p-Menthan-3-one, 4,8-epoxy-, cis-

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  • Identifiers

    CAS number
    7599-91-9

    Molecular formula
    C10H16O2

    SMILES
    C[C@@H]1CC[C@]2(C(=O)C1)C(O2)(C)C

  • Odor profile

    Woody 60.44%
    Herbal 58.65%
    Mint 57.48%
    Camphoreous 56.44%
    Sweet 52.85%
    Fresh 44.76%
    Tobacco 41.3%
    Cooling 41.01%
    Earthy 38.0%
    Green 37.01%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    219°C

    Flash point est.
    73.37 ˚C

  • Synonyms

    • p-Menthan-3-one, 4,8-epoxy-, cis-
    • 1-Oxaspiro[2.5]octan-4-one, 2,2,6-trimethyl-, trans-
    • cis-Pulegone Oxide
    • 7599-90-8
    • DTXSID80424063
    • OFUGTKAUAMKFPM-XCBNKYQSSA-N
    • 2,2,6-Trimethyl-1-oxaspiro[2.5]octan-4-one-, trans-
    • 1-Oxaspiro[2.5]octan-4-one, 2,2,6-trimethyl-, (3R,6S)-rel-

  • Applications

    p-Menthan-3-one, 4,8-epoxy-, cis- (CAS 7599-91-9) is an oxidized monoterpenoid in the menthone family, used primarily as a flavor and fragrance ingredient imparting minty, camphoraceous, herbal freshness to perfumes, personal-care products, and detergents by boosting brightness, balance, and longevity; in flavor applications, at very low dosage and where legally permitted, it modulates mint/eucalyptus facets in candies, chewing gum, and beverages; in organic synthesis it serves as an intermediate/terpenoid building block enabling selective epoxide ring-opening, access to menthone/menthol derivatives, and specialty odorants; in research it is employed as an analytical standard/marker for monoterpene oxidation products, as a model substrate for kinetics and catalytic epoxide opening, and in exploratory bioassays such as insect attractant/repellent behavior or antimicrobial screening; all uses require compliance with safety, purity, and regulatory frameworks (e.g., IFRA/food-grade) and storage away from light, heat, and oxygen to minimize odor changes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 264.62
    methanol 378.27
    isopropanol 200.65
    water 4.43
    ethyl acetate 158.57
    n-propanol 190.38
    acetone 222.9
    n-butanol 168.38
    acetonitrile 281.33
    DMF 244.02
    toluene 164.48
    isobutanol 141.49
    1,4-dioxane 360.32
    methyl acetate 187.05
    THF 439.75
    2-butanone 183.34
    n-pentanol 126.82
    sec-butanol 154.48
    n-hexane 16.18
    ethylene glycol 81.13
    NMP 251.8
    cyclohexane 42.42
    DMSO 168.58
    n-butyl acetate 139.28
    n-octanol 90.88
    chloroform 802.63
    n-propyl acetate 115.15
    acetic acid 258.78
    dichloromethane 597.91
    cyclohexanone 282.57
    propylene glycol 96.09
    isopropyl acetate 115.63
    DMAc 214.89
    2-ethoxyethanol 179.97
    isopentanol 140.84
    n-heptane 15.42
    ethyl formate 162.82
    1,2-dichloroethane 233.44
    n-hexanol 153.51
    2-methoxyethanol 286.04
    isobutyl acetate 93.87
    tetrachloromethane 129.21
    n-pentyl acetate 95.78
    transcutol 352.45
    n-heptanol 78.25
    ethylbenzene 95.18
    MIBK 112.33
    2-propoxyethanol 237.36
    tert-butanol 186.48
    MTBE 130.86
    2-butoxyethanol 136.58
    propionic acid 154.17
    o-xylene 107.13
    formic acid 136.54
    diethyl ether 126.05
    m-xylene 112.45
    p-xylene 140.25
    chlorobenzene 209.2
    dimethyl carbonate 77.39
    n-octane 8.58
    formamide 175.09
    cyclopentanone 296.56
    2-pentanone 138.44
    anisole 160.15
    cyclopentyl methyl ether 150.53
    gamma-butyrolactone 326.14
    1-methoxy-2-propanol 193.62
    pyridine 316.1
    3-pentanone 109.87
    furfural 339.14
    n-dodecane 10.86
    diethylene glycol 217.91
    diisopropyl ether 51.14
    tert-amyl alcohol 145.23
    acetylacetone 184.86
