Pinocarveol, (+/-)-

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  • Identifiers

    CAS number
    5947-36-4

    Molecular formula
    C10H16O

    SMILES
    CC1(C2CC1C(=C)C(C2)O)C

    Retention indicies (RI)

    • DB5: 1138.0
    • Carbowax: 1658.0

  • Odor profile

    Herbal 84.43%
    Mint 81.15%
    Camphoreous 81.15%
    Sweet 79.16%
    Woody 73.68%
    Cooling 69.8%
    Pine 69.13%
    Fresh 56.44%
    Spicy 52.77%
    Balsamic 49.01%

    Scent© AI

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    9.2 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point

    • 210.00 °C. @ 760.00 mm Hg

    Flash point est.
    74.05 ˚C

    Solubility expt.

    • Soluble in oils; Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Pinocarveol
    • 5947-36-4
    • 10-Pinen-3-ol
    • 2(10)-Pinen-3-ol
    • 6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
    • Pinocarveol, (+/-)-
    • FEMA No. 3587
    • 3917-59-7
    • trans-Pinocarveol
    • CHEBI:26137
    • 6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol
    • 3-Hydroxy-6,6-dimethyl-2-methylenebicyclo(3.1.1)heptane
    • Bicyclo[3.1.1]heptan-3-ol, 6,6-dimethyl-2-methylene-
    • EINECS 227-705-8
    • NSC 408847
    • 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol
    • AI3-23132
    • 6,6-Dimethyl-3-hydroxy-2-methylenebicyclo(3.1.1)heptane
    • DTXSID30863660
    • NSC-408847
    • Bicyclo(3.1.1)heptan-3-ol, 6,6-dimethyl-2-methylene-
    • (-)-trans-Pinocarveol
    • cis-Pinocarveol
    • 6,6-Dimethyl-2-methylene-Bicyclo(3.1.1)heptan-3-ol
    • 6,6-Dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol
    • (E)-Pinocarveol
    • Pinyl alcohol
    • 6,6-dimethyl-2-methylidenebicyclo(3.1.1)heptan-3-ol
    • UNII-0WG2C7KI43
    • laevo-pinocarveol
    • (Z)-Pinocarveol
    • EINECS 223-483-1
    • 6,6-dimethyl-2-methylene-norpinan-3-ol
    • 2(10)-Pinen-3-ol, (1S,3R,5S)-(-)-
    • SCHEMBL296319
    • 0WG2C7KI43
    • CHEMBL3109299
    • FEMA 3587
    • DTXCID20222323
    • Bicyclo[3.1.1]heptan-3-ol, 6,6-dimethyl-2-methylene-, [1S-(1.alpha.,3.alpha.,5.alpha.)]-
    • UAA88999
    • UAA89498
    • NSC146601
    • NSC408847
    • STL562482
    • AKOS037622959
    • AB86186
    • LMPR0102120025
    • NSC-146601
    • (1R-(1alpha,3alpha,5alpha))-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol
    • NS00013155
    • EN300-296441
    • 7,7-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
    • Bicyclo[3.1.1]heptan-3-ol,6-dimethyl-2-methylene-
    • Bicyclo3.1.1heptan-3-ol, 6,6-dimethyl-2-methylene-
    • Q27103091
    • 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol #
    • 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol, 9CI

