[4-(Prop-1-en-2-yl)cyclohexyl]methanol

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  • Identifiers

    CAS number
    18479-64-6

    Molecular formula
    C10H18O

    SMILES
    CC(=C)C1CCC(CC1)CO

    Retention indicies (RI)

    • Carbowax: 1978.0

  • Odor profile

    Floral 78.21%
    Herbal 60.36%
    Fresh 59.52%
    Citrus 53.06%
    Green 51.54%
    Clean 46.54%
    Rose 45.3%
    Woody 44.0%
    Sweet 42.44%
    Waxy 37.99%

    Scent© AI

  • Properties

    XLogP3-AA
    2.9

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    234°C

    Flash point est.
    100.36 ˚C

  • Synonyms

    • cis-isopulegone
    • trans-Shisool
    • (4-prop-1-en-2-ylcyclohexyl)methanol
    • [4-(prop-1-en-2-yl)cyclohexyl]methanol
    • 18479-64-6
    • 22521-57-9
    • Shisool
    • cis-p-Menth-8-en-7-ol
    • trans-p-Menth-8-en-7-ol
    • SCHEMBL3129182
    • SCHEMBL6756040
    • SCHEMBL10886649
    • SCHEMBL18071864
    • (4-Isopropenylcyclohexyl)methanol
    • GMYHXOPIKMGWOM-AOOOYVTPSA-N
    • GMYHXOPIKMGWOM-MGCOHNPYSA-N
    • GMYHXOPIKMGWOM-OKXAEBFBSA-N
    • DTXSID501268224
    • cis-4-isopropenyl-cyclohexylmethanol
    • (4-Isopropenylcyclohexyl)methanol #
    • cis-4-(1-Methylethenyl)cyclohexanemethanol
    • DS-018457

