Dihydroxyfumaric acid

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  • Identifiers

    CAS number
    133-38-0

    Molecular formula
    C4H4O6

    SMILES
    C(=C(/C(=O)O)\O)(\C(=O)O)/O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 54.38%
    Caramellic 38.95%
    Sour 36.08%
    Burnt 32.66%
    Sharp 26.7%
    Buttery 22.38%
    Sweet 22.29%
    Sulfurous 22.09%
    Winey 22.04%
    Clean 21.4%

     

    Flavor
    Odorless 58.08%
    Very mild 39.18%
    Sour 36.34%
    Nutty 32.05%
    Caramellic 30.46%
    Mild 24.83%
    Musty 24.68%
    Yeast 21.57%
    Urine 20.01%
    Acetoin 19.76%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    4.42 (weak acid)

    Molecular weight
    148.07 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    317°C

    Flash point

    • 196.02 ˚C est.

  • Synonyms

    • Dihydroxyfumaric acid
    • Dihydroxyfumarate
    • 133-38-0
    • 2-oxo-3,4,4-trihydroxy-3E-butenoic acid
    • DTXSID701030332
    • CHEBI:4593
    • RefChem:920265
    • GlyTouCan:G80475ZA
    • DTXCID901515429
    • G80475ZA
    • 205-106-2
    • 2,3-Dihydroxyfumaric acid
    • dihydroxybut-2-enedioic acid
    • (E)-2,3-dihydroxybut-2-enedioic acid
    • FUMARIC ACID, DIHYDROXY-
    • dihydroxybut-2-enedioicacid
    • dihydroxy-fumaric acid
    • (E)-2,3-Dihydroxyfumaric acid
    • (2E)-dihydroxybut-2-enedioic acid
    • 13096-38-3
    • 2-Butenedioic acid, 2,3-dihydroxy-, (E)-
    • (2E)-2,3-dihydroxybut-2-enedioic acid
    • Dihydroxyfumaricacid
    • 2-Butenedioic acid,3-dihydroxy-, (E)-
    • (E)-2,3-Dihydroxy-2-butenedioic acid
    • (2E)-2,3-dihydroxybut-2-enedioate
    • Acido diidrossifumarico
    • 2-Butenedioic acid, 2,3-dihydroxy-, (2E)-
    • Acido diidrossifumarico [Italian]
    • DHF
    • EINECS 205-106-2
    • NSC 20941
    • BRN 1724790
    • Dihydroxyfumarsaeure
    • (2-)dihydroxyfumarate
    • 3,4,4-trihydroxy-2-oxobut-3-enoic acid
    • Dihydroxy - maleic acid
    • L'Acido diidrossifumarico
    • SCHEMBL57215
    • 4-03-00-01975 (Beilstein Handbook Reference)
    • NSC20941
    • LMFA01060194
    • NSC-20941
    • NSC525548
    • 3,4,4-trihydroxy-2-oxobut-3-enoate
    • AKOS006221688
    • EBC-616006
    • FS-6811
    • NSC-525548
    • (2E)-2,3-Dihydroxy-2-butenedioic acid #
    • DB-230225
    • CS-0245735
    • NS00041390
    • C00975
    • EN300-310165
    • Q27106417
    • 133-38-0