  • Applications

    Pinocarveol, (+/−)- (CAS 5947-36-4) is a bicyclic monoterpenoid with pine–herbal–slightly camphoraceous notes, applied mainly in fragrance and research: (1) as a fragrance ingredient/modifier in fine fragrances, personal/home care, air care, and detergents to boost pine/woody/herbal facets, shape top notes in fougère, chypre, and citrus–aromatic accords, and help mask soapy bases; (2) investigated for flavor creation in foods and beverages with green–herbal–resinous nuances, subject to local regulatory permissions; (3) used as a GC–MS/GC–FID reference standard for identification, quantification, and fingerprinting of essential oils (e.g., pine, juniper, eucalyptus) and for supply-chain authentication of naturals; (4) employed as a marker of α-pinene oxidation in atmospheric chemistry, aiding instrument calibration and studies of secondary organic aerosol formation; (5) serving as a convenient synthetic intermediate to terpenoid derivatives (e.g., selective oxidation to pinocarvone, esterification, or other transformations to generate new aroma scaffolds) for perfumery and bioactivity research; (6) evaluated for antimicrobial, antifungal, insect-repellent, and malodor-control roles in cleaning formulations, surface coatings, bio-based packaging, and nature-derived agro formulations, with performance, stability, and safety determined by application context and compliance requirements.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 624.94
    methanol 652.58
    isopropanol 563.45
    water 12.68
    ethyl acetate 411.62
    n-propanol 486.61
    acetone 459.45
    n-butanol 396.77
    acetonitrile 431.75
    DMF 370.9
    toluene 135.86
    isobutanol 308.79
    1,4-dioxane 863.34
    methyl acetate 382.66
    THF 1189.92
    2-butanone 341.0
    n-pentanol 180.57
    sec-butanol 267.7
    n-hexane 15.72
    ethylene glycol 177.09
    NMP 135.97
    cyclohexane 22.15
    DMSO 337.29
    n-butyl acetate 263.09
    n-octanol 142.7
    chloroform 573.83
    n-propyl acetate 162.42
    acetic acid 280.54
    dichloromethane 401.27
    cyclohexanone 255.56
    propylene glycol 180.33
    isopropyl acetate 274.53
    DMAc 203.86
    2-ethoxyethanol 347.97
    isopentanol 295.43
    n-heptane 22.59
    ethyl formate 253.87
    1,2-dichloroethane 279.53
    n-hexanol 366.56
    2-methoxyethanol 692.19
    isobutyl acetate 112.29
    tetrachloromethane 134.94
    n-pentyl acetate 144.21
    transcutol 786.7
    n-heptanol 171.61
    ethylbenzene 70.14
    MIBK 212.87
    2-propoxyethanol 705.02
    tert-butanol 514.52
    MTBE 372.55
    2-butoxyethanol 327.93
    propionic acid 230.46
    o-xylene 82.75
    formic acid 190.33
    diethyl ether 389.3
    m-xylene 130.85
    p-xylene 94.93
    chlorobenzene 160.56
    dimethyl carbonate 142.77
    n-octane 12.72
    formamide 285.2
    cyclopentanone 421.17
    2-pentanone 300.15
    anisole 182.35
    cyclopentyl methyl ether 298.0
    gamma-butyrolactone 486.58
    1-methoxy-2-propanol 577.96
    pyridine 324.18
    3-pentanone 184.14
    furfural 353.78
    n-dodecane 9.5
    diethylene glycol 532.0
    diisopropyl ether 121.78
    tert-amyl alcohol 252.91
    acetylacetone 341.0
    n-hexadecane 10.66
    acetophenone 125.07
    methyl propionate 270.3
    isopentyl acetate 224.06
    trichloroethylene 444.35
