Piperitenone

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  • Identifiers

    CAS number
    491-09-8

    Molecular formula
    C10H14O

    SMILES
    CC1=CC(=O)C(=C(C)C)CC1

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1340.33
    • Carbowax: 1915.33

  • Odor profile

    Mint 80.87%
    Herbal 70.84%
    Camphoreous 48.8%
    Sweet 43.55%
    Tobacco 41.03%
    Ketonic 40.01%
    Spicy 38.83%
    Fruity 37.11%
    Phenolic 35.91%
    Caramellic 35.05%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    9.17 (weak base)

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 106.00 to 107.00 °C. @ 10.00 mm Hg

    Flash point est.
    93.42 ˚C

    Solubility expt.

    • insoluble in water; soluble in oils
    • miscible (in ethanol)

  • Synonyms

    • Piperitenone
    • 491-09-8
    • 3-Terpinolenone
    • Pulespenone
    • p-Mentha-1,4(8)-dien-3-one
    • 2-CYCLOHEXEN-1-ONE, 3-METHYL-6-(1-METHYLETHYLIDENE)-
    • 3-Methyl-6-(1-methylethylidene)cyclohex-2-en-1-one
    • FEMA No. 3560
    • 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one
    • 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one
    • 3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one
    • IKR841W74D
    • CHEBI:17304
    • p-Menth-1,4(8)-dien-3-one
    • 1-Methyl-4-isopropylidene-1-cyclohexen-3-one
    • EINECS 207-729-5
    • NSC667470
    • NSC-667470
    • DTXSID10883402
    • 3-Methyl-6-(propan-2-ylidene)cyclohex-2-enone
    • P-MENTHA-1,4(8)-DIEN-3-ONE [FHFI]
    • UNII-IKR841W74D
    • CHEMBL54161
    • SCHEMBL220677
    • FEMA 3560
    • HKZQJZIFODOLFR-UHFFFAOYSA-
    • DTXCID001022936
    • AAA49109
    • AKOS022504705
    • LMPR0102090056
    • NCI60_023460
    • 6-Isopropylidene-3-methyl-2-cyclohexenone
    • DB-323850
    • CS-0086696
    • NS00042900
    • 6-isopropylidene-3-methyl-cyclohex-2-en-1-one
    • C01951
    • EN300-126320
    • Q27102310
    • 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one #
    • Z1251353210
    • 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9CI
    • InChI=1/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3
    • 207-729-5

