Piperitone, L-

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    4573-50-6

    Molecular formula
    C10H16O

    SMILES
    CC1=CC(=O)[C@H](CC1)C(C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1271.0
    • Carbowax: 1739.0

  • Odor profile

    Mint 86.11%
    Herbal 83.78%
    Camphoreous 65.97%
    Cooling 53.05%
    Fresh 52.23%
    Spicy 48.13%
    Woody 43.94%
    Ketonic 37.59%
    Sweet 35.82%
    Phenolic 35.08%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    8.94 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    227°C

    Flash point est.
    85.42 ˚C

    Solubility expt.

    • Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • l-piperitone
    • 4573-50-6
    • (-)-piperitone
    • Piperitone, L-
    • (R)-6-(Isopropyl)-3-methylcyclohex-2-en-1-one
    • 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6R)-
    • 8GZY0Q0N20
    • (6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
    • CHEBI:48934
    • EINECS 224-957-0
    • L-PIPERITONE [FHFI]
    • FEMA NO. 4200
    • DTXSID10884090
    • (6R)-6-isopropyl-3-methylcyclohex-2-en-1-one
    • FEMA NO. 2910, L-
    • (6R)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
    • (6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one
    • (R)-Piperitone
    • piperiton
    • UNII-8GZY0Q0N20
    • (+/-)-Piperitone
    • (-)-p-Menth-1-en-3-one
    • SCHEMBL3508682
    • CHEMBL2229207
    • YSTPAHQEHQSRJD-SECBINFHSA-N
    • DTXCID001023560
    • MFCD23380212
    • NS00082958
    • P1783
    • (-)-6-Isopropyl-3-methyl-2-cyclohexen-1-one
    • (R)-6-Isopropyl-3-methylcyclohex-2-en-1-one
    • Q27121390
    • 224-957-0

