3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

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  • Identifiers

    CAS number
    771-03-9

    Molecular formula
    C8H8O4

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 49.14%
    Caramellic 37.06%
    Burnt 36.52%
    Nutty 28.24%
    Phenolic 27.85%
    Fruity 27.02%
    Roasted 26.14%
    Sweet 24.24%
    Creamy 20.31%
    Dry 20.26%

     

    Flavor
    Sweet 36.58%
    Phenolic 33.57%
    Nutty 33.34%
    Musty 29.24%
    Caramel 28.33%
    Burnt 24.74%
    Tobacco 24.73%
    Fruity 23.63%
    Woody 23.37%
    Creamy 22.88%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    6.59 (neutral)

    Molecular weight
    168.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    323°C

    Melting point expt.

    • 109 °C

    Flash point

    • 136.9 ˚C est.

  • Synonyms

    • 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
    • 771-03-9
    • DTXSID801015814
    • RefChem:1067258
    • DTXCID001160069
    • 2H-Pyran-2-one, 3-acetyl-4-hydroxy-6-methyl-
    • 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one
    • 3-acetyl-4-hydroxy-6-methylpyran-2-one
    • 2KAG279R6R
    • dehydroacetate
    • MFCD00006634
    • NSC-139150
    • 3-Acetyl-4-hydroxy-6-methyl-pyran-2-one
    • 45990-86-1
    • Dehydroacetic enol form
    • 3-acetyl-2-hydroxy-6-methyl-pyran-4-one
    • dehydroacetic-acid
    • EINECS 212-227-4
    • Caswell No. 278
    • DHA (VAN)
    • Dehydroacetic Acid [USAN]
    • UNII-2KAG279R6R
    • SCHEMBL17788
    • MLS001049074
    • HSDB 291
    • SCHEMBL1308058
    • DEHYDROACETIC ACID [II]
    • DEHYDROACETIC ACID [MI]
    • Kyselina dehydroacetova [Czech]
    • CHEMBL1724669
    • CHEMBL3306255
    • DEHYDROACETIC ACID [FCC]
    • SCHEMBL14447243
    • DEHYDROACETIC ACID [HSDB]
    • DTXSID20892343
    • DTXSID60892342
    • DTXSID70874033
    • HMS2267L15
    • DEHYDROACETIC ACID [MART.]
    • SMSSF-0055811
    • AAA77103
    • ALBB-021316
    • DEHYDROACETIC ACID [USP-RS]
    • EINECS 208-293-9
    • BDBM50012423
    • EBC-13466
    • STK801879
    • STL146176
    • AKOS000120795
    • AKOS003406223
    • AKOS004119848
    • EPA Pesticide Chemical Code 027801
    • NSC 139150
    • 2-Hydroxy-3-acetyl-6-methyl-4-pyrone
    • 3-acetyl-6-methyl-4-hydroxy-2-pyrone
    • BRN 0006129
    • 3-acetyl-6-methylpyran-2,4(3h)-dione
    • NCGC00246194-01
    • 3-Acetyl-6-methyl-4-hydroxypyran-2-one
    • 53488-80-5
    • SMR000386912
    • SY083793
    • AI3-01464
    • DB-365912
    • CS-0371456
    • NS00079672
    • 3-acetyl-4-hydroxy-6-methyl-2H -pyran-2-one
    • 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one #
    • 4H-Pyran-4-one, 3-acetyl-2-hydroxy-6-methyl-
    • 4-17-00-06699 (Beilstein Handbook Reference)
    • Q920725
    • 3-acetyl-6-methyl-3,4-dihydro-2H-2,4-pyrandione
    • 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione. enol form
    • F3282-0017
    • Z104500152
    • 2-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid, delta-lactone
    • 3-(1-Hydroxyethylidene)-6-methyl-2H-pyran-2,4(3H)-dione
    • 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione, ion(1-),
    • 4-Hexenoic acid, 2-acetyl-5-hydroxy-3-oxo-, delta-lactone
    • (3E)-3-(1-Hydroxyethylidene)-6-methyl-2H-pyran-2,4(3H)-dione
    • (Z)-3-(1-hydroxyethylidene)-6-methyl-2H-pyran-2,4(3H)-dione
    • Dehydroacetic acid;2-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid delta-lactone; DHA
    • 771-03-9

