Cyclohexanone, 5-methyl-2-(1-methylethenyl)-

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    529-00-0

    Molecular formula
    C10H16O

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1178.0

  • Odor profile

    Herbal 84.85%
    Mint 84.57%
    Green 73.65%
    Camphoreous 64.3%
    Fresh 61.65%
    Cooling 59.82%
    Woody 59.61%
    Spicy 46.36%
    Sweet 43.08%
    Citrus 42.24%

    Scent© AI

  • Properties

    XLogP3-AA
    2.8

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 101.00 to 102.00 °C. @ 17.00 mm Hg

    Flash point est.
    80.92 ˚C

    Solubility expt.

    • slightly
    • insoluble in water; soluble in alcohol and oils
    • miscible (in ethanol)

  • Synonyms

    • Isopulegone
    • 5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
    • 529-00-0
    • Cyclohexanone, 5-methyl-2-(1-methylethenyl)-
    • p-menth-8-en-3-one
    • 29606-79-9
    • 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one
    • 2-Isopropenyl-5-methylcyclohexanone #
    • (-)-trans-Isopulegone
    • SCHEMBL727954
    • CHEBI:37046
    • DTXSID40865498
    • (-)-trans-p-Menth-8-en-3-one
    • SAA88243
    • AKOS015907574
    • Cyclohexanone, 2-isopropylideno-5-methyl-
    • 5-methyl-2-(prop-1-en-2-yl)cyclohexanone
    • NS00096354
    • EN300-2968121
    • Q27117020
    • (2R-trans)-5-methyl-2-(1-methylethenyl)-cyclohexanone

