Menthyl pyrrolidone carboxylate, D-(-)-

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  • Identifiers

    CAS number
    68127-22-0

    Molecular formula
    C15H25NO3

    SMILES
    C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@H]2CCC(=O)N2)C(C)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 53.73%
    Mint 49.97%
    Cooling 49.08%
    Herbal 28.87%
    Woody 20.42%
    Spicy 19.07%
    Fresh 17.67%
    Animal 16.49%
    Lactonic 16.47%
    Camphoreous 15.53%

     

    Flavor
    Bitter 66.81%
    Odorless 22.76%
    Cedarleaf 22.33%
    Bland 21.08%
    Lovage 20.49%
    Sweet-like 19.91%
    Leaves 19.78%
    Basil 19.32%
    Ripe apricot 19.31%
    Parsley 19.31%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    7.2 (neutral)

    Molecular weight
    267.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    383°C

    Flash point

    • 159.37 ˚C est.

    Solubility expt.

    • Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 68127-22-0
    • Y27B4585KO
    • D-Proline, 5-oxo-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
    • DTXSID10887167
    • MENTHYL PYRROLIDONE CARBOXYLATE, D-(-)-
    • RefChem:810982
    • DTXCID901026480
    • FEMA NO. 4155, (-),D-
    • 5-Oxo-D-proline (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
    • (-)-Menthyl (+)-2-pyrrolidone-5-carboxylate
    • [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-5-oxopyrrolidine-2-carboxylate
    • (1R,2S,5R)-Menthyl (R)-Pyroglutamate
    • UNII-Y27B4585KO
    • EINECS 268-568-4
    • Menthyl pyrrolidone carboxylate, (-),D-
    • SLHPMAOXNSLXEH-YVECIDJPSA-N
    • D-(-)-menthyl pyrrolidone carboxylate
    • 127M220
    • Q27294168
    • (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 5-oxo-D-prolinate
    • ((1R,2S,5R)-2-ISOPROPYL-5-METHYL-CYCLOHEXYL) (2R)-5-OXOPYRROLIDINE-2-CARBOXYLATE
    • (1R-(1alpha,2beta,5alpha))-2-Isopropyl-5-methylcyclohexyl 5-oxo-D-prolinate
    • D-PROLINE, 5-OXO-, 5-METHYL-2-(1-METHYLETHYL)CYCLOHEXYL ESTER, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-
    • 68127-22-0

