cis-Piperitol

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  • Identifiers

    CAS number
    16721-38-3

    Molecular formula
    C10H18O

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

    Retention indicies (RI)

    • DB5: 1194.8
    • Carbowax: 1740.67

  • 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

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    219°C

    Flash point est.
    96.1 ˚C

  • Synonyms

    • cis-Piperitol
    • (+)-cis-Piperitol
    • 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R,6S)-rel-
    • 16721-38-3
    • (1R,6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
    • cis-p-Menth-1-en-3-ol
    • p-Menth-1-en-3-ol, cis-
    • 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, cis-
    • p-Menth-1-en-3-ol, cis-(+)-
    • FEMA No. 3179, cis-(+)-
    • p-Menth-1-en-3-ol, (3R,4S)-
    • 38KW3EQO0M
    • DTXSID90884932
    • EINECS 240-775-4
    • (1R,6S)-6-Isopropyl-3-methyl-cyclohex-2-en-1-ol
    • G7666796PG
    • p-Menth-1-en-3-ol, cis-(+/-)-
    • 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R,6S)-
    • 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R-cis)-
    • cis-6-(Isopropyl)-3-methylcyclohex-2-en-1-ol
    • 34350-53-3
    • (Z)-Piperitol
    • (+/-)-cis-Piperitol
    • UNII-38KW3EQO0M
    • SCHEMBL1301004
    • UNII-G7666796PG
    • CHEBI:167403
    • DTXCID501024349
    • FEMA NO. 3179, CIS-(+/-)-
    • 6-Isopropyl-3-methyl-2-cyclohexen-1-ol-, cis-
    • Q63408709
    • 3-METHYL-6-(1-METHYLETHYL)-2-CYCLOGEXEN-1-OL

  • Applications

    cis-Piperitol (CAS 16721-38-3) is a naturally occurring monoterpene alcohol found at trace levels in several essential oils (e.g., pepper, mint, eucalyptus) and is used primarily as a fragrance/flavor modifier imparting peppery, herbal, slightly minty nuances; as a raw material/intermediate to prepare esters, carbonates, and related monoterpene derivatives in aroma chemistry; as a reference standard for GC/GC–MS in essential‑oil fingerprinting, authenticity assessment, and monitoring aroma changes during storage/processing; as a chiral building block in asymmetric synthesis and studies of enantioselective catalysis; as a renewable scaffold from biomass for green‑chemistry routes; and it has been investigated in vitro for antimicrobial/antioxidant properties, in sensory science (odor thresholds, structure–odor relationships), and in encapsulation/controlled‑release systems to stabilize and deliver aromas (use subject to local regulations).

  • 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
Achillea abrotanoides Achillea abrotanoides (Vis.) Vis., fam. Asteraceae (Compositae) 0.05%
Angelica root (Finland) 1 8015-64-3 Angelica archangelica L., fam. Apiaceae (Umbelliferae) 0.05%
Armoise flower 8008-93-3 Artemisia vulgaris L., fam. Asteraceae (Compositae) 0.1%
Artemisia vestita (India) Artemisia vestita Wall. ex Dc., fam. Asteraceae (Compositae) 0.15%
Cymbopogon jwarancusa (India) Cymbopogon jwarancusa (Jones) Schult., fam. Poaceae (Gramineae) 15.2%
Eugenia javanica Eugenia javanica Lamk., fam. Myrtaceae 0.2%
Juniperus foetidissima leaf Juniperus foetidissima Willd., fam. Cupressaceae 0.3%
Mace 2 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Nutmeg (India) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.35%
Nutmeg (India) 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Nutmeg (Sri Lanka) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.45%
Nutmeg (India) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.01%
Orange leaf, sweet (North Africa) 1 Citrus sinensis (L.) Osbeck, cultivar Portuguese, fam. Rutaceae 0.48%
Orange leaf, sweet (North Africa) 4 Citrus sinensis (L.) Osbeck, cultivar Washington navel, fam. Rutaceae 0.23%
Peppermint (USA) 2 8006-90-4 Mentha piperita L. cultivar Mitcham, fam. Lamiaceae (Labiatae) 0.05%
Nutmeg (West Indies) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.8%
Zingiber cassumunar root (Indonesia) 1 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.01%
Pistacia khinjuk (Egypt) leaf Pistacia khinjuk Stocks, fam. Anacardiaceae 0.2%
Zingiber cassumunar root (Indonesia) 2 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.5%
Lepechinia urbanii Lepechinia urbanii (Briq.) Epling, fam. Lamiaceae (Labiatae) 0.01%
Nutmeg 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.15%
Wormwood (Mugwort) (Germany) 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.05%
Tea Tree (Australia) 7 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.01%
Achillea biebersteinii (Turkey) 1 Achillea biebersteinii Afan., fam. Asteraceae (Compositae) 0.17%
Cypress (Algeria) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.01%
Juniper leaf (France) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.01%
Blumea brevipes Blumea brevipes (Oliv. & Hiern) Willd., fam. Asteraceae (Compositae) 0.05%
Eucalyptus globulus (China) 2 fruit 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.73%
Artemisia moorcroftiana Artemisia moorcroftiana, fam. Asteraceae (Compositae) 0.44%
Orange leaf, sweet (Mauritius) Citrus sinensis (L.) Osbeck, fam. Rutaceae 26.42%
Rosemary (Turkey) 4 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.54%
Geum montanum root Geum montanum L., fam. Rosaceae 0.07%
Illicium griffithii fruit Illicium griffithii Hook. f. et Thoms., fam. Magnoliaceae (Illiciaceae) 0.05%
Achillea biebersteinii (Turkey) 2 Achillea biebersteinii Afan., fam. Asteraceae (Compositae) 0.5%
Mentha longifolia (Lithuania) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.12%
Orange leaf, sweet (Italy) 1 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.04%
Orange leaf, sweet (Italy) 2a Valencia Late Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.06%
Orange leaf, sweet (Italy) 2b Biondo Comune Citrus sinensis (L.) Osbeck, cultivar Biondo Comune, fam. Rutaceae 0.05%
Orange leaf, sweet (Italy) 2c Moro Citrus sinensis (L.) Osbeck, cultivar Moro, fam. Rutaceae 0.06%
Vitex agnus-castus leaf (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.1%
Vitex agnus-castus fruit (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.01%
Vitex agnus-castus inflorescence (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.1%
Tea Tree (USA-California) 2 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.23%
Keora (India) 4 Pandanus odoratissimus L. (P. fascicularis Lam.), fam. Pandanaceae 0.06%
Angelica (norvegica) root 8015-64-3 Angelica archangelica L. ssp. archangelica var. norvegica, fam. Apiaceae 2.5%
Camphor (Cuba) 8008-51-3 Cinnamomum camphora (L.) Nees et Ebermaier, fam. Lauraceae 0.01%
Dill herb (Reunion Island) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.1%
Cymbopogon nardus, var. confertiflorus Cymbopogon naruds (L.) Rendle, var., confertiflorus (Steud.), fam. Poaceae 0.4%
Cypress, Leyland (Poland) Cupressocyparis leylandii (Dall. et Jacks.) Dall., fam. Cupressaceae 0.01%
Artemisia verlotiorum (France) Artemisia verlotiorum Lamotte, fam. Asteraceae (Compositae) 0.01%