Isopiperitenone

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  • Identifiers

    CAS number
    529-01-1

    Molecular formula
    C10H14O

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

    Retention indicies (RI)

    • DB5: 1272.0
    • Carbowax: 1832.33

  • Odor profile

    Fruity 85.94%
    Mint 76.84%
    Herbal 66.42%
    Sweet 60.96%
    Spicy 45.09%
    Camphoreous 38.86%
    Tobacco 38.73%
    Woody 37.43%
    Green 36.85%
    Caramellic 33.68%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    232°C

    Flash point est.
    89.42 ˚C

  • Synonyms

    • Isopiperitenone
    • 529-01-1
    • Isopiperitenon
    • p-Mentha-1,8-dien-3-one
    • Iso-piperitenone
    • 3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-one
    • 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethenyl)-
    • NSC 120531
    • CHEBI:50110
    • (-)-Isoperitenone
    • NSC-120531
    • 3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one
    • 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one
    • 6-Isopropenyl-3-methyl-2-cyclohexen-1-one #
    • (S)-3-Methyl-6beta-isopropenyl-2-cyclohexene-1-one
    • 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enone
    • 1,8-para-Menthadien-3-one
    • SCHEMBL300586
    • C9MB368R8Y
    • DTXSID201316866
    • RAA75082
    • NSC120531
    • 6-Isopropenyl-3-methyl-2-cyclohexen-1-one
    • DS-004040
    • 2-Cyclohexen-1-one,3-methyl-6-(1-methylethenyl)-
    • Q27104748