  • Applications

    3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (CAS number: 771-03-9) is an alpha-pyrone derivative primarily used as a fragrance ingredient (odorant) in perfumery and may serve as a flavor precursor for certain food and beverage formulations; in cosmetics and personal care, it can be included as a scent component; in household cleaning and other consumer products it may be added to impart fragrance; in industrial manufacturing it serves as an intermediate in the synthesis of other aroma chemicals or specialty polymers; it can function as a building block in organic synthesis for additional aroma-related compounds; subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 72.98
    methanol 97.92
    isopropanol 59.69
    water 7.99
    ethyl acetate 193.44
    n-propanol 54.06
    acetone 314.19
    n-butanol 56.92
    acetonitrile 260.49
    DMF 673.67
    toluene 11.79
    isobutanol 42.15
    1,4-dioxane 262.76
    methyl acetate 186.22
    THF 508.0
    2-butanone 100.12
    n-pentanol 48.08
    sec-butanol 40.68
    n-hexane 3.32
    ethylene glycol 68.7
    NMP 494.28
    cyclohexane 2.61
    DMSO 434.27
    n-butyl acetate 70.23
    n-octanol 36.31
    chloroform 42.91
    n-propyl acetate 108.41
    acetic acid 237.4
    dichloromethane 63.67
    cyclohexanone 151.53
    propylene glycol 74.8
    isopropyl acetate 109.02
    DMAc 372.94
    2-ethoxyethanol 153.34
    isopentanol 52.0
    n-heptane 3.7
    ethyl formate 239.34
    1,2-dichloroethane 54.73
    n-hexanol 48.71
    2-methoxyethanol 343.55
    isobutyl acetate 54.54
    tetrachloromethane 7.06
    n-pentyl acetate 44.98
    transcutol 257.44
    n-heptanol 22.96
    ethylbenzene 11.68
    MIBK 89.73
    2-propoxyethanol 186.59
    tert-butanol 96.91
    MTBE 45.57
    2-butoxyethanol 71.1
    propionic acid 115.15
    o-xylene 12.88
    formic acid 144.89
    diethyl ether 55.45
    m-xylene 16.97
    p-xylene 16.51
    chlorobenzene 27.21
    dimethyl carbonate 193.96
    n-octane 1.93
    formamide 265.97
    cyclopentanone 277.99
    2-pentanone 137.24
    anisole 64.23
    cyclopentyl methyl ether 130.01
    gamma-butyrolactone 525.13
    1-methoxy-2-propanol 281.99
    pyridine 75.8
    3-pentanone 65.87
    furfural 424.4
    n-dodecane 3.05
    diethylene glycol 220.64
    diisopropyl ether 20.8
    tert-amyl alcohol 51.82
    acetylacetone 312.97
    n-hexadecane 3.51
    acetophenone 71.43
    methyl propionate 172.19
    isopentyl acetate 51.83
    trichloroethylene 90.8
    n-nonanol 33.49
    cyclohexanol 50.79
    benzyl alcohol 59.33
    2-ethylhexanol 31.29
    isooctanol 19.67
    dipropyl ether 41.76
    1,2-dichlorobenzene 32.82
    ethyl lactate 106.19
    propylene carbonate 315.34
    n-methylformamide 343.22
    2-pentanol 39.85
    n-pentane 2.61
    1-propoxy-2-propanol 113.65
    1-methoxy-2-propyl acetate 137.99
    2-(2-methoxypropoxy) propanol 109.23
