Piperitol

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  • Identifiers

    CAS number
    491-04-3

    Molecular formula
    C10H18O

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

    Retention indicies (RI)

    • Carbowax: 1671.5

  • Odor profile

    Herbal 83.32%
    Mint 78.77%
    Cooling 57.78%
    Camphoreous 56.0%
    Spicy 48.85%
    Fresh 45.78%
    Sweet 44.25%
    Woody 43.88%
    Musty 40.08%
    Earthy 39.18%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    9.98 (weak base)

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • MP: 36 °C; OPTICAL ROTATION: -246 DEG @ 17 °C (C= 2 IN BENZENE) /CIS-, L-/; MP: 28 °C /CIS-, DL-/
    • 96.00 to 97.00 °C. @ 760.00 mm Hg

    Boiling point

    • BP: 57 °C; SPECIFIC GRAVITY: 0.9217 @ 25 °C /TRANS-, DL-/
    • 230.00 to 232.00 °C. @ 760.00 mm Hg

    Flash point est.
    96.1 ˚C

  • Synonyms

    • p-Menth-1-en-3-ol
    • 491-04-3
    • 3-Carvomenthenol
    • 3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
    • Piperitol (monoterpene)
    • 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-
    • 6-(Isopropyl)-3-methylcyclohex-2-en-1-ol
    • 1-Methyl-4-isopropyl-1-cyclohexen-3-ol
    • HSDB 5666
    • EINECS 207-725-3
    • 3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol
    • 3-HYDROXY-4-ISOPROPYL-1-METHYLCYCLOHEXENE
    • (Z)-Piperitol
    • UNII-7UM0ILT6I7
    • 3Carvomenthenol
    • FEMA No. 3179
    • Piperitol?
    • 11063-75-5
    • pMenth1en3ol
    • PIPERITOL [HSDB]
    • 7UM0ILT6I7
    • 1Methyl4isopropyl1cyclohexen3ol
    • SCHEMBL1245098
    • DTXSID0052128
    • FEMA 3179
    • 6(Isopropyl)3methylcyclohex2en1ol
    • 3Methyl6(1methylethyl)2cyclohexen1ol
    • P-MENTH-1-EN-3-OL [FHFI]
    • 6-isopropyl-3-methyl-cyclohex-2-enol
    • AKOS025295367
    • 2Cyclohexen1ol, 3methyl6(1methylethyl)
    • 6-Isopropyl-3-methyl-2-cyclohexen-1-ol
    • DB-323839
    • NS00022231
    • 3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol, 9CI
    • Cyclohexane, 1-methyl-4-(1-methylethyl)-, didehydro monohydroxy deriv.