    n-nonanol 120.37
    cyclohexanol 165.3
    benzyl alcohol 137.78
    2-ethylhexanol 149.46
    isooctanol 127.86
    dipropyl ether 184.29
    1,2-dichlorobenzene 133.57
    ethyl lactate 105.05
    propylene carbonate 217.92
    n-methylformamide 373.95
    2-pentanol 242.88
    n-pentane 25.53
    1-propoxy-2-propanol 429.2
    1-methoxy-2-propyl acetate 335.2
    2-(2-methoxypropoxy) propanol 195.62
    mesitylene 84.4
    ε-caprolactone 230.86
    p-cymene 63.21
    epichlorohydrin 573.49
    1,1,1-trichloroethane 298.9
    2-aminoethanol 313.72
    morpholine-4-carbaldehyde 329.07
    sulfolane 281.07
    2,2,4-trimethylpentane 15.18
    2-methyltetrahydrofuran 439.37
    n-hexyl acetate 186.39
    isooctane 22.86
    2-(2-butoxyethoxy)ethanol 318.69
    sec-butyl acetate 122.43
    tert-butyl acetate 274.61
    decalin 14.46
    glycerin 248.8
    diglyme 532.51
    acrylic acid 171.49
    isopropyl myristate 74.37
    n-butyric acid 336.58
    acetyl acetate 219.59
    di(2-ethylhexyl) phthalate 66.8
    ethyl propionate 154.71
    nitromethane 471.41
    1,2-diethoxyethane 298.91
    benzonitrile 169.0
    trioctyl phosphate 58.75
    1-bromopropane 174.07
    gamma-valerolactone 530.85
    n-decanol 89.43
    triethyl phosphate 66.25
    4-methyl-2-pentanol 181.15
    propionitrile 338.0
    vinylene carbonate 221.33
    1,1,2-trichlorotrifluoroethane 279.27
    DMS 144.79
    cumene 58.82
    2-octanol 107.07
    2-hexanone 147.76
    octyl acetate 91.11
    limonene 71.87
    1,2-dimethoxyethane 461.74
    ethyl orthosilicate 68.89
    tributyl phosphate 62.38
    diacetone alcohol 302.19
    N,N-dimethylaniline 101.84
    acrylonitrile 357.29
    aniline 198.57
    1,3-propanediol 472.03
    bromobenzene 143.79
    dibromomethane 283.37
    1,1,2,2-tetrachloroethane 315.86
    2-methyl-cyclohexyl acetate 104.3
    tetrabutyl urea 67.75
    diisobutyl methanol 109.27
    2-phenylethanol 226.51
    styrene 72.26
    dioctyl adipate 78.33
    dimethyl sulfate 141.66
    ethyl butyrate 158.67
    methyl lactate 170.26
    butyl lactate 122.55
    diethyl carbonate 100.26
    propanediol butyl ether 216.98
    triethyl orthoformate 111.16
    p-tert-butyltoluene 69.98
    methyl 4-tert-butylbenzoate 145.9
    morpholine 713.62
    tert-butylamine 306.82
    n-dodecanol 65.16
    dimethoxymethane 462.06
    ethylene carbonate 204.62
    cyrene 124.89
    2-ethoxyethyl acetate 232.59
    2-ethylhexyl acetate 143.91
    1,2,4-trichlorobenzene 135.3
    4-methylpyridine 267.47
    dibutyl ether 120.63
    2,6-dimethyl-4-heptanol 109.27
    DEF 186.24
    dimethyl isosorbide 278.44
    tetrachloroethylene 233.56
    eugenol 158.04
    triacetin 136.08
    span 80 161.29
    1,4-butanediol 140.26
    1,1-dichloroethane 342.69
    2-methyl-1-pentanol 135.2
    methyl formate 295.34
    2-methyl-1-butanol 210.19
    n-decane 17.17
    butyronitrile 336.99
    3,7-dimethyl-1-octanol 134.49
    1-chlorooctane 66.73
    1-chlorotetradecane 25.23
    n-nonane 16.32
    undecane 12.38
    tert-butylcyclohexane 19.55
    cyclooctane 11.62
    cyclopentanol 225.97
    tetrahydropyran 488.8
    tert-amyl methyl ether 177.96
    2,5,8-trioxanonane 303.19
    1-hexene 57.3
    2-isopropoxyethanol 249.33
    2,2,2-trifluoroethanol 167.53
    methyl butyrate 165.12

