3,4-Dimethyl 1,2-cyclopentandione

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  • Identifiers

    CAS number
    13494-06-9

    Molecular formula
    C7H10O2

    SMILES
    CC1CC(=O)C(=O)C1C

  • Odor profile

    Fragrance
    Caramellic 85.4%
    Sweet 80.38%
    Burnt 66.39%
    Coffee 45.91%
    Nutty 36.54%
    Roasted 31.49%
    Tobacco 30.9%
    Woody 30.9%
    Phenolic 30.57%
    Hay 28.73%

     

    Flavor
    Sweet 77.37%
    Caramel 60.57%
    Maple 54.78%
    Sugar 41.15%
    Balsam 37.99%
    Candy 36.07%
    Tobacco 32.76%
    Almond 28.2%
    Minty 27.68%
    Licorice 26.98%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    7.22 (neutral)

    Molecular weight
    126.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    231°C

    Melting point expt.

    • 71 - 72 °C

    Flash point

    • 75.47 ˚C est.

  • Synonyms

    • 13494-06-9
    • 3,4-Dimethylcyclopentane-1,2-dione
    • 3,4-Dimethyl-1,2-cyclopentanedione
    • 3,4-Dimethyl-1,2-cyclopentadione
    • 1,2-Cyclopentanedione, 3,4-dimethyl-
    • FEMA No. 3268
    • Caramel Pentadione
    • 3,4-Dimethyl 1,2-cyclopentandione
    • EINECS 236-810-8
    • 50AIF51OCI
    • DTXSID2051689
    • 3,4-DIMETHYL 1,2-CYCLOPENTANDIONE [FCC]
    • 3,4-DIMETHYL 1,2-CYCLOPENTANDIONE, DL-
    • 3,4-DIMETHYL 1,2-CYCLOPENTANDIONE [FHFI]
    • 3,4-DIMETHYL 1,2-CYCLOPENTANDIONE, (+/-)-
    • UNII-50AIF51OCI
    • MFCD00143063
    • SCHEMBL872975
    • DTXCID5030244
    • FEMA 3268
    • CHEBI:195837
    • ,4-Dimethylcyclopentane-1,2-dione
    • AKOS015917414
    • CS-W011157
    • DS-9209
    • FD35600
    • D3782
    • NS00012293
    • D81912
    • EN300-6495712
    • 3,4-Dimethyl-1,2-cyclopentadione, >=97%, FG
    • Q27260782
    • 236-810-8

