(1S,5S)-2-methylidene-5-propan-2-ylcyclohex-3-en-1-ol

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  • Identifiers

    CAS number
    95259-30-6

    Molecular formula
    C10H16O

    SMILES
    CC(C)[C@@H]1C[C@@H](C(=C)C=C1)O

  • Odor profile

    Herbal 71.18%
    Mint 67.62%
    Spicy 62.54%
    Woody 54.47%
    Camphoreous 47.84%
    Cooling 44.98%
    Green 38.41%
    Fresh 32.56%
    Sweet 31.28%
    Earthy 30.95%

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  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    231°C

    Flash point est.
    92.63 ˚C

  • Applications

    The applications of (1R,5S)-2-Methylene-5-(1-methylethyl)-3-cyclohexen-1-ol (CAS 95259-30-6) center on its behavior as a monoterpenoid alcohol: used as a fragrance modifier in perfumery and flavors with minty, herbal, terpenic facets at low dosage; employed as a valuable intermediate en route to pulegone, menthone, and especially menthol via chemical or biotransformation; utilized as a substrate/analytical standard in studies of cytochrome P450s (e.g., limonene-3-hydroxylase) and in developing biocatalytic processes from limonene; leveraged as a chiral building block for asymmetric synthesis and derivatization (esters, carbonates, epoxides), including slow-release pro-fragrances; applied as a reference in chiral GC; and explored in mint–herbal flavor prototypes for foods/beverages and oral care, as well as in research-scale screening of insect-related olfactory bioactivity.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 163.95
    methanol 80.56
    isopropanol 186.55
    water 0.34
    ethyl acetate 96.7
    n-propanol 166.02
    acetone 89.98
    n-butanol 166.22
    acetonitrile 93.83
    DMF 94.09
    toluene 78.7
    isobutanol 118.08
    1,4-dioxane 242.88
    methyl acetate 99.18
    THF 308.41
    2-butanone 127.48
    n-pentanol 93.99
    sec-butanol 142.46
    n-hexane 15.72
    ethylene glycol 17.76
    NMP 67.54
    cyclohexane 28.09
    DMSO 92.79
    n-butyl acetate 137.91
    n-octanol 85.84
    chloroform 248.09
    n-propyl acetate 60.29
    acetic acid 60.62
    dichloromethane 170.42
    cyclohexanone 136.15
    propylene glycol 42.85
    isopropyl acetate 57.54
    DMAc 95.45
    2-ethoxyethanol 88.42
    isopentanol 131.41
    n-heptane 27.17
    ethyl formate 59.64
    1,2-dichloroethane 91.32
    n-hexanol 212.88
    2-methoxyethanol 142.03
    isobutyl acetate 47.81
    tetrachloromethane 46.08
    n-pentyl acetate 67.5
    transcutol 331.75
    n-heptanol 90.4
    ethylbenzene 46.86
    MIBK 62.94
    2-propoxyethanol 185.09
    tert-butanol 198.28
    MTBE 130.37
    2-butoxyethanol 110.09
    propionic acid 64.8
    o-xylene 53.45
    formic acid 14.85
    diethyl ether 117.28
    m-xylene 61.05
    p-xylene 58.33
    chlorobenzene 72.85
    dimethyl carbonate 21.59
    n-octane 11.11
    formamide 23.79
    cyclopentanone 136.82
    2-pentanone 96.22
    anisole 76.07
    cyclopentyl methyl ether 97.95
    gamma-butyrolactone 118.15
    1-methoxy-2-propanol 142.6
    pyridine 162.8
    3-pentanone 63.43
    furfural 110.87
    n-dodecane 9.3
    diethylene glycol 99.96
    diisopropyl ether 37.7
    tert-amyl alcohol 135.26
    acetylacetone 69.05
    n-hexadecane 10.57
    acetophenone 63.13
    methyl propionate 62.76
    isopentyl acetate 118.12
    trichloroethylene 169.98
    n-nonanol 72.85
    cyclohexanol 101.69
    benzyl alcohol 63.55
    2-ethylhexanol 114.37
    isooctanol 70.35
    dipropyl ether 108.05
    1,2-dichlorobenzene 59.91
    ethyl lactate 35.06
    propylene carbonate 77.09