    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
Amomum villosum Amomum villosum Lour., fam. Zingiberaceae 0.22%
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.07%
Coleonema pulchellum Coleonema pulchellum Williams (C. pulchrum Hook.), fam. Rutaceae 0.02%
Larix conifer bark Larix decidua Mill., fam. Pinaceae 3.0%
Pinus pinaster (Portugal) 2 needle 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.17%
Pinus sylvestris 7 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 0.78%
Xylopia parviflora fruit (Cameroon) Xylopia parviflora (A. Rich) Benth., fam. Annonaceae 2.7%
Eucalyptus viminalis (Uruguay) Eucalyptus viminalis Labill., fam. Myrtaceae 0.8%
Eucalyptus botryoides (Uruguay) Eucalyptus botryoides Sm., fam. Myrtaceae 1.4%
Eucalyptus grandis (Uruguay) Eucalyptus grandis W. Hill ex Maiden, fam. Myrtaceae 11.1%
Eucalyptus pellita (Uruguay) Eucalyptus pellita F. v. Muell., fam. Myrtaceae 2.8%
Eucalyptus amplifolia (Uruguay) Eucalyptus amplifolia Naud., fam. Myrtaceae 1.0%
Eucalyptus diversicolor (Uruguay) Eucalyptus diversicolor F. Muell., fam. Myrtaceae 2.5%
Eucalyptus affinis (Uruguay) Eucalyptus affinis Deane & Maiden, fam. Myrtaceae 1.2%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.17%
Carrot seed (France) 4 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.1%
Mastic gum (Greece) 2 61789-92-2 Pistacia lentiscus L., var. Chia, fam. Anacardiaceae 0.29%
Carrot seed (France) 3 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.27%
Myrtle leaf (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.09%
Myrtle flower (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.03%
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 3.4%
Thyme 3 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.01%
Thyme 4 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.02%
Avocado leaf Persea gratissima Gaertner (P. americana Mill.), fam. Lauraceae 0.01%
Pepper, black 5 8006-82-4 Piper nigrum L., fam. Piperaceae 1.4%
Eucalyptus camaldulensis (Burundi) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 0.3%
Tansy (Canada) 2a flowers 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 0.6%
Tansy (Canada) 2b stems & sheets 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 0.67%
Artemisia princeps (China) Artemisia princeps Pamp., fam. Asteraceae (Compositae) 1.38%
Illicium simonsii fruit (China) Illicium simonsii Maxim., fam. Magnoliaceae (Illiciaceae) 0.16%
Neolitsea oblongifolia (China) Neolitsea oblongifolia Merr. et Chun., fam. Lauraceae 1.87%
Eucalyptus tereticornis (China) Eucalyptus tereticornis Smith, fam. Myrtaceae 2.65%
Geum montanum root Geum montanum L., fam. Rosaceae 0.3%
Lippia multiflora leaf (Benin) Lippia multiflora Moldenke (syn.L.adoensis & L.grandiflora) fam.Verbenacea 0.8%
Cardamom, large (Nepalese) (India) 2 Amomum subulatum Roxb., fam. Zingiberaceae 0.11%
Artemisia campestris (Italy) 1 Artemisia campestris L. ssp. borealis (Pallas), H.M. Hall et Clements 3.8%
Artemisia genipi (Italy) Artemisia genipi Weber, fam. Asteraceae (Compositae) 0.2%
Wormwood (Mugwort) (Italy) 2 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.01%
Artemisia chamaemelifolia (Italy) Artemisia chamaemelifolia Vill., fam. Asteraceae (Compositae) 0.1%
Artemisia glacialis (Italy) Artemisia glacialis L., fam. Asteraceae (Compositae) 0.8%
Artemisia campestris (Italy) 2 Artemisia campestris L. ssp. campestris, fam. Asteraceae (Compositae) 2.7%
Annual wormwood (Italy) Artemisia annua L., fam. Asteraceae (Compositae) 5.5%
Artemisia verlotiorum (Italy) Artemisia verlotiorum Lamotte, fam. Asteraceae (Compositae) 0.01%
Armoise (Italy) 8008-93-3 Artemisia vulgaris L., fam. Asteraceae (Compositae) 0.2%
Thymus pulegioides (Italy) Thymus pulegioides L., fam. Lamiaceae (Labiatae) 0.2%
Sage, dalmatian (Italy) 6 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 6.65%
Rosemary (France) 2 Corsica 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.9%
Calanthe sieboldii flower headspace (Japan) Calanthe sieboldii, fam. Orchidaceae 0.1%
Pelargonium sidoides Pelargonium sidoides DC., fam. Geraniaceae 0.6%
Pelargonium reniforme Pelargonium reniforme Curt., fam. Geraniaceae 0.3%