Pinane

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  • Identifiers

    CAS number
    473-55-2

    Molecular formula
    C10H18

    SMILES
    CC1CCC2CC1C2(C)C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 985.0
    • Carbowax: 1075.0

  • Odor profile

    Woody 74.51%
    Pine 63.25%
    Herbal 62.34%
    Fresh 61.6%
    Camphoreous 55.14%
    Sweet 54.32%
    Terpenic 48.5%
    Spicy 43.96%
    Balsamic 43.45%
    Green 42.74%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    9.56 (weak base)

    Molecular weight
    138.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Melting point expt.

    • -53 °C

    Boiling point

    • 304 °F at 760 mmHg (NTP, 1992)
    • 169 °C

    Flash point est.
    35.4 ˚C

    Flash point expt.

    • 104 °F (NTP, 1992)

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)

  • Synonyms

    • Pinane
    • 473-55-2
    • 2,6,6-Trimethylbicyclo[3.1.1]heptane
    • DIHYDROPINENE
    • Pinane, endo + exo
    • Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-
    • HSDB 5664
    • EINECS 207-467-1
    • Bicyclo(3.1.1)heptane, 2,6,6-trimethyl-
    • NSC 76674
    • 2,6,6-Trimethylbicyclo(3.1.1)heptane
    • DTXSID7025922
    • UNII-140V20YT81
    • CHEBI:35710
    • 1a,2b,5a-2,6,6-Trimethylbicyclo(3.1.1)heptane
    • DTXCID705922
    • (1S)-(-)-trans-Pinane
    • NSC-76674
    • PINANE (2-D1)
    • PINANE (3-D1)
    • 6876-13-7
    • CAS-473-55-2
    • 2,6,6-trimethylbicyclo(3.1.1)heptane;pinane
    • 2,6,6-trimethylbicyclo[3.1.1]heptane;pinane
    • Pinane, didehydro derivative
    • Pinane (8CI)
    • Caswell No. 664
    • DIHYDROPINENE [HSDB]
    • NCIOpen2_000688
    • UNII-996299PUKB
    • CHEMBL1422299
    • 996299PUKB
    • NSC76674
    • EINECS 215-533-6
    • Tox21_202039
    • Tox21_303280
    • 2,6-Trimethylbicyclo[3.1.1]heptane
    • AKOS015960556
    • AKOS037643346
    • 140V20YT81
    • EPA Pesticide Chemical Code 067001
    • 2,6,6Trimethylbicyclo(3.1.1)heptane
    • Bicyclo[3.1.1]heptane,6,6-trimethyl-
    • NCGC00090847-01
    • NCGC00090847-02
    • NCGC00257210-01
    • NCGC00259588-01
    • AS-14849
    • LS-13860
    • Bicyclo(3.1.1)heptane, 2,6,6trimethyl
    • 2,6,6-Trimethylbicyclo[3.1.1]heptane #
    • DB-329663
    • NS00077419
    • E75920
    • 1a,2b,5a2,6,6Trimethylbicyclo(3.1.1)heptane
    • 2,6,6-TRIMETHYLBICYCLO(3,1,1)HEPTANE
    • 2,7,7-TRIMETHYLBICYCLO(3.1.1)HEPTANE
    • Q2095373
    • Bicyclo(3.1.1)heptane, 2,6,6-trimethyl-, didehydro deriv.
    • Bicyclo[3.1.1]heptane, 2,6,6-trimethyl-, [1R-(1.alpha.,2.beta.,5.alpha.)]-

