Dimethyl (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioate

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  • Identifiers

    CAS number
    56158-55-5

    Molecular formula
    C13H16O8

    SMILES
    COC(=O)[C@H]([C@](CC1=CC(=C(C=C1)O)O)(C(=O)OC)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 57.02%
    Sweet 36.63%
    Caramellic 34.8%
    Vanilla 32.72%
    Milky 32.68%
    Fruity 30.42%
    Creamy 28.91%
    Buttery 24.71%
    Dairy 23.18%
    Burnt 22.41%

     

    Flavor
    Bitter 54.31%
    Odorless 51.42%
    Bland 38.46%
    Very mild 30.34%
    Mild 29.87%
    Sweet-like 25.27%
    Yeast 18.91%
    Orange flower 18.86%
    Heather 18.79%
    Fruity 18.72%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    7.07 (neutral)

    Molecular weight
    300.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    540°C

    Flash point

    • 213.46 ˚C est.

  • Synonyms

    • DTXSID001118656
    • Dimethyl (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioate
    • 56158-55-5
    • Butanedioic acid, 2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxy-, dimethyl ester, [S-(R*,S*)]-
    • 56158-55-5

  • Applications

    Dimethyl (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioate (CAS 56158-55-5) is a tartrate-derived dimethyl ester featuring a catechol-containing aryl substituent, serving primarily as a chiral building block and intermediate in organic synthesis. In industrial practice, it is used as a precursor for asymmetric transformations and for constructing polyphenol-containing motifs. The catechol moiety offers potential antioxidant and stabilizing roles in polymer formulations and coatings, and the compound may be considered as a fragrance ingredient for perfumery and cosmetic applications. Additionally, it can function as a polymerizable or crosslinking component in tartrate-based polyesters, enabling applications in specialty plastics and coatings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 207.12
    methanol 373.86
    isopropanol 85.27
    water 16.27
    ethyl acetate 22.4
    n-propanol 85.45
    acetone 80.75
    n-butanol 44.76
    acetonitrile 14.83
    DMF 385.04
    toluene 3.52
    isobutanol 27.7
    1,4-dioxane 98.52
    methyl acetate 24.71
    THF 243.96
    2-butanone 32.76
    n-pentanol 22.23
    sec-butanol 42.65
    n-hexane 0.67
    ethylene glycol 280.06
    NMP 184.14
    cyclohexane 1.93
    DMSO 1047.15
    n-butyl acetate 3.68
    n-octanol 10.22
    chloroform 2.14
    n-propyl acetate 7.0
    acetic acid 99.32
    dichloromethane 3.69
    cyclohexanone 30.54
    propylene glycol 148.99
    isopropyl acetate 11.11
    DMAc 295.3
    2-ethoxyethanol 236.23
    isopentanol 24.35
    n-heptane 1.41
    ethyl formate 17.99
    1,2-dichloroethane 6.94
    n-hexanol 15.7
    2-methoxyethanol 570.63
    isobutyl acetate 1.91
    tetrachloromethane 0.82
    n-pentyl acetate 5.34
    transcutol 102.67
    n-heptanol 13.27
    ethylbenzene 2.42
    MIBK 13.77
    2-propoxyethanol 90.42
    tert-butanol 102.69
    MTBE 18.64
    2-butoxyethanol 42.83
    propionic acid 35.15
    o-xylene 4.14
    formic acid 408.26
    diethyl ether 28.46
    m-xylene 3.22
    p-xylene 2.16
    chlorobenzene 1.19
    dimethyl carbonate 42.6
    n-octane 0.91
    formamide 604.13
    cyclopentanone 71.83
    2-pentanone 29.41
    anisole 12.13
    cyclopentyl methyl ether 36.98
    gamma-butyrolactone 95.87
    1-methoxy-2-propanol 284.27
    pyridine 22.27
    3-pentanone 18.07
