Mesoxalic acid

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  • Identifiers

    CAS number
    473-90-5

    Molecular formula
    C3H2O5

    SMILES
    C(=O)(C(=O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 63.77%
    Sour 51.82%
    Caramellic 42.25%
    Burnt 41.2%
    Sharp 33.59%
    Winey 28.13%
    Buttery 23.48%
    Clean 22.09%
    Pungent 20.98%
    Creamy 19.78%

     

    Flavor
    Odorless 56.67%
    Sour 43.48%
    Very mild 35.61%
    Nutty 32.59%
    Caramellic 32.27%
    Musty 23.59%
    Yeast 21.3%
    Mild 21.18%
    Urine 20.55%
    Sharp 20.36%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    4.76 (weak acid)

    Molecular weight
    118.04 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    251°C

    Flash point

    • 178.34 ˚C est.

  • Synonyms

    • MESOXALIC ACID
    • Ketomalonic acid
    • Oxomalonic acid
    • 473-90-5
    • 2-oxopropanedioic acid
    • ALPHA-KETOMALONIC ACID
    • Oxomalonate
    • 62R514HE48
    • CHEBI:30842
    • RefChem:156683
    • 207-473-4
    • 2-Oxomalonic acid
    • Mesoxalate
    • Oxopropanedioic acid
    • Propanedioic acid, oxo- (9CI)
    • Ketomalonic acid; Mesoxalate
    • 2-Oxomalonsaeure
    • CCRIS 1453
    • Propanedioic acid, oxo-
    • EINECS 207-473-4
    • BRN 1754123
    • UNII-62R514HE48
    • Mesoxalic acid, 8CI
    • MESOXALIC ACID [MI]
    • SCHEMBL28953
    • 3-03-00-01355 (Beilstein Handbook Reference)
    • orb1701941
    • DTXSID3021649
    • AKOS006282599
    • DB03589
    • DB-352625
    • HY-114634
    • CS-0063624
    • NS00022212
    • C00830
    • Q2823289
    • F8881-6998
    • 473-90-5

