Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate

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  • Identifiers

    CAS number
    89-49-6

    Molecular formula
    C12H20O2

    SMILES
    CC1CCC(C(C1)OC(=O)C)C(=C)C

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1271.5
    • Carbowax: 1585.0

  • Odor profile

    Fruity 83.11%
    Green 74.83%
    Herbal 68.64%
    Sweet 67.38%
    Mint 66.8%
    Floral 62.15%
    Woody 62.03%
    Fresh 52.17%
    Spicy 44.69%
    Cooling 44.42%

    Scent© AI

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    8.73 (weak base)

    Molecular weight
    196.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    235°C

    Flash point est.
    99.97 ˚C

  • Synonyms

    • Isopulegol acetate
    • 89-49-6
    • p-Menth-8-en-3-yl acetate
    • Isopropenylcyclohexan-3-ol acetate
    • (5-methyl-2-prop-1-en-2-ylcyclohexyl) acetate
    • AI3-02180
    • 1-Methyl-4-isopropenylcyclohexan-3-yl acetate
    • 5-Methyl-2-(1-methylethenyl)cyclohexanol acetate
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl), acetate
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate
    • 2-Isopropenyl-5-methylcyclohexyl acetate
    • ISOPULEGOLACETATE
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate, [1R-(1.alpha.,2.beta.,5.alpha.)]-
    • neo-isopulegol acetate
    • neo-iso-isopulegol acetate
    • isopulegylacetat
    • NSC403868
    • 5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate
    • (-)-Isopulegyl acetate
    • SCHEMBL560314
    • DTXSID60861679
    • AKOS024286269
    • (2-isopropenyl-5-methyl-cyclohexyl) acetate
    • NS00012774
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate, (1R-(1alpha,2beta,5alpha))-
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate, {[1R-(1.alpha.,2.beta.,5.alpha.)]-}

