(1R)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-en-2-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    53585-45-8

    Molecular formula
    C10H14O

    SMILES
    CC1=CCC2[C@@H](C1=O)C2(C)C

    Retention indicies (RI)

    • Carbowax: 1881.0

  • Odor profile

    Woody 64.06%
    Mint 58.35%
    Camphoreous 55.29%
    Herbal 54.16%
    Spicy 44.17%
    Tobacco 36.74%
    Fresh 34.6%
    Cedar 34.51%
    Sweet 33.0%
    Cooling 32.51%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    215°C

    Flash point est.
    74.08 ˚C

  • Synonyms

    • 53585-45-8
    • DTXSID30788581
    • (1R)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-en-2-one
    • (1R)-3,7,7-Trimethylbicyclo(4.1.0)hept-3-en-2-one
    • DTXCID60739324

  • Applications

    (1R)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-en-2-one (CAS 53585-45-8) is a chiral monoterpenoid ketone featuring a strained norcarane skeleton and an activated enone, and is therefore used as a chiral-pool building block for asymmetric synthesis, an intermediate toward terpenoid fragrance ingredients and bicyclic motifs in pharma/agrochemical leads, a reference standard for GC/GC–MS and chiral separations (e.g., cyclodextrin columns) in developing/validating monoterpene analytical methods, and a model substrate to probe reaction mechanisms (Michael additions, selective reductions, Baeyer–Villiger oxidations, ring-opening) and the photo/thermochemistry of strained enones; additionally, in fragrance R&D it serves as a precursor/trace-level odor modulator to create or fine-tune pine–woody–camphoraceous facets with enantio-dependent character, and is used in sensory studies, stereoselective metabolism/toxicity work, and SAR library construction for bioactivity discovery.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 508.98
    methanol 504.44
    isopropanol 518.65
    water 6.25
    ethyl acetate 501.96
    n-propanol 431.15
    acetone 733.58
    n-butanol 394.9
    acetonitrile 551.84
    DMF 631.47
    toluene 310.98
    isobutanol 355.07
    1,4-dioxane 907.65
    methyl acetate 566.34
    THF 1056.69
    2-butanone 590.32
    n-pentanol 258.6
    sec-butanol 377.34
    n-hexane 76.2
    ethylene glycol 172.58
    NMP 370.76
    cyclohexane 86.21
    DMSO 384.14
    n-butyl acetate 317.49
    n-octanol 211.23
    chloroform 1244.15
    n-propyl acetate 318.79
    acetic acid 344.29
    dichloromethane 905.84
    cyclohexanone 535.69
    propylene glycol 214.92
    isopropyl acetate 379.78
    DMAc 414.54
    2-ethoxyethanol 422.1
    isopentanol 348.24
    n-heptane 46.95
    ethyl formate 298.03
    1,2-dichloroethane 552.87
    n-hexanol 348.98
    2-methoxyethanol 656.3
    isobutyl acetate 239.74
    tetrachloromethane 242.96
    n-pentyl acetate 246.32
    transcutol 839.29
    n-heptanol 209.8
    ethylbenzene 216.63
    MIBK 345.98
    2-propoxyethanol 598.89
    tert-butanol 490.84
    MTBE 471.65
    2-butoxyethanol 369.57
    propionic acid 304.11
    o-xylene 205.55
    formic acid 162.53
    diethyl ether 533.09
    m-xylene 274.68
    p-xylene 283.27
    chlorobenzene 344.77
    dimethyl carbonate 246.18
    n-octane 30.74
    formamide 252.08
    cyclopentanone 708.92
    2-pentanone 489.76
    anisole 379.86
    cyclopentyl methyl ether 489.68
    gamma-butyrolactone 708.82
    1-methoxy-2-propanol 559.14
    pyridine 519.45
    3-pentanone 362.23
    furfural 541.9
    n-dodecane 26.69
    diethylene glycol 449.39
    diisopropyl ether 220.11
    tert-amyl alcohol 367.8
    acetylacetone 504.87
    n-hexadecane 30.65
    acetophenone 298.83
    methyl propionate 396.45