  • Applications

    Mesoxalic acid (CAS 473-90-5) is a useful intermediate in organic synthesis, commonly employed as a precursor to various dicarboxylic acid derivatives, esters, and anhydrides for downstream transformations. In industry and materials research, it is viewed as a building block for developing monomers and specialized polymers and material systems. It can also serve as a ligand or metal-coordination building block in coordination chemistry, contributing to the design of metal complexes and multifunctional organic compounds. Additionally, mesoxalic acid has been explored as a precursor for the synthesis of heterocycles and other intermediates for chemical materials research. Subject to local regulations and formulation limits, its use is considered for synthesis and processing of chemicals within applicable regulatory frameworks.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 96.83
    methanol 168.26
    isopropanol 74.26
    water 45.22
    ethyl acetate 10.2
    n-propanol 64.95
    acetone 46.65
    n-butanol 41.13
    acetonitrile 16.6
    DMF 503.21
    toluene 1.2
    isobutanol 35.91
    1,4-dioxane 12.77
    methyl acetate 13.25
    THF 78.16
    2-butanone 29.16
    n-pentanol 26.87
    sec-butanol 40.83
    n-hexane 1.15
    ethylene glycol 120.63
    NMP 282.64
    cyclohexane 0.71
    DMSO 873.25
    n-butyl acetate 7.12
    n-octanol 11.74
    chloroform 0.72
    n-propyl acetate 8.31
    acetic acid 29.48
    dichloromethane 1.51
    cyclohexanone 17.59
    propylene glycol 118.9
    isopropyl acetate 8.28
    DMAc 274.78
    2-ethoxyethanol 102.55
    isopentanol 28.83
    n-heptane 2.18
    ethyl formate 14.7
    1,2-dichloroethane 3.75
    n-hexanol 17.84
    2-methoxyethanol 198.74
    isobutyl acetate 2.93
    tetrachloromethane 0.36
    n-pentyl acetate 6.92
    transcutol 85.86
    n-heptanol 12.28
    ethylbenzene 0.84
    MIBK 16.64
    2-propoxyethanol 71.2
    tert-butanol 68.65
    MTBE 13.85
    2-butoxyethanol 36.46
    propionic acid 33.85
    o-xylene 1.85
    formic acid 72.36
    diethyl ether 13.63
    m-xylene 1.72
    p-xylene 0.83
    chlorobenzene 0.46
    dimethyl carbonate 18.53
    n-octane 0.85
    formamide 144.17
    cyclopentanone 43.31
    2-pentanone 28.38
    anisole 3.7
    cyclopentyl methyl ether 21.68
    gamma-butyrolactone 55.62
    1-methoxy-2-propanol 201.57
    pyridine 7.25
    3-pentanone 17.32
    furfural 29.12
    n-dodecane 0.58
    diethylene glycol 95.06
    diisopropyl ether 4.75
    tert-amyl alcohol 42.64
    acetylacetone 20.2
    n-hexadecane 0.6
    acetophenone 6.54
    methyl propionate 25.23
    isopentyl acetate 4.99
    trichloroethylene 2.42
    n-nonanol 10.95
    cyclohexanol 15.83
    benzyl alcohol 8.48
    2-ethylhexanol 7.59
    isooctanol 9.15
    dipropyl ether 12.15
    1,2-dichlorobenzene 0.51
    ethyl lactate 23.78
    propylene carbonate 14.48
    n-methylformamide 179.98
    2-pentanol 30.58
    n-pentane 2.15
    1-propoxy-2-propanol 52.66
    1-methoxy-2-propyl acetate 18.48
    2-(2-methoxypropoxy) propanol 35.56
    mesitylene 1.65
    ε-caprolactone 17.89
    p-cymene 1.78
    epichlorohydrin 30.64
    1,1,1-trichloroethane 0.96
    2-aminoethanol 149.57
    morpholine-4-carbaldehyde 117.26
    sulfolane 170.86
    2,2,4-trimethylpentane 0.95
    2-methyltetrahydrofuran 25.14
    n-hexyl acetate 8.74
    isooctane 0.94
    2-(2-butoxyethoxy)ethanol 49.68
    sec-butyl acetate 4.34
    tert-butyl acetate 11.14
    decalin 0.45
    glycerin 164.58
    diglyme 62.85
    acrylic acid 34.99
    isopropyl myristate 4.85
    n-butyric acid 25.06
    acetyl acetate 3.21
    di(2-ethylhexyl) phthalate 4.87
    ethyl propionate 10.05
    nitromethane 61.63
    1,2-diethoxyethane 13.04
    benzonitrile 2.81
    trioctyl phosphate 6.47
    1-bromopropane 2.85
    gamma-valerolactone 58.59
    n-decanol 8.37
    triethyl phosphate 5.12
    4-methyl-2-pentanol 16.38
    propionitrile 13.76
    vinylene carbonate 8.97
    1,1,2-trichlorotrifluoroethane 38.19
    DMS 5.88
    cumene 0.96
    2-octanol 8.35
    2-hexanone 12.28
    octyl acetate 6.85
    limonene 3.3
    1,2-dimethoxyethane 62.3
    ethyl orthosilicate 4.56
    tributyl phosphate 5.45
    diacetone alcohol 52.4
    N,N-dimethylaniline 6.92
    acrylonitrile 20.67
    aniline 5.01
    1,3-propanediol 108.65
    bromobenzene 0.26
    dibromomethane 1.22
    1,1,2,2-tetrachloroethane 3.34
    2-methyl-cyclohexyl acetate 4.6
    tetrabutyl urea 13.72
    diisobutyl methanol 7.22
    2-phenylethanol 6.67
    styrene 0.74
    dioctyl adipate 7.58
    dimethyl sulfate 53.24
    ethyl butyrate 7.9
    methyl lactate 67.08
    butyl lactate 15.4
    diethyl carbonate 4.1
    propanediol butyl ether 44.21
    triethyl orthoformate 6.55
    p-tert-butyltoluene 2.08
    methyl 4-tert-butylbenzoate 13.93
    morpholine 41.88
    tert-butylamine 28.18
    n-dodecanol 6.06
    dimethoxymethane 117.81
    ethylene carbonate 7.82
    cyrene 51.2
    2-ethoxyethyl acetate 9.2
    2-ethylhexyl acetate 3.39
    1,2,4-trichlorobenzene 0.76
    4-methylpyridine 7.62
    dibutyl ether 6.4
    2,6-dimethyl-4-heptanol 7.22
    DEF 62.75
    dimethyl isosorbide 41.21
    tetrachloroethylene 1.86
    eugenol 16.97
    triacetin 10.19
    span 80 26.21
    1,4-butanediol 56.16
    1,1-dichloroethane 1.83
    2-methyl-1-pentanol 15.19
    methyl formate 68.08
    2-methyl-1-butanol 25.91
    n-decane 0.94
    butyronitrile 12.24
    3,7-dimethyl-1-octanol 8.4
    1-chlorooctane 2.4
    1-chlorotetradecane 1.16
    n-nonane 0.95
    undecane 0.73
    tert-butylcyclohexane 0.51
    cyclooctane 0.58
    cyclopentanol 30.76
    tetrahydropyran 10.61
    tert-amyl methyl ether 15.39
    2,5,8-trioxanonane 55.82
    1-hexene 2.59
    2-isopropoxyethanol 50.6
    2,2,2-trifluoroethanol 22.43
    methyl butyrate 13.9

    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