3,6-bis(hydroxymethyl)-2-methyl-4H-pyran-4-one

Overview IFRA Request a quote

  • Identifiers

    CAS number
    131123-56-3

    Molecular formula
    C8H10O4

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

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 59.03%
    Sweet 55.38%
    Fruity 38.34%
    Creamy 34.88%
    Burnt 34.23%
    Milky 33.62%
    Buttery 32.97%
    Nutty 32.79%
    Vanilla 31.61%
    Roasted 30.1%

     

    Flavor
    Sweet 45.05%
    Caramel 42.36%
    Fruity 34.81%
    Creamy 34.08%
    Fatty 32.63%
    Musty 32.27%
    Mild 29.0%
    Bread 28.98%
    Milky 28.72%
    Bitter 28.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    7.42 (neutral)

    Molecular weight
    170.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    496°C

    Melting point expt.

    • 122 - 123 °C

    Flash point

    • 152.37 ˚C est.

  • Synonyms

    • Herierin III
    • 131123-56-3
    • 6-Methyl-2,5-dihydroxymethyl-gamma pyranone
    • 3,6-Bis(hydroxymethyl)-2-methyl-4H-pyran-4-one
    • DTXSID10156906
    • 4H-Pyran-4-one, 3,6-bis(hydroxymethyl)-2-methyl-
    • RefChem:145797
    • DTXCID5079397
    • 3,6-bis(hydroxymethyl)-2-methylpyran-4-one
    • CHEBI:173779
    • 6-Methyl-2,5-dihydroxymethyl-gamma-pyranone III
    • 131123-56-3

