3-Pinanone

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  • Identifiers

    CAS number
    15358-88-0

    Molecular formula
    C10H16O

    SMILES
    CC1C2CC(C2(C)C)CC1=O

    Retention indicies (RI)

    • DB5: 1173.0
    • Carbowax: 1534.33

  • Odor profile

    Herbal 80.17%
    Camphoreous 76.57%
    Mint 72.55%
    Woody 68.42%
    Fresh 59.89%
    Pine 59.5%
    Cooling 58.97%
    Spicy 51.84%
    Earthy 42.12%
    Green 41.81%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    230°C

    Flash point est.
    68.65 ˚C

    Solubility expt.

    • Practically insoluble to insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 3-Pinanone
    • 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one
    • (E)-Pinocamphone
    • 15358-88-0
    • (1alpha,2beta,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
    • Bicyclo[3.1.1]heptan-3-one, 2,6,6-trimethyl-
    • Bicyclo[3.1.1]heptan-3-one, 2,6,6-trimethyl-, (1.alpha.,2.alpha.,5.alpha.)-
    • Bicyclo(3.1.1)heptan-3-one, 2,6,6-trimethyl-
    • 1S,2R,5R-3-Pinanone
    • D-Pinocamphone
    • 2,6,6-trimethylnorpinan-3-one
    • pinan-3-one
    • Pinocamphone, trans
    • SCHEMBL7839978
    • DTXSID60862166
    • CHEBI:171963
    • AAA47362
    • MFCD31630144
    • SY224505
    • NS00084069
    • NS00084366
    • NS00085303
    • 2,7,7-trimethyl-bicyclo[3.1.1]heptan-3-one
    • Bicyclo3.1.1heptan-3-one, 2,6,6-trimethyl-
    • 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one, 9CI
    • Q67865674
    • 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one, (1.alpha.,2.alpha.,5.alpha.)-