    n-hexadecane 12.36
    acetophenone 151.81
    methyl propionate 122.68
    isopentyl acetate 142.92
    trichloroethylene 499.79
    n-nonanol 83.12
    cyclohexanol 161.79
    benzyl alcohol 148.36
    2-ethylhexanol 86.19
    isooctanol 64.29
    dipropyl ether 70.5
    1,2-dichlorobenzene 193.57
    ethyl lactate 80.72
    propylene carbonate 227.02
    n-methylformamide 171.89
    2-pentanol 106.98
    n-pentane 20.33
    1-propoxy-2-propanol 155.39
    1-methoxy-2-propyl acetate 149.68
    2-(2-methoxypropoxy) propanol 141.23
    mesitylene 74.04
    ε-caprolactone 245.2
    p-cymene 66.61
    epichlorohydrin 341.85
    1,1,1-trichloroethane 279.57
    2-aminoethanol 136.02
    morpholine-4-carbaldehyde 288.73
    sulfolane 274.41
    2,2,4-trimethylpentane 15.73
    2-methyltetrahydrofuran 265.44
    n-hexyl acetate 151.81
    isooctane 13.67
    2-(2-butoxyethoxy)ethanol 181.87
    sec-butyl acetate 92.28
    tert-butyl acetate 122.44
    decalin 26.17
    glycerin 130.76
    diglyme 272.14
    acrylic acid 149.42
    isopropyl myristate 69.78
    n-butyric acid 187.22
    acetyl acetate 149.47
    di(2-ethylhexyl) phthalate 78.48
    ethyl propionate 106.14
    nitromethane 330.12
    1,2-diethoxyethane 126.01
    benzonitrile 231.28
    trioctyl phosphate 55.47
    1-bromopropane 155.25
    gamma-valerolactone 372.45
    n-decanol 64.21
    triethyl phosphate 68.37
    4-methyl-2-pentanol 76.86
    propionitrile 200.75
    vinylene carbonate 240.21
    1,1,2-trichlorotrifluoroethane 249.71
    DMS 135.9
    cumene 69.7
    2-octanol 60.11
    2-hexanone 123.44
    octyl acetate 83.44
    limonene 75.84
    1,2-dimethoxyethane 275.11
    ethyl orthosilicate 65.85
    tributyl phosphate 63.62
    diacetone alcohol 136.72
    N,N-dimethylaniline 106.69
    acrylonitrile 242.1
    aniline 169.58
    1,3-propanediol 187.07
    bromobenzene 217.69
    dibromomethane 371.87
    1,1,2,2-tetrachloroethane 356.77
    2-methyl-cyclohexyl acetate 114.72
    tetrabutyl urea 76.35
    diisobutyl methanol 57.78
    2-phenylethanol 164.69
    styrene 107.72
    dioctyl adipate 92.55
    dimethyl sulfate 109.22
    ethyl butyrate 115.98
    methyl lactate 92.95
    butyl lactate 90.93
    diethyl carbonate 94.82
    propanediol butyl ether 133.84
    triethyl orthoformate 89.12
    p-tert-butyltoluene 64.45
    methyl 4-tert-butylbenzoate 127.78
    morpholine 338.29
    tert-butylamine 130.02
    n-dodecanol 50.18
    dimethoxymethane 178.32
    ethylene carbonate 193.85
    cyrene 148.66
    2-ethoxyethyl acetate 125.16
    2-ethylhexyl acetate 114.19
    1,2,4-trichlorobenzene 224.15
    4-methylpyridine 282.7
    dibutyl ether 73.6
    2,6-dimethyl-4-heptanol 57.78
    DEF 133.79
    dimethyl isosorbide 214.06
    tetrachloroethylene 250.79
    eugenol 130.61
    triacetin 139.31
    span 80 125.61
    1,4-butanediol 87.99
    1,1-dichloroethane 291.37
    2-methyl-1-pentanol 113.41
    methyl formate 159.74
    2-methyl-1-butanol 128.08
    n-decane 15.66
    butyronitrile 209.95
    3,7-dimethyl-1-octanol 88.61
    1-chlorooctane 58.72
    1-chlorotetradecane 29.47
    n-nonane 13.38
    undecane 12.72
    tert-butylcyclohexane 23.02
    cyclooctane 14.91
    cyclopentanol 182.34
    tetrahydropyran 266.34
    tert-amyl methyl ether 95.28
    2,5,8-trioxanonane 204.15
    1-hexene 56.58
    2-isopropoxyethanol 129.5
    2,2,2-trifluoroethanol 110.7
    methyl butyrate 135.35

    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
Mentha arvensis, Glabrata Ray variety Mentha arvensis (L.) var. glabrata Ray, fam. Lamiaceae (Labiatae) 0.6%
Hesperozygis ringens (Brazil) Hesperozygis ringens (Benth.) Epling, fam. Lamiaceae (Labiatae) 0.6%