N-((Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide

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  • Identifiers

    CAS number
    68489-14-5

    Molecular formula
    C15H27NO3

    SMILES
    CCOC(=O)CNC(=O)[C@@H]1C[C@@H](CC[C@H]1C(C)C)C

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Cooling 56.76%
    Mint 50.8%
    Odorless 44.9%
    Herbal 26.31%
    Savory 21.12%
    Fresh 19.76%
    Animal 17.98%
    Grapefruit 17.8%
    Woody 14.98%
    Citrus 14.91%

     

    Flavor
    Fruity 39.88%
    Odorless 27.93%
    Bitter 25.76%
    Mild 23.35%
    Bland 21.88%
    Cedarleaf 19.78%
    Broom 19.49%
    Heather 19.48%
    Genet 19.47%
    Parsley 19.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.25 (neutral)

    Molecular weight
    269.38 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    362°C

    Flash point

    • 166.74 ˚C est.

    Solubility expt.

    • Practically insoluble or insoluble in water; slightly soluble in heptane; very slightly soluble in propylene glycol and ethyl acetate
    • Soluble (in ethanol)

  • Synonyms

    • N-((ETHOXYCARBONYL)METHYL)-P-MENTHANE-3-CARBOXAMIDE
    • FEMA No. 4309
    • 68489-14-5
    • ethyl 2-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate
    • WINSENSE WS-5
    • Q6CA504696
    • Ethyl 2-(((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanecarbonyl)amino)acetate
    • Glycine, N-(((1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl)carbonyl)-, ethyl ester
    • MENTHANE CARBOXAMIDOETHYL ACETATE
    • N-((Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide [FIFH]
    • MENTHANE CARBOXAMIDOETHYL ACETATE (INCHI)
    • N-[[(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester
    • Glycine, N-((5-methyl-2-(1-methylethyl)cyclohexyl)carbonyl)-, ethyl ester, (1R-(1alpha,2beta,5alpha))-
    • N-((ETHOXYCARBONYL)METHYL)-P-MENTHANE-3-CARBOXAMIDE [FHFI]
    • N-((ETHOXYCARBONYL)METHYL)-2-ISOPROPYL-5-METHYLCYCLOHEXANECARBOXAMIDE
    • N-((ETHOXYCARBONYL)METHYL)-2-ISOPROPYL-5-METHYLCYCLOHEXANECARBOXAMIDE, (1R,2S,5R)-
    • GLYCINE, N-((5-METHYL-2-(1-METHYLETHYL)CYCLOHEXYL)CARBONYL)-, ETHYL ESTER, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-
    • Ethyl 3-(p-Menthane-3-carboxamido)acetate
    • N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide
    • N-((Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide (FIFH)
    • UNII-Q6CA504696
    • ethyl 2-(((1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl)amino)acetate
    • Glycine, N-[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]-, ethyl ester
    • N-(((1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl)carbonyl)glycine ethyl ester
    • N-[[(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine Ethyl Ester; CPS 337; FEMA 4309;
    • SCHEMBL4884297
    • GWRCTWAPTXBPHW-FRRDWIJNSA-N
    • DTXSID501134437
    • HY-W423502
    • MENTHANE CARBOXAMIDOETHYL ACETATE [INCI]
    • Q27287054
    • ethyl 2-((1r,2s,5r)-2-isopropyl-5-methylcyclohexanecarboxamido)acetate
    • 695-735-2

