergrass (India) 5 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 2.78%
Pepper, black (variety Muntok) 8006-82-4 Piper nigrum L., variety Muntok, fam. Piperaceae 0.5%
Fitweed seed Eryngium foetidum L., fam. Apiaceae (Umbelliferae) 0.27%
Parsley herb (Cuba) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.03%
Pistacia lentiscus (Spain) 3 whole plant 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.3%
Eucalyptus globulus (Spain) 2a old leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.01%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.02%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.05%
Prostanthera staurophylla Prostanthera staurophylla F. Muell., fam. Lamiaceae (Labiatae) 0.4%
Zataria multiflora (Iran) 1a bud Zataria multiflora Boiss., fam. Lamiaceae (Labiatae) 1.79%
Zataria multiflora (Iran) 1b flower Zataria multiflora Boiss., fam. Lamiaceae (Labiatae) 1.05%
Zataria multiflora (Iran) 2 flowering tops Zataria multiflora Boiss., fam. Lamiaceae (Labiatae) 0.15%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.1%