Coumalic acid

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  • Identifiers

    CAS number
    500-05-0

    Molecular formula
    C6H4O4

    SMILES
    C1=CC(=O)OC=C1C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.4%
    Burnt 43.13%
    Caramellic 39.57%
    Sour 37.05%
    Nutty 29.0%
    Sharp 25.79%
    Phenolic 23.31%
    Balsamic 21.39%
    Bitter 20.74%
    Buttery 19.39%

     

    Flavor
    Odorless 42.09%
    Sweet 38.79%
    Sour 37.05%
    Balsam 33.47%
    Nutty 31.88%
    Faint 31.78%
    Balsamic 28.35%
    Phenolic 26.13%
    Almond 26.09%
    Mild 25.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.0

    pKa est.
    5.75 (weak acid)

    Molecular weight
    140.09 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    325°C

    Flash point

    • 141.74 ˚C est.

  • Synonyms

    • Coumalic acid
    • 500-05-0
    • 2-Oxo-2H-pyran-5-carboxylic acid
    • Cumalic acid
    • 6-oxopyran-3-carboxylic acid
    • 2H-Pyran-5-carboxylic acid, 2-oxo-
    • 2-Oxopyran-5-carboxylic acid
    • .alpha.-Pyrone-5-carboxylic acid
    • 2-Pyrone-5-carboxylic acid
    • alpha-Pyrone-5-carboxylic acid
    • OB1JPY343G
    • EINECS 207-899-0
    • MFCD00006644
    • NSC 22978
    • NSC-22978
    • 2-Oxo-1,2H-pyran-5-carboxylic acid
    • COUMALIC ACID [MI]
    • DTXSID60870569
    • 2-Pentenedioic acid, 4-(hydroxymethylene)-, delta-lactone
    • 2-Pentenedioic acid, 4-(hydroxymethylene)-, .delta.-lactone
    • 2-OXO-1(2H)-PYRAN-5-CARBOXYLIC ACID
    • Coumalicacid
    • GLUTACONIC ACID, 4-(HYDROXYMETHYLENE)-, .DELTA.-LACTONE
    • UNII-OB1JPY343G
    • Coumalic acid, 97%
    • 2Oxopyran5carboxylic acid
    • alphaPyrone5carboxylic acid
    • 2Oxo2Hpyran5carboxylic acid
    • SCHEMBL258740
    • 2HPyran5carboxylic acid, 2oxo
    • 6-oxo-pyran-3-carboxylic acid
    • CHEMBL216734
    • DTXCID20818280
    • .alpha.-Pyrone-3-carboxylic acid
    • CHEBI:180952
    • ALBB-033465
    • NSC22978
    • BBL009090
    • STK329418
    • 2-Oxo-2H-pyran-5-carboxylic acid #
    • 2-Pentenedioic acid, .delta.-lactone
    • AKOS000119258
    • SB40457
    • NCGC00336326-01
    • 1ST40242
    • AS-17705
    • BP-12397
    • HY-32004
    • SY020314
    • DB-051716
    • CS-0001427
    • NS00043036
    • EN300-19035
    • AB00990923-01
    • AB00990923-03
    • 2Pentenedioic acid, 4(hydroxymethylene), deltalactone
    • Q19903002
    • F2170-0001
    • Z104472302
    • GLUTACONIC ACID, 4-(HYDROXYMETHYLENE)-, DELTA-LACTONE
    • 207-899-0