    furfural 48.58
    n-dodecane 0.6
    diethylene glycol 189.33
    diisopropyl ether 4.51
    tert-amyl alcohol 57.71
    acetylacetone 49.26
    n-hexadecane 0.63
    acetophenone 12.9
    methyl propionate 38.38
    isopentyl acetate 3.28
    trichloroethylene 7.43
    n-nonanol 10.03
    cyclohexanol 27.08
    benzyl alcohol 18.81
    2-ethylhexanol 5.41
    isooctanol 8.53
    dipropyl ether 10.3
    1,2-dichlorobenzene 1.55
    ethyl lactate 18.24
    propylene carbonate 17.19
    n-methylformamide 202.77
    2-pentanol 23.36
    n-pentane 1.17
    1-propoxy-2-propanol 36.77
    1-methoxy-2-propyl acetate 14.88
    2-(2-methoxypropoxy) propanol 33.26
    mesitylene 2.19
    ε-caprolactone 26.22
    p-cymene 1.99
    epichlorohydrin 70.11
    1,1,1-trichloroethane 1.73
    2-aminoethanol 252.5
    morpholine-4-carbaldehyde 173.04
    sulfolane 172.79
    2,2,4-trimethylpentane 0.51
    2-methyltetrahydrofuran 54.64
    n-hexyl acetate 7.4
    isooctane 0.29
    2-(2-butoxyethoxy)ethanol 53.4
    sec-butyl acetate 3.82
    tert-butyl acetate 17.6
    decalin 0.57
    glycerin 326.41
    diglyme 88.08
    acrylic acid 42.74
    isopropyl myristate 3.81
    n-butyric acid 26.21
    acetyl acetate 9.81
    di(2-ethylhexyl) phthalate 5.13
    ethyl propionate 10.1
    nitromethane 172.7
    1,2-diethoxyethane 16.51
    benzonitrile 4.29
    trioctyl phosphate 4.92
    1-bromopropane 2.82
    gamma-valerolactone 113.4
    n-decanol 7.48
    triethyl phosphate 4.99
    4-methyl-2-pentanol 11.1
    propionitrile 9.49
    vinylene carbonate 13.26
    1,1,2-trichlorotrifluoroethane 79.98
    DMS 9.38
    cumene 1.69
    2-octanol 7.26
    2-hexanone 8.8
    octyl acetate 5.86
    limonene 3.38
    1,2-dimethoxyethane 138.35
    ethyl orthosilicate 4.88
    tributyl phosphate 3.61
    diacetone alcohol 71.33
    N,N-dimethylaniline 11.5
    acrylonitrile 15.97
    aniline 12.46
    1,3-propanediol 233.91
    bromobenzene 0.81
    dibromomethane 2.13
    1,1,2,2-tetrachloroethane 8.76
    2-methyl-cyclohexyl acetate 4.92
    tetrabutyl urea 8.64
    diisobutyl methanol 4.55
    2-phenylethanol 11.63
    styrene 2.27
    dioctyl adipate 6.52
    dimethyl sulfate 83.7
    ethyl butyrate 5.0
    methyl lactate 70.1
    butyl lactate 8.71
    diethyl carbonate 3.69
    propanediol butyl ether 33.26
    triethyl orthoformate 5.54
    p-tert-butyltoluene 2.27
    methyl 4-tert-butylbenzoate 17.56
    morpholine 147.48
    tert-butylamine 26.13
    n-dodecanol 5.36
    dimethoxymethane 299.21
    ethylene carbonate 11.63
    cyrene 53.58
    2-ethoxyethyl acetate 12.67
    2-ethylhexyl acetate 2.17
    1,2,4-trichlorobenzene 2.51
    4-methylpyridine 12.84
    dibutyl ether 4.95
    2,6-dimethyl-4-heptanol 4.55
    DEF 58.84
    dimethyl isosorbide 41.57
    tetrachloroethylene 7.25
    eugenol 18.84
    triacetin 12.67
    span 80 24.01
    1,4-butanediol 82.02
    1,1-dichloroethane 2.13
    2-methyl-1-pentanol 13.17
    methyl formate 129.0
    2-methyl-1-butanol 22.96
    n-decane 1.01
    butyronitrile 7.57
    3,7-dimethyl-1-octanol 6.42
    1-chlorooctane 2.46
    1-chlorotetradecane 1.18
    n-nonane 0.93
    undecane 0.76
    tert-butylcyclohexane 0.41
    cyclooctane 0.95
    cyclopentanol 48.99
    tetrahydropyran 33.8
    tert-amyl methyl ether 19.88
    2,5,8-trioxanonane 69.91
    1-hexene 2.04
    2-isopropoxyethanol 76.21
    2,2,2-trifluoroethanol 56.74
    methyl butyrate 11.55

    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