    isopentyl acetate 319.57
    trichloroethylene 1001.73
    n-nonanol 182.2
    cyclohexanol 327.46
    benzyl alcohol 259.38
    2-ethylhexanol 190.98
    isooctanol 177.42
    dipropyl ether 216.16
    1,2-dichlorobenzene 309.12
    ethyl lactate 183.26
    propylene carbonate 396.88
    n-methylformamide 370.73
    2-pentanol 328.9
    n-pentane 77.85
    1-propoxy-2-propanol 383.37
    1-methoxy-2-propyl acetate 367.16
    2-(2-methoxypropoxy) propanol 268.41
    mesitylene 181.97
    ε-caprolactone 455.82
    p-cymene 120.36
    epichlorohydrin 881.23
    1,1,1-trichloroethane 622.53
    2-aminoethanol 286.95
    morpholine-4-carbaldehyde 540.7
    sulfolane 522.5
    2,2,4-trimethylpentane 48.75
    2-methyltetrahydrofuran 639.46
    n-hexyl acetate 363.55
    isooctane 54.66
    2-(2-butoxyethoxy)ethanol 377.21
    sec-butyl acetate 254.72
    tert-butyl acetate 380.24
    decalin 63.11
    glycerin 260.17
    diglyme 632.8
    acrylic acid 273.45
    isopropyl myristate 143.37
    n-butyric acid 367.52
    acetyl acetate 330.57
    di(2-ethylhexyl) phthalate 128.34
    ethyl propionate 306.73
    nitromethane 595.52
    1,2-diethoxyethane 344.35
    benzonitrile 330.64
    trioctyl phosphate 99.17
    1-bromopropane 380.62
    gamma-valerolactone 757.27
    n-decanol 136.17
    triethyl phosphate 120.14
    4-methyl-2-pentanol 232.34
    propionitrile 419.63
    vinylene carbonate 382.06
    1,1,2-trichlorotrifluoroethane 471.69
    DMS 315.96
    cumene 159.26
    2-octanol 164.69
    2-hexanone 335.43
    octyl acetate 171.59
    limonene 141.09
    1,2-dimethoxyethane 613.14
    ethyl orthosilicate 120.39
    tributyl phosphate 112.49
    diacetone alcohol 381.78
    N,N-dimethylaniline 232.95
    acrylonitrile 478.81
    aniline 299.04
    1,3-propanediol 374.09
    bromobenzene 357.61
    dibromomethane 629.73
    1,1,2,2-tetrachloroethane 741.79
    2-methyl-cyclohexyl acetate 198.83
    tetrabutyl urea 125.49
    diisobutyl methanol 137.79
    2-phenylethanol 300.07
    styrene 219.08
    dioctyl adipate 161.54
    dimethyl sulfate 273.42
    ethyl butyrate 225.45
    methyl lactate 236.32
    butyl lactate 196.2
    diethyl carbonate 164.81
    propanediol butyl ether 309.86
    triethyl orthoformate 165.55
    p-tert-butyltoluene 124.31
    methyl 4-tert-butylbenzoate 266.86
    morpholine 768.27
    tert-butylamine 325.21
    n-dodecanol 105.49
    dimethoxymethane 573.01
    ethylene carbonate 322.5
    cyrene 237.68
    2-ethoxyethyl acetate 322.93
    2-ethylhexyl acetate 235.05
    1,2,4-trichlorobenzene 358.0
    4-methylpyridine 510.97
    dibutyl ether 205.64
    2,6-dimethyl-4-heptanol 137.79
    DEF 349.79
    dimethyl isosorbide 371.21
    tetrachloroethylene 497.79
    eugenol 249.07
    triacetin 262.57
    span 80 230.74
    1,4-butanediol 174.11
    1,1-dichloroethane 684.04
    2-methyl-1-pentanol 240.47
    methyl formate 320.16
    2-methyl-1-butanol 314.2
    n-decane 42.95
    butyronitrile 395.57
    3,7-dimethyl-1-octanol 194.08
    1-chlorooctane 141.59
    1-chlorotetradecane 63.17
    n-nonane 41.64
    undecane 33.07
    tert-butylcyclohexane 67.01
    cyclooctane 44.56
    cyclopentanol 350.22
    tetrahydropyran 658.45
    tert-amyl methyl ether 299.43
    2,5,8-trioxanonane 360.69
    1-hexene 198.03
    2-isopropoxyethanol 333.79
    2,2,2-trifluoroethanol 209.55
    methyl butyrate 339.6

    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
Cymbopogon jwarancusa (Himalaya) Cymbopogon jwarancusa (Jones) Schult., fam. Poaceae (Gramineae) 0.22%
Cypress (Algeria) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.01%