(1R,5S)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hex-3-en-2-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    546-78-1

    Molecular formula
    C10H14O

    SMILES
    CC1=CC(=O)[C@@]2([C@H]1C2)C(C)C

    Retention indicies (RI)

    • DB5: 1171.2
    • Carbowax: 1629.0

  • Odor profile

    Mint 60.93%
    Woody 53.73%
    Herbal 47.9%
    Spicy 44.37%
    Camphoreous 43.46%
    Cooling 37.85%
    Fresh 31.55%
    Cedar 25.85%
    Warm 23.0%
    Pine 22.73%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    8.0 (neutral)

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    229°C

    Flash point est.
    69.34 ˚C

  • Synonyms

    • Umbellulone
    • 546-78-1
    • (-)-Umbellulone
    • (R)-Umbellulone
    • (1R,5S)-4-Methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one
    • (1R,5S)-4-Methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one
    • [1R,5S,(-)]-4-Methyl-1-isopropylbicyclo[3.1.0]hexa-3-ene-2-one
    • C09911
    • AC1L9CYT
    • Umbellol
    • Umbellulone?
    • (1R,5S)-4-Methyl-1-(1-methylethyl)bicyclo(3.1.0)hex-3-en-2-one
    • (1R,5S)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hex-3-en-2-one
    • SureCN435454
    • SCHEMBL435454
    • CHEBI:9860
    • DTXSID301016986
    • AKOS040740954
    • NCGC00485432-01
    • DA-68469
    • MS-22850
    • HY-135013
    • CS-0109051
    • G14311
    • (1R,5S)-1-isopropyl-4-methyl-bicyclo[3.1.0]hex-3-en-2-one
    • (1R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one

