Digallic Acid

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  • Identifiers

    CAS number
    536-08-3

    Molecular formula
    C14H10O9

    SMILES
    C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 78.68%
    Phenolic 38.58%
    Balsamic 25.29%
    Burnt 25.06%
    Smoky 15.61%
    Savory 15.53%
    Milky 14.95%
    Vanilla 13.82%
    Dry 13.82%
    Bitter 13.78%

     

    Flavor
    Bitter 68.7%
    Odorless 48.85%
    Mild 35.53%
    Bland 31.73%
    Very mild 26.95%
    Sweet-like 24.34%
    Phenolic 23.94%
    Faint 21.67%
    Eugenol 21.37%
    Nitrile 20.55%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    7.73 (neutral)

    Molecular weight
    322.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    631°C

    Flash point

    • 272.65 ˚C est.

  • Synonyms

    • Digallic acid
    • 536-08-3
    • m-Digallic acid
    • m-Galloylgallic acid
    • Gallic acid 3-monogallate
    • 3,4-Dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoic acid
    • DTXSID50871747
    • 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid
    • 3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoic acid
    • NSC-59263
    • gallic acid 5,6-dihydroxy-3-carboxyphenyl ester
    • 404KO0584X
    • 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
    • CHEBI:30814
    • RefChem:133616
    • DTXCID60819377
    • 208-624-7
    • Gallic acid, 3-gallate
    • CHEMBL366356
    • NSC59263
    • 5,6-Dihydroxy-3-carboxyphenyl ester of gallic acid
    • 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoic acid
    • Benzoic acid, 3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)-
    • m-Galloyl gallic acid
    • 3-Galloyl gallic acid
    • NSC 59263
    • Digallussaure
    • Benzoic acid, 3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
    • UNII-404KO0584X
    • COVFEVWNJUOYRL-UHFFFAOYSA-N
    • C14H10O9
    • EINECS 208-624-7
    • BRN 2177723
    • 3-galloyloxy-4,5-dihydroxy-benzoic acid
    • DIGALLIC ACID, M-
    • DIGALLIC ACID, META
    • DIGALLIC ACID [MI]
    • NCIOpen2_007819
    • SCHEMBL39415
    • 3-10-00-02086 (Beilstein Handbook Reference)
    • orb1697437
    • SCHEMBL29836990
    • BDBM50056937
    • MFCD00068961
    • AKOS040751568
    • DISCONTINUED. Please see D445080
    • 4,5-DIHYDROXYBENZOIC ACID MONOGALLATE
    • CS-0066290
    • NS00043027
    • ST50985282
    • C01572
    • G91394
    • Q4140499
    • Benzoic acid,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
    • 4,5-dihydroxy-3-(3,4,5-trihydroxyphenylcarbonyloxy)benzoic acid
    • 536-08-3

