Cyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)-

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  • Identifiers

    CAS number
    39711-79-0

    Molecular formula
    C13H25NO

    SMILES
    CCNC(=O)C1CC(CCC1C(C)C)C

  • Odor profile

    Fragrance
    Cooling 64.61%
    Mint 62.33%
    Odorless 32.22%
    Herbal 27.2%
    Savory 25.87%
    Grapefruit 24.0%
    Spicy 21.76%
    Animal 20.73%
    Fishy 19.82%
    Cheesy 19.1%

     

    Flavor
    Herbal 39.54%
    Herb 25.17%
    Minty 24.56%
    Green 23.11%
    Odorless 22.73%
    Mild 22.04%
    Cedarleaf 20.88%
    Fruity 20.45%
    Mentholic 20.24%
    Green tea 20.23%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    8.24 (weak base)

    Molecular weight
    211.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    306°C

    Melting point expt.

    • 91 - 93 °C

    Flash point

    • 130.41 ˚C est.

    Solubility expt.

    • Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 39711-79-0
    • N-Ethyl-p-menthane-3-carboxamide
    • N-Ethyl-2-isopropyl-5-methylcyclohexanecarboxamide
    • Ethyl menthane carboxamide
    • WS 3
    • Cyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)-
    • N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide
    • N-ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
    • FEMA No. 3455
    • N-Ethyl-4-menthane-3-carboxamide
    • EINECS 254-599-0
    • N-Ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
    • DTXSID5047039
    • N-Ethyl-2-isopropyl-5-methylcyclohexane carboxamide
    • UNII-6S7S02945H
    • MFCD00130071
    • 6S7S02945H
    • N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide
    • DTXCID3027039
    • N-Ethyl 5-methyl-2-iso-propylcyclohexanecarboxamide
    • ETHYL MENTHANE CARBOXAMIDE [MI]
    • N-ethyl-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide
    • N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide
    • ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE [FHFI]
    • Framidice 3
    • TRPM8 agonist WS-3
    • TRPM8 antagonist WS-3
    • Menthol Carboxamide WS-3
    • SCHEMBL33290
    • GTPL2475
    • CHEMBL3185043
    • N-Ethyl-p-methane-3-carboxamide
    • CHEBI:168845
    • VUNOFAIHSALQQH-UHFFFAOYSA-N
    • Tox21_302336
    • N-Ethyl-(P)-menthane-3-carboxamide
    • s6122
    • AKOS015842655
    • CS-W015041
    • HY-W014325
    • N-Ethyl-p-menthane-3-carboxamide 99%
    • ETHYL MENTHANE CARBOXAMIDE [INCI]
    • NCGC00256167-01
    • AS-15567
    • SY013238
    • CAS-39711-79-0
    • DB-049468
    • DB-255709
    • E0796
    • NS00013664
    • O12022
    • Q27089232
    • N-Ethyl-2-isopropyl-5-methylcyclohexanecarboxamide, 99%, FG
    • 39711-29-0
    • N-Ethyl-p-methane-3-carboxamide, Ethyl menthane carboxamide, Framidice 3, Menthol Carboxamide WS-3

