Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-

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  • Identifiers

    CAS number
    24903-95-5

    Molecular formula
    C9H14O

    SMILES
    CC1(C2CCC(=O)C1C2)C

    Retention indicies (RI)

    • DB5: 1132.75
    • Carbowax: 1565.33

  • Odor profile

    Woody 79.69%
    Camphoreous 78.25%
    Herbal 75.48%
    Mint 73.04%
    Pine 60.64%
    Fresh 54.16%
    Cooling 53.92%
    Spicy 47.74%
    Cedar 46.28%
    Earthy 41.28%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    8.18 (weak base)

    Molecular weight
    138.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    210°C

    Flash point est.
    60.11 ˚C

  • Synonyms

    • 6,6-Dimethylbicyclo[3.1.1]heptan-2-one
    • Nopinone
    • 24903-95-5
    • Nopinon
    • beta-Pinone
    • Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-
    • .beta.-Pinone
    • 2-Norpinanone, 6,6-dimethyl-
    • EINECS 246-520-3
    • NSC 135004
    • 6,6-Dimethylbicyclo(3.1.1)heptan-2-one
    • Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-
    • DTXSID20865173
    • 6,6-dimethylnorpinan-2-one
    • MFCD08447116
    • 6,6-dimethyl-bicyclo[3.1.1]heptan-2-one
    • (1R)-(+)-Norinone
    • 2-Norpinanone,6-dimethyl-
    • SCHEMBL720591
    • DTXCID80813610
    • CHEBI:181453
    • NSC135004
    • NSC250997
    • 2-Norpinanone, 6,6-dimethyl-(8CI)
    • AKOS004907716
    • NSC-135004
    • SB45077
    • (1R,5R)-6,6-Dimethylnorpinan-2-one
    • LS-13665
    • SY211609
    • Bicyclo[3.1.1]heptan-2-one,6-dimethyl-
    • DB-013534
    • DB-286121
    • CS-0101275
    • NS00049623
    • EN300-182727
    • (1R)-6,6-DIMETHYLDICYCLO[3.1.1]HEPTAN-2-ONE