  • Applications

    Isopiperitenone (CAS 529-01-1) is an unsaturated monoterpene ketone that acts as an intermediate in the menthol biosynthetic pathway of Mentha; in practice it is used mainly as an analytical reference standard to identify/quantify trace levels in mint essential oils by GC-MS/GC-FID for authenticity testing and post-harvest change monitoring, as a substrate/matrix in enzymology and metabolism studies (e.g., probing p-menthane dehydrogenases/reductases and isotope tracing of pathway flux), and as a synthetic building block to prepare or transform related monoterpene ketones (pulegone, menthone/isomenthone and fragrance derivatives), and it is leveraged in biochemical and metabolic-engineering work to reconstruct mint aroma pathways in microbes; additionally, its occurrence profile serves as a chemotaxonomic marker to distinguish Mentha species/chemotypes and to study cultivation effects, and it is sometimes used as a reference in in vitro screening of enone bioactivities, though direct use in flavors and fragrances is typically limited and must follow safety regulations because enones are reactive, so it should be handled with good ventilation, limited exposure to air/light, and appropriate PPE.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 597.4
    methanol 703.78
    isopropanol 524.88
    water 1.09
    ethyl acetate 324.62
    n-propanol 445.84
    acetone 434.91
    n-butanol 486.22
    acetonitrile 750.06
    DMF 494.61
    toluene 281.39
    isobutanol 333.81
    1,4-dioxane 1019.75
    methyl acetate 303.97
    THF 1031.44
    2-butanone 363.46
    n-pentanol 296.01
    sec-butanol 380.03
    n-hexane 106.04
    ethylene glycol 55.8
    NMP 383.87
    cyclohexane 202.18
    DMSO 261.26
    n-butyl acetate 368.66
    n-octanol 216.87
    chloroform 1341.05
    n-propyl acetate 214.75
    acetic acid 391.9
    dichloromethane 912.9
    cyclohexanone 641.56
    propylene glycol 105.07
    isopropyl acetate 185.54
    DMAc 270.72
    2-ethoxyethanol 233.97
    isopentanol 360.19
    n-heptane 97.45
    ethyl formate 305.75
    1,2-dichloroethane 412.23
    n-hexanol 485.72
    2-methoxyethanol 443.75
    isobutyl acetate 140.63
    tetrachloromethane 198.02
    n-pentyl acetate 181.61
    transcutol 933.11
    n-heptanol 182.63
    ethylbenzene 145.21
    MIBK 191.53
    2-propoxyethanol 463.58
    tert-butanol 513.97
    MTBE 313.64
    2-butoxyethanol 234.03
    propionic acid 260.67
    o-xylene 150.07
    formic acid 122.96
    diethyl ether 421.67
    m-xylene 191.76
    p-xylene 187.32
    chlorobenzene 357.48
    dimethyl carbonate 89.61
    n-octane 31.4
    formamide 175.33
    cyclopentanone 518.17
    2-pentanone 304.29
    anisole 233.48
    cyclopentyl methyl ether 375.46
    gamma-butyrolactone 557.89
    1-methoxy-2-propanol 329.62
    pyridine 604.65
    3-pentanone 206.49
    furfural 492.31
    n-dodecane 24.84
    diethylene glycol 266.31
    diisopropyl ether 118.4
    tert-amyl alcohol 332.51
    acetylacetone 244.73
    n-hexadecane 28.96
    acetophenone 190.53
    methyl propionate 200.05
    isopentyl acetate 299.17
    trichloroethylene 817.29
    n-nonanol 178.04
    cyclohexanol 452.76
    benzyl alcohol 224.0
    2-ethylhexanol 245.46
    isooctanol 143.38
    dipropyl ether 247.75
    1,2-dichlorobenzene 268.04
    ethyl lactate 108.53
    propylene carbonate 375.26
    n-methylformamide 293.74
    2-pentanol 302.0
    n-pentane 107.14
    1-propoxy-2-propanol 348.08
    1-methoxy-2-propyl acetate 262.78
    2-(2-methoxypropoxy) propanol 251.95
    mesitylene 118.07
    ε-caprolactone 451.25
    p-cymene 118.85
    epichlorohydrin 601.18
    1,1,1-trichloroethane 524.9
    2-aminoethanol 164.96
    morpholine-4-carbaldehyde 464.13
    sulfolane 377.3
    2,2,4-trimethylpentane 40.56
    2-methyltetrahydrofuran 707.8
    n-hexyl acetate 291.48
    isooctane 39.57
    2-(2-butoxyethoxy)ethanol 365.22
    sec-butyl acetate 142.01
    tert-butyl acetate 198.44
    decalin 65.67
    glycerin 127.42
    diglyme 560.41
    acrylic acid 194.2
    isopropyl myristate 121.72
    n-butyric acid 475.32
    acetyl acetate 198.91
    di(2-ethylhexyl) phthalate 119.98
    ethyl propionate 169.83
    nitromethane 490.98
    1,2-diethoxyethane 346.23
    benzonitrile 387.28
    trioctyl phosphate 87.24
    1-bromopropane 364.38
    gamma-valerolactone 628.06
    n-decanol 132.23
    triethyl phosphate 106.86
    4-methyl-2-pentanol 158.05
    propionitrile 467.17
    vinylene carbonate 359.6
    1,1,2-trichlorotrifluoroethane 330.09
    DMS 174.89
    cumene 102.51
    2-octanol 135.31
    2-hexanone 257.55
    octyl acetate 149.96
    limonene 174.38
    1,2-dimethoxyethane 490.15
    ethyl orthosilicate 107.3
    tributyl phosphate 109.83
    diacetone alcohol 229.45
    N,N-dimethylaniline 150.47
    acrylonitrile 444.63
    aniline 320.38
    1,3-propanediol 268.86
    bromobenzene 345.23
    dibromomethane 679.48
    1,1,2,2-tetrachloroethane 610.18
    2-methyl-cyclohexyl acetate 192.07
    tetrabutyl urea 130.14
    diisobutyl methanol 134.82
    2-phenylethanol 281.01
    styrene 171.48
    dioctyl adipate 161.64
    dimethyl sulfate 105.19
    ethyl butyrate 227.37
    methyl lactate 111.07
    butyl lactate 159.08
    diethyl carbonate 169.06
    propanediol butyl ether 239.18
    triethyl orthoformate 171.49
    p-tert-butyltoluene 113.24
    methyl 4-tert-butylbenzoate 188.2
    morpholine 1017.56
    tert-butylamine 373.89
    n-dodecanol 102.86
    dimethoxymethane 308.81
    ethylene carbonate 307.47
    cyrene 186.3
    2-ethoxyethyl acetate 222.96
    2-ethylhexyl acetate 236.82
    1,2,4-trichlorobenzene 301.83
    4-methylpyridine 575.44
    dibutyl ether 227.66
    2,6-dimethyl-4-heptanol 134.82
    DEF 275.75
    dimethyl isosorbide 375.19
    tetrachloroethylene 391.07
    eugenol 186.33
    triacetin 215.06
    span 80 243.88
    1,4-butanediol 99.49
    1,1-dichloroethane 544.63
    2-methyl-1-pentanol 245.13
    methyl formate 231.14
    2-methyl-1-butanol 318.75
    n-decane 43.5
    butyronitrile 580.93
    3,7-dimethyl-1-octanol 197.13
    1-chlorooctane 139.14
    1-chlorotetradecane 58.28
    n-nonane 43.62
    undecane 31.8
    tert-butylcyclohexane 59.72
    cyclooctane 59.26
    cyclopentanol 399.41
    tetrahydropyran 913.59
    tert-amyl methyl ether 200.3
    2,5,8-trioxanonane 381.41
    1-hexene 257.54
    2-isopropoxyethanol 168.7
    2,2,2-trifluoroethanol 112.57
    methyl butyrate 245.45

