3-Acetyl-6-methylpyran-2,4-dione

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  • Identifiers

    CAS number
    520-45-6

    Molecular formula
    C8H8O4

    SMILES
    CC1=CC(=O)C(C(=O)O1)C(=O)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 66.89%
    Caramellic 62.68%
    Burnt 50.62%
    Sweet 48.41%
    Nutty 34.19%
    Tobacco 31.29%
    Winey 28.7%
    Spicy 28.1%
    Mint 27.44%
    Roasted 27.42%

     

    Flavor
    Fruity 30.9%
    Caramel 29.51%
    Nutty 23.91%
    Phenolic 23.08%
    Cotton candy 21.56%
    Extremely sweet 21.27%
    Molasses 21.2%
    Toffee 21.12%
    Seedy 20.92%
    Fenugreek 20.43%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    6.33 (neutral)

    Molecular weight
    168.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    318°C

    Flash point

    • 115.17 ˚C est.

  • Synonyms

    • DEHYDROACETIC ACID
    • 520-45-6
    • 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione
    • 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-
    • 3-Acetyl-6-methyl-2,4-pyrandione
    • 3-acetyl-6-methylpyran-2,4-dione
    • 16807-48-0
    • 3-Acetyl-6-methyl-pyran-2,4-dione
    • MFCD00066709
    • DTXSID6020014
    • 3-Acetyl-6-methylpyrandione-2,4
    • 3-acetyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
    • 2-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid, .delta.-lactone
    • SCHEMBL17787
    • Dehydroacetic acid (Standard)
    • HY-B1211R
    • PGRHXDWITVMQBC-UHFFFAOYSA-
    • MSK2505
    • 4-Hexenoic acid, .delta.-lactone
    • HMS3264K05
    • Pharmakon1600-01301016
    • HY-B1211
    • 2H-Pyran-2, 3-acetyl-6-methyl-
    • Tox21_302764
    • WLN: T6OV DV CHJ CV1 F1
    • BBL013155
    • NSC760135
    • STL163953
    • Dehydroacetic acid, >=98.0% (T)
    • AKOS000119576
    • AKOS016038058
    • CCG-213725
    • CS-4810
    • NSC-760135
    • 3-acetyl-6-methyl-3H-pyran-2,4-dione
    • NCGC00256469-01
    • 3-Acetyl-6-methyl-2,4(3H)-pyrandione
    • AC-10441
    • CAS-520-45-6
    • DS-15291
    • SY012826
    • DB-252330
    • D0039
    • NS00003021
    • 3-Acetyl-6-Methyldihydropyrandione-2,4(3H)
    • EN300-20186
    • 3-Acetyl-6-methyl-2,3-dihydropyran-2,4-dione
    • AB01510434_02
    • AH-034/32463001
    • SR-01000389026
    • Dehydroacetic acid 1000 microg/mL in Ethyl acetate
    • SR-01000389026-1
    • BRD-A17300716-001-01-5
    • Q63088091
    • 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione, enol form
    • 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione, ion(1-)
    • F0191-0260
    • 4-Hexenoic acid, 2-acetyl-5-hydroxy-3-oxo-, .delta.-lactone
    • Dehydroacetic acid, United States Pharmacopeia (USP) Reference Standard
    • Dehydroacetic acid, Pharmaceutical Secondary Standard; Certified Reference Material
    • InChI=1/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3