  • Applications

    Featuring a highly reactive vicinal diketone scaffold, 3,4-Dimethyl-1,2-cyclopentadione is utilized by organic laboratories as a versatile building block for assembling complex cyclic architectures, especially along synthetic routes to prostaglandin derivatives, modified steroids and antimicrobial compounds; its adjacent carbonyls enable facile enaminone formation, Michael additions, aldol condensations and metal-chelating ligand synthesis, so the molecule is also harnessed for preparing homogeneous catalysts based on chelates, while the two asymmetric methyl groups provide a convenient platform for stereochemical studies; additionally, it functions as a chromatographic reference standard, a precursor to miniature anthraquinone dyes, a research material for electrochemical sensors detecting heavy-metal ions, and an intermediate in flavor chemistry whose diketone core can join Maillard reactions to impart subtle caramel notes to premium food-flavor formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 314.68
    methanol 427.86
    isopropanol 251.87
    water 98.66
    ethyl acetate 238.26
    n-propanol 219.44
    acetone 387.31
    n-butanol 165.45
    acetonitrile 348.29
    DMF 334.25
    toluene 51.77
    isobutanol 171.7
    1,4-dioxane 517.81
    methyl acetate 333.54
    THF 375.75
    2-butanone 250.86
    n-pentanol 138.11
    sec-butanol 208.16
    n-hexane 11.07
    ethylene glycol 186.4
    NMP 370.1
    cyclohexane 17.54
    DMSO 351.23
    n-butyl acetate 155.98
    n-octanol 101.19
    chloroform 842.79
    n-propyl acetate 147.53
    acetic acid 802.06
    dichloromethane 611.72
    cyclohexanone 302.73
    propylene glycol 171.27
    isopropyl acetate 141.98
    DMAc 265.19
    2-ethoxyethanol 290.44
    isopentanol 173.01
    n-heptane 7.57
    ethyl formate 198.29
    1,2-dichloroethane 342.7
    n-hexanol 142.61
    2-methoxyethanol 442.71
    isobutyl acetate 91.59
    tetrachloromethane 128.51
    n-pentyl acetate 121.38
    transcutol 1036.9
    n-heptanol 101.68
    ethylbenzene 58.59
    MIBK 129.43
    2-propoxyethanol 260.09
    tert-butanol 305.38
    MTBE 164.54
    2-butoxyethanol 194.89
    propionic acid 364.52
    o-xylene 70.42
    formic acid 535.7
    diethyl ether 141.61
    m-xylene 60.3
    p-xylene 111.23
    chlorobenzene 186.34
    dimethyl carbonate 92.25
    n-octane 5.98
    formamide 736.06
    cyclopentanone 362.84
    2-pentanone 162.4
    anisole 166.67
    cyclopentyl methyl ether 135.95
    gamma-butyrolactone 532.22
    1-methoxy-2-propanol 281.68
    pyridine 296.08
    3-pentanone 123.81
    furfural 519.16
    n-dodecane 6.46
    diethylene glycol 305.89
    diisopropyl ether 53.12
    tert-amyl alcohol 243.59
    acetylacetone 260.89
    n-hexadecane 7.22
    acetophenone 171.61
    methyl propionate 174.63
    isopentyl acetate 161.41
    trichloroethylene 776.32
    n-nonanol 88.49
    cyclohexanol 158.27
    benzyl alcohol 156.39
    2-ethylhexanol 85.84
    isooctanol 88.65
    dipropyl ether 55.52
    1,2-dichlorobenzene 210.79
    ethyl lactate 101.68
    propylene carbonate 303.73
    n-methylformamide 320.81
    2-pentanol 135.88
    n-pentane 10.23
    1-propoxy-2-propanol 177.45
    1-methoxy-2-propyl acetate 172.61
    2-(2-methoxypropoxy) propanol 205.53
    mesitylene 48.17
    ε-caprolactone 299.9
    p-cymene 45.43
    epichlorohydrin 487.44
    1,1,1-trichloroethane 376.62
    2-aminoethanol 278.72
    morpholine-4-carbaldehyde 434.91
    sulfolane 517.19
    2,2,4-trimethylpentane 12.59
    2-methyltetrahydrofuran 276.62
    n-hexyl acetate 192.27
    isooctane 9.84
    2-(2-butoxyethoxy)ethanol 286.52
    sec-butyl acetate 100.97
    tert-butyl acetate 164.92
    decalin 15.56
    glycerin 268.17
    diglyme 460.81
    acrylic acid 409.01
    isopropyl myristate 67.91
    n-butyric acid 317.47
    acetyl acetate 196.97
    di(2-ethylhexyl) phthalate 81.86
    ethyl propionate 119.74
    nitromethane 1007.39
    1,2-diethoxyethane 205.38
    benzonitrile 221.09
    trioctyl phosphate 57.51
    1-bromopropane 121.21
    gamma-valerolactone 480.78
    n-decanol 62.79
    triethyl phosphate 64.25
    4-methyl-2-pentanol 97.83
    propionitrile 186.93
    vinylene carbonate 310.7
    1,1,2-trichlorotrifluoroethane 455.96
    DMS 185.14
    cumene 56.18
    2-octanol 75.64
    2-hexanone 143.22
    octyl acetate 91.13
    limonene 56.64
    1,2-dimethoxyethane 318.28
    ethyl orthosilicate 63.32
    tributyl phosphate 68.82
    diacetone alcohol 225.45
    N,N-dimethylaniline 105.95
    acrylonitrile 291.66
    aniline 146.42
    1,3-propanediol 293.67
    bromobenzene 153.3
    dibromomethane 350.6
    1,1,2,2-tetrachloroethane 610.25
    2-methyl-cyclohexyl acetate 109.22
    tetrabutyl urea 82.6
    diisobutyl methanol 58.34
    2-phenylethanol 169.22
    styrene 68.02
    dioctyl adipate 98.58
    dimethyl sulfate 177.45
    ethyl butyrate 105.8
    methyl lactate 133.71
    butyl lactate 114.82
    diethyl carbonate 87.17
    propanediol butyl ether 220.46
    triethyl orthoformate 79.61
    p-tert-butyltoluene 42.13
    methyl 4-tert-butylbenzoate 171.42
    morpholine 435.72
    tert-butylamine 160.77
    n-dodecanol 45.49
    dimethoxymethane 188.6
    ethylene carbonate 227.09
    cyrene 174.46
    2-ethoxyethyl acetate 184.18
    2-ethylhexyl acetate 113.25
    1,2,4-trichlorobenzene 250.03
    4-methylpyridine 240.74
    dibutyl ether 72.46
    2,6-dimethyl-4-heptanol 58.34
    DEF 176.6
    dimethyl isosorbide 286.51
    tetrachloroethylene 476.5
    eugenol 186.83
    triacetin 194.44
    span 80 168.58
    1,4-butanediol 148.29
    1,1-dichloroethane 376.75
    2-methyl-1-pentanol 143.77
    methyl formate 290.65
    2-methyl-1-butanol 154.5
    n-decane 10.12
    butyronitrile 156.91
    3,7-dimethyl-1-octanol 98.5
    1-chlorooctane 50.7
    1-chlorotetradecane 20.26
    n-nonane 8.89
    undecane 7.91
    tert-butylcyclohexane 15.37
    cyclooctane 6.23
    cyclopentanol 193.1
    tetrahydropyran 235.03
    tert-amyl methyl ether 112.52
    2,5,8-trioxanonane 307.66
    1-hexene 43.61
    2-isopropoxyethanol 194.27
    2,2,2-trifluoroethanol 421.3
    methyl butyrate 167.13

    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