  • Applications

    Menthyl pyrrolidone carboxylate, D-(-) (CAS 68127-22-0) is commonly employed as a chiral solvent and a synthetic intermediate in fine chemicals and pharmaceutical manufacturing, and it can function as a processing aid or solvent in coatings, inks, and adhesives. The menthyl moiety provides mint-related aroma attributes, so the compound may be used as a fragrance component or fixative in perfumery, while it may also be evaluated as a solvent or carrier in cosmetic and personal care formulations. In polymer and plastics processing, it can act as a specialty plasticizer or processing aid, and it may serve as a building block for other functional materials. Use and handling are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 714.04
    methanol 1031.0
    isopropanol 502.68
    water 1.92
    ethyl acetate 369.96
    n-propanol 415.69
    acetone 518.69
    n-butanol 382.42
    acetonitrile 217.27
    DMF 443.8
    toluene 117.85
    isobutanol 285.29
    1,4-dioxane 439.15
    methyl acetate 265.67
    THF 740.8
    2-butanone 355.14
    n-pentanol 209.75
    sec-butanol 289.22
    n-hexane 3.29
    ethylene glycol 55.38
    NMP 384.03
    cyclohexane 9.08
    DMSO 428.18
    n-butyl acetate 300.24
    n-octanol 70.99
    chloroform 928.44
    n-propyl acetate 217.32
    acetic acid 719.24
    dichloromethane 706.32
    cyclohexanone 530.97
    propylene glycol 122.59
    isopropyl acetate 286.12
    DMAc 448.72
    2-ethoxyethanol 339.95
    isopentanol 307.53
    n-heptane 1.63
    ethyl formate 288.7
    1,2-dichloroethane 364.7
    n-hexanol 179.03
    2-methoxyethanol 601.65
    isobutyl acetate 163.29
    tetrachloromethane 60.73
    n-pentyl acetate 170.63
    transcutol 999.12
    n-heptanol 83.74
    ethylbenzene 53.64
    MIBK 206.19
    2-propoxyethanol 380.81
    tert-butanol 337.49
    MTBE 181.09
    2-butoxyethanol 232.48
    propionic acid 309.62
    o-xylene 72.89
    formic acid 269.08
    diethyl ether 156.89
    m-xylene 90.32
    p-xylene 92.46
    chlorobenzene 209.66
    dimethyl carbonate 86.16
    n-octane 1.56
    formamide 334.48
    cyclopentanone 550.02
    2-pentanone 315.62
    anisole 131.05
    cyclopentyl methyl ether 228.65
    gamma-butyrolactone 631.39
    1-methoxy-2-propanol 450.44
    pyridine 385.78
    3-pentanone 160.98
    furfural 529.02
    n-dodecane 2.15
    diethylene glycol 277.5
    diisopropyl ether 44.31
    tert-amyl alcohol 222.87
    acetylacetone 352.99
    n-hexadecane 2.55
    acetophenone 173.73
    methyl propionate 212.65
    isopentyl acetate 262.66
    trichloroethylene 830.29
    n-nonanol 65.81
    cyclohexanol 241.27
    benzyl alcohol 189.06
    2-ethylhexanol 80.54
    isooctanol 68.57
    dipropyl ether 42.53
    1,2-dichlorobenzene 181.98
    ethyl lactate 105.24
    propylene carbonate 395.99
    n-methylformamide 318.86
    2-pentanol 209.31
    n-pentane 3.65
    1-propoxy-2-propanol 234.57
    1-methoxy-2-propyl acetate 267.57
    2-(2-methoxypropoxy) propanol 173.0
    mesitylene 48.89
    ε-caprolactone 519.73
    p-cymene 32.92
    epichlorohydrin 627.56
    1,1,1-trichloroethane 290.95
    2-aminoethanol 192.77
    morpholine-4-carbaldehyde 442.09
    sulfolane 490.75
    2,2,4-trimethylpentane 5.32
    2-methyltetrahydrofuran 478.78
    n-hexyl acetate 200.71
    isooctane 4.09
    2-(2-butoxyethoxy)ethanol 277.46
    sec-butyl acetate 155.56
    tert-butyl acetate 208.06
    decalin 7.56
    glycerin 158.04
    diglyme 470.75
    acrylic acid 241.99
    isopropyl myristate 55.91
    n-butyric acid 611.96
    acetyl acetate 243.73
    di(2-ethylhexyl) phthalate 80.78
    ethyl propionate 135.45
    nitromethane 685.06
    1,2-diethoxyethane 232.61
    benzonitrile 220.87
    trioctyl phosphate 51.04
    1-bromopropane 156.66
    gamma-valerolactone 816.88
    n-decanol 44.84
    triethyl phosphate 62.13
    4-methyl-2-pentanol 120.83
    propionitrile 163.72
    vinylene carbonate 336.05
    1,1,2-trichlorotrifluoroethane 442.05
    DMS 159.96
    cumene 40.64
    2-octanol 55.13
    2-hexanone 190.07
    octyl acetate 78.79
    limonene 43.06
    1,2-dimethoxyethane 372.33
    ethyl orthosilicate 60.93
    tributyl phosphate 65.91
    diacetone alcohol 253.31
    N,N-dimethylaniline 84.29
    acrylonitrile 199.71
    aniline 197.76
    1,3-propanediol 387.52
    bromobenzene 192.21
    dibromomethane 420.37
    1,1,2,2-tetrachloroethane 616.65
    2-methyl-cyclohexyl acetate 117.84
    tetrabutyl urea 76.74
    diisobutyl methanol 42.68
    2-phenylethanol 173.41
    styrene 67.46
    dioctyl adipate 88.66
    dimethyl sulfate 136.12
    ethyl butyrate 133.04
    methyl lactate 136.61
    butyl lactate 152.99
    diethyl carbonate 89.24
    propanediol butyl ether 213.32
    triethyl orthoformate 93.78
    p-tert-butyltoluene 30.33
    methyl 4-tert-butylbenzoate 133.23
    morpholine 577.32
    tert-butylamine 125.75
    n-dodecanol 31.23
    dimethoxymethane 252.42
    ethylene carbonate 298.89
    cyrene 172.66
    2-ethoxyethyl acetate 256.85
    2-ethylhexyl acetate 181.19
    1,2,4-trichlorobenzene 220.46
    4-methylpyridine 406.71
    dibutyl ether 60.53
    2,6-dimethyl-4-heptanol 42.68
    DEF 255.51
    dimethyl isosorbide 268.46
    tetrachloroethylene 365.28
    eugenol 151.39
    triacetin 183.16
    span 80 144.48
    1,4-butanediol 129.09
    1,1-dichloroethane 422.96
    2-methyl-1-pentanol 198.93
    methyl formate 229.42
    2-methyl-1-butanol 242.28
    n-decane 3.49
    butyronitrile 241.78
    3,7-dimethyl-1-octanol 78.14
    1-chlorooctane 29.7
    1-chlorotetradecane 10.34
    n-nonane 2.63
    undecane 2.63
    tert-butylcyclohexane 6.3
    cyclooctane 2.96
    cyclopentanol 270.11
    tetrahydropyran 409.83
    tert-amyl methyl ether 113.63
    2,5,8-trioxanonane 273.2
    1-hexene 27.4
    2-isopropoxyethanol 230.96
    2,2,2-trifluoroethanol 237.26
    methyl butyrate 218.8

    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