  • Applications

    3,6-bis(hydroxymethyl)-2-methyl-4H-pyran-4-one (CAS 131123-56-3) is primarily used as a reactive building block in organic synthesis, with the two hydroxymethyl groups providing sites for further functionalization to access more complex pyranone derivatives relevant in pharmaceutical and agrochemical research. It also serves as a polyol-type intermediate in polymer and resin chemistry, where its hydroxyl functionalities can participate in crosslinking to form polyurethane, polyester, or epoxy systems. In coatings, inks and adhesives, it can act as a hydroxyl-rich monomer or crosslinking agent, enhancing network formation and adhesion. In fragrance and flavor applications, pyranone-based frameworks and the hydroxy groups can function as aroma precursors or odorants, potentially supporting perfumery formulations. In cosmetics/personal care, it may be evaluated as a reactive building block for functional ingredients or humectant-like components, subject to formulation limits and regulatory constraints. Overall, the compound is principally employed as an intermediate and polyol-building block with potential as a fragrance precursor, with usage governed by local regulations and formulation specifics.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 76.92
    methanol 163.8
    isopropanol 46.79
    water 15.59
    ethyl acetate 51.39
    n-propanol 50.46
    acetone 126.38
    n-butanol 40.18
    acetonitrile 87.73
    DMF 463.44
    toluene 7.99
    isobutanol 32.85
    1,4-dioxane 144.63
    methyl acetate 67.02
    THF 249.08
    2-butanone 60.77
    n-pentanol 31.43
    sec-butanol 34.28
    n-hexane 1.32
    ethylene glycol 127.57
    NMP 330.08
    cyclohexane 1.78
    DMSO 1126.13
    n-butyl acetate 31.23
    n-octanol 19.35
    chloroform 24.62
    n-propyl acetate 31.85
    acetic acid 92.47
    dichloromethane 67.23
    cyclohexanone 96.5
    propylene glycol 49.8
    isopropyl acetate 27.3
    DMAc 285.68
    2-ethoxyethanol 108.14
    isopentanol 34.99
    n-heptane 2.4
    ethyl formate 63.92
    1,2-dichloroethane 65.02
    n-hexanol 33.95
    2-methoxyethanol 230.27
    isobutyl acetate 15.67
    tetrachloromethane 8.03
    n-pentyl acetate 18.35
    transcutol 111.03
    n-heptanol 17.79
    ethylbenzene 7.58
    MIBK 38.37
    2-propoxyethanol 85.22
    tert-butanol 78.14
    MTBE 28.9
    2-butoxyethanol 39.38
    propionic acid 62.99
    o-xylene 12.84
    formic acid 142.22
    diethyl ether 30.21
    m-xylene 12.38
    p-xylene 9.92
    chlorobenzene 16.6
    dimethyl carbonate 46.53
    n-octane 0.96
    formamide 219.22
    cyclopentanone 169.53
    2-pentanone 59.89
    anisole 32.94
    cyclopentyl methyl ether 61.99
    gamma-butyrolactone 243.85
    1-methoxy-2-propanol 124.71
    pyridine 45.24
    3-pentanone 41.24
    furfural 169.33
    n-dodecane 1.08
    diethylene glycol 127.82
    diisopropyl ether 8.44
    tert-amyl alcohol 52.87
    acetylacetone 85.98
    n-hexadecane 1.22
    acetophenone 43.37
    methyl propionate 66.74
    isopentyl acetate 25.09
    trichloroethylene 73.48
    n-nonanol 17.32
    cyclohexanol 38.58
    benzyl alcohol 37.07
    2-ethylhexanol 20.69
    isooctanol 15.48
    dipropyl ether 19.6
    1,2-dichlorobenzene 23.61
    ethyl lactate 36.12
    propylene carbonate 84.22
    n-methylformamide 230.36
    2-pentanol 23.37
    n-pentane 1.38
    1-propoxy-2-propanol 52.09
    1-methoxy-2-propyl acetate 46.4
    2-(2-methoxypropoxy) propanol 45.12
    mesitylene 9.32
    ε-caprolactone 85.1
    p-cymene 10.49
    epichlorohydrin 199.21
    1,1,1-trichloroethane 28.27
    2-aminoethanol 97.07
    morpholine-4-carbaldehyde 217.42
    sulfolane 380.33
    2,2,4-trimethylpentane 1.56
    2-methyltetrahydrofuran 93.55
    n-hexyl acetate 27.15
    isooctane 1.24
    2-(2-butoxyethoxy)ethanol 53.6
    sec-butyl acetate 17.25
    tert-butyl acetate 36.24
    decalin 2.06
    glycerin 119.4
    diglyme 109.44
    acrylic acid 71.91
    isopropyl myristate 12.24
    n-butyric acid 60.34
    acetyl acetate 33.4
    di(2-ethylhexyl) phthalate 17.62
    ethyl propionate 33.18
    nitromethane 255.32
    1,2-diethoxyethane 28.96
    benzonitrile 36.85
    trioctyl phosphate 14.96
    1-bromopropane 19.9
    gamma-valerolactone 188.91
    n-decanol 13.31
    triethyl phosphate 23.45
    4-methyl-2-pentanol 16.77
    propionitrile 47.37
    vinylene carbonate 75.21
    1,1,2-trichlorotrifluoroethane 126.47
    DMS 32.27
    cumene 8.08
    2-octanol 12.45
    2-hexanone 34.95
    octyl acetate 17.32
    limonene 15.08
    1,2-dimethoxyethane 152.24
    ethyl orthosilicate 19.59
    tributyl phosphate 16.28
    diacetone alcohol 73.07
    N,N-dimethylaniline 30.59
    acrylonitrile 78.87
    aniline 26.15
    1,3-propanediol 106.15
    bromobenzene 12.28
    dibromomethane 33.8
    1,1,2,2-tetrachloroethane 56.36
    2-methyl-cyclohexyl acetate 26.63
    tetrabutyl urea 25.62
    diisobutyl methanol 13.58
    2-phenylethanol 32.83
    styrene 7.44
    dioctyl adipate 21.39
    dimethyl sulfate 129.13
    ethyl butyrate 29.39
    methyl lactate 66.73
    butyl lactate 23.88
    diethyl carbonate 23.66
    propanediol butyl ether 38.79
    triethyl orthoformate 22.18
    p-tert-butyltoluene 10.1
    methyl 4-tert-butylbenzoate 42.64
    morpholine 151.29
    tert-butylamine 29.59
    n-dodecanol 10.02
    dimethoxymethane 158.77
    ethylene carbonate 61.88
    cyrene 70.52
    2-ethoxyethyl acetate 27.87
    2-ethylhexyl acetate 19.78
    1,2,4-trichlorobenzene 28.59
    4-methylpyridine 49.08
    dibutyl ether 12.81
    2,6-dimethyl-4-heptanol 13.58
    DEF 101.57
    dimethyl isosorbide 85.53
    tetrachloroethylene 36.68
    eugenol 40.54
    triacetin 32.55
    span 80 32.91
    1,4-butanediol 47.99
    1,1-dichloroethane 30.17
    2-methyl-1-pentanol 27.46
    methyl formate 192.74
    2-methyl-1-butanol 31.48
    n-decane 1.67
    butyronitrile 43.02
    3,7-dimethyl-1-octanol 18.17
    1-chlorooctane 8.84
    1-chlorotetradecane 3.72
    n-nonane 1.46
    undecane 1.32
    tert-butylcyclohexane 2.0
    cyclooctane 1.07
    cyclopentanol 57.89
    tetrahydropyran 61.65
    tert-amyl methyl ether 27.76
    2,5,8-trioxanonane 79.31
    1-hexene 5.12
    2-isopropoxyethanol 58.26
    2,2,2-trifluoroethanol 66.65
    methyl butyrate 49.54

    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