  • Applications

    6,6-Dimethylbicyclo[3.1.1]heptan-2-one (CAS 24903-95-5), commonly known as pinan-2-one, is a monoterpene ketone with a fresh pine–camphor odor; in practice it serves as a fragrance ingredient to impart cleanliness and mask malodors in functional perfumes and home care products (surface cleaners, deodorizers, floor cleaners, dishwashing liquids), and as a versatile pinene-derived intermediate for synthesis: it undergoes Baeyer–Villiger oxidation to pleasant-smelling lactones, selective reductions to alcohols/hydrocarbons, formation of oximes/hydrazones and amine derivatives for pharma/agro research, and in enantioenriched form can act as a chiral building block or auxiliary/ligand for asymmetric catalysis; it is also employed as a model substrate in studies of photocatalysis, selective oxidations, asymmetric hydrogenation and kinetic resolution, and in teaching to illustrate ring strain and stereochemical features of bridged frameworks.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 379.75
    methanol 502.21
    isopropanol 292.54
    water 18.72
    ethyl acetate 379.89
    n-propanol 298.39
    acetone 424.78
    n-butanol 254.35
    acetonitrile 532.7
    DMF 327.31
    toluene 216.15
    isobutanol 195.11
    1,4-dioxane 765.58
    methyl acetate 370.79
    THF 745.9
    2-butanone 305.43
    n-pentanol 147.33
    sec-butanol 183.91
    n-hexane 32.44
    ethylene glycol 128.15
    NMP 286.68
    cyclohexane 61.96
    DMSO 253.12
    n-butyl acetate 244.3
    n-octanol 123.3
    chloroform 1271.95
    n-propyl acetate 192.01
    acetic acid 458.42
    dichloromethane 883.58
    cyclohexanone 375.94
    propylene glycol 128.19
    isopropyl acetate 239.71
    DMAc 219.39
    2-ethoxyethanol 250.28
    isopentanol 211.05
    n-heptane 29.97
    ethyl formate 239.92
    1,2-dichloroethane 448.1
    n-hexanol 248.66
    2-methoxyethanol 436.03
    isobutyl acetate 139.42
    tetrachloromethane 237.63
    n-pentyl acetate 161.05
    transcutol 1007.46
    n-heptanol 137.52
    ethylbenzene 116.33
    MIBK 200.69
    2-propoxyethanol 439.17
    tert-butanol 282.24
    MTBE 235.56
    2-butoxyethanol 249.34
    propionic acid 298.32
    o-xylene 144.03
    formic acid 276.52
    diethyl ether 311.58
    m-xylene 171.08
    p-xylene 173.0
    chlorobenzene 315.17
    dimethyl carbonate 143.22
    n-octane 14.63
    formamide 353.73
    cyclopentanone 458.9
    2-pentanone 266.52
    anisole 230.96
    cyclopentyl methyl ether 293.47
    gamma-butyrolactone 577.07
    1-methoxy-2-propanol 339.9
    pyridine 479.01
    3-pentanone 200.74
    furfural 494.84
    n-dodecane 11.94
    diethylene glycol 360.28
    diisopropyl ether 123.82
    tert-amyl alcohol 174.23
    acetylacetone 314.71
    n-hexadecane 13.63
    acetophenone 191.52
    methyl propionate 258.03
    isopentyl acetate 219.97
    trichloroethylene 876.16
    n-nonanol 112.76
    cyclohexanol 206.8
    benzyl alcohol 168.18
    2-ethylhexanol 125.55
    isooctanol 105.92
    dipropyl ether 156.79
    1,2-dichlorobenzene 277.41
    ethyl lactate 106.13
    propylene carbonate 322.65
    n-methylformamide 332.19
    2-pentanol 174.0
    n-pentane 43.47
    1-propoxy-2-propanol 273.39
    1-methoxy-2-propyl acetate 289.41
    2-(2-methoxypropoxy) propanol 214.41
    mesitylene 116.56
    ε-caprolactone 369.55
    p-cymene 80.76
    epichlorohydrin 624.15
    1,1,1-trichloroethane 547.23
    2-aminoethanol 226.29
    morpholine-4-carbaldehyde 442.73
    sulfolane 389.93
    2,2,4-trimethylpentane 22.99
    2-methyltetrahydrofuran 430.18
    n-hexyl acetate 239.9
    isooctane 24.79
    2-(2-butoxyethoxy)ethanol 310.66
    sec-butyl acetate 145.45
    tert-butyl acetate 235.46
    decalin 32.81
    glycerin 193.91
    diglyme 530.62
    acrylic acid 292.04
    isopropyl myristate 93.54
    n-butyric acid 331.16
    acetyl acetate 284.76
    di(2-ethylhexyl) phthalate 92.39
    ethyl propionate 172.69
    nitromethane 657.08
    1,2-diethoxyethane 326.51
    benzonitrile 275.31
    trioctyl phosphate 66.75
    1-bromopropane 266.39
    gamma-valerolactone 607.45
    n-decanol 82.3
    triethyl phosphate 87.21
    4-methyl-2-pentanol 128.34
    propionitrile 336.83
    vinylene carbonate 349.4
    1,1,2-trichlorotrifluoroethane 376.4
    DMS 227.3
    cumene 91.59
    2-octanol 83.53
    2-hexanone 171.27
    octyl acetate 112.18
    limonene 94.77
    1,2-dimethoxyethane 359.88
    ethyl orthosilicate 87.69
    tributyl phosphate 85.63
    diacetone alcohol 229.9
    N,N-dimethylaniline 137.45
    acrylonitrile 402.33
    aniline 277.33
    1,3-propanediol 276.03
    bromobenzene 315.79
    dibromomethane 571.85
    1,1,2,2-tetrachloroethane 614.4
    2-methyl-cyclohexyl acetate 138.64
    tetrabutyl urea 85.67
    diisobutyl methanol 92.64
    2-phenylethanol 224.59
    styrene 129.98
    dioctyl adipate 116.95
    dimethyl sulfate 168.22
    ethyl butyrate 166.4
    methyl lactate 149.29
    butyl lactate 133.9
    diethyl carbonate 125.21
    propanediol butyl ether 197.18
    triethyl orthoformate 132.57
    p-tert-butyltoluene 81.62
    methyl 4-tert-butylbenzoate 180.15
    morpholine 640.78
    tert-butylamine 204.6
    n-dodecanol 60.67
    dimethoxymethane 309.13
    ethylene carbonate 292.03
    cyrene 154.1
    2-ethoxyethyl acetate 263.15
    2-ethylhexyl acetate 160.48
    1,2,4-trichlorobenzene 307.55
    4-methylpyridine 379.47
    dibutyl ether 134.0
    2,6-dimethyl-4-heptanol 92.64
    DEF 210.22
    dimethyl isosorbide 318.09
    tetrachloroethylene 461.28
    eugenol 177.75
    triacetin 229.28
    span 80 178.56
    1,4-butanediol 99.76
    1,1-dichloroethane 570.17
    2-methyl-1-pentanol 125.92
    methyl formate 276.53
    2-methyl-1-butanol 167.32
    n-decane 20.85
    butyronitrile 294.42
    3,7-dimethyl-1-octanol 125.24
    1-chlorooctane 79.83
    1-chlorotetradecane 33.11
    n-nonane 19.36
    undecane 15.17
    tert-butylcyclohexane 31.64
    cyclooctane 25.5
    cyclopentanol 233.24
    tetrahydropyran 506.48
    tert-amyl methyl ether 148.35
    2,5,8-trioxanonane 333.44
    1-hexene 97.22
    2-isopropoxyethanol 187.76
    2,2,2-trifluoroethanol 246.64
    methyl butyrate 191.17

    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
Pinus pinaster (Portugal) 1 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Santolina chamaecyparisus (France) 2 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.03%
Hyssop (Montenegro) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.08%
Olibanum, African (Oman) 8016-36-2 Boswellia frereana Birdwood, fam. Burseraceae 0.3%
Eucalyptus alba (Burkina Faso) Eucalyptus alba Muell., fam. Myrtaceae 0.2%
Teucrium heterophyllum (Canary Islands) Teucrium heterophyllum L'Her. (T. canariensis), fam. Lamiaceae (Labiatae) 0.2%
Eucalyptus botryoides (Rwanda) Eucalyptus botyroides Sm., fam. Myrtaceae 0.01%
Nepeta heliotropifolia Nepeta heliotropifolia Lam., fam. Lamiaceae (Labiatae) 2.9%
Cyperus maculatus rhizome Cyperus maculatus Boeck, fam. Cyperaceae 1.1%
Galbanum stem (Iran) 9000-24-2 Ferula galbaniflua Boiss. et Buhse, fam. Apiaceae (Umbelliferae) 0.2%
Eucalyptus resinifera (Cuba) Eucalyptus resinifera Smith, fam. Myrtaceae 0.2%
Eucalyptus tereticornis (Cuba) Eucalyptus tereticornis Smith, fam. Myrtaceae 1.5%