  • Applications

    Coumalic acid (CAS 500-05-0) is primarily used as an intermediate in organic synthesis to access a range of specialty chemicals; it serves as a building block for dye and pigment precursors, and as a reactive component in polymer and plastic resin production, including polyester and crosslinked systems; it is employed in coatings and inks formulations to modify resin matrices; it is commonly evaluated as an intermediate in pharmaceutical and agrochemical synthesis; and it may appear in other industrial syntheses under applicable regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.93
    methanol 42.73
    isopropanol 19.64
    water 2.87
    ethyl acetate 19.82
    n-propanol 18.3
    acetone 35.53
    n-butanol 15.22
    acetonitrile 14.37
    DMF 132.76
    toluene 2.58
    isobutanol 13.48
    1,4-dioxane 73.13
    methyl acetate 27.2
    THF 88.66
    2-butanone 28.56
    n-pentanol 14.65
    sec-butanol 17.12
    n-hexane 0.31
    ethylene glycol 20.78
    NMP 231.71
    cyclohexane 0.3
    DMSO 127.68
    n-butyl acetate 18.06
    n-octanol 24.31
    chloroform 0.63
    n-propyl acetate 16.65
    acetic acid 30.72
    dichloromethane 2.39
    cyclohexanone 28.42
    propylene glycol 19.93
    isopropyl acetate 15.4
    DMAc 155.94
    2-ethoxyethanol 57.84
    isopentanol 18.59
    n-heptane 0.88
    ethyl formate 17.58
    1,2-dichloroethane 4.81
    n-hexanol 13.64
    2-methoxyethanol 80.5
    isobutyl acetate 7.2
    tetrachloromethane 0.22
    n-pentyl acetate 23.69
    transcutol 277.46
    n-heptanol 18.94
    ethylbenzene 1.86
    MIBK 17.4
    2-propoxyethanol 51.59
    tert-butanol 30.72
    MTBE 20.6
    2-butoxyethanol 48.65
    propionic acid 24.63
    o-xylene 4.52
    formic acid 43.14
    diethyl ether 16.38
    m-xylene 3.47
    p-xylene 2.31
    chlorobenzene 1.89
    dimethyl carbonate 25.48
    n-octane 0.53
    formamide 75.88
    cyclopentanone 56.4
    2-pentanone 21.99
    anisole 13.32
    cyclopentyl methyl ether 28.68
    gamma-butyrolactone 85.19
    1-methoxy-2-propanol 63.52
    pyridine 22.21
    3-pentanone 18.16
    furfural 69.23
    n-dodecane 0.88
    diethylene glycol 57.4
    diisopropyl ether 5.81
    tert-amyl alcohol 28.1
    acetylacetone 32.08
    n-hexadecane 0.99
    acetophenone 20.18
    methyl propionate 28.52
    isopentyl acetate 16.96
    trichloroethylene 5.01
    n-nonanol 23.01
    cyclohexanol 13.17
    benzyl alcohol 15.55
    2-ethylhexanol 9.75
    isooctanol 15.21
    dipropyl ether 11.97
    1,2-dichlorobenzene 2.63
    ethyl lactate 19.28
    propylene carbonate 31.51
    n-methylformamide 59.86
    2-pentanol 13.04
    n-pentane 0.44
    1-propoxy-2-propanol 38.96
    1-methoxy-2-propyl acetate 35.2
    2-(2-methoxypropoxy) propanol 70.64
    mesitylene 2.89
    ε-caprolactone 42.65
    p-cymene 4.04
    epichlorohydrin 59.05
    1,1,1-trichloroethane 1.49
    2-aminoethanol 28.61
    morpholine-4-carbaldehyde 155.22
    sulfolane 115.81
    2,2,4-trimethylpentane 0.71
    2-methyltetrahydrofuran 48.8
    n-hexyl acetate 39.59
    isooctane 0.5
    2-(2-butoxyethoxy)ethanol 100.6
    sec-butyl acetate 10.93
    tert-butyl acetate 22.27
    decalin 0.49
    glycerin 44.25
    diglyme 131.45
    acrylic acid 30.66
    isopropyl myristate 15.53
    n-butyric acid 19.22
    acetyl acetate 12.88
    di(2-ethylhexyl) phthalate 16.93
    ethyl propionate 16.44
    nitromethane 76.75
    1,2-diethoxyethane 42.48
    benzonitrile 10.5
    trioctyl phosphate 13.81
    1-bromopropane 1.98
    gamma-valerolactone 92.11
    n-decanol 17.29
    triethyl phosphate 12.02
    4-methyl-2-pentanol 9.98
    propionitrile 10.67
    vinylene carbonate 23.96
    1,1,2-trichlorotrifluoroethane 43.73
    DMS 29.22
    cumene 2.2
    2-octanol 13.89
    2-hexanone 17.72
    octyl acetate 22.53
    limonene 5.98
    1,2-dimethoxyethane 64.84
    ethyl orthosilicate 10.67
    tributyl phosphate 14.11
    diacetone alcohol 45.75
    N,N-dimethylaniline 13.64
    acrylonitrile 17.14
    aniline 9.45
    1,3-propanediol 34.28
    bromobenzene 1.14
    dibromomethane 0.92
    1,1,2,2-tetrachloroethane 5.0
    2-methyl-cyclohexyl acetate 15.64
    tetrabutyl urea 25.04
    diisobutyl methanol 7.5
    2-phenylethanol 16.41
    styrene 1.99
    dioctyl adipate 24.06
    dimethyl sulfate 55.13
    ethyl butyrate 15.53
    methyl lactate 36.09
    butyl lactate 25.47
    diethyl carbonate 10.84
    propanediol butyl ether 61.66
    triethyl orthoformate 14.55
    p-tert-butyltoluene 3.99
    methyl 4-tert-butylbenzoate 41.08
    morpholine 74.79
    tert-butylamine 11.45
    n-dodecanol 12.16
    dimethoxymethane 69.04
    ethylene carbonate 19.1
    cyrene 62.79
    2-ethoxyethyl acetate 44.78
    2-ethylhexyl acetate 12.82
    1,2,4-trichlorobenzene 4.98
    4-methylpyridine 20.32
    dibutyl ether 17.22
    2,6-dimethyl-4-heptanol 7.5
    DEF 48.25
    dimethyl isosorbide 81.64
    tetrachloroethylene 3.01
    eugenol 39.7
    triacetin 46.75
    span 80 49.3
    1,4-butanediol 18.01
    1,1-dichloroethane 1.86
    2-methyl-1-pentanol 15.21
    methyl formate 43.47
    2-methyl-1-butanol 15.78
    n-decane 1.31
    butyronitrile 8.89
    3,7-dimethyl-1-octanol 17.8
    1-chlorooctane 5.21
    1-chlorotetradecane 2.66
    n-nonane 1.03
    undecane 1.08
    tert-butylcyclohexane 0.54
    cyclooctane 0.29
    cyclopentanol 21.07
    tetrahydropyran 24.02
    tert-amyl methyl ether 19.85
    2,5,8-trioxanonane 112.22
    1-hexene 1.27
    2-isopropoxyethanol 40.77
    2,2,2-trifluoroethanol 21.7
    methyl butyrate 18.95

    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