Bicyclo(3.1.0)hexan-2-one, 5-(1-methylethyl)-

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  • Identifiers

    CAS number
    513-20-2

    Molecular formula
    C9H14O

    SMILES
    CC(C)C12CCC(=O)C1C2

    Retention indicies (RI)

    • DB5: 1164.5
    • Carbowax: 1624.0

  • Odor profile

    Woody 84.28%
    Herbal 67.38%
    Spicy 60.55%
    Mint 55.29%
    Camphoreous 53.48%
    Fresh 47.35%
    Green 43.94%
    Cooling 42.01%
    Cedar 41.13%
    Pine 40.72%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    138.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 218.00 to 219.00 °C. @ 760.00 mm Hg

    Flash point est.
    64.11 ˚C

  • Synonyms

    • Sabinaketone
    • Sabina ketone
    • 5-Isopropylbicyclo[3.1.0]hexan-2-one
    • 513-20-2
    • Bicyclo[3.1.0]hexan-2-one, 5-(1-methylethyl)-
    • 5-Isopropylbicyclo(3.1.0)hexan-2-one
    • EINECS 208-153-7
    • 5-(propan-2-yl)bicyclo[3.1.0]hexan-2-one
    • DTXSID80883414
    • Bicyclo(3.1.0)hexan-2-one, 5-(1-methylethyl)-
    • 5-isopropyl-bicyclo[3.1.0]hexan-2-one
    • Bicyclo[3.1.0]hexan-2-one, 5-isopropyl-
    • 5-(1-Methylethyl)-Bicyclo(3.1.0)hexan-2-one
    • 5-(1-Methylethyl)-Bicyclo[3.1.0]hexan-2-one
    • Sabine ketone
    • 5-propan-2-ylbicyclo[3.1.0]hexan-2-one
    • SCHEMBL11518938
    • CHEBI:188423
    • DTXCID901022945
    • NS00043578
    • 5-(1-methylethyl)bicyclo[3.1.0]hexan-2-one
    • EN300-7356750
    • 5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one, 9CI