    mesitylene 13.15
    ε-caprolactone 173.27
    p-cymene 13.25
    epichlorohydrin 351.0
    1,1,1-trichloroethane 52.54
    2-aminoethanol 81.0
    morpholine-4-carbaldehyde 471.04
    sulfolane 510.64
    2,2,4-trimethylpentane 2.67
    2-methyltetrahydrofuran 178.89
    n-hexyl acetate 75.56
    isooctane 2.65
    2-(2-butoxyethoxy)ethanol 144.84
    sec-butyl acetate 58.7
    tert-butyl acetate 115.78
    decalin 4.26
    glycerin 152.66
    diglyme 232.92
    acrylic acid 135.52
    isopropyl myristate 35.81
    n-butyric acid 150.17
    acetyl acetate 190.63
    di(2-ethylhexyl) phthalate 41.57
    ethyl propionate 120.71
    nitromethane 731.49
    1,2-diethoxyethane 67.7
    benzonitrile 77.21
    trioctyl phosphate 35.03
    1-bromopropane 22.7
    gamma-valerolactone 487.34
    n-decanol 27.8
    triethyl phosphate 48.49
    4-methyl-2-pentanol 32.64
    propionitrile 108.85
    vinylene carbonate 271.26
    1,1,2-trichlorotrifluoroethane 213.13
    DMS 101.8
    cumene 12.04
    2-octanol 20.04
    2-hexanone 82.52
    octyl acetate 47.62
    limonene 18.87
    1,2-dimethoxyethane 323.26
    ethyl orthosilicate 40.58
    tributyl phosphate 45.06
    diacetone alcohol 182.88
    N,N-dimethylaniline 45.21
    acrylonitrile 174.05
    aniline 41.02
    1,3-propanediol 121.92
    bromobenzene 19.52
    dibromomethane 30.67
    1,1,2,2-tetrachloroethane 69.3
    2-methyl-cyclohexyl acetate 53.53
    tetrabutyl urea 60.28
    diisobutyl methanol 24.89
    2-phenylethanol 59.53
    styrene 12.27
    dioctyl adipate 61.24
    dimethyl sulfate 283.42
    ethyl butyrate 76.08
    methyl lactate 199.07
    butyl lactate 56.87
    diethyl carbonate 65.32
    propanediol butyl ether 87.3
    triethyl orthoformate 54.05
    p-tert-butyltoluene 13.73
    methyl 4-tert-butylbenzoate 82.3
    morpholine 247.82
    tert-butylamine 39.97
    n-dodecanol 22.85
    dimethoxymethane 409.43
    ethylene carbonate 217.51
    cyrene 153.6
    2-ethoxyethyl acetate 79.16
    2-ethylhexyl acetate 37.86
    1,2,4-trichlorobenzene 39.46
    4-methylpyridine 93.11
    dibutyl ether 35.11
    2,6-dimethyl-4-heptanol 24.89
    DEF 181.87
    dimethyl isosorbide 228.75
    tetrachloroethylene 33.03
    eugenol 91.88
    triacetin 95.69
    span 80 88.13
    1,4-butanediol 54.84
    1,1-dichloroethane 48.93
    2-methyl-1-pentanol 39.34
    methyl formate 446.49
    2-methyl-1-butanol 40.2
    n-decane 4.12
    butyronitrile 121.69
    3,7-dimethyl-1-octanol 37.59
    1-chlorooctane 16.99
    1-chlorotetradecane 9.83
    n-nonane 3.62
    undecane 3.53
    tert-butylcyclohexane 4.67
    cyclooctane 1.5
    cyclopentanol 85.85
    tetrahydropyran 105.47
    tert-amyl methyl ether 42.73
    2,5,8-trioxanonane 190.78
    1-hexene 13.63
    2-isopropoxyethanol 96.03
    2,2,2-trifluoroethanol 138.11
    methyl butyrate 153.88

    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