  • Applications

    Cyclohexanone, 5-methyl-2-(1-methylethenyl)- (CAS 529-00-0) finds use largely in flavor–fragrance and as a synthesis intermediate: employed as a minty–herbal note modifier in perfumery, oral-care, and confectionery; incorporated into mint, caraway, and herbal flavor accords; serves as a versatile monoterpene building block convertible to menthone/menthol, carvone, piperitone/pulegone and other p-menthane derivatives via isomerization, hydrogenation/oxidation, or Baeyer–Villiger routes to fragrant lactones; used to access fine-chemical scaffolds, aroma ingredients, and APIs owing to its terpenoid framework and chiral potential; explored as a precursor for certain agrochemical actives and semiochemicals (repellents/attractants) of terpenoid origin; and adopted in research as a model substrate for selective reductions/oxidations, Michael additions, and asymmetric catalysis, enabling greener synthetic pathways from essential oils; food/cosmetic use typically requires level control and regulatory compliance because related pulegone/piperitone isomers have defined safety limits.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1982.05
    methanol 2293.53
    isopropanol 1677.28
    water 2.08
    ethyl acetate 713.75
    n-propanol 1282.59
    acetone 1098.38
    n-butanol 1239.51
    acetonitrile 1956.41
    DMF 843.37
    toluene 499.65
    isobutanol 915.67
    1,4-dioxane 2031.21
    methyl acetate 628.25
    THF 2308.55
    2-butanone 791.53
    n-pentanol 714.96
    sec-butanol 920.52
    n-hexane 194.81
    ethylene glycol 147.38
    NMP 653.16
    cyclohexane 367.37
    DMSO 596.26
    n-butyl acetate 849.69
    n-octanol 432.88
    chloroform 3121.48
    n-propyl acetate 429.7
    acetic acid 983.86
    dichloromethane 2097.47
    cyclohexanone 1384.83
    propylene glycol 260.65
    isopropyl acetate 416.59
    DMAc 403.63
    2-ethoxyethanol 503.46
    isopentanol 890.98
    n-heptane 167.18
    ethyl formate 672.73
    1,2-dichloroethane 910.56
    n-hexanol 1205.69
    2-methoxyethanol 1040.69
    isobutyl acetate 285.25
    tetrachloromethane 425.15
    n-pentyl acetate 372.63
    transcutol 1789.4
    n-heptanol 375.07
    ethylbenzene 247.24
    MIBK 404.8
    2-propoxyethanol 1049.26
    tert-butanol 1279.54
    MTBE 756.76
    2-butoxyethanol 466.13
    propionic acid 624.52
    o-xylene 262.83
    formic acid 281.39
    diethyl ether 993.9
    m-xylene 337.21
    p-xylene 323.72
    chlorobenzene 738.17
    dimethyl carbonate 139.81
    n-octane 51.07
    formamide 352.96
    cyclopentanone 1128.89
    2-pentanone 689.54
    anisole 395.9
    cyclopentyl methyl ether 778.97
    gamma-butyrolactone 1224.0
    1-methoxy-2-propanol 713.28
    pyridine 1246.74
    3-pentanone 396.58
    furfural 1005.01
    n-dodecane 38.51
    diethylene glycol 564.93
    diisopropyl ether 250.64
    tert-amyl alcohol 711.06
    acetylacetone 506.93
    n-hexadecane 45.51
    acetophenone 316.14
    methyl propionate 387.62
    isopentyl acetate 680.93
    trichloroethylene 1772.94
    n-nonanol 329.98
    cyclohexanol 972.53
    benzyl alcohol 413.89
    2-ethylhexanol 515.46
    isooctanol 290.92
    dipropyl ether 489.73
    1,2-dichlorobenzene 509.8
    ethyl lactate 173.8
    propylene carbonate 737.26
    n-methylformamide 625.42
    2-pentanol 712.26
    n-pentane 208.22
    1-propoxy-2-propanol 735.58
    1-methoxy-2-propyl acetate 521.0
    2-(2-methoxypropoxy) propanol 402.76
    mesitylene 208.36
    ε-caprolactone 971.98
    p-cymene 202.62
    epichlorohydrin 1296.65
    1,1,1-trichloroethane 1072.6
    2-aminoethanol 419.59
    morpholine-4-carbaldehyde 828.61
    sulfolane 772.24
    2,2,4-trimethylpentane 70.29
    2-methyltetrahydrofuran 1539.75
    n-hexyl acetate 579.17
    isooctane 73.93
    2-(2-butoxyethoxy)ethanol 621.02
    sec-butyl acetate 272.68
    tert-butyl acetate 401.81
    decalin 104.59
    glycerin 279.15
    diglyme 1007.47
    acrylic acid 445.63
    isopropyl myristate 206.36
    n-butyric acid 1158.99
    acetyl acetate 375.01
    di(2-ethylhexyl) phthalate 192.5
    ethyl propionate 300.39
    nitromethane 1140.53
    1,2-diethoxyethane 683.71
    benzonitrile 796.06
    trioctyl phosphate 145.29
    1-bromopropane 796.04
    gamma-valerolactone 1353.08
    n-decanol 228.58
    triethyl phosphate 156.94
    4-methyl-2-pentanol 356.77
    propionitrile 1140.79
    vinylene carbonate 694.53
    1,1,2-trichlorotrifluoroethane 673.1
    DMS 282.66
    cumene 166.37
    2-octanol 272.28
    2-hexanone 538.4
    octyl acetate 257.37
    limonene 312.4
    1,2-dimethoxyethane 968.01
    ethyl orthosilicate 163.76
    tributyl phosphate 182.51
    diacetone alcohol 429.42
    N,N-dimethylaniline 228.53
    acrylonitrile 1030.22
    aniline 648.87
    1,3-propanediol 738.32
    bromobenzene 729.32
    dibromomethane 1511.49
    1,1,2,2-tetrachloroethane 1262.33
    2-methyl-cyclohexyl acetate 325.1
    tetrabutyl urea 209.74
    diisobutyl methanol 257.65
    2-phenylethanol 533.62
    styrene 311.07
    dioctyl adipate 264.68
    dimethyl sulfate 170.51
    ethyl butyrate 425.8
    methyl lactate 189.34
    butyl lactate 294.97
    diethyl carbonate 275.98
    propanediol butyl ether 457.63
    triethyl orthoformate 288.06
    p-tert-butyltoluene 187.4
    methyl 4-tert-butylbenzoate 301.8
    morpholine 2089.19
    tert-butylamine 909.29
    n-dodecanol 169.51
    dimethoxymethane 564.37
    ethylene carbonate 606.4
    cyrene 284.85
    2-ethoxyethyl acetate 415.3
    2-ethylhexyl acetate 484.88
    1,2,4-trichlorobenzene 545.32
    4-methylpyridine 1186.49
    dibutyl ether 431.9
    2,6-dimethyl-4-heptanol 257.65
    DEF 513.86
    dimethyl isosorbide 605.09
    tetrachloroethylene 823.43
    eugenol 288.51
    triacetin 362.34
    span 80 410.46
    1,4-butanediol 242.49
    1,1-dichloroethane 1304.5
    2-methyl-1-pentanol 546.43
    methyl formate 470.59
    2-methyl-1-butanol 748.24
    n-decane 71.36
    butyronitrile 1476.73
    3,7-dimethyl-1-octanol 369.29
    1-chlorooctane 252.83
    1-chlorotetradecane 93.92
    n-nonane 75.85
    undecane 50.61
    tert-butylcyclohexane 95.91
    cyclooctane 96.08
    cyclopentanol 982.91
    tetrahydropyran 2109.22
    tert-amyl methyl ether 400.99
    2,5,8-trioxanonane 609.37
    1-hexene 532.42
    2-isopropoxyethanol 339.36
    2,2,2-trifluoroethanol 237.54
    methyl butyrate 463.99

    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
Celery seed (India) 3 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.16%
Satureja boliviana (Peru) 1 Satureja boliviana Briq. (Micromeria boliviana Benth.), fam. Lamiaceae 5.45%
Satureja gilliesii Satureja gilliesii (Grah.) Briq., fam. Lamiaceae (Labiatae) 14.0%
Hesperozygis ringens (Brazil) Hesperozygis ringens (Benth.) Epling, fam. Lamiaceae (Labiatae) 1.2%
Hesperozygis rhododon (Brazil) Hesperozygis rhododon Epling, fam. Lamiaceae (Labiatae) 2.4%
Jasmine rose absolute (India) Gardenia jasminoides Ellis, fam. Rubiaceae 0.21%
Acinos suaveolens (Greece) 2 Acinos suaveolens (Sibt. et Smith) G. Don f., fam. Lamiaceae (Labiatae) 3.1%
Calamintha nepeta (Greece) 3 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball,fam. Lamiaceae 0.7%
Plectranthus glandulosus (Cameroon) 2 Plectranthus glandulosus Hook f., fam. Lamiaceae (Labiatae) 1.8%
Lemongrass 3a 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 1.68%
Lemongrass 3b headspace neat oil 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 2.47%
Lemongrass 3c headspace heated oil 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.62%
Peppermint (Mexico) 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.3%
Tanacetum khorassanicum (Iran) Tanacetum khorassanicum (Krasch.) Parsa, fam. Asteraceae (Compositae) 13.4%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.1%