  • Applications

    [4-(Prop-1-en-2-yl)cyclohexyl]methanol (CAS 18479-64-6) is a terpenoid-like primary alcohol with a terminal double bond, commonly leveraged as a versatile intermediate: esterification to fragrance esters (acetates/propionates) for perfumery and personal care; functionalization (acrylation, ethoxylation, urethane formation) to prepare reactive diluents or chain extenders for UV/PU/epoxy coatings, inks and resins, enhancing hydrophobicity and durability; double-bond transformations (oxidation/reduction, hydroboration–oxidation, epoxidation, hydrosilylation) to build derivative libraries for medicinal and agrochemical discovery while tuning lipophilicity and membrane permeability; as a precursor to specialty surfactants, plasticizers and lubricant additives; and as a reference/internal standard in GC/LC of terpenic alcohols as well as a convenient building block for academic organic synthesis.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6558.63
    methanol 6907.38
    isopropanol 5483.11
    water 1.68
    ethyl acetate 5433.53
    n-propanol 5962.18
    acetone 5852.76
    n-butanol 5695.49
    acetonitrile 4971.8
    DMF 3341.47
    toluene 1340.38
    isobutanol 3575.09
    1,4-dioxane 5935.0
    methyl acetate 3500.62
    THF 7673.62
    2-butanone 4406.36
    n-pentanol 2145.84
    sec-butanol 3699.67
    n-hexane 324.29
    ethylene glycol 570.7
    NMP 1702.76
    cyclohexane 545.08
    DMSO 4223.95
    n-butyl acetate 3536.03
    n-octanol 543.53
    chloroform 5921.4
    n-propyl acetate 2279.05
    acetic acid 3491.95
    dichloromethane 4467.88
    cyclohexanone 3795.14
    propylene glycol 1012.27
    isopropyl acetate 2668.79
    DMAc 1319.27
    2-ethoxyethanol 2551.75
    isopentanol 3930.64
    n-heptane 203.42
    ethyl formate 2648.6
    1,2-dichloroethane 3363.66
    n-hexanol 2592.75
    2-methoxyethanol 5701.23
    isobutyl acetate 952.93
    tetrachloromethane 1423.29
    n-pentyl acetate 1101.44
    transcutol 7794.37
    n-heptanol 737.75
    ethylbenzene 432.51
    MIBK 1696.06
    2-propoxyethanol 3605.48
    tert-butanol 6011.32
    MTBE 4746.55
    2-butoxyethanol 1436.79
    propionic acid 3041.24
    o-xylene 573.52
    formic acid 1091.39
    diethyl ether 5516.81
    m-xylene 739.32
    p-xylene 484.95
    chlorobenzene 1555.15
    dimethyl carbonate 655.92
    n-octane 46.06
    formamide 2185.9
    cyclopentanone 4132.53
    2-pentanone 3932.48
    anisole 1152.56
    cyclopentyl methyl ether 3200.71
    gamma-butyrolactone 4623.71
    1-methoxy-2-propanol 3766.12
    pyridine 3868.54
    3-pentanone 2235.69
    furfural 3069.35
    n-dodecane 20.32
    diethylene glycol 1743.05
    diisopropyl ether 1161.9
    tert-amyl alcohol 3267.38
    acetylacetone 2564.56
    n-hexadecane 24.29
    acetophenone 746.05
    methyl propionate 2767.05
    isopentyl acetate 2325.1
    trichloroethylene 5143.1
    n-nonanol 436.8
    cyclohexanol 2755.39
    benzyl alcohol 909.61
    2-ethylhexanol 1143.47
    isooctanol 537.11
    dipropyl ether 2010.19
    1,2-dichlorobenzene 1119.35
    ethyl lactate 551.26
    propylene carbonate 2098.15
    n-methylformamide 3969.55
    2-pentanol 3062.28
    n-pentane 438.06
    1-propoxy-2-propanol 2789.32
    1-methoxy-2-propyl acetate 2324.83
    2-(2-methoxypropoxy) propanol 816.4
    mesitylene 449.05
    ε-caprolactone 3018.05
    p-cymene 307.6
    epichlorohydrin 4838.25
    1,1,1-trichloroethane 3389.98
    2-aminoethanol 2012.17
    morpholine-4-carbaldehyde 2506.71
    sulfolane 3049.17
    2,2,4-trimethylpentane 143.08
    2-methyltetrahydrofuran 5198.17
    n-hexyl acetate 1173.17
    isooctane 153.65
    2-(2-butoxyethoxy)ethanol 1603.47
    sec-butyl acetate 1222.59
    tert-butyl acetate 2384.98
    decalin 129.14
    glycerin 1037.66
    diglyme 3273.45
    acrylic acid 1832.02
    isopropyl myristate 299.92
    n-butyric acid 5633.0
    acetyl acetate 1652.62
    di(2-ethylhexyl) phthalate 266.65
    ethyl propionate 1611.25
    nitromethane 5213.64
    1,2-diethoxyethane 3409.29
    benzonitrile 1463.04
    trioctyl phosphate 203.88
    1-bromopropane 2178.37
    gamma-valerolactone 4827.74
    n-decanol 278.24
    triethyl phosphate 397.7
    4-methyl-2-pentanol 1309.51
    propionitrile 3990.05
    vinylene carbonate 1793.45
    1,1,2-trichlorotrifluoroethane 2556.09
    DMS 642.24
    cumene 254.28
    2-octanol 419.35
    2-hexanone 1999.56
    octyl acetate 376.9
    limonene 536.15
    1,2-dimethoxyethane 4080.88
    ethyl orthosilicate 472.81
    tributyl phosphate 309.56
    diacetone alcohol 2123.18
    N,N-dimethylaniline 511.14
    acrylonitrile 3473.46
    aniline 2347.31
    1,3-propanediol 3659.26
    bromobenzene 1427.96
    dibromomethane 3203.85
    1,1,2,2-tetrachloroethane 3916.94
    2-methyl-cyclohexyl acetate 705.97
    tetrabutyl urea 312.5
    diisobutyl methanol 658.47
    2-phenylethanol 1112.58
    styrene 639.67
    dioctyl adipate 393.12
    dimethyl sulfate 693.06
    ethyl butyrate 1950.23
    methyl lactate 804.97
    butyl lactate 805.48
    diethyl carbonate 953.98
    propanediol butyl ether 1057.22
    triethyl orthoformate 1140.43
    p-tert-butyltoluene 317.47
    methyl 4-tert-butylbenzoate 568.32
    morpholine 7382.76
    tert-butylamine 3966.61
    n-dodecanol 184.17
    dimethoxymethane 2899.7
    ethylene carbonate 1742.7
    cyrene 505.82
    2-ethoxyethyl acetate 1509.29
    2-ethylhexyl acetate 1542.19
    1,2,4-trichlorobenzene 1250.15
    4-methylpyridine 3284.09
    dibutyl ether 1074.14
    2,6-dimethyl-4-heptanol 658.47
    DEF 2820.22
    dimethyl isosorbide 1226.94
    tetrachloroethylene 3059.77
    eugenol 533.99
    triacetin 715.4
    span 80 762.33
    1,4-butanediol 751.55
    1,1-dichloroethane 3987.34
    2-methyl-1-pentanol 1432.56
    methyl formate 2124.42
    2-methyl-1-butanol 3050.01
    n-decane 49.33
    butyronitrile 4211.33
    3,7-dimethyl-1-octanol 665.04
    1-chlorooctane 294.76
    1-chlorotetradecane 70.96
    n-nonane 52.23
    undecane 29.86
    tert-butylcyclohexane 136.0
    cyclooctane 139.4
    cyclopentanol 2625.97
    tetrahydropyran 6964.85
    tert-amyl methyl ether 2095.4
    2,5,8-trioxanonane 1465.22
    1-hexene 1138.03
    2-isopropoxyethanol 1510.36
    2,2,2-trifluoroethanol 810.04
    methyl butyrate 2209.19

    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
Perilla acuta 68132-21-8 Perilla acuta (Thunb.) Nakai & P. acuta Nakai forma viridis (Makino) Nakai 5.5%
Laser tribolum (Turkey) Laser tribolum (L.) Borkh. (Laserpitium t.L., Siler t.Crantz),fam.Apiaceae 0.23%
Nutmeg 5a 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 1.8%
Limnophila chinensis, aromatica Limnophila chinensis (Osb.) Merrill ssp. aromatica (Lam.) Yamazaki 0.65%