Bicyclo(4.1.0)heptane, 3-ethenyl-3,7,7-trimethyl-2-(1-methylethenyl)-, (1R-(1alpha,2alpha,3beta,6alpha))-

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  • Identifiers

    CAS number
    32531-56-9

    Molecular formula
    C15H24

    SMILES
    CC(=C)[C@H]1[C@H]2[C@H](C2(C)C)CC[C@@]1(C)C=C

    Retention indicies (RI)

    • Carbowax: 1487.67

  • Odor profile

    Woody 83.68%
    Herbal 57.11%
    Sweet 56.86%
    Citrus 47.02%
    Green 46.87%
    Terpenic 44.88%
    Pine 42.78%
    Spicy 41.83%
    Fresh 40.65%
    Oily 37.65%

    Scent© AI

  • Properties

    XLogP3-AA
    5.5

    pKa est.
    9.69 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    243°C

    Flash point est.
    77.54 ˚C

  • Synonyms

    • Bicycloelemene
    • (-)-Bicycloelemene
    • 32531-56-9
    • Bicyclo(4.1.0)heptane, 3-ethenyl-3,7,7-trimethyl-2-(1-methylethenyl)-, (1R-(1alpha,2alpha,3beta,6alpha))-
    • DTXSID50186242
    • CHEBI:172935
    • Q67879752

