(1S,5S)-1-[(2R)-6-methylhept-5-en-2-yl]-4-methylidenebicyclo[3.1.0]hexane

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    58319-04-3

    Molecular formula
    C15H24

    SMILES
    C[C@H](CCC=C(C)C)[C@@]12CCC(=C)[C@@H]1C2

  • Odor profile

    Woody 78.99%
    Sweet 46.54%
    Balsamic 42.36%
    Green 42.12%
    Oily 41.26%
    Herbal 37.93%
    Waxy 36.65%
    Citrus 35.84%
    Spicy 34.58%
    Fresh 33.29%

    Scent© AI

  • Properties

    XLogP3-AA
    5.1

    pKa est.
    9.98 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    269°C

    Flash point est.
    84.26 ˚C

  • Synonyms

    • 58319-04-3
    • DTXSID001018183
    • 1-(1,5-Dimethyl-4-hexenyl)-4-methylenebicyclo[3.1.0]hexane

  • Applications

    This hydrophobic bicyclic sesquiterpene occurs in various plant essential oils and is applied mainly in three areas: (1) fragrance and flavor – as a nuance ingredient imparting woody, spicy, and herbal facets to perfumes, personal care, and flavor accords (often as a modifier and base-note enhancer); (2) analytics – as a reference standard/retention index marker in GC–MS, for chiral GC method development, source authentication, and terpene profiling of natural materials; (3) research – as a terpene scaffold for selective functionalization of the exocyclic double bond, for biosynthetic and semiochemical studies, and it is explored for in vitro/preclinical antimicrobial, antioxidant, and insect-repellent potential; it is also considered in essential-oil formulation (microencapsulation, oxidation control) and as a starting point for synthesizing odorants or analytical tracers.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2416.65
    methanol 822.5
    isopropanol 2660.31
    water 0.16
    ethyl acetate 3610.75
    n-propanol 2219.16
    acetone 1950.5
    n-butanol 2662.68
    acetonitrile 951.25
    DMF 782.63
    toluene 2381.72
    isobutanol 1574.99
    1,4-dioxane 5346.76
    methyl acetate 1619.65
    THF 6333.08
    2-butanone 2134.21
    n-pentanol 1168.77
    sec-butanol 1846.76
    n-hexane 782.89
    ethylene glycol 98.41
    NMP 354.77
    cyclohexane 1341.65
    DMSO 458.23
    n-butyl acetate 2681.11
    n-octanol 504.59
    chloroform 2861.98
    n-propyl acetate 1241.51
    acetic acid 448.61
    dichloromethane 2128.27
    cyclohexanone 1667.01
    propylene glycol 276.65
    isopropyl acetate 3060.56
    DMAc 861.73
    2-ethoxyethanol 1339.92
    isopentanol 2322.55
    n-heptane 548.65
    ethyl formate 676.79
    1,2-dichloroethane 1801.52
    n-hexanol 2236.94
    2-methoxyethanol 2073.78
    isobutyl acetate 1042.88
    tetrachloromethane 654.33
    n-pentyl acetate 882.49
    transcutol 5634.11
    n-heptanol 569.24
    ethylbenzene 752.25
    MIBK 2012.51
    2-propoxyethanol 2977.21
    tert-butanol 2797.26
    MTBE 6557.42
    2-butoxyethanol 1003.98
    propionic acid 479.88
    o-xylene 858.01
    formic acid 74.85
    diethyl ether 7888.46
    m-xylene 1395.35
    p-xylene 811.97
    chlorobenzene 1039.61
    dimethyl carbonate 466.6
    n-octane 166.77
    formamide 164.8
    cyclopentanone 1417.99
    2-pentanone 2405.69
    anisole 1448.56
    cyclopentyl methyl ether 2920.98
    gamma-butyrolactone 1057.23
    1-methoxy-2-propanol 2273.47
    pyridine 2301.59
    3-pentanone 1698.58
    furfural 733.87
    n-dodecane 96.01
    diethylene glycol 1132.43
    diisopropyl ether 2947.91
    tert-amyl alcohol 1647.87
    acetylacetone 1959.22
    n-hexadecane 114.09
    acetophenone 698.98
    methyl propionate 1689.39
    isopentyl acetate 2686.97
    trichloroethylene 2049.7
    n-nonanol 506.89
    cyclohexanol 1431.18
    benzyl alcohol 619.74
    2-ethylhexanol 1190.17
    isooctanol 507.92
    dipropyl ether 3353.06
    1,2-dichlorobenzene 753.37
