Menthyl acetoacetate, (-)-

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  • Identifiers

    CAS number
    59557-05-0

    Molecular formula
    C14H24O3

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

  • Odor profile

    Fragrance
    Fruity 74.5%
    Mint 69.78%
    Floral 59.43%
    Herbal 59.09%
    Sweet 50.03%
    Cooling 45.11%
    Fresh 43.92%
    Woody 38.26%
    Rose 32.44%
    Berry 27.83%

     

    Flavor
    Fruity 68.82%
    Tropical 42.99%
    Sweet 39.48%
    Herbal 37.25%
    Minty 34.23%
    Berry 33.66%
    Woody 31.95%
    Fruit 30.43%
    Floral 29.2%
    Mint 28.05%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.74 (neutral)

    Molecular weight
    240.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    289°C

    Flash point

    • 119.5 ˚C est.

    Solubility expt.

    • Sparingly soluble in water; soluble in many non-polar solvents
    • Soluble (in ethanol)

  • Synonyms

    • 59557-05-0
    • Menthol acetoacetate
    • (-)-menthyl acetoacetate
    • Butanoic acid, 3-oxo-,(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
    • Menthyl acetoacetate, (-)-
    • 7Y94FXH95P
    • laevo-menthyl acetoacetate
    • FEMA NO. 4327
    • MENTHYL ACETOACETATE, L-
    • Butanoic acid, 3-oxo-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
    • (1R,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXYL 3-OXOBUTANOATE
    • (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoate
    • [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 3-oxobutanoate
    • BUTANOIC ACID, 3-OXO-, 5-METHYL-2-(1-METHYLETHYL)CYCLOHEXYL ESTER, (1R-(1.ALPHA.,2.BETA.,5.ALPHA.))-
    • UNII-7Y94FXH95P
    • L-MENTHYL ACETOACETATE [FHFI]
    • BRN 4679794
    • 2-06-00-00048 (Beilstein Handbook Reference)
    • SCHEMBL12994248
    • LAEVO-MENTHOL ACETOACETATE
    • LAEVO- MENTHOL ACETOACETATE
    • AKOS037647300
    • (1R,3R,4S)-p-Menth-3-yl Acetoacetate
    • AS-73223
    • (1R, 3R, 4S)-p-Menth-3-yl Acetoacetate
    • D93018
    • Q27269017
    • 611-852-3
    • Butanoic acid, 3-oxo-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1R-(1-alpha,2-beta,5-alpha))-
    • BUTANOIC ACID, 3-OXO-, 5-METHYL-2-(1-METHYLETHYL)CYCLOHEXYL ESTER, (1R-(1ALPHA,2BETA,5ALPHA))-
    • Butanoic acid, 3-oxo-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1theta-(1alpha,2beta,5alpha))-

