(+)-trans-Isopiperitenol

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  • Identifiers

    CAS number
    4017-77-0

    Molecular formula
    C10H16O

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

    Retention indicies (RI)

    • Carbowax: 1673.0

  • Odor profile

    Herbal 81.57%
    Mint 72.37%
    Green 57.21%
    Fruity 54.72%
    Floral 52.75%
    Spicy 52.55%
    Sweet 48.5%
    Fresh 48.28%
    Woody 48.26%
    Cooling 44.93%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    225°C

    Flash point est.
    99.19 ˚C

  • Synonyms

    • 4017-77-0
    • (1R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-ol
    • (+)-trans-isopiperitenol
    • (1R,6S)-isopiperitenol
    • SCHEMBL5904277
    • DTXSID00468848
    • trans-p-mentha-1,8-diene-3-ol
    • CHEBI:169979
    • (1R,6S)-p-mentha-1,8-dien-3-ol
    • (1R,6S)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-ol

  • Applications

    (+)-trans-Isopiperitenol (CAS 4017-77-0) is a monoterpene alcohol best known as a key intermediate in menthol biosynthesis in mint; in practice it is used as an analytical reference standard for profiling mint pathways in essential oils, as a chiral building block/precursor for synthesizing menthane-based flavors, fragrances and bioactive molecules, as a reference substrate/product in enzymology studies (e.g., limonene-3-hydroxylase and isopiperitenol dehydrogenase), and as a model compound in metabolic engineering toward menthol production, and it is also evaluated for its characteristic minty–herbal odor and typical monoterpene-alcohol bioactivities (e.g., antimicrobial, antioxidant), although its commercial role is more often as a precursor or intermediate than as a final perfuming agent.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1394.2
    methanol 1465.08
    isopropanol 1032.02
    water 1.28
    ethyl acetate 364.31
    n-propanol 932.6
    acetone 438.83
    n-butanol 867.67
    acetonitrile 778.86
    DMF 387.59
    toluene 178.17
    isobutanol 493.53
    1,4-dioxane 1374.33
    methyl acetate 310.39
    THF 1528.25
    2-butanone 363.47
    n-pentanol 431.2
    sec-butanol 563.3
    n-hexane 76.27
    ethylene glycol 76.46
    NMP 217.06
    cyclohexane 161.92
    DMSO 329.0
    n-butyl acetate 403.6
    n-octanol 228.5
    chloroform 819.46
    n-propyl acetate 209.53
    acetic acid 444.31
    dichloromethane 541.34
    cyclohexanone 459.13
    propylene glycol 153.39
    isopropyl acetate 193.8
    DMAc 198.09
    2-ethoxyethanol 353.08
    isopentanol 493.88
    n-heptane 113.69
    ethyl formate 305.36
    1,2-dichloroethane 272.97
    n-hexanol 735.28
    2-methoxyethanol 738.69
    isobutyl acetate 129.47
    tetrachloromethane 128.74
    n-pentyl acetate 165.61
    transcutol 1071.51
    n-heptanol 238.91
    ethylbenzene 73.22
    MIBK 182.03
    2-propoxyethanol 649.93
    tert-butanol 795.58
    MTBE 440.52
    2-butoxyethanol 299.31
    propionic acid 265.73
    o-xylene 91.05
    formic acid 150.69
    diethyl ether 704.35
    m-xylene 118.5
    p-xylene 91.18
    chlorobenzene 200.52
    dimethyl carbonate 62.14
    n-octane 27.11
    formamide 207.01
    cyclopentanone 427.74
    2-pentanone 315.42
    anisole 161.73
    cyclopentyl methyl ether 394.69
    gamma-butyrolactone 443.92
    1-methoxy-2-propanol 499.94
    pyridine 517.12
    3-pentanone 179.84
    furfural 357.75
    n-dodecane 18.86
    diethylene glycol 329.04
    diisopropyl ether 138.38
    tert-amyl alcohol 412.41
    acetylacetone 197.39
    n-hexadecane 21.36
    acetophenone 116.52
