4-Hydroxypiperitone

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  • Identifiers

    CAS number
    41853-05-8

    Molecular formula
    C10H18O2

    SMILES
    CC1CC(=O)C(CC1O)C(C)C

    Retention indicies (RI)

    • Carbowax: 2014.0

  • Odor profile

    Mint 62.69%
    Herbal 53.04%
    Woody 50.24%
    Camphoreous 49.45%
    Cooling 49.08%
    Sweet 38.36%
    Spicy 33.58%
    Earthy 32.63%
    Phenolic 30.85%
    Fresh 30.51%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    170.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    292°C

    Flash point est.
    111.45 ˚C

  • Synonyms

    • 4-Hydroxypiperitone
    • NCNOFEZLRJLBDH-UHFFFAOYSA-N

  • Applications

    4‑Hydroxypiperitone is a hydroxylated monoterpenoid enone; in research and industry it is mainly employed as a synthetic intermediate to assemble complex monoterpenoid frameworks and piperitone derivatives for drug discovery (e.g., antimicrobial, anti‑inflammatory, antioxidant leads), terpene‑based biopesticide development, and as a platform to benchmark asymmetric catalysis (selective reductions, epoxidations, Michael/aldol reactions); the C4‑OH increases polarity and derivatization flexibility (esters, ethers, carbamates, oximes), enabling fine‑tuning of solubility, stability, and bioactivity; in flavor and fragrance work it serves as a starting material for transformations yielding minty/herbal odorants and as a reference compound to study odor impact of terpene enones; it is also used as a substrate for microbial biotransformations, as an analytical standard (HPLC/GC‑MS) for impurity profiling and reaction monitoring, and as a bio‑derived feedstock from essential oils to support greener processes and small‑scale functional materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 296.92
    methanol 394.82
    isopropanol 280.89
    water 6.12
    ethyl acetate 59.38
    n-propanol 215.83
    acetone 102.89
    n-butanol 177.27
    acetonitrile 141.2
    DMF 155.82
    toluene 52.84
    isobutanol 151.14
    1,4-dioxane 291.74
    methyl acetate 81.17
    THF 300.25
    2-butanone 94.3
    n-pentanol 110.88
    sec-butanol 156.76
    n-hexane 6.15
    ethylene glycol 77.18
    NMP 131.83
    cyclohexane 13.72
    DMSO 157.16
    n-butyl acetate 83.49
    n-octanol 82.27
    chloroform 426.99
    n-propyl acetate 50.42
    acetic acid 177.69
    dichloromethane 273.94
    cyclohexanone 164.6
    propylene glycol 99.1
    isopropyl acetate 45.59
    DMAc 120.01
    2-ethoxyethanol 131.38
    isopentanol 124.66
    n-heptane 7.55
    ethyl formate 85.98
    1,2-dichloroethane 112.23
    n-hexanol 150.4
    2-methoxyethanol 233.34
    isobutyl acetate 42.33
    tetrachloromethane 57.04
    n-pentyl acetate 59.77
    transcutol 257.01
    n-heptanol 86.3
    ethylbenzene 39.25
    MIBK 54.6
    2-propoxyethanol 191.31
    tert-butanol 219.7
    MTBE 78.88
    2-butoxyethanol 120.98
    propionic acid 128.06
    o-xylene 46.9
    formic acid 89.67
    diethyl ether 64.14
    m-xylene 45.79
    p-xylene 57.35
    chlorobenzene 90.54
    dimethyl carbonate 21.6
    n-octane 5.08
    formamide 87.51
    cyclopentanone 179.46
    2-pentanone 69.46
    anisole 76.24
    cyclopentyl methyl ether 80.77
    gamma-butyrolactone 201.02
    1-methoxy-2-propanol 164.83
    pyridine 170.42
    3-pentanone 44.94
    furfural 208.1
    n-dodecane 5.49
    diethylene glycol 167.8
    diisopropyl ether 22.2
    tert-amyl alcohol 131.87
    acetylacetone 71.85
    n-hexadecane 6.17
    acetophenone 73.41
    methyl propionate 47.96
    isopentyl acetate 83.45
    trichloroethylene 241.73
    n-nonanol 68.77
    cyclohexanol 120.52
    benzyl alcohol 88.18
    2-ethylhexanol 75.68
    isooctanol 66.57
    dipropyl ether 43.1
    1,2-dichlorobenzene 84.57