    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
Armoise flower 8008-93-3 Artemisia vulgaris L., fam. Asteraceae (Compositae) 0.03%
Mentha x villosa (Belgium) Mentha x villosa H. nm. alopecuroides (M. x alopecuroides; M. x velutina) 0.7%
Pennyroyal 1 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.05%
Pennyroyal 3 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.25%
Calamintha nepeta (Greece) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.05%
Ziziphora tenuior (Turkey) Ziziphora tenuior L.(Z.acutifolia Montbret & Aucher ex Bentham), Lamiaceae 0.71%
Tagetes 2 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.05%
Pistacia lentiscus (Israel) 1a fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 2.21%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Gingergrass (India) 5 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 0.11%
Calamintha nepeta (Turkey) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.9%
Eucalyptus dealbata (Morocco) Eucalyptus dealbata A. Cunn. ex Schau, fam. Myrtaceae 0.01%
Fokienia hodginsii Fokienia hodginsii (Dunn) Henry et Thomas, fam. Cupressaceae 0.54%
Oenothera odorata flower concrete (China) Oenothera odorata Jacq., fam. Onagraceae 0.64%
Hyptis mutabilis Hyptis mutabilis (Rich.) Briq., fam. Lamiaceae (Labiatae) 0.25%
Dill herb (Cuba) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.4%
Calamintha incana (Turkey) Calamintha incana (Sm.) Boiss., fam. Lamiaceae (Labiatae) 1.03%
Lime (Persian) (Japan) Citrus latifolia Tanaka, fam. Rutaceae 0.01%
Minthostachys spicata Minthostachys spicata (Benth.) Epl., fam Lamiaceae (Labiatae) 0.2%
Mentha longifolia (Lithuania) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.25%
Tagetes (Turkey) 8016-84-0 Tagetes minuta L. (T. glandulifera Schrank), fam. Asteraceae (Compositae) 0.26%
Citrus japonica peel (Vietnam) Citrus japonica L., fam. Rutaceae 0.05%
Verbena officinalis leaf (Morocco) Verbena officinalis L., fam. Verbenaceae 0.96%
Mentha spicata (Cuba) Chemotype Mentha spicata L., fam. Lamiaceae (Labiatae) 0.6%
Rosemary (Japan) 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.13%
Rosemary (Brazil) 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Salvia aramiensis (Turkey) Salvia aramiensis Rech. fil., fam. Lamiaceae (Labiatae) 0.05%
Calamintha vardarensis Calamintha vardarensis (Greuter et Burdet) Silic, fam.Lamiaceae (Labiatae) 0.1%
Mentha longifolia (Iran) 3 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 1.0%
Calamintha nepeta (Montenegro) Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.2%
Cymbopogon giganteus (Mali) Cymbopogon giganteus (Hochst.) Chiov., fam. Poaceae (Gramineae) 0.15%
Prostanthera staurophylla Prostanthera staurophylla F. Muell., fam. Lamiaceae (Labiatae) 0.7%
Tanacetum balsamita Tanacetum balsamita L., fam. Asteraceae (Compositae) 0.1%
Calamintha sylvatica (Yugoslavia) Calamintha sylvatica Bromf., ssp. sylvatica, fam. Lamiaceae (Labiatae) 0.9%
Pennyroyal (Greece) 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 3.0%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.05%
Mentha longifolia (Jordan) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.5%