  • Applications

    In research and industry, (1R,5S)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hex-3-en-2-one is a valuable chiral monoterpenoid ketone used as a stereodefined building block in asymmetric synthesis (access to chiral alcohols, amines, epoxides and pharma/flavor intermediates; scaffolds for chiral ligands/catalysts), as a precursor/intermediate for transformations such as hydrogenation, epoxidation, Michael/aldol additions and cyclizations to generate p-menthane derivative libraries, evaluated in fragrance/flavor research as a note or modulator with a characteristic terpenone character (supporting citrus–herbal–mint accords) in experimental formulations, employed as a GC/GC-MS reference/internal standard for essential oils and monoterpenoid profiling, supporting chemical-ecology and crop-protection studies as a potential semiochemical/insect-behavior modifier or its precursor, and serving as an academic model to probe small-ring enone reactivity (stereocontrol, ring-strain effects, photochemistry) and structure–odor relationships; it also provides a platform for designing longer-lasting aroma materials, encapsulation/dispersion systems, and bio-based terpene-derived polymers for materials R&D.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 919.67
    methanol 991.96
    isopropanol 860.82
    water 16.22
    ethyl acetate 844.07
    n-propanol 805.49
    acetone 1348.19
    n-butanol 659.74
    acetonitrile 1246.94
    DMF 1134.3
    toluene 605.02
    isobutanol 617.39
    1,4-dioxane 1852.4
    methyl acetate 966.51
    THF 1977.12
    2-butanone 1012.63
    n-pentanol 403.01
    sec-butanol 631.42
    n-hexane 119.92
    ethylene glycol 294.26
    NMP 694.3
    cyclohexane 180.04
    DMSO 723.41
    n-butyl acetate 453.39
    n-octanol 270.61
    chloroform 2460.43
    n-propyl acetate 503.4
    acetic acid 629.14
    dichloromethane 1941.87
    cyclohexanone 983.5
    propylene glycol 317.62
    isopropyl acetate 630.76
    DMAc 701.78
    2-ethoxyethanol 683.48
    isopentanol 539.02
    n-heptane 63.74
    ethyl formate 508.19
    1,2-dichloroethane 1227.03
    n-hexanol 474.91
    2-methoxyethanol 1144.75
    isobutyl acetate 357.86
    tetrachloromethane 538.38
    n-pentyl acetate 368.98
    transcutol 1129.28
    n-heptanol 278.54
    ethylbenzene 347.17
    MIBK 545.85
    2-propoxyethanol 860.27
    tert-butanol 840.49
    MTBE 867.81
    2-butoxyethanol 506.96
    propionic acid 538.07
    o-xylene 365.02
    formic acid 313.74
    diethyl ether 1029.8
    m-xylene 466.37
    p-xylene 482.86
    chlorobenzene 666.03
    dimethyl carbonate 425.22
    n-octane 40.99
    formamide 552.35
    cyclopentanone 1319.7
    2-pentanone 815.76
    anisole 663.07
    cyclopentyl methyl ether 856.93
    gamma-butyrolactone 1309.7
    1-methoxy-2-propanol 863.79
    pyridine 1105.78
    3-pentanone 643.46
    furfural 1001.45
    n-dodecane 34.84
    diethylene glycol 656.05
    diisopropyl ether 360.91
    tert-amyl alcohol 587.92
    acetylacetone 885.89
    n-hexadecane 41.04
    acetophenone 479.19
    methyl propionate 681.39
    isopentyl acetate 457.74
    trichloroethylene 1994.28
    n-nonanol 240.9
    cyclohexanol 536.4
    benzyl alcohol 433.64
    2-ethylhexanol 255.06
    isooctanol 236.76
    dipropyl ether 307.26
    1,2-dichlorobenzene 564.76
    ethyl lactate 251.09
    propylene carbonate 673.45
    n-methylformamide 705.71
    2-pentanol 505.71
    n-pentane 123.65
    1-propoxy-2-propanol 503.26
    1-methoxy-2-propyl acetate 537.32
    2-(2-methoxypropoxy) propanol 377.79
    mesitylene 305.72
    ε-caprolactone 795.01
    p-cymene 174.7
    epichlorohydrin 1701.94
    1,1,1-trichloroethane 1299.86
    2-aminoethanol 489.47
    morpholine-4-carbaldehyde 948.98
    sulfolane 987.6
    2,2,4-trimethylpentane 70.77
    2-methyltetrahydrofuran 1273.02
    n-hexyl acetate 520.72
    isooctane 74.53
    2-(2-butoxyethoxy)ethanol 512.44
    sec-butyl acetate 389.58
    tert-butyl acetate 608.15
    decalin 97.52
    glycerin 394.26
    diglyme 959.06
    acrylic acid 478.52
    isopropyl myristate 205.39
    n-butyric acid 621.88
    acetyl acetate 547.17
    di(2-ethylhexyl) phthalate 180.03
    ethyl propionate 487.43
    nitromethane 1165.72
    1,2-diethoxyethane 524.56
    benzonitrile 613.72
    trioctyl phosphate 135.25
    1-bromopropane 753.99
    gamma-valerolactone 1364.61
    n-decanol 175.98
    triethyl phosphate 172.02
    4-methyl-2-pentanol 323.55
    propionitrile 922.3
    vinylene carbonate 639.82
    1,1,2-trichlorotrifluoroethane 793.25
    DMS 499.85
    cumene 245.64
    2-octanol 222.74
    2-hexanone 526.42
    octyl acetate 245.68
    limonene 204.16
    1,2-dimethoxyethane 1062.59
    ethyl orthosilicate 171.81
    tributyl phosphate 152.64
    diacetone alcohol 576.53
    N,N-dimethylaniline 375.54
    acrylonitrile 1050.27
    aniline 602.73
    1,3-propanediol 661.0
    bromobenzene 708.45
    dibromomethane 1318.71
    1,1,2,2-tetrachloroethane 1429.29
    2-methyl-cyclohexyl acetate 275.09
    tetrabutyl urea 176.41
    diisobutyl methanol 176.45
    2-phenylethanol 458.23
    styrene 387.65
    dioctyl adipate 235.43
    dimethyl sulfate 476.18
    ethyl butyrate 329.59
    methyl lactate 353.56
    butyl lactate 258.1
    diethyl carbonate 243.57
    propanediol butyl ether 385.4
    triethyl orthoformate 236.48
    p-tert-butyltoluene 177.55
    methyl 4-tert-butylbenzoate 410.64
    morpholine 1535.86
    tert-butylamine 537.15
    n-dodecanol 133.88
    dimethoxymethane 1008.51
    ethylene carbonate 558.31
    cyrene 332.94
    2-ethoxyethyl acetate 502.62
    2-ethylhexyl acetate 340.62
    1,2,4-trichlorobenzene 632.68
    4-methylpyridine 1029.68
    dibutyl ether 293.92
    2,6-dimethyl-4-heptanol 176.45
    DEF 614.8
    dimethyl isosorbide 551.76
    tetrachloroethylene 1029.06
    eugenol 382.63
    triacetin 381.78
    span 80 316.38
    1,4-butanediol 275.34
    1,1-dichloroethane 1472.07
    2-methyl-1-pentanol 361.1
    methyl formate 607.7
    2-methyl-1-butanol 517.22
    n-decane 56.11
    butyronitrile 736.99
    3,7-dimethyl-1-octanol 248.67
    1-chlorooctane 200.07
    1-chlorotetradecane 88.51
    n-nonane 53.65
    undecane 43.14
    tert-butylcyclohexane 96.96
    cyclooctane 76.39
    cyclopentanol 644.25
    tetrahydropyran 1281.48
    tert-amyl methyl ether 507.84
    2,5,8-trioxanonane 544.0
    1-hexene 309.34
    2-isopropoxyethanol 501.33
    2,2,2-trifluoroethanol 359.39
    methyl butyrate 534.09

    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 (India) Cymbopogon jwarancusa (Jones) Schult., fam. Poaceae (Gramineae) 4.7%
Cypress cones (Egypt) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.1%
Tansy (Canada) 2a flowers 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 1.86%
Tansy (Canada) 2b stems & sheets 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 0.84%
Cypress (Algeria) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.16%
Juniper leaf (France) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.01%
Artemisia aksaiensis (China) Artemisia aksaiensis Y.R. Ling, fam. Asteraceae (Compositae) 0.31%
Eucalyptus globulus (Algeria) 1 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.6%
Oregano, mexican (U.S.A.) 2 Lippia graveolens HBK., fam. Verbenaceae 0.01%
Pennyroyal (Cuba) 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.74%
Keora (India) 4 Pandanus odoratissimus L. (P. fascicularis Lam.), fam. Pandanaceae 0.07%
Helichrysum stoechas (France) 8023-85-8 Helichrysum stoechas L., fam. Asteraceae (Compositae) 0.01%
Tansy (Poland) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 0.1%
Tansy (Argentina) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 0.01%
Tansy (Finland) 2b 8016-87-3 Tanacetum vulgare L. umbellulone chemotype, fam. Asteraceae (Compositae) 56.8%
Tansy (U.S.A.) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 24.7%
Ocimum gratissimum (Benin) 1 Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 0.25%
Eucalyptus globulus (Italy) 1a hydrodistiled 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.6%
Eucalyptus globulus (Italy) 1b CO2-extract 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.2%
Salvadora persica root Salvadora persica L., fam. Salvadoraceae 0.4%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Eucalyptus resinifera (Cuba) Eucalyptus resinifera Smith, fam. Myrtaceae 0.01%