  • Applications

    N-((Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide is primarily used as an intermediate in organic synthesis, offering a chiral menthane framework and a carbamate-protected amine that enable selective transformations in multi-step routes. The N-(ethoxycarbonyl)methyl carbamate moiety acts as a protective group for amines, allowing sequential functionalization without disturbing other parts of the molecule. In fragrance and cosmetics chemistry, it can serve as a precursor to menthane-derived fragrance compounds and related cosmetic ingredients. It is also evaluated as a specialized intermediate for developing menthol-derived derivatives with potential applications in polymer, coating, and formulation contexts. CAS 68489-14-5.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 332.08
    methanol 497.8
    isopropanol 237.75
    water 0.52
    ethyl acetate 204.18
    n-propanol 219.17
    acetone 234.51
    n-butanol 169.25
    acetonitrile 107.16
    DMF 308.19
    toluene 83.57
    isobutanol 141.57
    1,4-dioxane 278.38
    methyl acetate 143.38
    THF 401.96
    2-butanone 170.28
    n-pentanol 112.81
    sec-butanol 138.56
    n-hexane 1.46
    ethylene glycol 35.94
    NMP 268.7
    cyclohexane 4.61
    DMSO 429.41
    n-butyl acetate 153.13
    n-octanol 30.1
    chloroform 380.3
    n-propyl acetate 101.89
    acetic acid 332.65
    dichloromethane 354.83
    cyclohexanone 304.38
    propylene glycol 75.04
    isopropyl acetate 149.09
    DMAc 334.35
    2-ethoxyethanol 206.0
    isopentanol 146.08
    n-heptane 0.67
    ethyl formate 146.5
    1,2-dichloroethane 247.93
    n-hexanol 96.91
    2-methoxyethanol 355.79
    isobutyl acetate 79.11
    tetrachloromethane 39.04
    n-pentyl acetate 75.16
    transcutol 486.0
    n-heptanol 37.65
    ethylbenzene 36.62
    MIBK 106.7
    2-propoxyethanol 209.03
    tert-butanol 214.62
    MTBE 109.86
    2-butoxyethanol 112.8
    propionic acid 145.28
    o-xylene 55.97
    formic acid 130.55
    diethyl ether 81.04
    m-xylene 57.97
    p-xylene 54.06
    chlorobenzene 134.06
    dimethyl carbonate 45.61
    n-octane 0.76
    formamide 149.8
    cyclopentanone 329.74
    2-pentanone 153.36
    anisole 81.22
    cyclopentyl methyl ether 120.91
    gamma-butyrolactone 385.69
    1-methoxy-2-propanol 235.28
    pyridine 222.97
    3-pentanone 88.48
    furfural 347.24
    n-dodecane 0.93
    diethylene glycol 164.36
    diisopropyl ether 22.02
    tert-amyl alcohol 138.74
    acetylacetone 205.94
    n-hexadecane 1.12
    acetophenone 103.38
    methyl propionate 116.52
    isopentyl acetate 145.43
    trichloroethylene 444.56
    n-nonanol 28.64
    cyclohexanol 130.45
    benzyl alcohol 116.66
    2-ethylhexanol 43.88
    isooctanol 32.83
    dipropyl ether 20.92
    1,2-dichlorobenzene 117.31
    ethyl lactate 56.31
    propylene carbonate 213.99
    n-methylformamide 172.01
    2-pentanol 83.04
    n-pentane 1.47
    1-propoxy-2-propanol 125.11
    1-methoxy-2-propyl acetate 150.83
    2-(2-methoxypropoxy) propanol 99.6
    mesitylene 31.79
    ε-caprolactone 281.45
    p-cymene 23.27
    epichlorohydrin 396.78
    1,1,1-trichloroethane 177.56
    2-aminoethanol 112.03
    morpholine-4-carbaldehyde 276.99
    sulfolane 390.36
    2,2,4-trimethylpentane 2.81
    2-methyltetrahydrofuran 245.69
    n-hexyl acetate 86.56
    isooctane 2.0
    2-(2-butoxyethoxy)ethanol 143.45
    sec-butyl acetate 80.68
    tert-butyl acetate 137.03
    decalin 4.88
    glycerin 100.3
    diglyme 254.02
    acrylic acid 126.35
    isopropyl myristate 25.37
    n-butyric acid 271.38
    acetyl acetate 140.16
    di(2-ethylhexyl) phthalate 45.3
    ethyl propionate 74.25
    nitromethane 326.8
    1,2-diethoxyethane 114.38
    benzonitrile 124.95
    trioctyl phosphate 28.64
    1-bromopropane 89.67
    gamma-valerolactone 473.6
    n-decanol 19.73
    triethyl phosphate 40.13
    4-methyl-2-pentanol 51.2
    propionitrile 94.78
    vinylene carbonate 179.73
    1,1,2-trichlorotrifluoroethane 282.97
    DMS 84.89
    cumene 28.07
    2-octanol 23.94
    2-hexanone 89.32
    octyl acetate 36.08
    limonene 29.03
    1,2-dimethoxyethane 235.83
    ethyl orthosilicate 38.58
    tributyl phosphate 35.25
    diacetone alcohol 164.94
    N,N-dimethylaniline 57.39
    acrylonitrile 121.92
    aniline 134.26
    1,3-propanediol 210.19
    bromobenzene 121.13
    dibromomethane 207.99
    1,1,2,2-tetrachloroethane 381.96
    2-methyl-cyclohexyl acetate 67.34
    tetrabutyl urea 44.7
    diisobutyl methanol 24.21
    2-phenylethanol 103.25
    styrene 45.22
    dioctyl adipate 48.12
    dimethyl sulfate 94.21
    ethyl butyrate 71.69
    methyl lactate 74.93
    butyl lactate 76.4
    diethyl carbonate 52.29
    propanediol butyl ether 107.32
    triethyl orthoformate 50.82
    p-tert-butyltoluene 22.23
    methyl 4-tert-butylbenzoate 85.76
    morpholine 349.44
    tert-butylamine 81.53
    n-dodecanol 13.84
    dimethoxymethane 153.11
    ethylene carbonate 157.82
    cyrene 112.96
    2-ethoxyethyl acetate 132.5
    2-ethylhexyl acetate 99.15
    1,2,4-trichlorobenzene 137.1
    4-methylpyridine 229.45
    dibutyl ether 24.48
    2,6-dimethyl-4-heptanol 24.21
    DEF 146.65
    dimethyl isosorbide 169.16
    tetrachloroethylene 220.65
    eugenol 92.16
    triacetin 87.54
    span 80 82.36
    1,4-butanediol 83.71
    1,1-dichloroethane 213.19
    2-methyl-1-pentanol 106.0
    methyl formate 131.11
    2-methyl-1-butanol 124.06
    n-decane 1.53
    butyronitrile 114.08
    3,7-dimethyl-1-octanol 37.24
    1-chlorooctane 13.4
    1-chlorotetradecane 4.6
    n-nonane 1.2
    undecane 1.14
    tert-butylcyclohexane 3.9
    cyclooctane 1.37
    cyclopentanol 144.61
    tetrahydropyran 219.45
    tert-amyl methyl ether 70.23
    2,5,8-trioxanonane 155.41
    1-hexene 13.35
    2-isopropoxyethanol 136.48
    2,2,2-trifluoroethanol 107.97
    methyl butyrate 114.34

    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