  • Applications

    Piperitol (CAS 491-04-3) is a monoterpenoid alcohol with a herbaceous-minty, slightly peppery odor, used primarily in flavor and fragrance to create or fine-tune minty/green nuances in perfumes, candles, personal-care products, and food flavors; in aroma chemistry as an intermediate for preparing related terpenoid aroma chemicals and as a trace-level odor modulator; in essential-oil analytics as a reference standard and marker for GC-MS method calibration, batch chemoprofiling, and chemotaxonomy studies of Mentha materials; in R&D as a natural scaffold screened in vitro for antimicrobial, antioxidant, and insect-repellent properties, and as a chiral building block in small-scale organic synthesis; it is also considered for controlled-release and microencapsulation systems to enhance odor stability in consumer matrices, subject to IFRA safety assessment and local food/cosmetic regulatory limits.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1304.45
    methanol 1231.79
    isopropanol 1078.05
    water 0.89
    ethyl acetate 371.92
    n-propanol 936.34
    acetone 543.9
    n-butanol 874.54
    acetonitrile 882.82
    DMF 327.51
    toluene 211.81
    isobutanol 524.43
    1,4-dioxane 1331.23
    methyl acetate 336.43
    THF 1752.29
    2-butanone 407.8
    n-pentanol 449.79
    sec-butanol 587.08
    n-hexane 142.88
    ethylene glycol 62.47
    NMP 240.73
    cyclohexane 274.09
    DMSO 314.61
    n-butyl acetate 506.94
    n-octanol 271.59
    chloroform 1191.26
    n-propyl acetate 240.26
    acetic acid 411.7
    dichloromethane 791.62
    cyclohexanone 559.05
    propylene glycol 120.42
    isopropyl acetate 202.76
    DMAc 167.71
    2-ethoxyethanol 307.81
    isopentanol 521.58
    n-heptane 173.68
    ethyl formate 301.67
    1,2-dichloroethane 379.3
    n-hexanol 829.83
    2-methoxyethanol 620.88
    isobutyl acetate 154.22
    tetrachloromethane 210.75
    n-pentyl acetate 212.17
    transcutol 935.73
    n-heptanol 286.55
    ethylbenzene 97.16
    MIBK 195.74
    2-propoxyethanol 651.14
    tert-butanol 844.97
    MTBE 506.04
    2-butoxyethanol 336.36
    propionic acid 279.87
    o-xylene 113.68
    formic acid 106.74
    diethyl ether 755.74
    m-xylene 141.09
    p-xylene 131.99
    chlorobenzene 253.64
    dimethyl carbonate 54.33
    n-octane 46.64
    formamide 142.2
    cyclopentanone 550.19
    2-pentanone 364.24
    anisole 164.37
    cyclopentyl methyl ether 438.49
    gamma-butyrolactone 520.8
    1-methoxy-2-propanol 423.74
    pyridine 609.19
    3-pentanone 203.35
    furfural 379.92
    n-dodecane 31.54
    diethylene glycol 284.67
    diisopropyl ether 161.03
    tert-amyl alcohol 437.37
    acetylacetone 203.32
    n-hexadecane 35.88
    acetophenone 124.25
    methyl propionate 194.07
    isopentyl acetate 376.6
    trichloroethylene 612.11
    n-nonanol 220.75
    cyclohexanol 488.62
    benzyl alcohol 159.04
    2-ethylhexanol 362.33
    isooctanol 198.0
    dipropyl ether 458.19
    1,2-dichlorobenzene 181.86
    ethyl lactate 84.53
    propylene carbonate 299.89
    n-methylformamide 249.05
    2-pentanol 453.18
    n-pentane 181.2
    1-propoxy-2-propanol 471.32
    1-methoxy-2-propyl acetate 269.05
    2-(2-methoxypropoxy) propanol 216.35
    mesitylene 95.59
    ε-caprolactone 429.31
    p-cymene 109.06
    epichlorohydrin 592.48
    1,1,1-trichloroethane 439.28
    2-aminoethanol 203.31
    morpholine-4-carbaldehyde 353.42
    sulfolane 322.7
    2,2,4-trimethylpentane 51.08
    2-methyltetrahydrofuran 982.36
    n-hexyl acetate 298.41
    isooctane 54.53
    2-(2-butoxyethoxy)ethanol 354.09
    sec-butyl acetate 141.76
    tert-butyl acetate 201.8
    decalin 66.1
    glycerin 134.06
    diglyme 546.16
    acrylic acid 171.26
    isopropyl myristate 113.53
    n-butyric acid 592.82
    acetyl acetate 163.63
    di(2-ethylhexyl) phthalate 102.17
    ethyl propionate 155.01
    nitromethane 428.75
    1,2-diethoxyethane 446.03
    benzonitrile 288.8
    trioctyl phosphate 84.27
    1-bromopropane 464.83
    gamma-valerolactone 616.22
    n-decanol 153.29
    triethyl phosphate 88.47
    4-methyl-2-pentanol 214.86
    propionitrile 626.13
    vinylene carbonate 261.59
    1,1,2-trichlorotrifluoroethane 269.93
    DMS 120.73
    cumene 75.57
    2-octanol 179.33
    2-hexanone 266.07
    octyl acetate 141.99
    limonene 191.41
    1,2-dimethoxyethane 570.39
    ethyl orthosilicate 100.49
    tributyl phosphate 96.93
    diacetone alcohol 208.14
    N,N-dimethylaniline 100.48
    acrylonitrile 442.42
    aniline 261.43
    1,3-propanediol 396.83
    bromobenzene 239.92
    dibromomethane 652.49
    1,1,2,2-tetrachloroethane 465.36
    2-methyl-cyclohexyl acetate 190.25
    tetrabutyl urea 109.35
    diisobutyl methanol 181.92
    2-phenylethanol 238.85
    styrene 117.27
    dioctyl adipate 132.06
    dimethyl sulfate 60.22
    ethyl butyrate 263.76
    methyl lactate 84.31
    butyl lactate 156.21
    diethyl carbonate 145.16
    propanediol butyl ether 245.91
    triethyl orthoformate 188.69
    p-tert-butyltoluene 110.47
    methyl 4-tert-butylbenzoate 146.35
    morpholine 1356.74
    tert-butylamine 646.24
    n-dodecanol 113.12
    dimethoxymethane 308.53
    ethylene carbonate 252.62
    cyrene 142.58
    2-ethoxyethyl acetate 226.17
    2-ethylhexyl acetate 298.31
    1,2,4-trichlorobenzene 191.05
    4-methylpyridine 486.88
    dibutyl ether 286.56
    2,6-dimethyl-4-heptanol 181.92
    DEF 240.76
    dimethyl isosorbide 298.86
    tetrachloroethylene 316.84
    eugenol 144.25
    triacetin 171.05
    span 80 243.73
    1,4-butanediol 105.43
    1,1-dichloroethane 558.78
    2-methyl-1-pentanol 286.73
    methyl formate 157.47
    2-methyl-1-butanol 418.93
    n-decane 60.56
    butyronitrile 807.17
    3,7-dimethyl-1-octanol 217.24
    1-chlorooctane 163.73
    1-chlorotetradecane 59.23
    n-nonane 62.33
    undecane 42.3
    tert-butylcyclohexane 62.47
    cyclooctane 78.87
    cyclopentanol 484.15
    tetrahydropyran 1461.89
    tert-amyl methyl ether 248.59
    2,5,8-trioxanonane 343.47
    1-hexene 325.82
    2-isopropoxyethanol 197.52
    2,2,2-trifluoroethanol 86.28
    methyl butyrate 221.52

