2,3-Dihydroxy-2-((4-hydroxyphenyl)methyl)butanedioic acid

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  • Identifiers

    CAS number
    469-65-8

    Molecular formula
    C11H12O7

    SMILES
    C1=CC(=CC=C1CC(C(C(=O)O)O)(C(=O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 54.3%
    Sweet 44.23%
    Caramellic 27.67%
    Bitter 27.37%
    Balsamic 25.41%
    Vanilla 24.69%
    Milky 24.59%
    Savory 23.78%
    Phenolic 23.64%
    Creamy 23.04%

     

    Flavor
    Odorless 66.28%
    Very mild 36.67%
    Mild 34.7%
    Bland 30.68%
    Bitter 24.65%
    Sweet-like 24.64%
    Sour 22.53%
    Yeast 21.69%
    Faint 20.24%
    Cadaverous 19.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    5.22 (weak acid)

    Molecular weight
    256.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    488°C

    Melting point expt.

    • 186 - 187 °C

    Flash point

    • 255.09 ˚C est.

  • Synonyms

    • 469-65-8
    • 2,3-dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid
    • 2,3-Dihydroxy-2-((4-hydroxyphenyl)methyl)butanedioic acid
    • DTXSID90963695
    • RefChem:1059394
    • DTXCID90876458
    • Piscidein
    • (2R,3S)-Piscidic acid
    • 2,3-DIHYDROXY-2-(4-HYDROXYBENZYL)SUCCINIC ACID
    • Piscidinsaure
    • Tartaric acid, (p-hydroxybenzyl)-
    • SpecPlus_000029
    • DivK1c_006125
    • SCHEMBL782199
    • orb1991869
    • CHEMBL1474079
    • KBio1_001069
    • DTXSID90276232
    • CHEBI:138667
    • GLXC-19159
    • HY-N11707
    • AKOS022665281
    • FS-7320
    • NCGC00160142-01
    • DA-76929
    • FP180526
    • XP180499
    • CS-0783424
    • H61428
    • 469-65-8

