4,7,7-Trimethylbicyclo[3.2.0]hept-3-en-6-one

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  • Identifiers

    CAS number
    4613-37-0

    Molecular formula
    C10H14O

    SMILES
    CC1=CCC2C1C(=O)C2(C)C

  • Odor profile

    Woody 57.64%
    Herbal 56.01%
    Mint 53.16%
    Camphoreous 50.55%
    Spicy 45.23%
    Fresh 38.77%
    Tobacco 33.29%
    Cooling 32.47%
    Earthy 31.25%
    Citrus 30.11%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    213°C

    Flash point est.
    75.37 ˚C

  • Synonyms

    • Filifolone
    • 4,7,7-trimethylbicyclo[3.2.0]hept-3-en-6-one
    • 4613-37-0
    • 2,6,6-Trimethylbicyclo[3.2.0]hept-2-en-7-one
    • 2,6,6-TRIMETHYLBICYCLO[3.2.0]HEPTA-2-ENE-7-ONE
    • DTXSID50487221
    • JVEJBTZZORGEKF-UHFFFAOYSA-N
    • 4,7,7-trimethyl-bicyclo[3.2.0]hept-3-en-6-one
    • Bicyclo[3.2.0]hept-3-en-6-one, 4,7,7-trimethyl-

  • Applications

    4,7,7-Trimethylbicyclo[3.2.0]hept-3-en-6-one (CAS 4613-37-0) is a terpenoid-like bicyclic ketone used and studied chiefly as a synthetic intermediate to access monoterpene derivatives and other strained frameworks (reductions, epoxidation, Michael addition, Baeyer–Villiger oxidation, ring-opening, etc.), as a fragrance raw material and target in aroma R&D due to the resinous/herbal odor profile typical of such bicyclic ketones and the tunability of its notes upon chemical modification, as a compact lipophilic scaffold in medicinal/agrochemical chemistry, as a model substrate for asymmetric catalysis (hydrogenation, conjugate addition), for probing the reactivity of strained enones and photochemistry, as a reference/standard in analytical methods (GC/MS, NMR), and as a starting point to prepare functionalized lactones, thioethers, and allylic alcohols for odorants, aroma modulators, and small-molecule materials studies.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1108.84
    methanol 1170.6
    isopropanol 1124.6
    water 44.51
    ethyl acetate 1181.41
    n-propanol 947.99
    acetone 1752.67
    n-butanol 841.66
    acetonitrile 1432.04
    DMF 1578.76
    toluene 736.09
    isobutanol 780.36
    1,4-dioxane 1842.93
    methyl acetate 1356.35
    THF 1879.99
    2-butanone 1296.76
    n-pentanol 521.15
    sec-butanol 793.95
    n-hexane 154.47
    ethylene glycol 405.13
    NMP 802.02
    cyclohexane 185.79
    DMSO 800.71
    n-butyl acetate 626.18
    n-octanol 440.18
    chloroform 3124.45
    n-propyl acetate 699.26
    acetic acid 786.36
    dichloromethane 2182.97
    cyclohexanone 1129.35
    propylene glycol 473.94
    isopropyl acetate 867.08
    DMAc 1006.81
    2-ethoxyethanol 919.97
    isopentanol 726.08
    n-heptane 90.84
    ethyl formate 764.9
    1,2-dichloroethane 1238.46
    n-hexanol 678.65
    2-methoxyethanol 1439.93
    isobutyl acetate 488.7
    tetrachloromethane 739.82
    n-pentyl acetate 505.07
    transcutol 1682.81
    n-heptanol 433.19
    ethylbenzene 511.3
    MIBK 747.31
    2-propoxyethanol 1167.18
    tert-butanol 1040.82
    MTBE 999.33
    2-butoxyethanol 761.18
    propionic acid 711.61
    o-xylene 526.68
    formic acid 453.11
    diethyl ether 1045.08
    m-xylene 661.82
    p-xylene 748.86
    chlorobenzene 847.98
    dimethyl carbonate 614.83
    n-octane 61.78
    formamide 743.74
    cyclopentanone 1478.85
    2-pentanone 1061.78
    anisole 897.08
    cyclopentyl methyl ether 928.59
    gamma-butyrolactone 1506.69
    1-methoxy-2-propanol 1154.02
    pyridine 1214.76
    3-pentanone 789.39
    furfural 1311.48
    n-dodecane 52.8
    diethylene glycol 870.81
    diisopropyl ether 459.3
    tert-amyl alcohol 779.23
    acetylacetone 1211.62
    n-hexadecane 60.85
    acetophenone 704.18
    methyl propionate 921.71
    isopentyl acetate 622.72
    trichloroethylene 2537.3
    n-nonanol 373.63
    cyclohexanol 651.87
    benzyl alcohol 612.75
    2-ethylhexanol 368.81
    isooctanol 359.86
    dipropyl ether 427.27
    1,2-dichlorobenzene 773.67