  • Applications

    3-Pinanone (CAS 15358-88-0) is a monoterpene ketone with a characteristic camphoraceous, pine-like odour used as a fragrance and flavour ingredient to impart fresh pine/minty notes in perfumes, deodorants, household and industrial cleaners, air-care products and candles; it also serves as a versatile pinane-based intermediate in organic synthesis to access terpenoid derivatives (e.g., enantioselective reductions to pinanol, formation of oximes/hydrazones, and Baeyer–Villiger oxidations to lactones), fragrance modulators, and intermediates en route to pharmaceutical and agrochemical targets; it is employed as a chiral building block or precursor to pinane-derived auxiliaries/ligands for stereoselective catalysis, and as a model substrate in R&D for optimizing ketone reductions, hydrogenations, selective oxidations and biocatalytic KRED screens from lab to pilot scale; in sensory and analytical work it is used as an odour standard and to fine-tune aroma profiles in formulations; additionally, its volatility and solvent compatibility make it useful as an aromatic co-solvent, solubility modifier and fragrance carrier in certain consumer product systems.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 335.5
    methanol 412.85
    isopropanol 273.79
    water 13.4
    ethyl acetate 401.77
    n-propanol 269.71
    acetone 359.2
    n-butanol 216.19
    acetonitrile 426.7
    DMF 342.1
    toluene 229.12
    isobutanol 171.17
    1,4-dioxane 708.21
    methyl acetate 392.18
    THF 579.4
    2-butanone 280.44
    n-pentanol 103.75
    sec-butanol 145.43
    n-hexane 15.4
    ethylene glycol 126.73
    NMP 164.59
    cyclohexane 32.55
    DMSO 206.36
    n-butyl acetate 240.12
    n-octanol 95.26
    chloroform 998.23
    n-propyl acetate 161.4
    acetic acid 262.65
    dichloromethane 667.15
    cyclohexanone 290.01
    propylene glycol 113.02
    isopropyl acetate 251.67
    DMAc 223.84
    2-ethoxyethanol 214.62
    isopentanol 173.53
    n-heptane 16.71
    ethyl formate 235.2
    1,2-dichloroethane 385.65
    n-hexanol 210.0
    2-methoxyethanol 435.88
    isobutyl acetate 112.65
    tetrachloromethane 182.67
    n-pentyl acetate 140.22
    transcutol 837.49
    n-heptanol 112.26
    ethylbenzene 118.77
    MIBK 165.06
    2-propoxyethanol 439.59
    tert-butanol 250.82
    MTBE 211.0
    2-butoxyethanol 234.91
    propionic acid 230.65
    o-xylene 139.38
    formic acid 176.09
    diethyl ether 258.07
    m-xylene 180.18
    p-xylene 174.17
    chlorobenzene 307.14
    dimethyl carbonate 154.91
    n-octane 8.99
    formamide 268.86
    cyclopentanone 350.56
    2-pentanone 225.9
    anisole 243.2
    cyclopentyl methyl ether 217.14
    gamma-butyrolactone 454.41
    1-methoxy-2-propanol 335.41
    pyridine 458.37
    3-pentanone 180.57
    furfural 444.11
    n-dodecane 7.64
    diethylene glycol 368.56
    diisopropyl ether 99.32
    tert-amyl alcohol 142.41
    acetylacetone 316.63
    n-hexadecane 8.86
    acetophenone 187.95
    methyl propionate 275.36
    isopentyl acetate 209.9
    trichloroethylene 748.72
    n-nonanol 87.5
    cyclohexanol 142.75
    benzyl alcohol 167.52
    2-ethylhexanol 101.64
    isooctanol 86.19
    dipropyl ether 123.69
    1,2-dichlorobenzene 256.96
    ethyl lactate 99.06
    propylene carbonate 257.11
    n-methylformamide 309.96
    2-pentanol 133.17
    n-pentane 21.64
    1-propoxy-2-propanol 272.48
    1-methoxy-2-propyl acetate 312.99
    2-(2-methoxypropoxy) propanol 185.98
    mesitylene 116.73
    ε-caprolactone 272.86
    p-cymene 77.45
    epichlorohydrin 547.17
    1,1,1-trichloroethane 448.76
    2-aminoethanol 205.0
    morpholine-4-carbaldehyde 387.44
    sulfolane 276.64
    2,2,4-trimethylpentane 13.1
    2-methyltetrahydrofuran 294.57
    n-hexyl acetate 189.39
    isooctane 15.43
    2-(2-butoxyethoxy)ethanol 264.74
    sec-butyl acetate 124.15
    tert-butyl acetate 230.45
    decalin 21.38
    glycerin 166.52
    diglyme 484.57
    acrylic acid 208.5
    isopropyl myristate 76.75
    n-butyric acid 287.84
    acetyl acetate 296.37
    di(2-ethylhexyl) phthalate 74.95
    ethyl propionate 163.89
    nitromethane 523.59
    1,2-diethoxyethane 292.47
    benzonitrile 252.54
    trioctyl phosphate 53.63
    1-bromopropane 193.21
    gamma-valerolactone 563.5
    n-decanol 62.66
    triethyl phosphate 78.8
    4-methyl-2-pentanol 101.64
    propionitrile 296.38
    vinylene carbonate 302.68
    1,1,2-trichlorotrifluoroethane 321.4
    DMS 208.99
    cumene 87.52
    2-octanol 65.16
    2-hexanone 130.19
    octyl acetate 91.69
    limonene 77.13
    1,2-dimethoxyethane 319.89
    ethyl orthosilicate 78.42
    tributyl phosphate 65.54
    diacetone alcohol 222.4
    N,N-dimethylaniline 134.87
    acrylonitrile 390.66
    aniline 268.27
    1,3-propanediol 279.48
    bromobenzene 302.35
    dibromomethane 406.92
    1,1,2,2-tetrachloroethane 516.45
    2-methyl-cyclohexyl acetate 118.04
    tetrabutyl urea 70.43
    diisobutyl methanol 76.61
    2-phenylethanol 233.61
    styrene 132.1
    dioctyl adipate 92.05
    dimethyl sulfate 169.18
    ethyl butyrate 156.41
    methyl lactate 153.02
    butyl lactate 120.05
    diethyl carbonate 119.49
    propanediol butyl ether 172.91
    triethyl orthoformate 115.73
    p-tert-butyltoluene 79.94
    methyl 4-tert-butylbenzoate 164.33
    morpholine 548.92
    tert-butylamine 160.99
    n-dodecanol 46.05
    dimethoxymethane 322.42
    ethylene carbonate 258.18
    cyrene 128.9
    2-ethoxyethyl acetate 255.92
    2-ethylhexyl acetate 151.95
    1,2,4-trichlorobenzene 274.9
    4-methylpyridine 375.67
    dibutyl ether 91.17
    2,6-dimethyl-4-heptanol 76.61
    DEF 182.77
    dimethyl isosorbide 283.53
    tetrachloroethylene 381.89
    eugenol 165.48
    triacetin 181.72
    span 80 136.74
    1,4-butanediol 86.12
    1,1-dichloroethane 443.07
    2-methyl-1-pentanol 85.73
    methyl formate 257.54
    2-methyl-1-butanol 130.86
    n-decane 12.97
    butyronitrile 243.65
    3,7-dimethyl-1-octanol 102.16
    1-chlorooctane 57.85
    1-chlorotetradecane 24.34
    n-nonane 11.54
    undecane 9.65
    tert-butylcyclohexane 21.51
    cyclooctane 14.2
    cyclopentanol 154.26
    tetrahydropyran 371.31
    tert-amyl methyl ether 124.12
    2,5,8-trioxanonane 291.71
    1-hexene 54.91
    2-isopropoxyethanol 156.2
    2,2,2-trifluoroethanol 189.92
    methyl butyrate 167.55