  • Applications

    Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, acetate (CAS 89-49-6) is a monoterpene ester used mainly as a fragrance and flavor ingredient: it imparts minty–herbal–woody, slightly citrus facets and is employed in fine fragrances, soaps, detergents, fabric softeners, candles, and air-care/deodorizing products; in flavors it is blended to reinforce spearmint, caraway, herbal, and citrus notes in confectionery, chewing gum, beverages, and oral-care flavors; it also serves as a synthetic intermediate in aroma chemistry (amenable to hydrolysis/transformation to the corresponding alcohol and other monoterpene derivatives) and as a co-solvent/compatibilizer for fragrance oils in certain delivery systems.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1663.55
    methanol 2197.44
    isopropanol 1679.81
    water 2.2
    ethyl acetate 608.66
    n-propanol 1191.04
    acetone 940.24
    n-butanol 1116.12
    acetonitrile 812.8
    DMF 1063.71
    toluene 435.25
    isobutanol 906.21
    1,4-dioxane 1906.49
    methyl acetate 515.46
    THF 2338.18
    2-butanone 615.19
    n-pentanol 628.7
    sec-butanol 951.4
    n-hexane 62.52
    ethylene glycol 198.38
    NMP 759.63
    cyclohexane 176.32
    DMSO 899.0
    n-butyl acetate 577.2
    n-octanol 320.13
    chloroform 2776.18
    n-propyl acetate 347.8
    acetic acid 843.0
    dichloromethane 1998.56
    cyclohexanone 1153.71
    propylene glycol 437.5
    isopropyl acetate 403.7
    DMAc 545.42
    2-ethoxyethanol 481.05
    isopentanol 861.05
    n-heptane 49.71
    ethyl formate 553.32
    1,2-dichloroethane 843.39
    n-hexanol 871.72
    2-methoxyethanol 1095.97
    isobutyl acetate 257.27
    tetrachloromethane 267.26
    n-pentyl acetate 307.33
    transcutol 1691.94
    n-heptanol 288.97
    ethylbenzene 207.61
    MIBK 357.99
    2-propoxyethanol 876.19
    tert-butanol 1359.44
    MTBE 612.13
    2-butoxyethanol 420.02
    propionic acid 589.08
    o-xylene 251.08
    formic acid 274.12
    diethyl ether 572.64
    m-xylene 294.76
    p-xylene 291.51
    chlorobenzene 596.77
    dimethyl carbonate 150.14
    n-octane 20.2
    formamide 325.36
    cyclopentanone 1045.64
    2-pentanone 547.31
    anisole 387.21
    cyclopentyl methyl ether 669.15
    gamma-butyrolactone 1124.38
    1-methoxy-2-propanol 922.72
    pyridine 1059.16
    3-pentanone 282.53
    furfural 977.09
    n-dodecane 20.79
    diethylene glycol 562.25
    diisopropyl ether 155.88
    tert-amyl alcohol 802.41
    acetylacetone 534.2
    n-hexadecane 24.4
    acetophenone 322.15
    methyl propionate 353.18
    isopentyl acetate 512.45
    trichloroethylene 1622.59
    n-nonanol 256.32
    cyclohexanol 1003.43
    benzyl alcohol 428.76
    2-ethylhexanol 367.79
    isooctanol 222.91
    dipropyl ether 290.48
    1,2-dichlorobenzene 451.26
    ethyl lactate 177.93
    propylene carbonate 719.24
    n-methylformamide 578.17
    2-pentanol 626.21
    n-pentane 71.47
    1-propoxy-2-propanol 633.91
    1-methoxy-2-propyl acetate 482.27
    2-(2-methoxypropoxy) propanol 396.69
    mesitylene 170.74
    ε-caprolactone 875.18
    p-cymene 151.69
    epichlorohydrin 1262.1
    1,1,1-trichloroethane 853.67
    2-aminoethanol 516.49
    morpholine-4-carbaldehyde 931.29
    sulfolane 891.03
    2,2,4-trimethylpentane 38.46
    2-methyltetrahydrofuran 1368.44
    n-hexyl acetate 486.89
    isooctane 34.89
    2-(2-butoxyethoxy)ethanol 603.72
    sec-butyl acetate 232.91
    tert-butyl acetate 391.18
    decalin 60.04
    glycerin 426.25
    diglyme 900.29
    acrylic acid 404.58
    isopropyl myristate 176.18
    n-butyric acid 1015.14
    acetyl acetate 388.27
    di(2-ethylhexyl) phthalate 212.69
    ethyl propionate 259.58
    nitromethane 982.45
    1,2-diethoxyethane 519.59
    benzonitrile 642.11
    trioctyl phosphate 146.69
    1-bromopropane 597.65
    gamma-valerolactone 1409.18
    n-decanol 187.93
    triethyl phosphate 144.36
    4-methyl-2-pentanol 327.07
    propionitrile 646.87
    vinylene carbonate 672.28
    1,1,2-trichlorotrifluoroethane 706.25
    DMS 295.15
    cumene 146.18
    2-octanol 209.65
    2-hexanone 369.28
    octyl acetate 233.14
    limonene 239.96
    1,2-dimethoxyethane 888.81
    ethyl orthosilicate 141.37
    tributyl phosphate 176.28
    diacetone alcohol 482.41
    N,N-dimethylaniline 246.17
    acrylonitrile 634.57
    aniline 599.52
    1,3-propanediol 789.67
    bromobenzene 604.98
    dibromomethane 1316.3
    1,1,2,2-tetrachloroethane 1295.89
    2-methyl-cyclohexyl acetate 298.3
    tetrabutyl urea 211.72
    diisobutyl methanol 190.04
    2-phenylethanol 493.08
    styrene 261.08
    dioctyl adipate 269.79
    dimethyl sulfate 203.19
    ethyl butyrate 335.12
    methyl lactate 230.61
    butyl lactate 288.84
    diethyl carbonate 231.52
    propanediol butyl ether 515.8
    triethyl orthoformate 228.88
    p-tert-butyltoluene 151.94
    methyl 4-tert-butylbenzoate 317.63
    morpholine 2151.33
    tert-butylamine 793.57
    n-dodecanol 143.22
    dimethoxymethane 608.6
    ethylene carbonate 570.5
    cyrene 344.89
    2-ethoxyethyl acetate 391.99
    2-ethylhexyl acetate 373.94
    1,2,4-trichlorobenzene 518.3
    4-methylpyridine 1111.54
    dibutyl ether 287.0
    2,6-dimethyl-4-heptanol 190.04
    DEF 464.16
    dimethyl isosorbide 660.45
    tetrachloroethylene 714.1
    eugenol 313.05
    triacetin 364.88
    span 80 441.23
    1,4-butanediol 290.12
    1,1-dichloroethane 1051.07
    2-methyl-1-pentanol 508.55
    methyl formate 439.26
    2-methyl-1-butanol 719.52
    n-decane 33.33
    butyronitrile 898.78
    3,7-dimethyl-1-octanol 304.98
    1-chlorooctane 160.47
    1-chlorotetradecane 65.01
    n-nonane 31.16
    undecane 25.73
    tert-butylcyclohexane 54.88
    cyclooctane 39.6
    cyclopentanol 982.26
    tetrahydropyran 1717.85
    tert-amyl methyl ether 353.59
    2,5,8-trioxanonane 629.66
    1-hexene 259.09
    2-isopropoxyethanol 342.18
    2,2,2-trifluoroethanol 213.55
    methyl butyrate 383.79

    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
Chenopodium ambrosioides Chenopodium ambrosioides L., fam. Chenopodiaceae 0.08%
Satureja gilliesii Satureja gilliesii (Grah.) Briq., fam. Lamiaceae (Labiatae) 27.7%
Mentha arvensis ssp. austriaca 2 Mentha arvensis L. ssp. austriaca, fam. Lamiaceae (Labiatae) 0.15%
Calamintha nepeta (Italy) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 2.3%
Cypress, Leyland (Poland) Cupressocyparis leylandii (Dall. et Jacks.) Dall., fam. Cupressaceae 0.01%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.3%
Douglas fir (Bulgaria) Pseudotsuga menziesii (Mirbel) Franco, fam. Pinaceae 0.05%