Bicyclo(4.1.0)heptan-3-one, 1-methyl-4-(1-methylethylidene)-7-(3-oxobutyl)-, (1S,6R,7R)-

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  • Identifiers

    CAS number
    100347-96-4

    Molecular formula
    C15H22O2

    SMILES
    CC(=C1C[C@@H]2[C@H]([C@@]2(CC1=O)C)CCC(=O)C)C

  • Odor profile

    Woody 78.83%
    Floral 50.07%
    Fruity 47.56%
    Dry 42.83%
    Tobacco 37.71%
    Orris 36.67%
    Mint 36.53%
    Cedar 34.72%
    Herbal 33.88%
    Berry 31.64%

    Scent© AI

  • Properties

    XLogP3-AA
    2.4

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    380°C

    Flash point est.
    125.48 ˚C

  • Synonyms

    • Curcumenone
    • 100347-96-4
    • (1S,6beta)-1beta-Methyl-4-(1-methylethylidene)-7beta-(3-oxobutyl)bicyclo[4.1.0]heptan-3-one
    • Bicyclo(4.1.0)heptan-3-one, 1-methyl-4-(1-methylethylidene)-7-(3-oxobutyl)-, (1S,6R,7R)-
    • SCHEMBL3300327
    • CHEMBL4643848
    • CHEBI:81130
    • DTXSID30905433
    • AKOS040760356
    • FS-7460
    • DA-62540
    • HY-115363
    • CS-0035133
    • C17492
    • F92720
    • Q27155088
    • (1S,6R,7R)-1-methyl-7-(3-oxobutyl)-4-propan-2-ylidenebicyclo[4.1.0]heptan-3-one
    • 1-METHYL-7-(3-OXOBUTYL)-4-(PROPAN-2-YLIDENE)BICYCLO[4.1.0]HEPTAN-3-ONE