  • Applications

    Menthyl acetoacetate, (-)- (CAS 59557-05-0) is an acetoacetate ester bearing a menthyl group, used primarily as a synthetic intermediate and fragrance ingredient; in the fragrance industry it is regarded as a chiral intermediate and may function as a fragrance fixative in perfume formulations; in cosmetics and personal care it participates in fragrance formulations for creams, lotions, and soaps; in flavor research it may be evaluated as an aroma precursor; it can also serve as a building block or intermediate in the synthesis of pharmaceutical and other specialty chemicals, and in household and cleaning products it may be used as an added fragrance component to improve odor profiles.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 736.38
    methanol 875.61
    isopropanol 810.19
    water 1.56
    ethyl acetate 512.01
    n-propanol 541.4
    acetone 880.49
    n-butanol 519.08
    acetonitrile 463.22
    DMF 867.57
    toluene 297.72
    isobutanol 475.43
    1,4-dioxane 1219.18
    methyl acetate 441.27
    THF 2111.03
    2-butanone 523.57
    n-pentanol 311.53
    sec-butanol 495.38
    n-hexane 51.78
    ethylene glycol 129.49
    NMP 1040.11
    cyclohexane 134.24
    DMSO 877.19
    n-butyl acetate 410.85
    n-octanol 189.05
    chloroform 2117.99
    n-propyl acetate 302.36
    acetic acid 874.47
    dichloromethane 1334.76
    cyclohexanone 1194.53
    propylene glycol 339.2
    isopropyl acetate 377.33
    DMAc 707.57
    2-ethoxyethanol 323.54
    isopentanol 514.28
    n-heptane 24.48
    ethyl formate 363.52
    1,2-dichloroethane 798.14
    n-hexanol 482.38
    2-methoxyethanol 720.64
    isobutyl acetate 238.78
    tetrachloromethane 228.25
    n-pentyl acetate 263.46
    transcutol 1524.08
    n-heptanol 175.18
    ethylbenzene 165.55
    MIBK 357.0
    2-propoxyethanol 646.71
    tert-butanol 939.11
    MTBE 497.68
    2-butoxyethanol 316.63
    propionic acid 569.94
    o-xylene 208.13
    formic acid 241.72
    diethyl ether 382.29
    m-xylene 251.67
    p-xylene 236.94
    chlorobenzene 530.21
    dimethyl carbonate 165.5
    n-octane 11.79
    formamide 258.64
    cyclopentanone 1263.82
    2-pentanone 482.8
    anisole 304.93
    cyclopentyl methyl ether 696.01
    gamma-butyrolactone 1387.5
    1-methoxy-2-propanol 661.06
    pyridine 704.57
    3-pentanone 306.35
    furfural 975.54
    n-dodecane 11.75
    diethylene glycol 446.64
    diisopropyl ether 142.01
    tert-amyl alcohol 583.45
    acetylacetone 610.08
    n-hexadecane 14.18
    acetophenone 304.68
    methyl propionate 367.47
    isopentyl acetate 399.88
    trichloroethylene 1623.59
    n-nonanol 165.79
    cyclohexanol 788.97
    benzyl alcohol 314.6
    2-ethylhexanol 229.24
    isooctanol 149.99
    dipropyl ether 185.88
    1,2-dichlorobenzene 440.82
    ethyl lactate 171.74
    propylene carbonate 763.55
    n-methylformamide 403.06
    2-pentanol 384.19
    n-pentane 43.27
    1-propoxy-2-propanol 468.91
    1-methoxy-2-propyl acetate 441.08
    2-(2-methoxypropoxy) propanol 366.47
    mesitylene 168.7
    ε-caprolactone 944.49
    p-cymene 106.53
    epichlorohydrin 1316.59
    1,1,1-trichloroethane 885.81
    2-aminoethanol 306.46
    morpholine-4-carbaldehyde 898.84
    sulfolane 1321.37
    2,2,4-trimethylpentane 31.79
    2-methyltetrahydrofuran 1257.2
    n-hexyl acetate 435.05
    isooctane 25.69
    2-(2-butoxyethoxy)ethanol 503.94
    sec-butyl acetate 223.19
    tert-butyl acetate 420.81
    decalin 54.13
    glycerin 364.64
    diglyme 781.01
    acrylic acid 434.34
    isopropyl myristate 154.35
    n-butyric acid 832.38
    acetyl acetate 400.95
    di(2-ethylhexyl) phthalate 184.2
    ethyl propionate 245.99
    nitromethane 924.35
    1,2-diethoxyethane 383.88
    benzonitrile 417.92
    trioctyl phosphate 127.72
    1-bromopropane 447.45
    gamma-valerolactone 1423.53
    n-decanol 121.23
    triethyl phosphate 133.45
    4-methyl-2-pentanol 249.08
    propionitrile 353.92
    vinylene carbonate 614.67
    1,1,2-trichlorotrifluoroethane 842.22
    DMS 318.33
    cumene 121.89
    2-octanol 133.18
    2-hexanone 331.47
    octyl acetate 203.76
    limonene 163.87
    1,2-dimethoxyethane 598.36
    ethyl orthosilicate 133.22
    tributyl phosphate 162.59
    diacetone alcohol 515.06
    N,N-dimethylaniline 207.31
    acrylonitrile 389.56
    aniline 454.61
    1,3-propanediol 485.6
    bromobenzene 532.48
    dibromomethane 930.77
    1,1,2,2-tetrachloroethane 1526.24
    2-methyl-cyclohexyl acetate 264.22
    tetrabutyl urea 194.98
    diisobutyl methanol 133.12
    2-phenylethanol 365.58
    styrene 190.94
    dioctyl adipate 239.12
    dimethyl sulfate 278.21
    ethyl butyrate 235.74
    methyl lactate 252.89
    butyl lactate 268.54
    diethyl carbonate 169.29
    propanediol butyl ether 412.64
    triethyl orthoformate 179.59
    p-tert-butyltoluene 106.5
    methyl 4-tert-butylbenzoate 316.54
    morpholine 1400.13
    tert-butylamine 516.12
    n-dodecanol 92.45
    dimethoxymethane 473.96
    ethylene carbonate 554.75
    cyrene 357.93
    2-ethoxyethyl acetate 364.84
    2-ethylhexyl acetate 300.88
    1,2,4-trichlorobenzene 565.42
    4-methylpyridine 764.45
    dibutyl ether 197.59
    2,6-dimethyl-4-heptanol 133.12
    DEF 434.64
    dimethyl isosorbide 619.83
    tetrachloroethylene 865.46
    eugenol 299.15
    triacetin 380.72
    span 80 382.17
    1,4-butanediol 180.51
    1,1-dichloroethane 982.92
    2-methyl-1-pentanol 312.93
    methyl formate 352.71
    2-methyl-1-butanol 409.02
    n-decane 19.87
    butyronitrile 454.86
    3,7-dimethyl-1-octanol 210.32
    1-chlorooctane 118.15
    1-chlorotetradecane 46.57
    n-nonane 18.77
    undecane 14.73
    tert-butylcyclohexane 48.58
    cyclooctane 33.56
    cyclopentanol 809.27
    tetrahydropyran 1266.35
    tert-amyl methyl ether 311.48
    2,5,8-trioxanonane 526.31
    1-hexene 183.34
    2-isopropoxyethanol 272.89
    2,2,2-trifluoroethanol 307.24
    methyl butyrate 347.15

    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