2,10-Epoxypinane

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  • Identifiers

    CAS number
    6931-54-0

    Molecular formula
    C10H16O

    SMILES
    CC1(C2CCC3(C1C2)CO3)C

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1154.5

  • Odor profile

    Woody 68.67%
    Herbal 65.44%
    Camphoreous 60.81%
    Fresh 57.83%
    Pine 57.76%
    Green 48.91%
    Mint 48.03%
    Sweet 47.85%
    Spicy 47.68%
    Cooling 43.58%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.03 (neutral)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    198°C

    Flash point est.
    65.65 ˚C

  • Synonyms

    • 2,10-Epoxypinane
    • 6931-54-0
    • beta-Pinene oxide
    • 6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,2'-oxirane]
    • beta-Pinene epoxide
    • Pinane, 2,10-epoxy-
    • .beta.-Pinene oxide
    • CCRIS 3760
    • Spiro[bicyclo[3.1.1]heptane-2,2'-oxirane], 6,6-dimethyl-
    • (+)-Beta-Pinene oxide
    • EINECS 230-055-8
    • BRN 0105830
    • Spiro(bicyclo(3.1.1)heptane-2,2'-oxirane), 6,6-dimethyl-
    • DTXSID70863962
    • 5-17-01-00423 (Beilstein Handbook Reference)
    • 6,6-dimethylspiro(bicyclo(3.1.1)heptane-2,2'-oxirane)
    • ss-Pinenoxyd
    • beta pinene oxide
    • .beta.-Pinene epoxide
    • SCHEMBL260525
    • DTXCID90219301
    • GAA93154
    • AKOS006227869
    • NS00012358
    • G47255
    • EN300-1601456
    • Z1198147162
    • 230-055-8