  • Applications

    L-Piperitone (Piperitone, L-, CAS 4573-50-6) is a monoterpene ketone with a minty, camphoraceous odor used in fragrance and flavor formulations to impart fresh, herbaceous, cooling notes; as a versatile chiral intermediate for the synthesis of menthol/menthone/isomenthone, thymol/carvacrol and other terpenoid derivatives; as a renewable feedstock sourced from essential oils (e.g., Eucalyptus dives, Mentha species) for green-chemistry processes; in personal care, cleaning and household products as an aroma or masking agent, and it is actively studied for antimicrobial, insect-repellent and fumigant activities; it also serves as an analytical reference standard in GC-MS for essential-oil and flavor quality control, and as an asymmetric building block in organic synthesis and in encapsulation/controlled-release systems to stabilize and tailor sensory delivery.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 777.97
    methanol 872.9
    isopropanol 719.0
    water 1.17
    ethyl acetate 379.11
    n-propanol 584.08
    acetone 567.02
    n-butanol 600.19
    acetonitrile 1101.48
    DMF 484.51
    toluene 351.66
    isobutanol 433.39
    1,4-dioxane 1105.64
    methyl acetate 380.04
    THF 1273.73
    2-butanone 465.36
    n-pentanol 358.94
    sec-butanol 472.15
    n-hexane 159.61
    ethylene glycol 60.85
    NMP 472.22
    cyclohexane 299.53
    DMSO 287.53
    n-butyl acetate 481.76
    n-octanol 267.72
    chloroform 2177.4
    n-propyl acetate 254.29
    acetic acid 496.06
    dichloromethane 1505.47
    cyclohexanone 848.62
    propylene glycol 108.45
    isopropyl acetate 218.43
    DMAc 264.93
    2-ethoxyethanol 238.78
    isopentanol 440.4
    n-heptane 130.36
    ethyl formate 371.49
    1,2-dichloroethane 624.53
    n-hexanol 597.12
    2-methoxyethanol 464.89
    isobutyl acetate 170.12
    tetrachloromethane 345.25
    n-pentyl acetate 240.87
    transcutol 881.09
    n-heptanol 235.06
    ethylbenzene 183.99
    MIBK 230.11
    2-propoxyethanol 517.82
    tert-butanol 590.58
    MTBE 400.6
    2-butoxyethanol 276.89
    propionic acid 338.21
    o-xylene 189.85
    formic acid 127.21
    diethyl ether 525.09
    m-xylene 230.81
    p-xylene 248.54
    chlorobenzene 519.44
    dimethyl carbonate 90.42
    n-octane 46.92
    formamide 181.05
    cyclopentanone 740.74
    2-pentanone 383.91
    anisole 257.46
    cyclopentyl methyl ether 456.56
    gamma-butyrolactone 775.94
    1-methoxy-2-propanol 335.08
    pyridine 818.71
    3-pentanone 257.37
    furfural 604.64
    n-dodecane 36.2
    diethylene glycol 268.77
    diisopropyl ether 142.94
    tert-amyl alcohol 381.79
    acetylacetone 276.07
    n-hexadecane 42.23
    acetophenone 225.63
    methyl propionate 232.58
    isopentyl acetate 389.22
    trichloroethylene 1272.61
    n-nonanol 210.92
    cyclohexanol 550.24
    benzyl alcohol 253.31
    2-ethylhexanol 293.98
    isooctanol 182.48
    dipropyl ether 286.33
    1,2-dichlorobenzene 387.13
    ethyl lactate 110.35
    propylene carbonate 476.79
    n-methylformamide 322.12
    2-pentanol 376.06
    n-pentane 153.55
    1-propoxy-2-propanol 373.42
    1-methoxy-2-propyl acetate 289.23
    2-(2-methoxypropoxy) propanol 250.8
    mesitylene 151.77
    ε-caprolactone 600.37
    p-cymene 153.78
    epichlorohydrin 805.52
    1,1,1-trichloroethane 806.12
    2-aminoethanol 176.0
    morpholine-4-carbaldehyde 495.5
    sulfolane 528.11
    2,2,4-trimethylpentane 54.45
    2-methyltetrahydrofuran 904.57
    n-hexyl acetate 377.87
    isooctane 50.97
    2-(2-butoxyethoxy)ethanol 352.38
    sec-butyl acetate 159.93
    tert-butyl acetate 222.61
    decalin 93.15
    glycerin 126.17
    diglyme 568.09
    acrylic acid 262.76
    isopropyl myristate 146.43
    n-butyric acid 624.16
    acetyl acetate 213.81
    di(2-ethylhexyl) phthalate 138.73
    ethyl propionate 191.42
    nitromethane 588.8
    1,2-diethoxyethane 366.81
    benzonitrile 523.86
    trioctyl phosphate 104.29
    1-bromopropane 563.57
    gamma-valerolactone 791.13
    n-decanol 153.57
    triethyl phosphate 119.59
    4-methyl-2-pentanol 184.67
    propionitrile 680.2
    vinylene carbonate 460.29
    1,1,2-trichlorotrifluoroethane 424.92
    DMS 201.18
    cumene 132.09
    2-octanol 177.81
    2-hexanone 319.46
    octyl acetate 182.45
    limonene 226.73
    1,2-dimethoxyethane 505.14
    ethyl orthosilicate 123.7
    tributyl phosphate 127.03
    diacetone alcohol 239.93
    N,N-dimethylaniline 166.11
    acrylonitrile 643.29
    aniline 383.67
    1,3-propanediol 306.22
    bromobenzene 539.2
    dibromomethane 1132.43
    1,1,2,2-tetrachloroethane 931.96
    2-methyl-cyclohexyl acetate 225.13
    tetrabutyl urea 151.92
    diisobutyl methanol 158.43
    2-phenylethanol 318.57
    styrene 226.5
    dioctyl adipate 189.22
    dimethyl sulfate 114.06
    ethyl butyrate 262.82
    methyl lactate 111.32
    butyl lactate 190.45
    diethyl carbonate 189.42
    propanediol butyl ether 259.84
    triethyl orthoformate 193.41
    p-tert-butyltoluene 144.09
    methyl 4-tert-butylbenzoate 216.64
    morpholine 1112.47
    tert-butylamine 458.75
    n-dodecanol 117.41
    dimethoxymethane 300.21
    ethylene carbonate 382.66
    cyrene 194.56
    2-ethoxyethyl acetate 267.96
    2-ethylhexyl acetate 306.4
    1,2,4-trichlorobenzene 419.55
    4-methylpyridine 760.61
    dibutyl ether 267.02
    2,6-dimethyl-4-heptanol 158.43
    DEF 307.89
    dimethyl isosorbide 384.55
    tetrachloroethylene 612.19
    eugenol 202.88
    triacetin 248.78
    span 80 258.46
    1,4-butanediol 109.24
    1,1-dichloroethane 903.33
    2-methyl-1-pentanol 295.58
    methyl formate 249.35
    2-methyl-1-butanol 400.74
    n-decane 63.75
    butyronitrile 827.78
    3,7-dimethyl-1-octanol 224.16
    1-chlorooctane 193.89
    1-chlorotetradecane 78.07
    n-nonane 66.11
    undecane 46.5
    tert-butylcyclohexane 80.79
    cyclooctane 87.57
    cyclopentanol 534.28
    tetrahydropyran 1183.02
    tert-amyl methyl ether 236.77
    2,5,8-trioxanonane 362.56
    1-hexene 375.04
    2-isopropoxyethanol 174.5
    2,2,2-trifluoroethanol 136.49
    methyl butyrate 284.64

    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
Pennyroyal 2 8013-99-8 Mentha pulegium L. (C.R. variety), fam. Lamiaceae (Labiatae) 0.09%
Pennyroyal 3 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.45%
Peppermint (USA) 2 8006-90-4 Mentha piperita L. cultivar Mitcham, fam. Lamiaceae (Labiatae) 0.5%