4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    80-57-9

    Molecular formula
    C10H14O

    SMILES
    CC1=CC(=O)C2CC1C2(C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1209.71
    • Carbowax: 1717.14

  • Odor profile

    Fragrance
    Fruity 75.71%
    Woody 68.9%
    Mint 67.03%
    Herbal 58.76%
    Camphoreous 57.51%
    Spicy 57.45%
    Tobacco 42.97%
    Sweet 39.64%
    Cedar 35.59%
    Fresh 34.67%

     

    Flavor
    Minty 40.38%
    Fresh 31.56%
    Camphor 26.49%
    Bitter 23.73%
    Woody 22.62%
    Basil 21.86%
    Ripe apricot 21.49%
    Red fruit 21.47%
    Cedarleaf 20.88%
    Mint 20.54%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    8.07 (weak base)

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    233°C

    Flash point

    • 75.39 ˚C est.

    Solubility expt.

    • Practically insoluble to insoluble in water; soluble in non-polar solvents
    • Soluble (in ethanol)

  • Synonyms

    • VERBENONE
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
    • 80-57-9
    • 2-Pinen-4-one
    • dl-Verbenone
    • d-Verbenone
    • NSC6832
    • ST069322
    • Verbinone
    • CHEBI:78315
    • Verbenone, (d)-
    • Verbenone, (L)-
    • (S)-(-)-Verbenone
    • Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-
    • 5480-12-6
    • S-Verbenone
    • NSC 6831
    • (-)-cis-verbenone
    • NSC 36846
    • Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-
    • 4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one
    • (1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-ene-2-one
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R,5R)-
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R-cis)-
    • NSC-6832
    • dextro-verbenone
    • 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one
    • 2-Pinen-4-one, (1S,5S)-(-)-
    • Verbenone (D,L-)
    • VERBENONE,(DL)
    • (-)-2-Pinen-4-one
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1S,5S)-
    • SCHEMBL118161
    • Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-
    • DTXSID2048115
    • (1s)-(-)-pin-2-en-4-one
    • BBL033979
    • STK801995
    • AKOS024283493
    • VS-12358
    • DB-061581
    • DB-075693
    • CS-0280756
    • NS00013256
    • NS00085225
    • V0072
    • EN300-89049
    • C09913
    • Q421151
    • (-)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one