  • Applications

    Bicyclo(3.1.0)hexan-2-one, 5-(1-methylethyl)- (CAS 513-20-2) is a compact, ring-strained bicyclic ketone used as a specialty intermediate in organic synthesis to install a rigid, hydrophobic scaffold and to undergo transformations such as reductions/oxidations, controlled ring opening, and ring expansion (e.g., Baeyer–Villiger) to access lactones, alcohols, and secondary amines; as a model substrate for mechanistic and stereochemical studies of enolate formation and nucleophilic additions to strained ketones; as a building block in medicinal and agrochemical discovery to probe how bicyclic motifs influence permeability, metabolic stability, and target selectivity; in fragrance and flavor research to develop bicyclic ketone-type odorants or act as a tonal modifier, and as a reference material for analytical method development (GC/GC-MS), retention-index calibration, and QC of related derivatives; it is also occasionally used to introduce a rigid motif into additives or research-scale material precursors to fine-tune physical properties.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 542.33
    methanol 595.36
    isopropanol 451.43
    water 5.53
    ethyl acetate 590.68
    n-propanol 439.52
    acetone 552.64
    n-butanol 350.73
    acetonitrile 603.02
    DMF 488.34
    toluene 282.52
    isobutanol 287.26
    1,4-dioxane 1074.14
    methyl acetate 580.9
    THF 776.23
    2-butanone 408.98
    n-pentanol 159.59
    sec-butanol 236.78
    n-hexane 16.05
    ethylene glycol 180.12
    NMP 177.65
    cyclohexane 36.1
    DMSO 301.74
    n-butyl acetate 269.19
    n-octanol 83.95
    chloroform 1149.41
    n-propyl acetate 213.6
    acetic acid 328.08
    dichloromethane 840.9
    cyclohexanone 354.16
    propylene glycol 179.15
    isopropyl acetate 368.13
    DMAc 341.85
    2-ethoxyethanol 357.69
    isopentanol 285.28
    n-heptane 15.62
    ethyl formate 288.39
    1,2-dichloroethane 516.97
    n-hexanol 238.21
    2-methoxyethanol 689.25
    isobutyl acetate 155.59
    tetrachloromethane 181.07
    n-pentyl acetate 141.5
    transcutol 1155.93
    n-heptanol 105.56
    ethylbenzene 135.93
    MIBK 236.59
    2-propoxyethanol 549.82
    tert-butanol 417.04
    MTBE 360.87
    2-butoxyethanol 266.68
    propionic acid 292.08
    o-xylene 149.37
    formic acid 196.34
    diethyl ether 420.61
    m-xylene 182.96
    p-xylene 193.33
    chlorobenzene 343.26
    dimethyl carbonate 197.46
    n-octane 8.04
    formamide 326.01
    cyclopentanone 406.3
    2-pentanone 329.72
    anisole 339.56
    cyclopentyl methyl ether 257.44
    gamma-butyrolactone 470.67
    1-methoxy-2-propanol 502.52
    pyridine 673.26
    3-pentanone 247.1
    furfural 476.87
    n-dodecane 7.59
    diethylene glycol 480.98
    diisopropyl ether 134.26
    tert-amyl alcohol 206.22
    acetylacetone 467.25
    n-hexadecane 8.91
    acetophenone 236.02
    methyl propionate 376.26
    isopentyl acetate 250.62
    trichloroethylene 851.78
    n-nonanol 82.18
    cyclohexanol 179.13
    benzyl alcohol 228.44
    2-ethylhexanol 106.08
    isooctanol 88.82
    dipropyl ether 141.41
    1,2-dichlorobenzene 273.85
    ethyl lactate 116.73
    propylene carbonate 259.66
    n-methylformamide 383.1
    2-pentanol 196.17
    n-pentane 23.84
    1-propoxy-2-propanol 311.65
    1-methoxy-2-propyl acetate 412.88
    2-(2-methoxypropoxy) propanol 236.64
    mesitylene 116.36
    ε-caprolactone 319.83
    p-cymene 75.79
    epichlorohydrin 698.1
    1,1,1-trichloroethane 518.04
    2-aminoethanol 303.85
    morpholine-4-carbaldehyde 490.33
    sulfolane 274.1
    2,2,4-trimethylpentane 14.02
    2-methyltetrahydrofuran 389.97
    n-hexyl acetate 186.61
    isooctane 18.02
    2-(2-butoxyethoxy)ethanol 338.6
    sec-butyl acetate 176.54
    tert-butyl acetate 324.77
    decalin 21.82
    glycerin 245.15
    diglyme 649.58
    acrylic acid 244.54
    isopropyl myristate 85.85
    n-butyric acid 373.28
    acetyl acetate 366.66
    di(2-ethylhexyl) phthalate 83.21
    ethyl propionate 223.31
    nitromethane 626.41
    1,2-diethoxyethane 395.13
    benzonitrile 308.49
    trioctyl phosphate 52.24
    1-bromopropane 266.62
    gamma-valerolactone 671.09
    n-decanol 60.34
    triethyl phosphate 86.91
    4-methyl-2-pentanol 147.86
    propionitrile 461.81
    vinylene carbonate 301.59
    1,1,2-trichlorotrifluoroethane 389.67
    DMS 263.4
    cumene 93.06
    2-octanol 62.79
    2-hexanone 181.75
    octyl acetate 95.04
    limonene 79.24
    1,2-dimethoxyethane 537.11
    ethyl orthosilicate 87.91
    tributyl phosphate 68.81
    diacetone alcohol 300.93
    N,N-dimethylaniline 170.93
    acrylonitrile 542.88
    aniline 336.02
    1,3-propanediol 419.2
    bromobenzene 340.4
    dibromomethane 511.52
    1,1,2,2-tetrachloroethane 611.27
    2-methyl-cyclohexyl acetate 135.73
    tetrabutyl urea 75.3
    diisobutyl methanol 88.21
    2-phenylethanol 263.53
    styrene 169.3
    dioctyl adipate 99.82
    dimethyl sulfate 188.47
    ethyl butyrate 185.66
    methyl lactate 186.92
    butyl lactate 119.61
    diethyl carbonate 142.13
    propanediol butyl ether 189.58
    triethyl orthoformate 140.53
    p-tert-butyltoluene 79.46
    methyl 4-tert-butylbenzoate 174.83
    morpholine 871.95
    tert-butylamine 252.69
    n-dodecanol 45.94
    dimethoxymethane 480.68
    ethylene carbonate 272.19
    cyrene 148.24
    2-ethoxyethyl acetate 308.37
    2-ethylhexyl acetate 180.1
    1,2,4-trichlorobenzene 304.74
    4-methylpyridine 522.68
    dibutyl ether 107.74
    2,6-dimethyl-4-heptanol 88.21
    DEF 255.74
    dimethyl isosorbide 313.68
    tetrachloroethylene 430.86
    eugenol 186.28
    triacetin 200.77
    span 80 160.8
    1,4-butanediol 135.56
    1,1-dichloroethane 627.04
    2-methyl-1-pentanol 133.62
    methyl formate 283.8
    2-methyl-1-butanol 207.53
    n-decane 12.32
    butyronitrile 354.74
    3,7-dimethyl-1-octanol 110.68
    1-chlorooctane 56.97
    1-chlorotetradecane 25.96
    n-nonane 10.53
    undecane 9.28
    tert-butylcyclohexane 22.54
    cyclooctane 13.39
    cyclopentanol 188.96
    tetrahydropyran 543.73
    tert-amyl methyl ether 180.35
    2,5,8-trioxanonane 382.18
    1-hexene 64.58
    2-isopropoxyethanol 249.34
    2,2,2-trifluoroethanol 188.02
    methyl butyrate 232.75