    ethyl lactate 395.77
    propylene carbonate 899.6
    n-methylformamide 1016.18
    2-pentanol 685.47
    n-pentane 168.01
    1-propoxy-2-propanol 749.41
    1-methoxy-2-propyl acetate 732.54
    2-(2-methoxypropoxy) propanol 542.15
    mesitylene 448.73
    ε-caprolactone 947.57
    p-cymene 257.35
    epichlorohydrin 1777.56
    1,1,1-trichloroethane 1733.86
    2-aminoethanol 636.77
    morpholine-4-carbaldehyde 1233.45
    sulfolane 1110.68
    2,2,4-trimethylpentane 102.99
    2-methyltetrahydrofuran 1239.24
    n-hexyl acetate 759.44
    isooctane 111.21
    2-(2-butoxyethoxy)ethanol 747.84
    sec-butyl acetate 541.12
    tert-butyl acetate 839.19
    decalin 129.93
    glycerin 556.75
    diglyme 1371.37
    acrylic acid 668.85
    isopropyl myristate 290.39
    n-butyric acid 862.11
    acetyl acetate 821.95
    di(2-ethylhexyl) phthalate 249.23
    ethyl propionate 677.87
    nitromethane 1651.39
    1,2-diethoxyethane 694.52
    benzonitrile 810.23
    trioctyl phosphate 190.2
    1-bromopropane 813.82
    gamma-valerolactone 1701.66
    n-decanol 273.41
    triethyl phosphate 232.94
    4-methyl-2-pentanol 476.29
    propionitrile 1012.74
    vinylene carbonate 915.83
    1,1,2-trichlorotrifluoroethane 1104.59
    DMS 689.86
    cumene 372.95
    2-octanol 349.12
    2-hexanone 700.98
    octyl acetate 356.6
    limonene 286.34
    1,2-dimethoxyethane 1324.35
    ethyl orthosilicate 232.15
    tributyl phosphate 221.42
    diacetone alcohol 800.24
    N,N-dimethylaniline 543.23
    acrylonitrile 1203.71
    aniline 757.38
    1,3-propanediol 825.79
    bromobenzene 876.56
    dibromomethane 1415.75
    1,1,2,2-tetrachloroethane 1844.03
    2-methyl-cyclohexyl acetate 375.57
    tetrabutyl urea 247.15
    diisobutyl methanol 253.57
    2-phenylethanol 639.86
    styrene 547.53
    dioctyl adipate 332.32
    dimethyl sulfate 671.18
    ethyl butyrate 483.69
    methyl lactate 532.78
    butyl lactate 397.86
    diethyl carbonate 341.8
    propanediol butyl ether 620.08
    triethyl orthoformate 330.01
    p-tert-butyltoluene 262.1
    methyl 4-tert-butylbenzoate 583.84
    morpholine 1528.45
    tert-butylamine 723.58
    n-dodecanol 204.59
    dimethoxymethane 1272.17
    ethylene carbonate 775.92
    cyrene 452.71
    2-ethoxyethyl acetate 648.82
    2-ethylhexyl acetate 446.75
    1,2,4-trichlorobenzene 868.86
    4-methylpyridine 1258.51
    dibutyl ether 403.48
    2,6-dimethyl-4-heptanol 253.57
    DEF 827.53
    dimethyl isosorbide 742.57
    tetrachloroethylene 1317.87
    eugenol 574.47
    triacetin 580.05
    span 80 452.61
    1,4-butanediol 379.47
    1,1-dichloroethane 1811.14
    2-methyl-1-pentanol 477.01
    methyl formate 918.99
    2-methyl-1-butanol 661.93
    n-decane 85.1
    butyronitrile 902.17
    3,7-dimethyl-1-octanol 387.48
    1-chlorooctane 288.31
    1-chlorotetradecane 124.15
    n-nonane 84.46
    undecane 64.96
    tert-butylcyclohexane 138.76
    cyclooctane 96.28
    cyclopentanol 720.77
    tetrahydropyran 1242.96
    tert-amyl methyl ether 641.41
    2,5,8-trioxanonane 795.99
    1-hexene 422.37
    2-isopropoxyethanol 686.28
    2,2,2-trifluoroethanol 570.08
    methyl butyrate 764.15

    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
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.76%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.18%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.83%
Artemisia judaica (Israel) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.6%
Rosemary (Japan) 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.11%
Tansy (Japan) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 1.0%
Artemisia barrelieri Artemisia barrelieri Besser, fam. Asteraceae (Compositae) 6.3%
Armoise (Algeria) 1b thujone type 8008-93-3 Artemisia herba-albe Asso, fam. Asteraceae (Compositae) 2.4%
Armoise (Algeria) 1a camphor type 8008-93-3 Artemisia herba-alba Asso, fam. Asteraceae (Compositae) 1.2%