  • Applications

    Piperitenone (CAS 491-09-8) is a natural monoterpene ketone with a minty-herbal odor found in Mentha and some Cymbopogon essential oils; it is used as a versatile synthetic intermediate (e.g., epoxidation to piperitenone oxide, Baeyer-Villiger rearrangements, selective hydrogenation/oxidation toward menthone/menthol derivatives), as a fragrance/flavor modifier in research to add cool, slightly spicy notes, as a chemical standard and chemotaxonomic marker in essential-oil analytics and phytochemistry, and as a reference scaffold in pharmaceutical and agrochemical studies to assess in vitro antimicrobial, antifungal, insecticidal/larvicidal, and antioxidant activities; it is also explored as a terpene-based starting material for biobased materials/monomers, while most uses remain at laboratory scale requiring control of purity, safe handling, and compliance with natural flavor/fragrance regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 321.91
    methanol 355.04
    isopropanol 320.1
    water 0.9
    ethyl acetate 290.3
    n-propanol 301.73
    acetone 364.47
    n-butanol 325.62
    acetonitrile 695.84
    DMF 407.79
    toluene 282.68
    isobutanol 232.46
    1,4-dioxane 841.61
    methyl acetate 297.58
    THF 878.38
    2-butanone 337.68
    n-pentanol 219.26
    sec-butanol 303.35
    n-hexane 148.52
    ethylene glycol 32.95
    NMP 412.88
    cyclohexane 254.45
    DMSO 173.52
    n-butyl acetate 307.41
    n-octanol 200.81
    chloroform 1455.49
    n-propyl acetate 196.61
    acetic acid 287.81
    dichloromethane 992.08
    cyclohexanone 598.53
    propylene glycol 59.15
    isopropyl acetate 161.42
    DMAc 249.61
    2-ethoxyethanol 165.82
    isopentanol 246.02
    n-heptane 120.03
    ethyl formate 264.61
    1,2-dichloroethane 454.34
    n-hexanol 355.66
    2-methoxyethanol 291.33
    isobutyl acetate 128.44
    tetrachloromethane 269.1
    n-pentyl acetate 184.53
    transcutol 520.14
    n-heptanol 172.81
    ethylbenzene 178.05
    MIBK 173.31
    2-propoxyethanol 316.57
    tert-butanol 353.53
    MTBE 275.84
    2-butoxyethanol 191.23
    propionic acid 213.5
    o-xylene 168.3
    formic acid 78.29
    diethyl ether 390.15
    m-xylene 188.68
    p-xylene 230.83
    chlorobenzene 376.62
    dimethyl carbonate 86.34
    n-octane 48.83
    formamide 136.16
    cyclopentanone 575.17
    2-pentanone 275.18
    anisole 239.01
    cyclopentyl methyl ether 363.85
    gamma-butyrolactone 565.99
    1-methoxy-2-propanol 223.9
    pyridine 589.93
    3-pentanone 212.47
    furfural 437.79
    n-dodecane 34.9
    diethylene glycol 157.05
    diisopropyl ether 115.81
    tert-amyl alcohol 275.39
    acetylacetone 214.32
    n-hexadecane 40.58
    acetophenone 201.72
    methyl propionate 196.93
    isopentyl acetate 250.35
    trichloroethylene 871.14
    n-nonanol 166.73
    cyclohexanol 369.18
    benzyl alcohol 195.37
    2-ethylhexanol 218.69
    isooctanol 134.93
    dipropyl ether 244.02
    1,2-dichlorobenzene 301.81
    ethyl lactate 93.35
    propylene carbonate 344.46
