(-)-beta-Bourbonene

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  • Identifiers

    CAS number
    5208-59-3

    Molecular formula
    C15H24

    SMILES
    CC(C)C1CCC2(C1C3C2CCC3=C)C

  • Odor profile

    Fragrance
    Woody 81.53%
    Herbal 63.08%
    Spicy 52.78%
    Green 51.83%
    Fresh 42.23%
    Fruity 41.95%
    Balsamic 39.41%
    Oily 39.12%
    Citrus 38.56%
    Floral 35.32%

     

    Flavor
    Woody 61.13%
    Herbal 52.93%
    Herb 52.57%
    Wood 50.31%
    Fruity 42.76%
    Spice 36.59%
    Citrus 33.72%
    Fruit 32.42%
    Pine 26.55%
    Fir needle 26.18%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    4.7

    pKa est.
    9.56 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    272°C

    Flash point

    • 69.76 ˚C est.

    Solubility expt.

    • Insoluble in water; soluble in most fixed oils
    • Soluble (in ethanol)

  • Synonyms

    • .beta.-Bourbonene
    • 5208-59-3
    • (-)-beta-Bourbonene
    • 1-methyl-5-methylidene-8-propan-2-yltricyclo[5.3.0.02,6]decane
    • (-)-.beta.-Bourbonene
    • CHEBI:88874
    • DTXSID90863505
    • YIRAHEODBQONHI-UHFFFAOYSA-N
    • [1S-[1.alpha.,3a.alpha.,3b.beta.,6a.beta.,6b.alpha.]]-Cyclobuta[1,2:3,4]dicyclopentene-decahydro-3a-methyl-6-methylene-1-[1-methylethyl]
    • Cyclobuta[1,2:3,4]dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1.alpha.,3a.alpha.,3b.beta.,6a.beta.,6b.alpha.)-
    • NSC288727
    • Q27160892
    • 3a-Methyl-6-methylidene-1-(propan-2-yl)decahydrocyclobuta[1,2-a:3,4-a']dicyclopentene
    • Cyclobuta[1,4]dicyclopentene, 1,2,3,3a,3b.beta.,4,5,6,6a.beta.,6b.alpha.-decahydro-1.alpha.-isopropyl-3a.alpha.-methyl-6-methylene-
    • Cyclobuta[1,4]dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, [1S-(1.alpha.,3a.alpha.,3b.beta.,6a.beta.,6b.alpha.)]-