    ethyl lactate 46.85
    propylene carbonate 123.11
    n-methylformamide 104.99
    2-pentanol 91.19
    n-pentane 7.08
    1-propoxy-2-propanol 130.82
    1-methoxy-2-propyl acetate 78.57
    2-(2-methoxypropoxy) propanol 95.51
    mesitylene 31.93
    ε-caprolactone 147.1
    p-cymene 37.41
    epichlorohydrin 189.68
    1,1,1-trichloroethane 125.44
    2-aminoethanol 152.42
    morpholine-4-carbaldehyde 176.04
    sulfolane 192.5
    2,2,4-trimethylpentane 6.71
    2-methyltetrahydrofuran 169.36
    n-hexyl acetate 86.2
    isooctane 6.43
    2-(2-butoxyethoxy)ethanol 130.7
    sec-butyl acetate 38.28
    tert-butyl acetate 54.68
    decalin 10.17
    glycerin 127.92
    diglyme 191.27
    acrylic acid 108.71
    isopropyl myristate 37.33
    n-butyric acid 149.47
    acetyl acetate 48.35
    di(2-ethylhexyl) phthalate 49.82
    ethyl propionate 39.98
    nitromethane 164.84
    1,2-diethoxyethane 80.01
    benzonitrile 119.22
    trioctyl phosphate 37.64
    1-bromopropane 74.01
    gamma-valerolactone 235.34
    n-decanol 50.96
    triethyl phosphate 35.88
    4-methyl-2-pentanol 59.44
    propionitrile 113.37
    vinylene carbonate 121.26
    1,1,2-trichlorotrifluoroethane 163.11
    DMS 53.84
    cumene 36.78
    2-octanol 59.56
    2-hexanone 61.21
    octyl acetate 48.38
    limonene 45.48
    1,2-dimethoxyethane 162.41
    ethyl orthosilicate 35.95
    tributyl phosphate 37.57
    diacetone alcohol 90.04
    N,N-dimethylaniline 56.94
    acrylonitrile 137.01
    aniline 87.67
    1,3-propanediol 188.7
    bromobenzene 81.36
    dibromomethane 171.86
    1,1,2,2-tetrachloroethane 207.14
    2-methyl-cyclohexyl acetate 63.5
    tetrabutyl urea 46.9
    diisobutyl methanol 46.22
    2-phenylethanol 103.87
    styrene 44.13
    dioctyl adipate 50.64
    dimethyl sulfate 42.22
    ethyl butyrate 55.04
    methyl lactate 50.23
    butyl lactate 64.22
    diethyl carbonate 40.11
    propanediol butyl ether 117.96
    triethyl orthoformate 45.63
    p-tert-butyltoluene 35.65
    methyl 4-tert-butylbenzoate 81.5
    morpholine 277.63
    tert-butylamine 125.23
    n-dodecanol 38.49
    dimethoxymethane 78.51
    ethylene carbonate 100.36
    cyrene 94.12
    2-ethoxyethyl acetate 71.54
    2-ethylhexyl acetate 61.78
    1,2,4-trichlorobenzene 100.49
    4-methylpyridine 137.7
    dibutyl ether 44.31
    2,6-dimethyl-4-heptanol 46.22
    DEF 63.52
    dimethyl isosorbide 139.44
    tetrachloroethylene 139.43
    eugenol 87.26
    triacetin 74.19
    span 80 96.35
    1,4-butanediol 83.8
    1,1-dichloroethane 144.33
    2-methyl-1-pentanol 91.27
    methyl formate 82.08
    2-methyl-1-butanol 111.72
    n-decane 9.01
    butyronitrile 128.58
    3,7-dimethyl-1-octanol 69.34
    1-chlorooctane 37.05
    1-chlorotetradecane 15.3
    n-nonane 7.88
    undecane 6.87
    tert-butylcyclohexane 10.73
    cyclooctane 4.88
    cyclopentanol 152.24
    tetrahydropyran 191.4
    tert-amyl methyl ether 54.8
    2,5,8-trioxanonane 142.73
    1-hexene 29.32
    2-isopropoxyethanol 93.71
    2,2,2-trifluoroethanol 67.6
    methyl butyrate 58.72

    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
Mentha longifolia ssp. himalaiensis 90063-99-3 Mentha longifolia (L.) Hudson, ssp. himalaiensis Briq., fam. Lamiaceae 2.8%
Calamintha nepeta (Greece) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 0.1%
Calamintha nepeta (Italy) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.6%
Erichtites hieracifolia (Brazil) Erichtites hieracifolia (L.) Raf. ex DC, fam. Asteraceae (Compositae) 1.2%
Thapsia garganica root Thapsia garganica L., fam. Apiaceae (Umbelliferae) 0.55%
Plectranthus glandulosus (Cameroon) 2 Plectranthus glandulosus Hook f., fam. Lamiaceae (Labiatae) 0.7%
Mentha longifolia (Jordan) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.2%