    n-methylformamide 244.64
    2-pentanol 231.77
    n-pentane 122.95
    1-propoxy-2-propanol 252.88
    1-methoxy-2-propyl acetate 205.8
    2-(2-methoxypropoxy) propanol 190.43
    mesitylene 127.64
    ε-caprolactone 432.69
    p-cymene 132.92
    epichlorohydrin 568.23
    1,1,1-trichloroethane 607.49
    2-aminoethanol 97.9
    morpholine-4-carbaldehyde 392.49
    sulfolane 379.0
    2,2,4-trimethylpentane 46.43
    2-methyltetrahydrofuran 636.34
    n-hexyl acetate 288.36
    isooctane 40.61
    2-(2-butoxyethoxy)ethanol 253.75
    sec-butyl acetate 132.19
    tert-butyl acetate 174.85
    decalin 88.37
    glycerin 73.44
    diglyme 414.72
    acrylic acid 162.46
    isopropyl myristate 123.03
    n-butyric acid 370.84
    acetyl acetate 175.96
    di(2-ethylhexyl) phthalate 110.71
    ethyl propionate 173.7
    nitromethane 397.71
    1,2-diethoxyethane 261.32
    benzonitrile 368.41
    trioctyl phosphate 80.96
    1-bromopropane 415.22
    gamma-valerolactone 564.0
    n-decanol 122.03
    triethyl phosphate 110.6
    4-methyl-2-pentanol 126.56
    propionitrile 459.98
    vinylene carbonate 327.8
    1,1,2-trichlorotrifluoroethane 285.46
    DMS 168.39
    cumene 126.85
    2-octanol 140.66
    2-hexanone 235.7
    octyl acetate 151.03
    limonene 183.37
    1,2-dimethoxyethane 386.63
    ethyl orthosilicate 111.26
    tributyl phosphate 98.42
    diacetone alcohol 182.7
    N,N-dimethylaniline 160.3
    acrylonitrile 429.4
    aniline 281.63
    1,3-propanediol 161.78
    bromobenzene 377.62
    dibromomethane 757.78
    1,1,2,2-tetrachloroethane 668.01
    2-methyl-cyclohexyl acetate 188.97
    tetrabutyl urea 124.96
    diisobutyl methanol 121.03
    2-phenylethanol 236.4
    styrene 194.9
    dioctyl adipate 155.62
    dimethyl sulfate 101.65
    ethyl butyrate 214.39
    methyl lactate 90.08
    butyl lactate 137.24
    diethyl carbonate 166.26
    propanediol butyl ether 167.36
    triethyl orthoformate 163.01
    p-tert-butyltoluene 124.96
    methyl 4-tert-butylbenzoate 188.57
    morpholine 812.77
    tert-butylamine 280.53
    n-dodecanol 93.36
    dimethoxymethane 261.18
    ethylene carbonate 281.44
    cyrene 167.15
    2-ethoxyethyl acetate 197.3
    2-ethylhexyl acetate 209.91
    1,2,4-trichlorobenzene 330.84
    4-methylpyridine 539.05
    dibutyl ether 223.07
    2,6-dimethyl-4-heptanol 121.03
    DEF 254.94
    dimethyl isosorbide 311.72
    tetrachloroethylene 456.83
    eugenol 173.65
    triacetin 192.89
    span 80 188.35
    1,4-butanediol 65.85
    1,1-dichloroethane 607.26
    2-methyl-1-pentanol 195.91
    methyl formate 193.46
    2-methyl-1-butanol 247.03
    n-decane 60.98
    butyronitrile 523.35
    3,7-dimethyl-1-octanol 163.01
    1-chlorooctane 165.89
    1-chlorotetradecane 68.64
    n-nonane 63.88
    undecane 44.93
    tert-butylcyclohexane 74.97
    cyclooctane 79.98
    cyclopentanol 347.0
    tetrahydropyran 795.72
    tert-amyl methyl ether 189.53
    2,5,8-trioxanonane 288.49
    1-hexene 296.04
    2-isopropoxyethanol 128.52
    2,2,2-trifluoroethanol 97.72
    methyl butyrate 232.75