  • Applications

    2,3-Dihydroxy-2-((4-hydroxyphenyl)methyl)butanedioic acid (CAS 469-65-8) is a multifunctional tartrate-derived diol that can serve as a chiral building block and intermediate in pharmaceutical synthesis, enabling asymmetric transformations to construct complex bioactive molecules. It may be used as a diol comonomer or intermediate in polymer and plastics manufacturing, contributing to polyester or specialty resin systems. The molecule’s phenolic and carboxylate groups suggest potential roles as a stabilizer or antioxidant and as a metal-chelating agent in cosmetic and household formulations, enhancing formulation stability and metal ion management. In coatings and inks, it can act as a resin precursor or crosslinking component to increase network formation. Additionally, it can serve as a versatile precursor in organic synthesis for catalytic ligands or as intermediates for other organic syntheses, depending on regulatory constraints and formulation requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 158.07
    methanol 328.7
    isopropanol 88.3
    water 66.99
    ethyl acetate 18.56
    n-propanol 77.69
    acetone 79.76
    n-butanol 42.99
    acetonitrile 9.75
    DMF 412.77
    toluene 4.13
    isobutanol 29.52
    1,4-dioxane 57.39
    methyl acetate 17.29
    THF 236.39
    2-butanone 35.05
    n-pentanol 23.22
    sec-butanol 52.22
    n-hexane 0.85
    ethylene glycol 464.8
    NMP 222.1
    cyclohexane 1.68
    DMSO 609.79
    n-butyl acetate 3.34
    n-octanol 6.22
    chloroform 0.15
    n-propyl acetate 5.54
    acetic acid 65.57
    dichloromethane 0.27
    cyclohexanone 21.97
    propylene glycol 215.91
    isopropyl acetate 12.66
    DMAc 411.75
    2-ethoxyethanol 352.58
    isopentanol 36.08
    n-heptane 2.51
    ethyl formate 12.22
    1,2-dichloroethane 1.19
    n-hexanol 22.53
    2-methoxyethanol 791.48
    isobutyl acetate 1.05
    tetrachloromethane 0.31
    n-pentyl acetate 3.06
    transcutol 58.0
    n-heptanol 14.27
    ethylbenzene 2.75
    MIBK 21.4
    2-propoxyethanol 128.95
    tert-butanol 162.36
    MTBE 25.41
    2-butoxyethanol 48.3
    propionic acid 25.92
    o-xylene 5.68
    formic acid 414.52
    diethyl ether 23.99
    m-xylene 4.1
    p-xylene 1.94
    chlorobenzene 0.35
    dimethyl carbonate 29.39
    n-octane 0.99
    formamide 723.37
    cyclopentanone 63.83
    2-pentanone 47.22
    anisole 10.06
    cyclopentyl methyl ether 51.66
    gamma-butyrolactone 61.72
    1-methoxy-2-propanol 421.49
    pyridine 13.67
    3-pentanone 18.81
    furfural 27.73
    n-dodecane 0.52
    diethylene glycol 236.98
    diisopropyl ether 7.23
    tert-amyl alcohol 93.93
    acetylacetone 51.65
    n-hexadecane 0.56
    acetophenone 8.97
    methyl propionate 35.37
    isopentyl acetate 2.77
    trichloroethylene 0.95
    n-nonanol 6.91
    cyclohexanol 31.23
    benzyl alcohol 15.32
    2-ethylhexanol 7.02
    isooctanol 8.61
    dipropyl ether 16.1
    1,2-dichlorobenzene 0.41
    ethyl lactate 16.77
    propylene carbonate 9.66
    n-methylformamide 232.2
    2-pentanol 40.66
    n-pentane 1.57
    1-propoxy-2-propanol 50.32
    1-methoxy-2-propyl acetate 14.73
    2-(2-methoxypropoxy) propanol 28.01
    mesitylene 3.21
    ε-caprolactone 19.03
    p-cymene 2.28
    epichlorohydrin 36.57
    1,1,1-trichloroethane 0.46
    2-aminoethanol 484.39
    morpholine-4-carbaldehyde 173.53
    sulfolane 123.16
    2,2,4-trimethylpentane 0.73
    2-methyltetrahydrofuran 67.14
    n-hexyl acetate 3.88
    isooctane 0.54
    2-(2-butoxyethoxy)ethanol 46.49
    sec-butyl acetate 3.71
    tert-butyl acetate 22.22
    decalin 0.63
    glycerin 450.92
    diglyme 77.54
    acrylic acid 27.51
    isopropyl myristate 2.34
    n-butyric acid 23.94
    acetyl acetate 5.15
    di(2-ethylhexyl) phthalate 2.29
    ethyl propionate 8.99
    nitromethane 103.75
    1,2-diethoxyethane 10.24
    benzonitrile 1.76
    trioctyl phosphate 2.65
    1-bromopropane 0.84
    gamma-valerolactone 97.27
    n-decanol 5.91
    triethyl phosphate 3.2
    4-methyl-2-pentanol 18.86
    propionitrile 6.24
    vinylene carbonate 4.94
    1,1,2-trichlorotrifluoroethane 45.49
    DMS 3.83
    cumene 1.82
    2-octanol 6.03
    2-hexanone 8.51
    octyl acetate 3.71
    limonene 3.82
    1,2-dimethoxyethane 158.06
    ethyl orthosilicate 3.46
    tributyl phosphate 1.61
    diacetone alcohol 112.64
    N,N-dimethylaniline 10.88
    acrylonitrile 9.09
    aniline 11.07
    1,3-propanediol 332.06
    bromobenzene 0.23
    dibromomethane 0.19
    1,1,2,2-tetrachloroethane 1.58
    2-methyl-cyclohexyl acetate 3.04
    tetrabutyl urea 5.69
    diisobutyl methanol 5.69
    2-phenylethanol 10.97
    styrene 1.89
    dioctyl adipate 3.04
    dimethyl sulfate 49.04
    ethyl butyrate 4.65
    methyl lactate 72.83
    butyl lactate 5.64
    diethyl carbonate 2.23
    propanediol butyl ether 28.31
    triethyl orthoformate 4.28
    p-tert-butyltoluene 2.61
    methyl 4-tert-butylbenzoate 13.65
    morpholine 120.33
    tert-butylamine 41.45
    n-dodecanol 4.54
    dimethoxymethane 268.58
    ethylene carbonate 4.83
    cyrene 52.09
    2-ethoxyethyl acetate 5.96
    2-ethylhexyl acetate 1.65
    1,2,4-trichlorobenzene 0.69
    4-methylpyridine 9.62
    dibutyl ether 3.27
    2,6-dimethyl-4-heptanol 5.69
    DEF 75.01
    dimethyl isosorbide 38.17
    tetrachloroethylene 1.74
    eugenol 15.45
    triacetin 5.01
    span 80 17.88
    1,4-butanediol 114.4
    1,1-dichloroethane 0.44
    2-methyl-1-pentanol 16.61
    methyl formate 93.43
    2-methyl-1-butanol 30.74
    n-decane 0.85
    butyronitrile 5.12
    3,7-dimethyl-1-octanol 4.43
    1-chlorooctane 1.32
    1-chlorotetradecane 0.76
    n-nonane 0.83
    undecane 0.65
    tert-butylcyclohexane 0.46
    cyclooctane 1.2
    cyclopentanol 54.11
    tetrahydropyran 27.24
    tert-amyl methyl ether 30.73
    2,5,8-trioxanonane 66.13
    1-hexene 2.2
    2-isopropoxyethanol 100.55
    2,2,2-trifluoroethanol 31.7
    methyl butyrate 11.23

    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