    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
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.25%
Cedarleaf 2 8000-27-9 Thuja occidentalis L., fam. Taxodiaceae 0.4%
Annual wormwood, leaf (U.S.A., Indiana) 1 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.14%
Annual wormwood, leaf (U.S.A., Indiana) 2 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.55%
Annual wormwood, flower (U.S.A., Indiana) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.23%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.03%
Artemisia persica (India) Artemisia persica Boiss., fam. Asteraceae (Compositae) 1.7%
Artemisia maritima (Himalaya) Artemisia maritima L., fam. Asteracae (Compositae) 0.67%
Artemisia gmelini (Himalaya) Artemisia gmelinii Web. ex Stechm., fam. Asteracae (Compositae) 1.53%
Artemisia roxburghiana (Himalaya) Artemisia roxburghiana Wall. ex Bies, var. hypolenca, fam. Asteraceae 3.0%
Artemisia moorcroftiana Artemisia moorcroftiana, fam. Asteraceae (Compositae) 0.01%
Nicotiana forgetiana flower Nicotiana forgetiana Hort. ex Hensley (subgenus Petunioides), Solanaceae 0.76%
Boldo leaf (Italy) Boldea fragrans Juss. (Peumus boldus Mol.) 0.78%
Boldo leaf (Chile) Boldea fragrans Juss. (Peumus boldus Mol.) 0.4%
Mentha longifolia (Israel) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.01%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.51%
Thapsia garganica root Thapsia garganica L., fam. Apiaceae (Umbelliferae) 0.01%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Artemisia coerulescens Artemisia coerulescens L. var. palmata Lam., fam. Asteraceae (Compsitae) 0.3%
Nepeta heliotropifolia Nepeta heliotropifolia Lam., fam. Lamiaceae (Labiatae) 1.9%
Laurel leaf (Czechia) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.4%
Laurel leaf (Turkey) 2a hydrodistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.3%
Laurel leaf (Turkey) 2b steamdistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Laurel leaf (Turkey) 2c CO2-extracted 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.5%