    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
Calamintha nepeta (Belgium) Calamintha nepeta (L.) Savi (Melissa nepeta L.), fam. Lamiaceae (Labiatae) 2.2%
Calamintha nepeta (Greece) 1 Calamintha nepeta (L.) Savi (Melissa nepeta L.), fam. Lamiaceae (Labiatae) 2.4%
Cymbopogon jwarancusa (India) Cymbopogon jwarancusa (Jones) Schult., fam. Poaceae (Gramineae) 6.5%
Hyssop (Himalaya) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.16%
Mentha cervina Mentha cervina L., fam. Lamiaceae (Labiatae) 34.0%
Mentha gentilis var. lanata Mentha gentilis (L.) var. lanata (Rydb.) Fujita et Fujita, fam. Lamiaceae 0.05%
Mentha longifolia (Italy) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.85%
Mentha longifolia ssp. longifolia (Greece) 90063-99-3 Mentha longifolia (L.) ssp. longifolia, fam. Lamiaceae (Labiatae) 1.1%
Mentha longifolia ssp. petiolata (Greece) 1 90063-99-3 Mentha longifolia (L.) ssp. petiolata (Chemotype I), fam. Lamiaceae 0.7%
Mentha rotundifolia (Greece) 1 Mentha x rotundifolia (L.) Hudson (Chemotype I), fam. Lamiaceae (Labiatae) 0.4%
Mentha rotundifolia (Japan) Mentha rotundifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.3%
Mentha spicata (Greece) Chemotype IIIa Mentha spicata L. (Chemotype IIIa), fam. Lamiaceae (Labiatae) 0.7%
Mentha spicata (Greece) Chemotype IV Mentha spicata L. (Chemotype IV), fam Lamiaceae (Labiatae) 0.55%
Mentha x dumetorum (Greece) Mentha x dumetorum, fam Lamiaceae (Labiatae) 0.07%
Mentha x spicata (Greece) Mentha x spicata L., fam. Lamiaceae (Labiatae) 0.06%
Mentha x villosa (Greece) 1 Mentha x villosa Hudson, fam. Lamiaceae (Labiatae) 0.52%
Mentha x villosa (Greece) 2 Mentha x villosa Hudson, fam. Lamiaceae (Labiatae) 2.01%
Mentha x villoso-nervata (Greece) 1 Mentha x villoso-nervata Opiz (M.longifolia L. x M.spicata L.) (Chemot.I) 1.0%
Mentha rotundifolia (Greece) 2 Mentha rotundifolia (L.) Hudson (Chemotype II), fam. Lamiaceae (Labiatae) 8.15%
Minthostachys glabrescens Minthostachys glabrescens Epling, fam. Lamiaceae (Labiatae) 0.8%
Orange leaf, sweet (North Africa) 1 Citrus sinensis (L.) Osbeck, cultivar Portuguese, fam. Rutaceae 0.12%
Orange leaf, sweet (North Africa) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 1.04%
Orange leaf, sweet (North Africa) 4 Citrus sinensis (L.) Osbeck, cultivar Washington navel, fam. Rutaceae 0.72%
Cornmint (Mentha arvensis) 68917-18-0 Mentha arvensis (L.) var. piperascens Malinv., fam. Lamiaceae (Labiatae) 0.01%
Pennyroyal 1 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 1.65%
Pennyroyal 2 8013-99-8 Mentha pulegium L. (C.R. variety), fam. Lamiaceae (Labiatae) 0.62%
Pennyroyal 3 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.45%
Mentha arvensis, Glabrata Ray variety Mentha arvensis (L.) var. glabrata Ray, fam. Lamiaceae (Labiatae) 0.3%
Scullcap Scutellaria lateriflora L., fam. Lamiaceae (Labiatae) 0.2%
Ziziphora hispanica Ziziphora hispanica L., fam. Lamiaceae (Labiatae) 14.7%
Calamintha nepeta (Turkey) 1 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 40.4%
Ziziphora clinopodioides (Turkey) 1 Ziziphora clinopodioides Lam., fam. Lamiaceae (Labiatae) 1.0%
Acinos suaveolens (Turkey) Acinos suaveolens (Sibt. et Smith) G. Don f., fam. Lamiaceae (Labiatae) 0.67%
Ziziphora clinopodioides (Turkey) 2 Ziziphora clinopodioides Lam., fam. Lamiaceae (Labiatae) 6.84%
Lippia carviodora (Kenya) Lippia carviodora Meikle, fam. Verbenaceae 1.15%
Ziziphora tenuior (Turkey) Ziziphora tenuior L.(Z.acutifolia Montbret & Aucher ex Bentham), Lamiaceae 0.04%
Daphne genkwa Daphne genkwa Sieb. et Zucc., fam. Thymelaeaceae 0.01%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.98%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.11%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.18%
Tagetes 2 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.04%
Orange, sweet, deterpenized 8008-57-9 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.2%
Pistacia lentiscus (Israel) 1a fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 2.3%
Peppermint (Canada) 1 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.35%
Peppermint (Greece) 3 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.1%
Gingergrass (India) 1 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 0.1%
Calamintha nepeta (Turkey) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.9%
Kaempferia galanga rhizome (Malaysia) Kaempferia galanga L. (Alpinia sessilis Kon.), fam. Zingiberaceae 0.56%
Calamintha arkansana Calamintha arkansana (Nutt.) Shinners, fam. Lamiaceae (Labiatae) 0.07%
Tagetes erecta (Portugal) Tagetes erecta L. (T. major Gaertn), fam. Asteraceae (Compositae) 2.7%