  • Applications

    2,10‑Epoxypinane (CAS 6931‑54‑0) is a stereodefined pinane‑framework monoterpene epoxide used as a chiral intermediate in the synthesis of fragrances, flavors, and bioactive compounds; its strained epoxide ring undergoes selective openings (acidic, basic, nucleophilic, or enzyme‑catalyzed) to furnish diols, amino alcohols, ethers, or halo derivatives that serve as versatile building blocks. It also functions as a model substrate for probing mechanisms of terpene rearrangements (e.g., pinane/campholenic‑type pathways under Lewis acid catalysis), for studying epoxide hydrolysis by epoxide hydrolases, and for developing asymmetric catalytic methods rooted in monoterpene scaffolds. In essential‑oil analysis and α‑pinene oxidation studies, 2,10‑epoxypinane can act as a GC–MS reference/benchmark to identify epoxidation products and monitor transformation routes; additionally, its rigid pinane core is useful for designing pinane‑based ligands and auxiliaries for stereocontrolled synthesis. At the materials/formulation interface, it is occasionally employed as a precursor to install functionality onto terpene skeletons to tune hydrophobicity, volatility, or odor character, supporting optimization of fragrance blends and specialty coatings.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 269.3
    methanol 285.43
    isopropanol 192.17
    water 4.69
    ethyl acetate 261.66
    n-propanol 216.94
    acetone 243.48
    n-butanol 193.91
    acetonitrile 282.72
    DMF 169.34
    toluene 180.77
    isobutanol 140.12
    1,4-dioxane 468.6
    methyl acetate 227.91
    THF 593.89
    2-butanone 190.56
    n-pentanol 101.55
    sec-butanol 126.61
    n-hexane 24.63
    ethylene glycol 77.22
    NMP 138.92
    cyclohexane 58.02
    DMSO 135.74
    n-butyl acetate 177.6
    n-octanol 74.6
    chloroform 726.01
    n-propyl acetate 129.49
    acetic acid 229.17
    dichloromethane 546.54
    cyclohexanone 243.97
    propylene glycol 78.58
    isopropyl acetate 187.8
    DMAc 119.9
    2-ethoxyethanol 171.63
    isopentanol 152.67
    n-heptane 29.21
    ethyl formate 153.83
    1,2-dichloroethane 275.62
    n-hexanol 176.61
    2-methoxyethanol 288.28
    isobutyl acetate 102.84
    tetrachloromethane 150.21
    n-pentyl acetate 107.16
    transcutol 580.82
    n-heptanol 87.18
    ethylbenzene 75.77
    MIBK 146.14
    2-propoxyethanol 300.13
    tert-butanol 170.4
    MTBE 163.42
    2-butoxyethanol 159.21
    propionic acid 157.09
    o-xylene 102.18
    formic acid 131.26
    diethyl ether 259.25
    m-xylene 129.71
    p-xylene 97.35
    chlorobenzene 200.69
    dimethyl carbonate 106.63
    n-octane 11.74
    formamide 167.32
    cyclopentanone 286.84
    2-pentanone 185.77
    anisole 143.42
    cyclopentyl methyl ether 237.7
    gamma-butyrolactone 322.23
    1-methoxy-2-propanol 222.81
    pyridine 298.83
    3-pentanone 136.07
    furfural 274.01
    n-dodecane 10.38
    diethylene glycol 242.09
    diisopropyl ether 97.06
    tert-amyl alcohol 110.7
    acetylacetone 209.37
    n-hexadecane 12.01
    acetophenone 113.21
    methyl propionate 174.72
    isopentyl acetate 165.96
    trichloroethylene 483.06
    n-nonanol 70.84
    cyclohexanol 145.79
    benzyl alcohol 103.99
    2-ethylhexanol 94.76
    isooctanol 70.43
    dipropyl ether 130.52
    1,2-dichlorobenzene 174.7
    ethyl lactate 77.66
    propylene carbonate 187.56
    n-methylformamide 161.67
    2-pentanol 126.42
    n-pentane 39.58
    1-propoxy-2-propanol 201.91
    1-methoxy-2-propyl acetate 228.88
    2-(2-methoxypropoxy) propanol 138.66
    mesitylene 88.18
    ε-caprolactone 229.73
    p-cymene 64.56
    epichlorohydrin 362.29
    1,1,1-trichloroethane 299.04
    2-aminoethanol 127.24
    morpholine-4-carbaldehyde 241.21
    sulfolane 202.91
    2,2,4-trimethylpentane 19.48
    2-methyltetrahydrofuran 304.26
    n-hexyl acetate 144.71
    isooctane 23.27
    2-(2-butoxyethoxy)ethanol 190.66
    sec-butyl acetate 104.51
    tert-butyl acetate 176.08
    decalin 26.25
    glycerin 117.36
    diglyme 324.82
    acrylic acid 142.28
    isopropyl myristate 66.69
    n-butyric acid 208.1
    acetyl acetate 197.99
    di(2-ethylhexyl) phthalate 59.38
    ethyl propionate 124.36
    nitromethane 308.09
    1,2-diethoxyethane 223.66
    benzonitrile 159.79
    trioctyl phosphate 46.19
    1-bromopropane 188.81
    gamma-valerolactone 366.1
    n-decanol 54.13
    triethyl phosphate 68.92
    4-methyl-2-pentanol 94.07
    propionitrile 213.42
    vinylene carbonate 204.8
    1,1,2-trichlorotrifluoroethane 205.37
    DMS 143.09
    cumene 58.83
    2-octanol 52.88
    2-hexanone 111.62
    octyl acetate 76.51
    limonene 75.98
    1,2-dimethoxyethane 239.76
    ethyl orthosilicate 70.69
    tributyl phosphate 57.52
    diacetone alcohol 156.68
    N,N-dimethylaniline 85.29
    acrylonitrile 220.73
    aniline 175.7
    1,3-propanediol 187.97
    bromobenzene 215.82
    dibromomethane 379.49
    1,1,2,2-tetrachloroethane 333.91
    2-methyl-cyclohexyl acetate 103.24
    tetrabutyl urea 57.31
    diisobutyl methanol 74.74
    2-phenylethanol 143.91
    styrene 86.85
    dioctyl adipate 76.37
    dimethyl sulfate 98.7
    ethyl butyrate 135.97
    methyl lactate 102.12
    butyl lactate 90.03
    diethyl carbonate 100.33
    propanediol butyl ether 118.34
    triethyl orthoformate 110.31
    p-tert-butyltoluene 64.61
    methyl 4-tert-butylbenzoate 109.97
    morpholine 409.34
    tert-butylamine 131.83
    n-dodecanol 42.29
    dimethoxymethane 236.57
    ethylene carbonate 187.92
    cyrene 99.68
    2-ethoxyethyl acetate 172.74
    2-ethylhexyl acetate 128.57
    1,2,4-trichlorobenzene 182.24
    4-methylpyridine 228.91
    dibutyl ether 96.01
    2,6-dimethyl-4-heptanol 74.74
    DEF 134.91
    dimethyl isosorbide 200.49
    tetrachloroethylene 253.24
    eugenol 104.79
    triacetin 142.02
    span 80 109.97
    1,4-butanediol 66.44
    1,1-dichloroethane 306.05
    2-methyl-1-pentanol 83.57
    methyl formate 141.78
    2-methyl-1-butanol 118.77
    n-decane 17.55
    butyronitrile 207.1
    3,7-dimethyl-1-octanol 82.33
    1-chlorooctane 56.05
    1-chlorotetradecane 26.24
    n-nonane 16.04
    undecane 13.1
    tert-butylcyclohexane 23.68
    cyclooctane 26.03
    cyclopentanol 147.63
    tetrahydropyran 361.32
    tert-amyl methyl ether 112.01
    2,5,8-trioxanonane 208.76
    1-hexene 67.52
    2-isopropoxyethanol 125.87
    2,2,2-trifluoroethanol 114.04
    methyl butyrate 130.72

    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
Juniperus foetidissima leaf Juniperus foetidissima Willd., fam. Cupressaceae 0.2%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.2%
Hemidesmus indicus Hemidesmus indicus R.Br., fam. Asclepiadaceae 0.01%
Lemon leaf (petitgrain) (USA) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.34%
Lemongrass (Argentine) 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 1.66%
Douglas fir (Bulgaria) Pseudotsuga menziesii (Mirbel) Franco, fam. Pinaceae 0.15%