    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 sylvestris var. incana Mentha sylvestris var. incana, fam Lamiacae (Labiatae) 44.8%
Achillea wilhelmsii (Egypt) Achillea wilhelmsii C. Koch (A. santolina Auct. Mult.), fam. Asteraceae 0.3%
Cymbopogon jwarancusa (Himalaya) Cymbopogon jwarancusa (Jones) Schult., fam. Poaceae (Gramineae) 0.2%
Mentha requienii 1 Mentha requienii Bentham, fam. Lamiaceae (Labiatae) 0.4%
Mentha requienii 2 Mentha requienii Bentham, fam. Lamiaceae (Labiatae) 0.3%
Pennyroyal 4 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.05%
Tea Tree (Australia) 1 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.07%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.09%
Cumin (India) 1 8014-30-9 Cuminum cyminum L., fam. Apiaceae (Umbelliferae) 1.72%
Annual wormwood (Yugoslavia) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.35%
Abies fragesii Abies fragesii Franch, fam. Pinaceae 2.26%
Artemisia indica (China) Artemisia indica Willd., fam. Asteraceae (Compositae) 2.83%
Artemisia occidentalis-sichaunensis (China) Artemisia occidentalis-sichuanensis Y.R. Ling et S.Y. Zhao,fam. Asteraceae 2.01%
Aegle marmelos leaf (India) 2 Aegle marmelos (L.) Correa, fam. Rutaceae 0.43%
Marjoram, sweet 2 8015-01-8 Majorana hortensis Moench, Origanum majorana L., fam. Lamiaceae (Labiatae) 0.8%
Nutmeg (India) 6 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.06%
Pelargonium sidoides Pelargonium sidoides DC., fam. Geraniaceae 0.2%
Santolina ligustica (Italy) Santolina ligustica Arrigonia, fam. Asteraceae (Compositae) 0.3%
Artemisia aucheri (Iran) 1 Artemisia aucheri Boiss., fam. Asteraceae (Compositae) 0.2%
Artemisia deserti (Iran) Artemisia deserti Krasch., fam. Asteraceae (Compositae) 1.4%
Eucalyptus camaldulensis (Israel) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 0.1%
Eucalyptus camaldulensis (Algeria) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 0.2%