  • Applications

    Beta-bourbonene (CAS 5208-59-3) is a sesquiterpene hydrocarbon naturally occurring in many essential oils and used as a fragrance ingredient to impart warm woody, balsamic, subtly peppery facets, enriching woody-amber, chypre and oriental accords and adding depth to soaps, detergents, candles and personal care products; in flavors it is occasionally applied at very low levels to add woody-herbal, lightly spicy nuances, while in analytics it serves as a marker/reference standard in GC-MS profiling for authenticity testing and quality control of essential oils and botanical extracts; preclinical work also explores typical sesquiterpene bioactivities (antimicrobial, antioxidant, anti-inflammatory) and possible effects on insect behavior, although medicinal applications remain unsubstantiated and require further evidence; because it is prone to oxidation, materials should be stored tightly closed, protected from light/air, and may include antioxidants to preserve odor quality.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 529.71
    methanol 272.95
    isopropanol 921.21
    water 0.71
    ethyl acetate 1178.8
    n-propanol 670.34
    acetone 1187.77
    n-butanol 857.31
    acetonitrile 750.67
    DMF 859.69
    toluene 1411.8
    isobutanol 638.53
    1,4-dioxane 2117.83
    methyl acetate 865.42
    THF 3945.28
    2-butanone 1097.03
    n-pentanol 351.87
    sec-butanol 615.38
    n-hexane 185.35
    ethylene glycol 58.96
    NMP 519.07
    cyclohexane 514.94
    DMSO 437.4
    n-butyl acetate 1455.81
    n-octanol 425.25
    chloroform 2067.6
    n-propyl acetate 616.32
    acetic acid 230.92
    dichloromethane 1661.07
    cyclohexanone 1525.43
    propylene glycol 129.94
    isopropyl acetate 1074.44
    DMAc 578.87
    2-ethoxyethanol 389.06
    isopentanol 808.35
    n-heptane 346.11
    ethyl formate 597.07
    1,2-dichloroethane 1099.55
    n-hexanol 956.17
    2-methoxyethanol 714.11
    isobutyl acetate 623.47
    tetrachloromethane 506.74
    n-pentyl acetate 691.77
    transcutol 1423.66
    n-heptanol 406.66
    ethylbenzene 541.63
    MIBK 925.53
    2-propoxyethanol 1088.59
    tert-butanol 1084.93
    MTBE 1464.7
    2-butoxyethanol 558.91
    propionic acid 316.13
    o-xylene 657.84
    formic acid 40.98
    diethyl ether 1378.98
    m-xylene 931.94
    p-xylene 701.55
    chlorobenzene 1032.45
    dimethyl carbonate 395.71
    n-octane 121.69
    formamide 97.66
    cyclopentanone 1862.1
    2-pentanone 1126.44
    anisole 802.85
    cyclopentyl methyl ether 1454.39
    gamma-butyrolactone 1523.48
    1-methoxy-2-propanol 834.12
    pyridine 1538.13
    3-pentanone 749.1
    furfural 918.98
    n-dodecane 97.47
    diethylene glycol 455.79
    diisopropyl ether 646.21
    tert-amyl alcohol 598.16
    acetylacetone 1176.75
    n-hexadecane 115.4
    acetophenone 602.86
    methyl propionate 752.99
    isopentyl acetate 1438.15
    trichloroethylene 1645.1
    n-nonanol 385.77
    cyclohexanol 774.19
    benzyl alcohol 470.7
    2-ethylhexanol 612.22
    isooctanol 357.79
    dipropyl ether 1165.63
    1,2-dichlorobenzene 797.27
    ethyl lactate 244.59
    propylene carbonate 931.41
    n-methylformamide 372.07
    2-pentanol 643.33
    n-pentane 276.94
    1-propoxy-2-propanol 971.54
    1-methoxy-2-propyl acetate 1259.79
    2-(2-methoxypropoxy) propanol 531.07
    mesitylene 630.94
    ε-caprolactone 1113.31
    p-cymene 562.44
    epichlorohydrin 1557.32
    1,1,1-trichloroethane 1279.21
    2-aminoethanol 164.65
    morpholine-4-carbaldehyde 855.48
    sulfolane 865.05
    2,2,4-trimethylpentane 129.54
    2-methyltetrahydrofuran 2056.89
    n-hexyl acetate 905.17
    isooctane 175.75
    2-(2-butoxyethoxy)ethanol 700.49
    sec-butyl acetate 556.24
    tert-butyl acetate 1128.29
    decalin 179.71
    glycerin 151.19
    diglyme 1386.29
    acrylic acid 209.97
    isopropyl myristate 465.59
    n-butyric acid 730.33
    acetyl acetate 752.73
    di(2-ethylhexyl) phthalate 322.17
    ethyl propionate 614.9
    nitromethane 526.76
    1,2-diethoxyethane 1122.44
    benzonitrile 821.08
    trioctyl phosphate 273.36
    1-bromopropane 1035.69
    gamma-valerolactone 1641.54
    n-decanol 305.22
    triethyl phosphate 344.6
    4-methyl-2-pentanol 527.17
    propionitrile 908.33
    vinylene carbonate 845.86
    1,1,2-trichlorotrifluoroethane 518.19
    DMS 580.19
    cumene 379.19
    2-octanol 309.77
    2-hexanone 625.11
    octyl acetate 497.48
    limonene 651.43
    1,2-dimethoxyethane 1133.6
    ethyl orthosilicate 361.43
    tributyl phosphate 320.84
    diacetone alcohol 726.13
    N,N-dimethylaniline 475.79
    acrylonitrile 799.84
    aniline 860.39
    1,3-propanediol 407.49
    bromobenzene 1250.69
    dibromomethane 1255.65
    1,1,2,2-tetrachloroethane 1210.72
    2-methyl-cyclohexyl acetate 634.24
    tetrabutyl urea 374.14
    diisobutyl methanol 517.87
    2-phenylethanol 740.29
    styrene 611.4
    dioctyl adipate 473.49
    dimethyl sulfate 346.75
    ethyl butyrate 962.07
    methyl lactate 269.47
    butyl lactate 419.15
    diethyl carbonate 583.04
    propanediol butyl ether 414.3
    triethyl orthoformate 669.65
    p-tert-butyltoluene 589.46
    methyl 4-tert-butylbenzoate 582.01
    morpholine 1754.34
    tert-butylamine 842.63
    n-dodecanol 246.44
    dimethoxymethane 1179.97
    ethylene carbonate 820.55
    cyrene 369.74
    2-ethoxyethyl acetate 811.77
    2-ethylhexyl acetate 1103.38
    1,2,4-trichlorobenzene 816.11
    4-methylpyridine 1580.88
    dibutyl ether 832.29
    2,6-dimethyl-4-heptanol 517.87
    DEF 742.57
    dimethyl isosorbide 1008.8
    tetrachloroethylene 739.69
    eugenol 461.59
    triacetin 602.08
    span 80 479.79
    1,4-butanediol 125.34
    1,1-dichloroethane 1314.3
    2-methyl-1-pentanol 354.02
    methyl formate 354.34
    2-methyl-1-butanol 592.36
    n-decane 160.35
    butyronitrile 1099.08
    3,7-dimethyl-1-octanol 499.31
    1-chlorooctane 423.84
    1-chlorotetradecane 183.93
    n-nonane 158.16
    undecane 122.19
    tert-butylcyclohexane 173.68
    cyclooctane 230.78
    cyclopentanol 786.95
    tetrahydropyran 2400.63
    tert-amyl methyl ether 716.62
    2,5,8-trioxanonane 837.18
    1-hexene 454.29
    2-isopropoxyethanol 367.09
    2,2,2-trifluoroethanol 118.06
    methyl butyrate 704.64

    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