  • Applications

    Dihydroxyfumaric acid (CAS 133-38-0) is a dicarboxylic acid bearing two hydroxyl groups, commonly regarded as a synthetic intermediate and a structural unit in polymers. In practice, it can serve as a building block for polyesters and specialty polymers, as well as a crosslinking or reactive component in coatings and resins. It may also function as a chelating agent and/or pH adjuster in cosmetic and household formulations, and as a chiral building block for enantioselective syntheses in pharmaceuticals. Additional potential applications include electronic materials and functional polymers, where it could be used as a monomer or modifier, and as an intermediate in agricultural chemical synthesis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 186.76
    methanol 302.68
    isopropanol 108.37
    water 276.26
    ethyl acetate 9.05
    n-propanol 102.6
    acetone 48.22
    n-butanol 63.33
    acetonitrile 9.08
    DMF 464.96
    toluene 2.85
    isobutanol 42.43
    1,4-dioxane 52.15
    methyl acetate 16.66
    THF 106.61
    2-butanone 28.61
    n-pentanol 31.23
    sec-butanol 66.35
    n-hexane 3.58
    ethylene glycol 315.75
    NMP 161.7
    cyclohexane 4.74
    DMSO 1351.04
    n-butyl acetate 4.25
    n-octanol 17.68
    chloroform 3.18
    n-propyl acetate 4.03
    acetic acid 26.2
    dichloromethane 6.08
    cyclohexanone 14.34
    propylene glycol 135.86
    isopropyl acetate 6.41
    DMAc 275.68
    2-ethoxyethanol 145.25
    isopentanol 32.71
    n-heptane 7.12
    ethyl formate 12.34
    1,2-dichloroethane 11.45
    n-hexanol 23.37
    2-methoxyethanol 322.0
    isobutyl acetate 0.8
    tetrachloromethane 3.17
    n-pentyl acetate 5.23
    transcutol 45.76
    n-heptanol 20.99
    ethylbenzene 2.43
    MIBK 10.18
    2-propoxyethanol 67.23
    tert-butanol 102.84
    MTBE 29.32
    2-butoxyethanol 45.25
    propionic acid 23.93
    o-xylene 5.25
    formic acid 138.71
    diethyl ether 35.76
    m-xylene 3.39
    p-xylene 1.72
    chlorobenzene 0.67
    dimethyl carbonate 17.06
    n-octane 3.81
    formamide 233.51
    cyclopentanone 30.78
    2-pentanone 22.44
    anisole 5.92
    cyclopentyl methyl ether 31.15
    gamma-butyrolactone 30.34
    1-methoxy-2-propanol 174.96
    pyridine 12.4
    3-pentanone 18.28
    furfural 17.57
    n-dodecane 1.87
    diethylene glycol 119.01
    diisopropyl ether 8.37
    tert-amyl alcohol 72.46
    acetylacetone 15.65
    n-hexadecane 1.89
    acetophenone 5.26
    methyl propionate 22.77
    isopentyl acetate 2.52
    trichloroethylene 6.13
    n-nonanol 15.78
    cyclohexanol 28.58
    benzyl alcohol 9.71
    2-ethylhexanol 8.49
    isooctanol 11.33
    dipropyl ether 16.39
    1,2-dichlorobenzene 0.89
    ethyl lactate 10.46
    propylene carbonate 5.45
    n-methylformamide 179.45
    2-pentanol 41.89
    n-pentane 8.63
    1-propoxy-2-propanol 37.52
    1-methoxy-2-propyl acetate 9.7
    2-(2-methoxypropoxy) propanol 20.55
    mesitylene 3.31
    ε-caprolactone 11.66
    p-cymene 2.75
    epichlorohydrin 37.27
    1,1,1-trichloroethane 2.73
    2-aminoethanol 256.47
    morpholine-4-carbaldehyde 107.13
    sulfolane 96.05
    2,2,4-trimethylpentane 2.31
    2-methyltetrahydrofuran 39.57
    n-hexyl acetate 6.24
    isooctane 1.66
    2-(2-butoxyethoxy)ethanol 38.92
    sec-butyl acetate 2.26
    tert-butyl acetate 9.23
    decalin 1.44
    glycerin 200.55
    diglyme 60.84
    acrylic acid 22.44
    isopropyl myristate 3.47
    n-butyric acid 15.32
    acetyl acetate 2.5
    di(2-ethylhexyl) phthalate 2.5
    ethyl propionate 5.78
    nitromethane 47.36
    1,2-diethoxyethane 13.62
    benzonitrile 1.83
    trioctyl phosphate 4.41
    1-bromopropane 7.36
    gamma-valerolactone 37.92
    n-decanol 12.56
    triethyl phosphate 3.27
    4-methyl-2-pentanol 14.65
    propionitrile 9.52
    vinylene carbonate 3.7
    1,1,2-trichlorotrifluoroethane 43.32
    DMS 3.82
    cumene 1.95
    2-octanol 12.62
    2-hexanone 7.17
    octyl acetate 5.31
    limonene 4.7
    1,2-dimethoxyethane 91.96
    ethyl orthosilicate 3.58
    tributyl phosphate 2.37
    diacetone alcohol 37.16
    N,N-dimethylaniline 11.17
    acrylonitrile 12.15
    aniline 8.59
    1,3-propanediol 189.83
    bromobenzene 0.52
    dibromomethane 4.87
    1,1,2,2-tetrachloroethane 10.41
    2-methyl-cyclohexyl acetate 2.16
    tetrabutyl urea 7.8
    diisobutyl methanol 6.91
    2-phenylethanol 7.72
    styrene 1.77
    dioctyl adipate 3.7
    dimethyl sulfate 51.58
    ethyl butyrate 4.06
    methyl lactate 39.74
    butyl lactate 8.09
    diethyl carbonate 2.08
    propanediol butyl ether 33.06
    triethyl orthoformate 4.06
    p-tert-butyltoluene 3.36
    methyl 4-tert-butylbenzoate 11.06
    morpholine 96.13
    tert-butylamine 46.18
    n-dodecanol 9.68
    dimethoxymethane 164.33
    ethylene carbonate 3.52
    cyrene 21.18
    2-ethoxyethyl acetate 7.21
    2-ethylhexyl acetate 1.91
    1,2,4-trichlorobenzene 1.26
    4-methylpyridine 8.05
    dibutyl ether 7.05
    2,6-dimethyl-4-heptanol 6.91
    DEF 65.17
    dimethyl isosorbide 19.89
    tetrachloroethylene 9.85
    eugenol 12.48
    triacetin 4.57
    span 80 15.36
    1,4-butanediol 87.93
    1,1-dichloroethane 4.0
    2-methyl-1-pentanol 14.85
    methyl formate 73.4
    2-methyl-1-butanol 35.12
    n-decane 3.1
    butyronitrile 7.86
    3,7-dimethyl-1-octanol 8.04
    1-chlorooctane 5.12
    1-chlorotetradecane 2.24
    n-nonane 3.37
    undecane 2.38
    tert-butylcyclohexane 1.09
    cyclooctane 3.71
    cyclopentanol 47.91
    tetrahydropyran 26.91
    tert-amyl methyl ether 29.7
    2,5,8-trioxanonane 46.35
    1-hexene 5.33
    2-isopropoxyethanol 51.98
    2,2,2-trifluoroethanol 25.95
    methyl butyrate 7.13

    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