  • Applications

    Bicyclo(4.1.0)heptan-3-one, 1-methyl-4-(1-methylethylidene)-7-(3-oxobutyl)-, (1S,6R,7R) (CAS 100347-96-4) is a strained, multifunctional bicyclic ketone used primarily in research as a stereodefined building block to assemble expanded terpene/norbornanone-type scaffolds, as an intermediate toward pharmaceutical and agrochemical targets, for probing stereoselective transformations (aldol, Michael, selective reductions), and as a reference material and analytical standard for LC–MS/GC–MS; its carbonyl groups and isopropylidene/oxobutyl side chains enable labeling, functional diversification, and derivative-library generation for bioactivity screening, while the rigid, high-strain framework can also serve as a reinforcing motif in functional organic materials studies and as a model scaffold/ligand platform for mechanistic investigations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 292.2
    methanol 330.43
    isopropanol 258.0
    water 1.31
    ethyl acetate 223.57
    n-propanol 211.79
    acetone 300.08
    n-butanol 180.31
    acetonitrile 228.23
    DMF 255.14
    toluene 141.28
    isobutanol 145.4
    1,4-dioxane 596.17
    methyl acetate 218.56
    THF 650.61
    2-butanone 203.91
    n-pentanol 113.77
    sec-butanol 133.39
    n-hexane 3.48
    ethylene glycol 58.75
    NMP 148.65
    cyclohexane 11.41
    DMSO 135.28
    n-butyl acetate 140.08
    n-octanol 55.68
    chloroform 593.19
    n-propyl acetate 133.45
    acetic acid 210.69
    dichloromethane 401.51
    cyclohexanone 252.82
    propylene glycol 106.88
    isopropyl acetate 156.74
    DMAc 202.4
    2-ethoxyethanol 215.75
    isopentanol 148.29
    n-heptane 3.74
    ethyl formate 145.42
    1,2-dichloroethane 173.64
    n-hexanol 132.41
    2-methoxyethanol 385.62
    isobutyl acetate 111.21
    tetrachloromethane 49.06
    n-pentyl acetate 85.89
    transcutol 619.55
    n-heptanol 60.63
    ethylbenzene 63.94
    MIBK 127.39
    2-propoxyethanol 318.77
    tert-butanol 239.63
    MTBE 141.79
    2-butoxyethanol 163.68
    propionic acid 132.97
    o-xylene 70.08
    formic acid 88.21
    diethyl ether 134.07
    m-xylene 85.83
    p-xylene 102.56
    chlorobenzene 155.76
    dimethyl carbonate 79.17
    n-octane 2.37
    formamide 151.92
    cyclopentanone 289.49
    2-pentanone 165.77
    anisole 166.63
    cyclopentyl methyl ether 152.36
    gamma-butyrolactone 287.75
    1-methoxy-2-propanol 300.12
    pyridine 339.99
    3-pentanone 99.47
    furfural 288.8
    n-dodecane 2.99
    diethylene glycol 268.55
    diisopropyl ether 40.86
    tert-amyl alcohol 123.17
    acetylacetone 244.83
    n-hexadecane 3.5
    acetophenone 147.81
    methyl propionate 145.24
    isopentyl acetate 143.75
    trichloroethylene 406.63
    n-nonanol 54.46
    cyclohexanol 126.07
    benzyl alcohol 154.28
    2-ethylhexanol 66.23
    isooctanol 50.43
    dipropyl ether 57.68
    1,2-dichlorobenzene 123.57
    ethyl lactate 81.93
    propylene carbonate 189.85
    n-methylformamide 148.11
    2-pentanol 101.92
    n-pentane 4.58
    1-propoxy-2-propanol 197.08
    1-methoxy-2-propyl acetate 204.98
    2-(2-methoxypropoxy) propanol 155.55
    mesitylene 45.27
    ε-caprolactone 233.29
    p-cymene 34.78
    epichlorohydrin 391.87
    1,1,1-trichloroethane 196.36
    2-aminoethanol 130.31
    morpholine-4-carbaldehyde 302.5
    sulfolane 176.64
    2,2,4-trimethylpentane 4.21
    2-methyltetrahydrofuran 295.91
    n-hexyl acetate 118.91
    isooctane 4.24
    2-(2-butoxyethoxy)ethanol 225.37
    sec-butyl acetate 104.58
    tert-butyl acetate 146.08
    decalin 7.64
    glycerin 134.84
    diglyme 355.94
    acrylic acid 113.26
    isopropyl myristate 49.31
    n-butyric acid 200.4
    acetyl acetate 169.98
    di(2-ethylhexyl) phthalate 63.35
    ethyl propionate 104.61
    nitromethane 309.76
    1,2-diethoxyethane 174.44
    benzonitrile 185.67
    trioctyl phosphate 40.44
    1-bromopropane 88.99
    gamma-valerolactone 449.11
    n-decanol 40.38
    triethyl phosphate 51.61
    4-methyl-2-pentanol 79.38
    propionitrile 161.11
    vinylene carbonate 204.45
    1,1,2-trichlorotrifluoroethane 233.26
    DMS 129.82
    cumene 42.51
    2-octanol 41.94
    2-hexanone 121.24
    octyl acetate 60.73
    limonene 39.37
    1,2-dimethoxyethane 346.03
    ethyl orthosilicate 51.28
    tributyl phosphate 49.35
    diacetone alcohol 182.97
    N,N-dimethylaniline 90.23
    acrylonitrile 195.09
    aniline 165.19
    1,3-propanediol 223.27
    bromobenzene 147.48
    dibromomethane 217.81
    1,1,2,2-tetrachloroethane 287.9
    2-methyl-cyclohexyl acetate 94.89
    tetrabutyl urea 58.17
    diisobutyl methanol 44.72
    2-phenylethanol 166.49
    styrene 76.0
    dioctyl adipate 72.46
    dimethyl sulfate 76.6
    ethyl butyrate 96.68
    methyl lactate 96.14
    butyl lactate 90.31
    diethyl carbonate 77.74
    propanediol butyl ether 152.07
    triethyl orthoformate 74.17
    p-tert-butyltoluene 33.79
    methyl 4-tert-butylbenzoate 102.03
    morpholine 546.51
    tert-butylamine 111.81
    n-dodecanol 30.33
    dimethoxymethane 248.81
    ethylene carbonate 173.28
    cyrene 141.41
    2-ethoxyethyl acetate 160.16
    2-ethylhexyl acetate 99.71
    1,2,4-trichlorobenzene 151.6
    4-methylpyridine 313.21
    dibutyl ether 56.24
    2,6-dimethyl-4-heptanol 44.72
    DEF 132.07
    dimethyl isosorbide 224.86
    tetrachloroethylene 170.57
    eugenol 118.83
    triacetin 136.02
    span 80 131.18
    1,4-butanediol 83.44
    1,1-dichloroethane 225.97
    2-methyl-1-pentanol 99.97
    methyl formate 120.46
    2-methyl-1-butanol 111.7
    n-decane 4.91
    butyronitrile 169.84
    3,7-dimethyl-1-octanol 62.87
    1-chlorooctane 26.53
    1-chlorotetradecane 11.61
    n-nonane 3.84
    undecane 3.73
    tert-butylcyclohexane 7.36
    cyclooctane 3.43
    cyclopentanol 142.99
    tetrahydropyran 332.58
    tert-amyl methyl ether 78.24
    2,5,8-trioxanonane 229.97
    1-hexene 25.24
    2-isopropoxyethanol 166.13
    2,2,2-trifluoroethanol 79.83
    methyl butyrate 137.76

    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
Curcuma xanthorrhiza (Indonesia) Curcuma xanthorrhiza Roxb., fam. Zingiberaceae 0.01%
Curcuma aeruginosa (Indonesia) Curcuma aeruginosa Roxb., fam. Zingiberaceae 1.9%
Curcuma heyneana (Indonesia) Curcuma heyneana Val., fam. Zingiberaceae 2.3%