  • Applications

    Bicyclo(4.1.0)heptane, 3-ethenyl-3,7,7-trimethyl-2-(1-methylethenyl)-, (1R-(1alpha,2alpha,3beta,6alpha)) (CAS 32531-56-9) is a bicyclic sesquiterpene diene whose two exocyclic double bonds make it valuable for: use as an intermediate in organic synthesis and terpene chemistry to access epoxides, allylic alcohols/ketones, hydroboration–oxidation products, ozonolysis fragments, and olefin-metathesis adducts, and as a chiral building block owing to its defined absolute configuration; serving as a reactive monomer/crosslinker for UV/thermal-cured resins and thiol–ene or hydrosilylation networks, acting as a reactive diluent in inks, coatings, and adhesives to increase hardness, enhance hydrophobicity, and reduce cure shrinkage; providing a precursor for terpene-like odorants and a GC/GC–MS reference/retention-index marker in quality control of sesquiterpene-rich essential oils; offering a scaffold in agrochemical and chemical-ecology studies for semiochemicals (attractants/repellents) and controlled-release tests thanks to moderate volatility; and functioning as a model compound in environmental and educational contexts to probe radical/ozone oxidation pathways and conformational strain in bicyclic systems.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 122.36
    methanol 60.67
    isopropanol 182.57
    water 0.17
    ethyl acetate 219.52
    n-propanol 156.2
    acetone 262.35
    n-butanol 177.23
    acetonitrile 116.04
    DMF 281.33
    toluene 303.72
    isobutanol 163.63
    1,4-dioxane 471.1
    methyl acetate 200.73
    THF 972.24
    2-butanone 293.45
    n-pentanol 123.69
    sec-butanol 172.61
    n-hexane 71.56
    ethylene glycol 24.1
    NMP 260.21
    cyclohexane 127.76
    DMSO 143.33
    n-butyl acetate 285.31
    n-octanol 171.49
    chloroform 398.87
    n-propyl acetate 164.76
    acetic acid 57.31
    dichloromethane 307.69
    cyclohexanone 421.94
    propylene glycol 56.26
    isopropyl acetate 223.84
    DMAc 250.03
    2-ethoxyethanol 134.46
    isopentanol 183.65
    n-heptane 103.09
    ethyl formate 115.36
    1,2-dichloroethane 238.04
    n-hexanol 276.86
    2-methoxyethanol 181.82
    isobutyl acetate 171.58
    tetrachloromethane 106.59
    n-pentyl acetate 207.56
    transcutol 293.23
    n-heptanol 161.41
    ethylbenzene 183.75
    MIBK 251.45
    2-propoxyethanol 326.24
    tert-butanol 249.78
    MTBE 362.86
    2-butoxyethanol 200.7
    propionic acid 84.4
    o-xylene 196.72
    formic acid 11.1
    diethyl ether 294.88
    m-xylene 262.0
    p-xylene 212.85
    chlorobenzene 229.44
    dimethyl carbonate 102.22
    n-octane 48.44
    formamide 22.01
    cyclopentanone 521.63
    2-pentanone 281.5
    anisole 250.07
    cyclopentyl methyl ether 451.87
    gamma-butyrolactone 395.49
    1-methoxy-2-propanol 220.75
    pyridine 312.81
    3-pentanone 223.51
    furfural 247.55
    n-dodecane 39.85
    diethylene glycol 157.25
    diisopropyl ether 170.62
    tert-amyl alcohol 205.66
    acetylacetone 282.6
    n-hexadecane 46.33
    acetophenone 199.31
    methyl propionate 192.11
    isopentyl acetate 327.31
    trichloroethylene 354.16
    n-nonanol 156.62
    cyclohexanol 222.29
    benzyl alcohol 154.66
    2-ethylhexanol 201.85
    isooctanol 147.46
    dipropyl ether 270.28
    1,2-dichlorobenzene 208.43
    ethyl lactate 98.06
    propylene carbonate 226.82
    n-methylformamide 86.22
    2-pentanol 166.67
    n-pentane 80.1
    1-propoxy-2-propanol 284.29
    1-methoxy-2-propyl acetate 314.56
    2-(2-methoxypropoxy) propanol 191.6
    mesitylene 192.16
    ε-caprolactone 308.46
    p-cymene 172.58
    epichlorohydrin 436.93
    1,1,1-trichloroethane 278.67
    2-aminoethanol 55.55
    morpholine-4-carbaldehyde 308.82
    sulfolane 356.76
    2,2,4-trimethylpentane 51.02
    2-methyltetrahydrofuran 586.57
    n-hexyl acetate 299.04
    isooctane 58.34
    2-(2-butoxyethoxy)ethanol 223.88
    sec-butyl acetate 157.06
    tert-butyl acetate 264.32
    decalin 77.08
    glycerin 58.75
    diglyme 351.26
    acrylic acid 64.92
    isopropyl myristate 153.02
    n-butyric acid 140.55
    acetyl acetate 145.17
    di(2-ethylhexyl) phthalate 126.74
    ethyl propionate 164.73
    nitromethane 111.48
    1,2-diethoxyethane 211.98
    benzonitrile 199.24
    trioctyl phosphate 111.71
    1-bromopropane 242.76
    gamma-valerolactone 443.28
    n-decanol 122.9
    triethyl phosphate 116.99
    4-methyl-2-pentanol 143.88
    propionitrile 167.56
    vinylene carbonate 184.79
    1,1,2-trichlorotrifluoroethane 193.45
    DMS 191.25
    cumene 143.65
    2-octanol 137.44
    2-hexanone 208.01
    octyl acetate 179.65
    limonene 217.42
    1,2-dimethoxyethane 306.77
    ethyl orthosilicate 111.75
    tributyl phosphate 111.6
    diacetone alcohol 236.27
    N,N-dimethylaniline 179.84
    acrylonitrile 141.62
    aniline 184.57
    1,3-propanediol 93.42
    bromobenzene 276.74
    dibromomethane 272.31
    1,1,2,2-tetrachloroethane 306.67
    2-methyl-cyclohexyl acetate 223.16
    tetrabutyl urea 139.41
    diisobutyl methanol 155.0
    2-phenylethanol 246.18
    styrene 182.93
    dioctyl adipate 159.22
    dimethyl sulfate 121.21
    ethyl butyrate 208.97
    methyl lactate 95.72
    butyl lactate 147.38
    diethyl carbonate 137.28
    propanediol butyl ether 170.65
    triethyl orthoformate 163.26
    p-tert-butyltoluene 184.41
    methyl 4-tert-butylbenzoate 222.34
    morpholine 447.58
    tert-butylamine 189.47
    n-dodecanol 100.16
    dimethoxymethane 296.9
    ethylene carbonate 171.42
    cyrene 176.42
    2-ethoxyethyl acetate 220.68
    2-ethylhexyl acetate 275.49
    1,2,4-trichlorobenzene 233.46
    4-methylpyridine 335.25
    dibutyl ether 201.36
    2,6-dimethyl-4-heptanol 155.0
    DEF 222.86
    dimethyl isosorbide 361.46
    tetrachloroethylene 194.98
    eugenol 177.49
    triacetin 207.62
    span 80 182.4
    1,4-butanediol 52.42
    1,1-dichloroethane 271.68
    2-methyl-1-pentanol 126.91
    methyl formate 80.25
    2-methyl-1-butanol 165.92
    n-decane 63.9
    butyronitrile 202.06
    3,7-dimethyl-1-octanol 179.94
    1-chlorooctane 159.05
    1-chlorotetradecane 74.95
    n-nonane 64.02
    undecane 49.85
    tert-butylcyclohexane 76.59
    cyclooctane 71.73
    cyclopentanol 248.9
    tetrahydropyran 554.16
    tert-amyl methyl ether 253.87
    2,5,8-trioxanonane 253.23
    1-hexene 145.84
    2-isopropoxyethanol 142.24
    2,2,2-trifluoroethanol 32.42
    methyl butyrate 191.84