  • Applications

    4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one (CAS 80-57-9) is commonly used as a fragrance ingredient and a potential fixative in perfumery, helping shape and stabilize scent notes. It may also be employed in cosmetics and personal care formulations as a fragrance component, and in household products such as cleaners and detergents as a scent additive. In industrial manufacturing, it can serve as an intermediate or chiral building block for the synthesis of specialty fragrances and related chemicals. In coatings and inks, it may be incorporated to provide a distinctive scent profile or as a processing aid.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 292.71
    methanol 371.58
    isopropanol 199.51
    water 8.79
    ethyl acetate 326.4
    n-propanol 235.97
    acetone 355.4
    n-butanol 205.73
    acetonitrile 488.6
    DMF 299.42
    toluene 272.64
    isobutanol 159.81
    1,4-dioxane 719.25
    methyl acetate 328.51
    THF 847.47
    2-butanone 279.18
    n-pentanol 125.01
    sec-butanol 153.51
    n-hexane 51.21
    ethylene glycol 83.82
    NMP 345.21
    cyclohexane 89.1
    DMSO 206.11
    n-butyl acetate 212.75
    n-octanol 113.99
    chloroform 898.68
    n-propyl acetate 160.02
    acetic acid 346.99
    dichloromethane 675.73
    cyclohexanone 408.15
    propylene glycol 84.02
    isopropyl acetate 205.66
    DMAc 179.7
    2-ethoxyethanol 180.93
    isopentanol 168.0
    n-heptane 42.19
    ethyl formate 209.57
    1,2-dichloroethane 396.8
    n-hexanol 234.09
    2-methoxyethanol 334.04
    isobutyl acetate 114.25
    tetrachloromethane 194.18
    n-pentyl acetate 140.33
    transcutol 596.71
    n-heptanol 120.16
    ethylbenzene 119.91
    MIBK 174.6
    2-propoxyethanol 365.48
    tert-butanol 210.93
    MTBE 210.17
    2-butoxyethanol 194.72
    propionic acid 238.01
    o-xylene 148.14
    formic acid 191.93
    diethyl ether 338.17
    m-xylene 197.78
    p-xylene 147.45
    chlorobenzene 292.9
    dimethyl carbonate 135.8
    n-octane 17.46
    formamide 227.17
    cyclopentanone 507.15
    2-pentanone 258.58
    anisole 198.0
    cyclopentyl methyl ether 378.86
    gamma-butyrolactone 593.81
    1-methoxy-2-propanol 255.6
    pyridine 439.58
    3-pentanone 199.6
    furfural 435.08
    n-dodecane 14.08
    diethylene glycol 273.16
    diisopropyl ether 122.82
    tert-amyl alcohol 146.58
    acetylacetone 276.79
    n-hexadecane 16.31
    acetophenone 158.06
    methyl propionate 245.3
    isopentyl acetate 189.15
    trichloroethylene 732.01
    n-nonanol 100.91
    cyclohexanol 215.55
    benzyl alcohol 139.05
    2-ethylhexanol 126.26
    isooctanol 94.58
    dipropyl ether 151.02
    1,2-dichlorobenzene 250.27
    ethyl lactate 90.17
    propylene carbonate 298.33
    n-methylformamide 277.74
    2-pentanol 149.5
    n-pentane 59.01
    1-propoxy-2-propanol 224.9
    1-methoxy-2-propyl acetate 235.0
    2-(2-methoxypropoxy) propanol 166.0
    mesitylene 125.73
    ε-caprolactone 358.16
    p-cymene 76.83
    epichlorohydrin 585.98
    1,1,1-trichloroethane 451.45
    2-aminoethanol 142.73
    morpholine-4-carbaldehyde 385.83
    sulfolane 396.2
    2,2,4-trimethylpentane 26.13
    2-methyltetrahydrofuran 500.08
    n-hexyl acetate 213.52
    isooctane 29.15
    2-(2-butoxyethoxy)ethanol 229.28
    sec-butyl acetate 121.52
    tert-butyl acetate 206.54
    decalin 40.01
    glycerin 125.37
    diglyme 376.53
    acrylic acid 229.07
    isopropyl myristate 85.15
    n-butyric acid 271.36
    acetyl acetate 230.7
    di(2-ethylhexyl) phthalate 83.4
    ethyl propionate 157.69
    nitromethane 532.54
    1,2-diethoxyethane 230.25
    benzonitrile 241.43
    trioctyl phosphate 64.84
    1-bromopropane 263.29
    gamma-valerolactone 573.11
    n-decanol 75.13
    triethyl phosphate 77.54
    4-methyl-2-pentanol 105.55
    propionitrile 303.79
    vinylene carbonate 312.71
    1,1,2-trichlorotrifluoroethane 300.66
    DMS 205.3
    cumene 85.4
    2-octanol 76.68
    2-hexanone 151.58
    octyl acetate 103.19
    limonene 95.41
    1,2-dimethoxyethane 283.17
    ethyl orthosilicate 79.06
    tributyl phosphate 75.96
    diacetone alcohol 202.78
    N,N-dimethylaniline 120.44
    acrylonitrile 351.29
    aniline 233.94
    1,3-propanediol 194.94
    bromobenzene 304.81
    dibromomethane 483.96
    1,1,2,2-tetrachloroethane 490.4
    2-methyl-cyclohexyl acetate 125.95
    tetrabutyl urea 81.77
    diisobutyl methanol 80.38
    2-phenylethanol 197.84
    styrene 132.57
    dioctyl adipate 101.88
    dimethyl sulfate 163.07
    ethyl butyrate 141.24
    methyl lactate 121.57
    butyl lactate 108.06
    diethyl carbonate 106.49
    propanediol butyl ether 149.21
    triethyl orthoformate 108.29
    p-tert-butyltoluene 77.85
    methyl 4-tert-butylbenzoate 162.08
    morpholine 621.34
    tert-butylamine 154.08
    n-dodecanol 57.93
    dimethoxymethane 301.63
    ethylene carbonate 262.69
    cyrene 138.53
    2-ethoxyethyl acetate 202.48
    2-ethylhexyl acetate 147.15
    1,2,4-trichlorobenzene 271.09
    4-methylpyridine 396.16
    dibutyl ether 120.93
    2,6-dimethyl-4-heptanol 80.38
    DEF 207.39
    dimethyl isosorbide 255.43
    tetrachloroethylene 353.07
    eugenol 149.47
    triacetin 175.81
    span 80 145.65
    1,4-butanediol 68.25
    1,1-dichloroethane 453.12
    2-methyl-1-pentanol 109.87
    methyl formate 249.66
    2-methyl-1-butanol 148.38
    n-decane 23.55
    butyronitrile 279.29
    3,7-dimethyl-1-octanol 110.82
    1-chlorooctane 84.29
    1-chlorotetradecane 35.83
    n-nonane 22.64
    undecane 17.7
    tert-butylcyclohexane 36.4
    cyclooctane 38.83
    cyclopentanol 240.18
    tetrahydropyran 562.91
    tert-amyl methyl ether 148.49
    2,5,8-trioxanonane 240.45
    1-hexene 114.35
    2-isopropoxyethanol 135.58
    2,2,2-trifluoroethanol 175.16
    methyl butyrate 169.77