    n-methylformamide 45.53
    2-pentanol 105.23
    n-pentane 19.03
    1-propoxy-2-propanol 170.04
    1-methoxy-2-propyl acetate 102.02
    2-(2-methoxypropoxy) propanol 103.76
    mesitylene 41.32
    ε-caprolactone 112.43
    p-cymene 50.97
    epichlorohydrin 157.66
    1,1,1-trichloroethane 115.05
    2-aminoethanol 50.64
    morpholine-4-carbaldehyde 115.7
    sulfolane 97.19
    2,2,4-trimethylpentane 12.57
    2-methyltetrahydrofuran 189.33
    n-hexyl acetate 96.76
    isooctane 13.92
    2-(2-butoxyethoxy)ethanol 141.01
    sec-butyl acetate 48.46
    tert-butyl acetate 67.65
    decalin 16.78
    glycerin 48.08
    diglyme 200.46
    acrylic acid 41.28
    isopropyl myristate 45.44
    n-butyric acid 113.65
    acetyl acetate 45.47
    di(2-ethylhexyl) phthalate 46.42
    ethyl propionate 49.07
    nitromethane 72.76
    1,2-diethoxyethane 129.91
    benzonitrile 84.7
    trioctyl phosphate 35.84
    1-bromopropane 100.5
    gamma-valerolactone 155.76
    n-decanol 54.64
    triethyl phosphate 38.09
    4-methyl-2-pentanol 69.4
    propionitrile 100.54
    vinylene carbonate 68.91
    1,1,2-trichlorotrifluoroethane 85.6
    DMS 50.4
    cumene 39.44
    2-octanol 60.64
    2-hexanone 71.41
    octyl acetate 55.34
    limonene 66.56
    1,2-dimethoxyethane 137.13
    ethyl orthosilicate 41.6
    tributyl phosphate 37.75
    diacetone alcohol 90.49
    N,N-dimethylaniline 55.54
    acrylonitrile 84.51
    aniline 82.84
    1,3-propanediol 95.17
    bromobenzene 75.76
    dibromomethane 138.47
    1,1,2,2-tetrachloroethane 137.16
    2-methyl-cyclohexyl acetate 72.32
    tetrabutyl urea 46.97
    diisobutyl methanol 65.86
    2-phenylethanol 98.92
    styrene 51.02
    dioctyl adipate 55.95
    dimethyl sulfate 28.01
    ethyl butyrate 82.38
    methyl lactate 37.35
    butyl lactate 59.07
    diethyl carbonate 48.53
    propanediol butyl ether 99.96
    triethyl orthoformate 60.35
    p-tert-butyltoluene 51.87
    methyl 4-tert-butylbenzoate 75.44
    morpholine 258.88
    tert-butylamine 133.03
    n-dodecanol 43.63
    dimethoxymethane 86.64
    ethylene carbonate 59.88
    cyrene 67.97
    2-ethoxyethyl acetate 89.59
    2-ethylhexyl acetate 92.76
    1,2,4-trichlorobenzene 72.5
    4-methylpyridine 134.32
    dibutyl ether 74.83
    2,6-dimethyl-4-heptanol 65.86
    DEF 69.12
    dimethyl isosorbide 140.66
    tetrachloroethylene 86.23
    eugenol 73.72
    triacetin 71.56
    span 80 96.42
    1,4-butanediol 32.77
    1,1-dichloroethane 131.76
    2-methyl-1-pentanol 84.97
    methyl formate 31.86
    2-methyl-1-butanol 112.19
    n-decane 15.2
    butyronitrile 131.3
    3,7-dimethyl-1-octanol 79.63
    1-chlorooctane 48.64
    1-chlorotetradecane 21.17
    n-nonane 14.15
    undecane 11.66
    tert-butylcyclohexane 17.91
    cyclooctane 12.07
    cyclopentanol 100.63
    tetrahydropyran 230.99
    tert-amyl methyl ether 79.68
    2,5,8-trioxanonane 143.15
    1-hexene 55.89
    2-isopropoxyethanol 76.42
    2,2,2-trifluoroethanol 19.09
    methyl butyrate 62.83

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1 3

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
Eucalyptus globulus (Spain) 2a old leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.67%
Eucalyptus globulus (Spain) 2b young leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.01%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.19%
Eucalyptus globulus (Yugoslavia) 1c branches 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.09%
Cymbopogon giganteus (Mali) Cymbopogon giganteus (Hochst.) Chiov., fam. Poaceae (Gramineae) 20.0%