    methyl propionate 190.17
    isopentyl acetate 301.13
    trichloroethylene 464.26
    n-nonanol 183.93
    cyclohexanol 441.72
    benzyl alcohol 156.69
    2-ethylhexanol 294.53
    isooctanol 161.54
    dipropyl ether 386.17
    1,2-dichlorobenzene 138.07
    ethyl lactate 87.67
    propylene carbonate 260.65
    n-methylformamide 297.64
    2-pentanol 436.34
    n-pentane 112.72
    1-propoxy-2-propanol 460.23
    1-methoxy-2-propyl acetate 264.89
    2-(2-methoxypropoxy) propanol 225.15
    mesitylene 74.58
    ε-caprolactone 364.85
    p-cymene 82.94
    epichlorohydrin 522.85
    1,1,1-trichloroethane 293.15
    2-aminoethanol 247.88
    morpholine-4-carbaldehyde 372.43
    sulfolane 259.7
    2,2,4-trimethylpentane 33.43
    2-methyltetrahydrofuran 846.53
    n-hexyl acetate 242.43
    isooctane 37.19
    2-(2-butoxyethoxy)ethanol 377.46
    sec-butyl acetate 129.03
    tert-butyl acetate 189.16
    decalin 39.25
    glycerin 167.77
    diglyme 583.28
    acrylic acid 161.59
    isopropyl myristate 95.18
    n-butyric acid 582.18
    acetyl acetate 157.46
    di(2-ethylhexyl) phthalate 90.7
    ethyl propionate 143.27
    nitromethane 454.8
    1,2-diethoxyethane 426.88
    benzonitrile 234.87
    trioctyl phosphate 71.09
    1-bromopropane 305.47
    gamma-valerolactone 545.18
    n-decanol 130.35
    triethyl phosphate 80.8
    4-methyl-2-pentanol 206.19
    propionitrile 511.2
    vinylene carbonate 233.5
    1,1,2-trichlorotrifluoroethane 256.71
    DMS 107.5
    cumene 57.84
    2-octanol 142.69
    2-hexanone 222.47
    octyl acetate 120.3
    limonene 143.78
    1,2-dimethoxyethane 606.36
    ethyl orthosilicate 90.23
    tributyl phosphate 83.28
    diacetone alcohol 218.12
    N,N-dimethylaniline 95.86
    acrylonitrile 371.77
    aniline 263.14
    1,3-propanediol 467.35
    bromobenzene 170.78
    dibromomethane 412.38
    1,1,2,2-tetrachloroethane 351.97
    2-methyl-cyclohexyl acetate 156.1
    tetrabutyl urea 95.61
    diisobutyl methanol 155.29
    2-phenylethanol 222.42
    styrene 89.4
    dioctyl adipate 118.68
    dimethyl sulfate 60.44
    ethyl butyrate 230.39
    methyl lactate 97.69
    butyl lactate 134.41
    diethyl carbonate 134.22
    propanediol butyl ether 246.33
    triethyl orthoformate 164.62
    p-tert-butyltoluene 83.62
    methyl 4-tert-butylbenzoate 130.76
    morpholine 1433.44
    tert-butylamine 551.84
    n-dodecanol 96.9
    dimethoxymethane 370.32
    ethylene carbonate 226.1
    cyrene 141.87
    2-ethoxyethyl acetate 202.39
    2-ethylhexyl acetate 224.12
    1,2,4-trichlorobenzene 151.69
    4-methylpyridine 408.24
    dibutyl ether 228.61
    2,6-dimethyl-4-heptanol 155.29
    DEF 248.75
    dimethyl isosorbide 303.36
    tetrachloroethylene 229.42
    eugenol 139.4
    triacetin 150.88
    span 80 234.09
    1,4-butanediol 123.59
    1,1-dichloroethane 383.02
    2-methyl-1-pentanol 269.44
    methyl formate 188.17
    2-methyl-1-butanol 412.39
    n-decane 36.69
    butyronitrile 664.39
    3,7-dimethyl-1-octanol 192.08
    1-chlorooctane 114.93
    1-chlorotetradecane 41.87
    n-nonane 36.92
    undecane 25.31
    tert-butylcyclohexane 39.3
    cyclooctane 44.56
    cyclopentanol 403.03
    tetrahydropyran 1292.76
    tert-amyl methyl ether 225.51
    2,5,8-trioxanonane 371.14
    1-hexene 215.44
    2-isopropoxyethanol 212.5
    2,2,2-trifluoroethanol 87.56
    methyl butyrate 205.47

    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
Ziziphora hispanica Ziziphora hispanica L., fam. Lamiaceae (Labiatae) 1.53%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%