    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
Amomum villosum Amomum villosum Lour., fam. Zingiberaceae 0.01%
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.35%
Cedarleaf 2 8000-27-9 Thuja occidentalis L., fam. Taxodiaceae 0.2%
Roman chamomile (India) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.03%
Rosemary (Tunisia) 1 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Eucalyptus globulus (Spain) 1 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.04%
Hinoki leaf Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 0.89%
Hinoki root Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 2.44%
Hinoki wood Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 0.29%
Ichtyothere terminalis (Brazil) Ichtyothere terminalis (common name: Mata-peixe or cunabi),fam. Asteraceae 0.84%
Lavandula dentata (Chemotype A) Lavandula dentata L. (Chemotype A), fam. Lamiaceae (Labiatae) 0.3%
Lavandula dentata (Chemotype B) Lavandula dentata L. (Chemotype B), fam. Lamiaceae (Labiatae) 0.4%
Lavandula luisieri (Chemotype A) Lavandula luisieri L., Chemotype A, fam. Lamiaceae (Labiatae) 1.7%
Lavandula luisieri (Chemotype B) Lavandula luisieri L., Chemotype B, fam. Lamiaceae (Labiatae) 2.1%
Lavandula stoechas (ssp. sampaioana A) Lavandula stoechas L. (ssp. sampaioana, Chemotype A), fam. Lamiaceae 0.2%
Lavandula stoechas (ssp. pedunculata A) Lavandula stoechas L. (ssp. pedunculata, Chemotype A), fam. Lamiaceae 0.4%
Lavandula stoechas (ssp. pedunculata B) Lavandula stoechas L. (ssp. pedunculata, Chemotype B), fam. Lamiaceae 2.0%
Lavandula stoechas (ssp. sampaioana B) Lavandula stoechas L. (ssp. sampaioana, Chemotype B), fam. Lamiaceae 2.0%
Lavandula stoechas (ssp. stoechas) Lavandula stoechas L. (ssp. stoechas), fam. Lamiaceae (Labiatae) 0.1%
Lavandula viridis Lavandula viridis L., fam. Lamiaceae (Labiatae) 0.7%
Myrtle leaf (Morocco) 1 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.05%
Myrtle leaf, wildgrowing (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.01%
Olibanum, Frankincense (Aden) 8016-36-2 Boswellia carterii Birdwood, fam. Burseraceae 6.5%
Pinus pinaster (Portugal) 1 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Pinus pinaster (France) 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Rosemary (Spain) 3 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 4.0%
Sideritis granatensis Sideritis granatensis (Pau) Rivas-Goday, fam. Lamiaceae (Labiatae) 0.05%
Rosemary (Argentina) 1 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.3%
Rosemary (Argentina) 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.7%
Guava leaf 1 91770-12-6 Psidium guajava L., fam. Myrtaceae 0.2%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.4%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 1.2%
Juniperus flaccida var. poblana Juniperus flaccida var. poblana Martinez, fam. Cupressaceae 0.3%
Seafennel 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.09%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.1%
Cypress cones (Egypt) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.9%
Pistacia khinjuk (Egypt) leaf Pistacia khinjuk Stocks, fam. Anacardiaceae 0.01%
Daphne genkwa Daphne genkwa Sieb. et Zucc., fam. Thymelaeaceae 0.01%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.04%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.3%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.11%
Pistacia lentiscus (Spain) 1a leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.08%
Mastic gum (Spain) 61789-92-2 Pistacia lentiscus L., fam. Anacardiaceae 0.12%
Thyme red (Spain) 3 8007-46-3 Thymus zygis L., fam. Lamiaceae (Labiatae) 0.14%
Rosemary (Italy) 4 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 4.76%
Rosemary (Italy) 3 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 8.36%
Annual wormwood (Yugoslavia) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 2.6%
Myrtle leaf (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.01%
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 2.0%
Thymus satureoides (Morocco) 8007-46-3 Thymus satureoides Boiss. et Reut., fam. Lamiaceae (Labiatae) 0.05%