  • Applications

    3-Acetyl-6-methylpyran-2,4-dione (CAS 520-45-6) is primarily used as an intermediate in the synthesis of heterocyclic compounds for pharmaceutical and agrochemical applications; it is also evaluated as a fragrance precursor in perfumery, where the carbonyl-rich scaffold can participate in odor-forming reactions or serve as a building block for more complex aroma compounds. In industrial organic synthesis, the compound may function as a ligand or chelating agent in catalytic processes and as a versatile scaffold for further functionalization, enabling the development of libraries of bioactive or functional materials. Some formulations consider it for polymer and coating research as a reactive intermediate for crosslinking or post-polymerization modification. Overall, its use is typically limited to research and production within regulated chemical synthesis, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.56
    methanol 32.24
    isopropanol 16.16
    water 12.17
    ethyl acetate 115.13
    n-propanol 16.81
    acetone 152.41
    n-butanol 16.67
    acetonitrile 197.54
    DMF 262.66
    toluene 10.17
    isobutanol 13.02
    1,4-dioxane 137.69
    methyl acetate 110.18
    THF 197.01
    2-butanone 37.07
    n-pentanol 14.41
    sec-butanol 13.17
    n-hexane 1.81
    ethylene glycol 27.31
    NMP 358.95
    cyclohexane 2.03
    DMSO 121.73
    n-butyl acetate 33.29
    n-octanol 16.2
    chloroform 45.75
    n-propyl acetate 55.19
    acetic acid 146.5
    dichloromethane 64.58
    cyclohexanone 75.87
    propylene glycol 27.44
    isopropyl acetate 57.03
    DMAc 255.19
    2-ethoxyethanol 56.57
    isopentanol 15.63
    n-heptane 1.67
    ethyl formate 153.0
    1,2-dichloroethane 37.69
    n-hexanol 15.07
    2-methoxyethanol 126.48
    isobutyl acetate 28.93
    tetrachloromethane 5.72
    n-pentyl acetate 21.31
    transcutol 131.5
    n-heptanol 8.38
    ethylbenzene 9.93
    MIBK 36.65
    2-propoxyethanol 71.79
    tert-butanol 25.9
    MTBE 14.06
    2-butoxyethanol 29.51
    propionic acid 61.8
    o-xylene 11.88
    formic acid 99.05
    diethyl ether 22.51
    m-xylene 12.56
    p-xylene 14.85
    chlorobenzene 24.11
    dimethyl carbonate 116.85
    n-octane 0.96
    formamide 164.44
    cyclopentanone 135.71
    2-pentanone 48.86
    anisole 49.02
    cyclopentyl methyl ether 57.21
    gamma-butyrolactone 303.35
    1-methoxy-2-propanol 92.56
    pyridine 63.14
    3-pentanone 30.5
    furfural 333.19
    n-dodecane 1.77
    diethylene glycol 95.32
    diisopropyl ether 8.55
    tert-amyl alcohol 17.52
    acetylacetone 172.47
    n-hexadecane 2.0
    acetophenone 61.29
    methyl propionate 98.94
    isopentyl acetate 25.55
    trichloroethylene 80.73
    n-nonanol 15.56
    cyclohexanol 21.47
    benzyl alcohol 37.33
    2-ethylhexanol 12.49
    isooctanol 8.05
    dipropyl ether 17.74
    1,2-dichlorobenzene 31.29
    ethyl lactate 60.04
    propylene carbonate 204.46
    n-methylformamide 158.01
    2-pentanol 11.23
    n-pentane 1.21
    1-propoxy-2-propanol 44.29
    1-methoxy-2-propyl acetate 71.37
    2-(2-methoxypropoxy) propanol 66.25
    mesitylene 9.59
    ε-caprolactone 105.01
    p-cymene 9.66
    epichlorohydrin 179.95
    1,1,1-trichloroethane 38.59
    2-aminoethanol 30.61
    morpholine-4-carbaldehyde 312.32
    sulfolane 243.89
    2,2,4-trimethylpentane 1.08
    2-methyltetrahydrofuran 70.57
    n-hexyl acetate 37.94
    isooctane 1.0
    2-(2-butoxyethoxy)ethanol 71.27
    sec-butyl acetate 31.03
    tert-butyl acetate 52.55
    decalin 3.14
    glycerin 62.17
    diglyme 121.13
    acrylic acid 85.38
    isopropyl myristate 19.98
    n-butyric acid 66.95
    acetyl acetate 137.96
    di(2-ethylhexyl) phthalate 27.77
    ethyl propionate 71.92
    nitromethane 497.34
    1,2-diethoxyethane 32.77
    benzonitrile 64.98
    trioctyl phosphate 19.38
    1-bromopropane 12.0
    gamma-valerolactone 274.99
    n-decanol 13.17
    triethyl phosphate 31.9
    4-methyl-2-pentanol 10.29
    propionitrile 57.64
    vinylene carbonate 203.52
    1,1,2-trichlorotrifluoroethane 128.88
    DMS 77.39
    cumene 9.76
    2-octanol 7.71
    2-hexanone 32.77
    octyl acetate 25.74
    limonene 11.26
    1,2-dimethoxyethane 140.72
    ethyl orthosilicate 24.29
    tributyl phosphate 26.35
    diacetone alcohol 73.88
    N,N-dimethylaniline 36.79
    acrylonitrile 112.92
    aniline 29.17
    1,3-propanediol 39.55
    bromobenzene 18.23
    dibromomethane 27.22
    1,1,2,2-tetrachloroethane 55.53
    2-methyl-cyclohexyl acetate 32.68
    tetrabutyl urea 38.29
    diisobutyl methanol 9.76
    2-phenylethanol 34.71
    styrene 11.39
    dioctyl adipate 37.3
    dimethyl sulfate 167.69
    ethyl butyrate 43.66
    methyl lactate 103.96
    butyl lactate 29.75
    diethyl carbonate 41.33
    propanediol butyl ether 39.04
    triethyl orthoformate 31.05
    p-tert-butyltoluene 8.9
    methyl 4-tert-butylbenzoate 53.81
    morpholine 107.78
    tert-butylamine 11.65
    n-dodecanol 11.24
    dimethoxymethane 168.62
    ethylene carbonate 146.54
    cyrene 109.86
    2-ethoxyethyl acetate 42.29
    2-ethylhexyl acetate 19.7
    1,2,4-trichlorobenzene 39.68
    4-methylpyridine 70.27
    dibutyl ether 17.06
    2,6-dimethyl-4-heptanol 9.76
    DEF 97.0
    dimethyl isosorbide 141.99
    tetrachloroethylene 30.11
    eugenol 60.31
    triacetin 71.19
    span 80 51.52
    1,4-butanediol 20.14
    1,1-dichloroethane 30.57
    2-methyl-1-pentanol 14.06
    methyl formate 225.33
    2-methyl-1-butanol 13.45
    n-decane 2.23
    butyronitrile 51.52
    3,7-dimethyl-1-octanol 17.82
    1-chlorooctane 9.19
    1-chlorotetradecane 5.74
    n-nonane 1.89
    undecane 1.98
    tert-butylcyclohexane 2.63
    cyclooctane 1.02
    cyclopentanol 32.11
    tetrahydropyran 44.51
    tert-amyl methyl ether 15.49
    2,5,8-trioxanonane 112.93
    1-hexene 6.26
    2-isopropoxyethanol 36.44
    2,2,2-trifluoroethanol 103.44
    methyl butyrate 86.21

    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