    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 (China) 1g leaf Amomum villosum Lour., fam. Zingiberaceae 1.0%
Eucalyptus globulus (Spain) 1 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.01%
Hyssop (France) 1 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 32.6%
Hyssop (USA) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 30.88%
Hyssop (Himalaya) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 5.28%
Mentha x gentilis nm. hirtella Mentha x gentilis (L.) nm hirtella Markl., fam Lamiaceae (Labiatae) 0.35%
Rosemary (Spain) 3 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Sideritis granatensis Sideritis granatensis (Pau) Rivas-Goday, fam. Lamiaceae (Labiatae) 0.3%
Santolina chamaecyparisus (France) 2 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.02%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.3%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 0.2%
Juniperus flaccida var. poblana Juniperus flaccida var. poblana Martinez, fam. Cupressaceae 0.2%
Sphaeranthus suaveolens (Egypt) Sphaeranthus suaveolens DC., fam. Asteraceae (Compositae) 33.5%
Hyssop flower 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.9%
Hyssop leaf 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.7%
Hyssop stem 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.1%
Hyssop root 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.6%
Artemisia alba (Belgium) 84775-75-7 Artemisia alba Turra, fam. Asteraceae (Compositae) 34.6%
Annual wormwood (Yugoslavia) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.05%
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 3.5%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Hyssop (Finland) 1 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 30.9%
Hyssop (Finland) 2 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 15.5%
Hyssop (Finland) 3 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.55%
Hyssop (Finland) 4 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 19.25%
Hyssop (Bulgaria) 8006-83-5 Hyssopus officinalis L. ssp officinalis, fam. Lamiaceae (Labiatae) 40.2%
Artemisia maritima (Himalaya) Artemisia maritima L., fam. Asteracae (Compositae) 0.54%
Artemisia gmelini (Himalaya) Artemisia gmelinii Web. ex Stechm., fam. Asteracae (Compositae) 0.34%
Rosemary (Morocco) 1 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.1%
Rosemary (France) 1 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.3%
Artemisia argentea (Madeira) Artemisia argentea L'Her., fam. Asteraceae (Compositae) 7.0%
Chloranthus spicatus flower head space Chloranthus spicatus (Thunb.) Makino, fam. Chloranthaceae 0.19%
Jasmine rose flower headspace (China) 2 Gardenia jasminoides Ellis var. fortuniana Lindl., fam. Rubiaceae 0.28%
Rosemary (Egypt) 1 8000-27-5 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 1.22%
Rosemary (Egypt) 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 2.88%
Annual wormwood (China) 2a 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.1%
Annual wormwood (China) 2b 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.05%
Patchouli (China) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.01%
Hyssop (Montenegro) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.28%
Juniperus rigida (Japan) 2 Juniperus rigida Mig., fam. Cupressaceae 0.05%
Juniperus rigida (China) Juniperus rigida Mig., fam. Cupressaceae 0.05%
Juniperus rigida (Korea) Juniperus rigida Mig., fam. Cupressaceae 0.05%
Sideritis lycia (Turkey) Sideritis lycia Boiss. et Heldr., fam. Lamiaceae (Labiatae) 0.4%
Hyssop (Spain) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 2.0%
Artemisia umbelliformis (Italy) Artemisia umbelliformis Lam., fam. Asteraceae (Compositae) 0.01%
Artemisia campestris (Italy) 1 Artemisia campestris L. ssp. borealis (Pallas), H.M. Hall et Clements 0.01%
Artemisia genipi (Italy) Artemisia genipi Weber, fam. Asteraceae (Compositae) 0.01%
Artemisia petrosa (Italy) Artemisia petrosa Baumg. ssp. eriantha Ten., fam. Asteraceae (Compositae) 0.01%
Artemisia vallesiaca (Italy) Artemisia vallesiaca All., fam. Asteraceae (Compositae) 0.01%
Wormwood (Mugwort) (Italy) 2 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.01%