    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
Davana 1 8016-03-3 Artemisia pallens Wall. ex DC., fam. Asteraceae (Compositae) 0.3%
Piper hancei (China) Piper hancei Maxim, fam. Piperaceae 0.07%
Vitex trifolia (Thailand) Vitex trifolia L., fam. Verbenaceae 0.42%
Idiospermum australiense Idiospermum australiense (Diels) S.T. Blake, fam. Idiospermaceae 6.0%
Lemon leaf (petitgrain) 2 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.62%
Teucrium betonicum (Madeira) Teucrium betonicum L'Her., fam. Lamiaceae (Labiatae) 6.8%
Uromyrtus australis (Australia) Uromyrtus australis A.J. Scott, fam. Myrtaceae 0.09%
St. John's wort (India) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 0.02%
Cubeb 2 8007-87-2 Piper cubeba L., fam. Piperaceae 0.05%
Tansy (Netherlands) 1a leaf 8016-87-3 Tanacetum vulgare L. chrysantenyl chemotype, fam. Asteraceae (Compositae) 0.1%
Tansy (Netherlands) 1b flower 8016-87-3 Tanacetum vulgare L. chrysantenyl chemotype, fam. Asteraceae (Compositae) 0.05%
Tansy (Netherlands) 2a leaf 8016-87-3 Tanacetum vulgare L. artemisia chemotype, fam. Asteraceae (Compositae) 1.7%
Tansy (Netherlands) 2b flower 8016-87-3 Tanacetum vulgare L. artemisia chemotype, fam. Asteraceae (Compositae) 0.05%
Tansy (Netherlands) 3a leaf 8016-87-3 Tanacetum vulgare L. beta-thujone chemotype, fam. Asteraceae (Compositae) 0.05%
Tansy (Netherlands) 3b flower 8016-87-3 Tanacetum vulgare L. beta-thujone chemotype, fam. Asteraceae (Compositae) 0.05%
Tansy (Netherlands) 4a leaf 8016-87-3 Tanacetum vulgare L. lyratol/acetate type, fam. Asteraceae (Compositae) 0.5%
Tansy (Netherlands) 4b flower 8016-87-3 Tanacetum vulgare L. lyratol/acetate type, fam. Asteraceae (Compositae) 0.05%
Citrus australasica leaf Citrus australasica, fam. Rutaceae 0.4%
Pentaceras australe leaf Pentaceras australe (F. Muell.) Benth., fam. Rutaceae 0.1%
Thymus fedtschenkoi var. handelii (Turkey) Thymus fedtschenkoi var. handelii, fam. Lamiaceae (Labiatae) 0.01%
Desmos goezeanus leaf (Australia) Desmos goezeanus (F. Muell.) L.W. Jessup, fam. Annonaceae 0.1%
Neolitsea australiensis leaf (Australia) Neolitsea australiensis Kosterm., fam. Lauraceae 0.6%
Neolitsea brassii leaf (Australia) Neolitsea brassii Allen, fam. Lauraceae 0.1%
Neolitsea dealbata leaf (Australia) Neolitsea dealbata (R. Br.) Merr., fam. Lauraceae 0.75%
Cinnamomum baileyanum (Australia) 1a leaf Cinnamomum baileyanum (F. Muell. ex F.M. Bailey) W.D. Francis, Lauraceae 0.2%
Cinnamomum laubatii leaf (Australia) Cinnamomum laubatii F. Muel., fam. Lauraceae 0.25%