    ethyl lactate 322.11
    propylene carbonate 709.31
    n-methylformamide 371.06
    2-pentanol 2145.92
    n-pentane 1124.06
    1-propoxy-2-propanol 2197.56
    1-methoxy-2-propyl acetate 2925.55
    2-(2-methoxypropoxy) propanol 1048.88
    mesitylene 886.73
    ε-caprolactone 1465.93
    p-cymene 562.19
    epichlorohydrin 2123.71
    1,1,1-trichloroethane 1701.62
    2-aminoethanol 403.25
    morpholine-4-carbaldehyde 1122.36
    sulfolane 542.24
    2,2,4-trimethylpentane 373.13
    2-methyltetrahydrofuran 4388.45
    n-hexyl acetate 1206.7
    isooctane 509.44
    2-(2-butoxyethoxy)ethanol 1583.59
    sec-butyl acetate 1372.54
    tert-butyl acetate 2917.46
    decalin 350.5
    glycerin 271.54
    diglyme 2956.74
    acrylic acid 237.25
    isopropyl myristate 585.53
    n-butyric acid 1425.15
    acetyl acetate 1381.42
    di(2-ethylhexyl) phthalate 340.86
    ethyl propionate 1310.63
    nitromethane 581.12
    1,2-diethoxyethane 4558.52
    benzonitrile 663.04
    trioctyl phosphate 229.19
    1-bromopropane 2279.77
    gamma-valerolactone 1751.07
    n-decanol 380.4
    triethyl phosphate 489.71
    4-methyl-2-pentanol 1491.99
    propionitrile 1336.82
    vinylene carbonate 573.37
    1,1,2-trichlorotrifluoroethane 673.39
    DMS 853.24
    cumene 504.52
    2-octanol 373.98
    2-hexanone 1182.6
    octyl acetate 570.84
    limonene 823.58
    1,2-dimethoxyethane 2863.28
    ethyl orthosilicate 592.12
    tributyl phosphate 321.99
    diacetone alcohol 1483.36
    N,N-dimethylaniline 726.04
    acrylonitrile 814.9
    aniline 1421.43
    1,3-propanediol 1073.77
    bromobenzene 1215.88
    dibromomethane 1837.56
    1,1,2,2-tetrachloroethane 1736.86
    2-methyl-cyclohexyl acetate 913.44
    tetrabutyl urea 343.9
    diisobutyl methanol 934.73
    2-phenylethanol 1100.96
    styrene 863.71
    dioctyl adipate 595.75
    dimethyl sulfate 290.39
    ethyl butyrate 1697.22
    methyl lactate 377.86
    butyl lactate 444.37
    diethyl carbonate 892.56
    propanediol butyl ether 586.4
    triethyl orthoformate 1238.26
    p-tert-butyltoluene 632.55
    methyl 4-tert-butylbenzoate 692.81
    morpholine 5476.44
    tert-butylamine 2465.84
    n-dodecanol 299.71
    dimethoxymethane 2539.81
    ethylene carbonate 678.66
    cyrene 376.1
    2-ethoxyethyl acetate 1517.1
    2-ethylhexyl acetate 1909.21
    1,2,4-trichlorobenzene 781.97
    4-methylpyridine 2176.99
    dibutyl ether 1750.05
    2,6-dimethyl-4-heptanol 934.73
    DEF 1506.56
    dimethyl isosorbide 1394.96
    tetrachloroethylene 1113.09
    eugenol 499.76
    triacetin 828.32
    span 80 670.25
    1,4-butanediol 258.41
    1,1-dichloroethane 2201.74
    2-methyl-1-pentanol 1012.93
    methyl formate 222.72
    2-methyl-1-butanol 1651.16
    n-decane 181.66
    butyronitrile 1810.76
    3,7-dimethyl-1-octanol 825.81
    1-chlorooctane 488.22
    1-chlorotetradecane 214.18
    n-nonane 179.9
    undecane 125.38
    tert-butylcyclohexane 377.39
    cyclooctane 515.33
    cyclopentanol 1017.81
    tetrahydropyran 7058.72
    tert-amyl methyl ether 2833.76
    2,5,8-trioxanonane 1716.33
    1-hexene 1515.05
    2-isopropoxyethanol 1118.59
    2,2,2-trifluoroethanol 126.08
    methyl butyrate 1218.82

    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
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Phoebe 1 Phoebe porosa Mez. (syn. Oreodaphne porosa Nees et Mart.), fam. Lauraceae 0.5%
Lavender (Bulgaria) 2 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.03%
Lavender (Ukraine) 8000-28-0 Lavandula angustifolia Mill., (L. officinalis Chaix), fam. Lamiaceae 0.06%
Lavender (Australia) 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.05%
Lavender (Moldova) 8000-28-0 Lavandula angustifolia Mill., (L. officinalis Chaix), fam. Lamiaceae 0.05%