  • Applications

    Pinane (CAS 473-55-2) is a saturated bicyclic monoterpene obtained mainly by hydrogenating α-pinene from turpentine; with its nonpolar character, mild odor, and greater oxidative stability than unsaturated terpenes, it is used as a solvent/diluent in coatings, printing inks, adhesives and terpene-based cleaners; as a volatile carrier/penetrant for agrochemical actives; as a chemical intermediate to access pinane derivatives such as pinanol, pinanone, pinanediol, and related chiral auxiliaries/ligands for advanced asymmetric synthesis; it is leveraged in materials chemistry to build bio-based resins, oligomers and surfactants; contributes hydrocarbon content to terpene and hydrogenated rosin resin streams; and is also investigated as a renewable high–energy-density jet-fuel blending component and employed as a model hydrocarbon in combustion, atmospheric-oxidation studies, and GC–MS calibration.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 718.89
    methanol 564.72
    isopropanol 582.68
    water 1.49
    ethyl acetate 1044.22
    n-propanol 678.02
    acetone 764.89
    n-butanol 742.0
    acetonitrile 814.46
    DMF 449.52
    toluene 678.15
    isobutanol 467.84
    1,4-dioxane 1519.24
    methyl acetate 744.51
    THF 2364.16
    2-butanone 717.93
    n-pentanol 360.1
    sec-butanol 450.77
    n-hexane 358.68
    ethylene glycol 87.78
    NMP 370.12
    cyclohexane 581.99
    DMSO 311.71
    n-butyl acetate 1439.73
    n-octanol 354.82
    chloroform 1494.0
    n-propyl acetate 490.47
    acetic acid 341.54
    dichloromethane 1255.18
    cyclohexanone 888.38
    propylene glycol 134.34
    isopropyl acetate 737.48
    DMAc 332.26
    2-ethoxyethanol 378.44
    isopentanol 595.99
    n-heptane 492.71
    ethyl formate 522.93
    1,2-dichloroethane 837.34
    n-hexanol 1084.33
    2-methoxyethanol 657.64
    isobutyl acetate 394.88
    tetrachloromethane 495.15
    n-pentyl acetate 464.95
    transcutol 1408.92
    n-heptanol 416.96
    ethylbenzene 260.78
    MIBK 556.81
    2-propoxyethanol 1122.06
    tert-butanol 674.95
    MTBE 1043.26
    2-butoxyethanol 502.52
    propionic acid 379.14
    o-xylene 326.54
    formic acid 104.34
    diethyl ether 1401.7
    m-xylene 485.07
    p-xylene 312.29
    chlorobenzene 606.04
    dimethyl carbonate 250.66
    n-octane 155.8
    formamide 167.53
    cyclopentanone 1036.68
    2-pentanone 729.55
    anisole 398.09
    cyclopentyl methyl ether 1063.13
    gamma-butyrolactone 1010.0
    1-methoxy-2-propanol 581.99
    pyridine 924.52
    3-pentanone 576.58
    furfural 647.96
    n-dodecane 90.45
    diethylene glycol 502.07
    diisopropyl ether 609.45
    tert-amyl alcohol 463.18
    acetylacetone 633.61
    n-hexadecane 100.86
    acetophenone 268.52
    methyl propionate 620.75
    isopentyl acetate 1059.41
    trichloroethylene 1062.9
    n-nonanol 328.09
    cyclohexanol 560.41
    benzyl alcohol 230.84
    2-ethylhexanol 679.49
    isooctanol 317.21
    dipropyl ether 1214.15
    1,2-dichlorobenzene 474.46
    ethyl lactate 166.98
    propylene carbonate 574.98
    n-methylformamide 353.24
    2-pentanol 520.99
    n-pentane 426.08
    1-propoxy-2-propanol 920.83
    1-methoxy-2-propyl acetate 893.5
    2-(2-methoxypropoxy) propanol 368.29
    mesitylene 361.05
    ε-caprolactone 746.01
    p-cymene 311.9
    epichlorohydrin 979.48
    1,1,1-trichloroethane 895.06
    2-aminoethanol 217.28
    morpholine-4-carbaldehyde 552.27
    sulfolane 534.33
    2,2,4-trimethylpentane 150.61
    2-methyltetrahydrofuran 1395.94
    n-hexyl acetate 595.04
    isooctane 187.45
    2-(2-butoxyethoxy)ethanol 559.34
    sec-butyl acetate 379.88
    tert-butyl acetate 724.8
    decalin 175.47
    glycerin 161.38
    diglyme 930.9
    acrylic acid 231.86
    isopropyl myristate 270.57
    n-butyric acid 727.14
    acetyl acetate 550.5
    di(2-ethylhexyl) phthalate 173.5
    ethyl propionate 460.93
    nitromethane 563.05
    1,2-diethoxyethane 1091.01
    benzonitrile 423.05
    trioctyl phosphate 157.77
    1-bromopropane 836.97
    gamma-valerolactone 1000.54
    n-decanol 250.73
    triethyl phosphate 251.93
    4-methyl-2-pentanol 377.11
    propionitrile 853.48
    vinylene carbonate 549.08
    1,1,2-trichlorotrifluoroethane 382.78
    DMS 372.91
    cumene 203.35
    2-octanol 253.0
    2-hexanone 450.5
    octyl acetate 305.46
    limonene 464.47
    1,2-dimethoxyethane 734.31
    ethyl orthosilicate 279.75
    tributyl phosphate 208.9
    diacetone alcohol 469.06
    N,N-dimethylaniline 247.81
    acrylonitrile 655.46
    aniline 554.59
    1,3-propanediol 391.87
    bromobenzene 686.46
    dibromomethane 1004.76
    1,1,2,2-tetrachloroethane 771.49
    2-methyl-cyclohexyl acetate 443.91
    tetrabutyl urea 206.18
    diisobutyl methanol 423.45
    2-phenylethanol 464.09
    styrene 294.99
    dioctyl adipate 254.57
    dimethyl sulfate 199.21
    ethyl butyrate 791.9
    methyl lactate 200.23
    butyl lactate 280.19
    diethyl carbonate 451.11
    propanediol butyl ether 295.97
    triethyl orthoformate 553.97
    p-tert-butyltoluene 326.72
    methyl 4-tert-butylbenzoate 310.08
    morpholine 1358.81
    tert-butylamine 639.57
    n-dodecanol 198.92
    dimethoxymethane 730.44
    ethylene carbonate 560.1
    cyrene 203.39
    2-ethoxyethyl acetate 582.77
    2-ethylhexyl acetate 874.37
    1,2,4-trichlorobenzene 446.14
    4-methylpyridine 788.81
    dibutyl ether 695.28
    2,6-dimethyl-4-heptanol 423.45
    DEF 543.98
    dimethyl isosorbide 620.29
    tetrachloroethylene 629.1
    eugenol 250.13
    triacetin 353.45
    span 80 320.58
    1,4-butanediol 125.75
    1,1-dichloroethane 911.74
    2-methyl-1-pentanol 305.08
    methyl formate 298.19
    2-methyl-1-butanol 474.77
    n-decane 156.38
    butyronitrile 901.55
    3,7-dimethyl-1-octanol 389.2
    1-chlorooctane 340.57
    1-chlorotetradecane 146.13
    n-nonane 170.91
    undecane 114.01
    tert-butylcyclohexane 173.11
    cyclooctane 275.44
    cyclopentanol 530.84
    tetrahydropyran 1659.4
    tert-amyl methyl ether 606.39
    2,5,8-trioxanonane 565.95
    1-hexene 557.8
    2-isopropoxyethanol 319.95
    2,2,2-trifluoroethanol 141.26
    methyl butyrate 464.37

    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
Oregano, spanish (Greece) 3 8007-11-2 Coridothymus capitatus Rchb. (Thymus capitatus Hoffm. et Link.), Lamiaceae 0.8%
Lavender (South Africa) 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.1%
Pinus sylvestris 8 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 0.05%
Pinus sylvestris (Lithuania) 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 0.01%