  • Applications

    Digallic Acid (CAS 536-08-3) is primarily used as an intermediate/building block in the synthesis of polyphenolic resins and crosslinking agents for coatings, adhesives, and plastics; it can function as a chelating agent for metal complexation in processing; it serves as a precursor for tannin-based materials and bio-based polymers; it is used as an antioxidant additive in polymer formulations and coatings due to its polyphenolic structure; and it is studied as a reagent in the development of functional materials and other specialty chemicals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.48
    methanol 25.11
    isopropanol 22.28
    water 0.87
    ethyl acetate 8.54
    n-propanol 25.12
    acetone 3.69
    n-butanol 13.21
    acetonitrile 2.36
    DMF 134.65
    toluene 0.38
    isobutanol 6.76
    1,4-dioxane 32.16
    methyl acetate 12.05
    THF 71.03
    2-butanone 11.16
    n-pentanol 4.96
    sec-butanol 25.09
    n-hexane 0.04
    ethylene glycol 63.85
    NMP 54.76
    cyclohexane 0.07
    DMSO 194.1
    n-butyl acetate 1.84
    n-octanol 5.43
    chloroform 0.03
    n-propyl acetate 2.49
    acetic acid 14.09
    dichloromethane 0.05
    cyclohexanone 2.82
    propylene glycol 60.97
    isopropyl acetate 4.72
    DMAc 207.21
    2-ethoxyethanol 160.57
    isopentanol 7.05
    n-heptane 0.18
    ethyl formate 2.89
    1,2-dichloroethane 0.15
    n-hexanol 3.32
    2-methoxyethanol 358.05
    isobutyl acetate 0.35
    tetrachloromethane 0.02
    n-pentyl acetate 2.73
    transcutol 77.54
    n-heptanol 5.84
    ethylbenzene 0.28
    MIBK 2.06
    2-propoxyethanol 63.35
    tert-butanol 31.07
    MTBE 13.25
    2-butoxyethanol 33.61
    propionic acid 13.75
    o-xylene 0.64
    formic acid 38.9
    diethyl ether 10.75
    m-xylene 0.33
    p-xylene 0.16
    chlorobenzene 0.03
    dimethyl carbonate 15.2
    n-octane 0.14
    formamide 132.42
    cyclopentanone 8.8
    2-pentanone 5.27
    anisole 4.08
    cyclopentyl methyl ether 11.24
    gamma-butyrolactone 18.97
    1-methoxy-2-propanol 223.83
    pyridine 6.31
    3-pentanone 4.37
    furfural 9.14
    n-dodecane 0.12
    diethylene glycol 78.73
    diisopropyl ether 1.65
    tert-amyl alcohol 32.0
    acetylacetone 6.51
    n-hexadecane 0.14
    acetophenone 2.57
    methyl propionate 18.52
    isopentyl acetate 1.39
    trichloroethylene 0.17
    n-nonanol 5.91
    cyclohexanol 6.33
    benzyl alcohol 3.89
    2-ethylhexanol 1.37
    isooctanol 3.4
    dipropyl ether 6.09
    1,2-dichlorobenzene 0.05
    ethyl lactate 7.94
    propylene carbonate 2.56
    n-methylformamide 58.03
    2-pentanol 10.39
    n-pentane 0.09
    1-propoxy-2-propanol 33.34
    1-methoxy-2-propyl acetate 9.75
    2-(2-methoxypropoxy) propanol 25.01
    mesitylene 0.22
    ε-caprolactone 8.19
    p-cymene 0.31
    epichlorohydrin 14.55
    1,1,1-trichloroethane 0.04
    2-aminoethanol 96.21
    morpholine-4-carbaldehyde 87.52
    sulfolane 30.44
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 22.31
    n-hexyl acetate 4.07
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 41.36
    sec-butyl acetate 1.76
    tert-butyl acetate 7.26
    decalin 0.04
    glycerin 158.51
    diglyme 70.18
    acrylic acid 12.84
    isopropyl myristate 1.95
    n-butyric acid 8.16
    acetyl acetate 1.66
    di(2-ethylhexyl) phthalate 1.4
    ethyl propionate 4.85
    nitromethane 35.0
    1,2-diethoxyethane 13.7
    benzonitrile 0.44
    trioctyl phosphate 1.64
    1-bromopropane 0.14
    gamma-valerolactone 37.28
    n-decanol 4.15
    triethyl phosphate 2.1
    4-methyl-2-pentanol 3.05
    propionitrile 2.5
    vinylene carbonate 1.54
    1,1,2-trichlorotrifluoroethane 20.54
    DMS 3.54
    cumene 0.17
    2-octanol 3.77
    2-hexanone 1.76
    octyl acetate 3.22
    limonene 0.48
    1,2-dimethoxyethane 84.09
    ethyl orthosilicate 2.33
    tributyl phosphate 1.16
    diacetone alcohol 29.26
    N,N-dimethylaniline 3.41
    acrylonitrile 3.96
    aniline 3.25
    1,3-propanediol 94.91
    bromobenzene 0.02
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.33
    2-methyl-cyclohexyl acetate 1.25
    tetrabutyl urea 3.41
    diisobutyl methanol 1.29
    2-phenylethanol 2.93
    styrene 0.22
    dioctyl adipate 2.78
    dimethyl sulfate 23.39
    ethyl butyrate 2.51
    methyl lactate 38.1
    butyl lactate 5.07
    diethyl carbonate 1.69
    propanediol butyl ether 23.68
    triethyl orthoformate 3.83
    p-tert-butyltoluene 0.43
    methyl 4-tert-butylbenzoate 7.69
    morpholine 85.85
    tert-butylamine 7.15
    n-dodecanol 2.79
    dimethoxymethane 119.94
    ethylene carbonate 1.42
    cyrene 16.9
    2-ethoxyethyl acetate 8.32
    2-ethylhexyl acetate 0.82
    1,2,4-trichlorobenzene 0.15
    4-methylpyridine 2.72
    dibutyl ether 3.55
    2,6-dimethyl-4-heptanol 1.29
    DEF 24.94
    dimethyl isosorbide 19.18
    tetrachloroethylene 0.21
    eugenol 8.29
    triacetin 5.62
    span 80 14.9
    1,4-butanediol 22.36
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 3.23
    methyl formate 17.16
    2-methyl-1-butanol 9.0
    n-decane 0.23
    butyronitrile 1.34
    3,7-dimethyl-1-octanol 2.63
    1-chlorooctane 0.55
    1-chlorotetradecane 0.27
    n-nonane 0.19
    undecane 0.16
    tert-butylcyclohexane 0.04
    cyclooctane 0.07
    cyclopentanol 11.28
    tetrahydropyran 10.22
    tert-amyl methyl ether 17.34
    2,5,8-trioxanonane 50.08
    1-hexene 0.17
    2-isopropoxyethanol 50.57
    2,2,2-trifluoroethanol 7.53
    methyl butyrate 3.89

    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