  • Applications

    N-Ethyl-2-isopropyl-5-methylcyclohexanecarboxamide (commonly known as WS-3) is an odorless, thermally stable, low-volatility cooling agent widely employed in the food industry (candies, chewing gum, non-alcoholic beverages, dairy products), pharmaceuticals (topical analgesic creams, cough lozenges, oral gels), cosmetics and personal-care items (lipsticks, toothpastes, mouthwashes, shampoos), e-cigarette liquids and flavor concentrates, as well as in pharmacological studies of the TRPM8 cold receptor; because it delivers a long-lasting, deep cooling sensation without bitterness or mucosal irritation, it is favored as a menthol substitute, serving to modify flavor, enhance palatability, impart freshness, mask unpleasant active ingredients, and, in certain contexts, act as a synthetic intermediate for other cyclohexane amide derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 574.58
    methanol 665.97
    isopropanol 577.41
    water 1.19
    ethyl acetate 166.92
    n-propanol 545.35
    acetone 265.54
    n-butanol 465.31
    acetonitrile 164.44
    DMF 396.13
    toluene 165.52
    isobutanol 416.29
    1,4-dioxane 505.55
    methyl acetate 164.11
    THF 670.32
    2-butanone 239.52
    n-pentanol 275.11
    sec-butanol 397.78
    n-hexane 28.32
    ethylene glycol 78.39
    NMP 356.21
    cyclohexane 71.34
    DMSO 249.08
    n-butyl acetate 271.91
    n-octanol 136.33
    chloroform 1000.48
    n-propyl acetate 125.48
    acetic acid 339.73
    dichloromethane 568.99
    cyclohexanone 506.6
    propylene glycol 156.25
    isopropyl acetate 152.32
    DMAc 284.75
    2-ethoxyethanol 214.89
    isopentanol 353.83
    n-heptane 16.97
    ethyl formate 194.54
    1,2-dichloroethane 314.07
    n-hexanol 367.74
    2-methoxyethanol 404.78
    isobutyl acetate 120.72
    tetrachloromethane 148.49
    n-pentyl acetate 158.5
    transcutol 379.43
    n-heptanol 164.63
    ethylbenzene 91.06
    MIBK 140.76
    2-propoxyethanol 350.34
    tert-butanol 442.44
    MTBE 253.55
    2-butoxyethanol 234.24
    propionic acid 249.47
    o-xylene 114.34
    formic acid 106.31
    diethyl ether 195.27
    m-xylene 116.98
    p-xylene 129.3
    chlorobenzene 266.8
    dimethyl carbonate 46.15
    n-octane 10.94
    formamide 92.7
    cyclopentanone 484.23
    2-pentanone 197.09
    anisole 128.36
    cyclopentyl methyl ether 219.63
    gamma-butyrolactone 452.68
    1-methoxy-2-propanol 297.27
    pyridine 501.77
    3-pentanone 125.1
    furfural 439.33
    n-dodecane 10.21
    diethylene glycol 230.05
    diisopropyl ether 62.23
    tert-amyl alcohol 306.32
    acetylacetone 165.01
    n-hexadecane 11.86
    acetophenone 132.48
    methyl propionate 112.89
    isopentyl acetate 252.18
    trichloroethylene 615.67
    n-nonanol 115.42
    cyclohexanol 369.07
    benzyl alcohol 168.29
    2-ethylhexanol 170.62
    isooctanol 129.95
    dipropyl ether 102.8
    1,2-dichlorobenzene 213.05
    ethyl lactate 79.94
    propylene carbonate 300.85
    n-methylformamide 204.67
    2-pentanol 257.75
    n-pentane 29.36
    1-propoxy-2-propanol 258.02
    1-methoxy-2-propyl acetate 179.91
    2-(2-methoxypropoxy) propanol 147.04
    mesitylene 77.95
    ε-caprolactone 397.47
    p-cymene 75.31
    epichlorohydrin 442.68
    1,1,1-trichloroethane 339.47
    2-aminoethanol 221.53
    morpholine-4-carbaldehyde 334.29
    sulfolane 401.11
    2,2,4-trimethylpentane 20.37
    2-methyltetrahydrofuran 417.81
    n-hexyl acetate 195.41
    isooctane 15.2
    2-(2-butoxyethoxy)ethanol 198.0
    sec-butyl acetate 101.87
    tert-butyl acetate 135.39
    decalin 28.96
    glycerin 169.35
    diglyme 301.66
    acrylic acid 203.85
    isopropyl myristate 70.63
    n-butyric acid 442.62
    acetyl acetate 121.15
    di(2-ethylhexyl) phthalate 95.34
    ethyl propionate 93.39
    nitromethane 238.48
    1,2-diethoxyethane 164.34
    benzonitrile 248.82
    trioctyl phosphate 70.39
    1-bromopropane 246.43
    gamma-valerolactone 599.24
    n-decanol 82.08
    triethyl phosphate 68.35
    4-methyl-2-pentanol 145.28
    propionitrile 223.88
    vinylene carbonate 281.84
    1,1,2-trichlorotrifluoroethane 336.9
    DMS 108.58
    cumene 70.12
    2-octanol 110.67
    2-hexanone 149.83
    octyl acetate 93.85
    limonene 98.08
    1,2-dimethoxyethane 303.78
    ethyl orthosilicate 71.47
    tributyl phosphate 74.5
    diacetone alcohol 170.47
    N,N-dimethylaniline 94.89
    acrylonitrile 235.92
    aniline 232.26
    1,3-propanediol 337.43
    bromobenzene 255.48
    dibromomethane 418.08
    1,1,2,2-tetrachloroethane 561.05
    2-methyl-cyclohexyl acetate 127.33
    tetrabutyl urea 90.44
    diisobutyl methanol 89.51
    2-phenylethanol 200.91
    styrene 109.14
    dioctyl adipate 94.74
    dimethyl sulfate 75.85
    ethyl butyrate 131.44
    methyl lactate 92.29
    butyl lactate 143.03
    diethyl carbonate 86.62
    propanediol butyl ether 201.31
    triethyl orthoformate 102.24
    p-tert-butyltoluene 69.42
    methyl 4-tert-butylbenzoate 137.31
    morpholine 596.94
    tert-butylamine 261.62
    n-dodecanol 60.94
    dimethoxymethane 166.01
    ethylene carbonate 239.61
    cyrene 143.74
    2-ethoxyethyl acetate 160.69
    2-ethylhexyl acetate 193.61
    1,2,4-trichlorobenzene 237.7
    4-methylpyridine 415.3
    dibutyl ether 93.09
    2,6-dimethyl-4-heptanol 89.51
    DEF 188.69
    dimethyl isosorbide 226.7
    tetrachloroethylene 383.17
    eugenol 151.68
    triacetin 130.25
    span 80 165.72
    1,4-butanediol 139.14
    1,1-dichloroethane 402.73
    2-methyl-1-pentanol 223.81
    methyl formate 147.55
    2-methyl-1-butanol 318.71
    n-decane 17.76
    butyronitrile 293.13
    3,7-dimethyl-1-octanol 116.42
    1-chlorooctane 76.88
    1-chlorotetradecane 30.27
    n-nonane 15.94
    undecane 13.01
    tert-butylcyclohexane 24.87
    cyclooctane 17.68
    cyclopentanol 377.71
    tetrahydropyran 574.42
    tert-amyl methyl ether 155.83
    2,5,8-trioxanonane 193.12
    1-hexene 110.5
    2-isopropoxyethanol 160.06
    2,2,2-trifluoroethanol 100.61
    methyl butyrate 153.21

    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