Diethyl [S-(R*,R*)]-tartrate

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  • Identifiers

    CAS number
    13811-71-7

    Molecular formula
    C8H14O6

    SMILES
    CCOC(=O)[C@H]([C@@H](C(=O)OCC)O)O

  • Odor profile

    Fragrance
    Fruity 84.73%
    Caramellic 63.18%
    Winey 56.52%
    Sweet 48.16%
    Buttery 41.0%
    Apple 32.96%
    Ethereal 31.21%
    Fatty 28.01%
    Creamy 27.46%
    Rummy 26.95%

     

    Flavor
    Odorless 44.9%
    Mild 33.35%
    Bitter 30.7%
    Very mild 30.39%
    Fruity 28.63%
    Bland 28.24%
    Sweet-like 24.61%
    Waxy 22.16%
    Yeast 22.13%
    Creamy 21.64%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    6.14 (neutral)

    Molecular weight
    206.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    272°C

    Flash point

    • 128.08 ˚C est.

  • Synonyms

    • 13811-71-7
    • (2S,3S)-Diethyl 2,3-dihydroxysuccinate
    • (-)-Diethyl D-tartrate
    • Diethyl D-(-)-Tartrate
    • diethyl D-tartrate
    • diethyl (2S,3S)-2,3-dihydroxybutanedioate
    • MFCD00064451
    • (-)-DIETHYL-D-TARTRATE
    • (-)-diethyl tartrate
    • Diethyl (S-(R*,R*))-tartrate
    • (S,S)-diethyl tartrate
    • EINECS 237-458-8
    • DIETHYL-D-TARTRATE
    • Diethyl [S-(R*,R*)]-tartrate
    • 1,4-diethyl (2S,3S)-2,3-dihydroxybutanedioate
    • D-(-)-Tartaric acid diethyl ester
    • C8H14O6
    • d-(-)-diethyl tartrate
    • diethyl (D)-tartrate
    • diethyl (s,s)-tartrate
    • diethyl (-)-d-tartrate
    • (+/-)-Diethyl tartrate
    • 3HB9XL6BGJ
    • (2S,3S)-Diethyl tartrate
    • Diethyl tartrate, (S,S)-
    • SCHEMBL112149
    • (s,s)-(-)-diethyl tartrate
    • DTXSID6058689
    • (2S,3S)-(-)-Diethyl tartrate
    • DTXSID801021118
    • HY-Y1361
    • (-)-Diethyl D-tartrate, >=99%
    • AC7856
    • AKOS015920333
    • AC-3437
    • CS-W020598
    • DS-12477
    • T1195
    • Rel-diethyl (2S,3S)-2,3-dihydroxysuccinate
    • EN300-1723566
    • Q55078682
    • F1905-7030
    • 237-458-8

  • Applications

    Diethyl [S-(R*,R*)]-tartrate (CAS 13811-71-7) is used as a chiral ligand/auxiliary in asymmetric synthesis, notably in Sharpless epoxidation to prepare enantioenriched epoxides from allylic alcohols. It also serves as a precursor for the synthesis of chiral tartrate-derived ligands and auxiliaries employed in asymmetric catalysis in both industry and academic research. Additionally, it provides a scaffold for constructing enantioenriched building blocks used in pharmaceutical and natural product synthesis, and it is employed in research and development to develop enantioselective manufacturing processes. As a tartrate ester with defined stereochemistry, it remains a core reagent in the development of asymmetric transformations from bench-scale to pilot-scale.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 58.66
    methanol 127.79
    isopropanol 39.79
    water 8.2
    ethyl acetate 65.71
    n-propanol 40.16
    acetone 141.75
    n-butanol 31.71
    acetonitrile 78.21
    DMF 579.73
    toluene 17.27
    isobutanol 27.9
    1,4-dioxane 109.54
    methyl acetate 94.44
    THF 168.72
    2-butanone 75.6
    n-pentanol 26.11
    sec-butanol 37.46
    n-hexane 3.81
    ethylene glycol 62.12
    NMP 732.45
    cyclohexane 9.82
    DMSO 1571.06
    n-butyl acetate 46.9
    n-octanol 15.87
    chloroform 83.22
    n-propyl acetate 34.4
    acetic acid 230.95
    dichloromethane 150.58
    cyclohexanone 150.06
    propylene glycol 42.69
    isopropyl acetate 34.74
    DMAc 558.21
    2-ethoxyethanol 96.74
    isopentanol 29.18
    n-heptane 3.98
    ethyl formate 70.62
    1,2-dichloroethane 145.0
    n-hexanol 23.76
    2-methoxyethanol 185.28
    isobutyl acetate 13.55
    tetrachloromethane 19.19
    n-pentyl acetate 27.37
    transcutol 162.03
    n-heptanol 14.21
    ethylbenzene 15.32
    MIBK 27.9
    2-propoxyethanol 67.88
    tert-butanol 65.75
    MTBE 41.83
    2-butoxyethanol 39.09
    propionic acid 111.08
    o-xylene 27.15
    formic acid 252.05
    diethyl ether 34.58
    m-xylene 15.15
    p-xylene 19.58
    chlorobenzene 35.4
    dimethyl carbonate 62.8
    n-octane 2.06
    formamide 417.58
    cyclopentanone 210.11
    2-pentanone 53.39
    anisole 35.0
    cyclopentyl methyl ether 64.29
    gamma-butyrolactone 349.21
    1-methoxy-2-propanol 98.82
    pyridine 110.18
    3-pentanone 55.64
    furfural 307.52
    n-dodecane 1.53
    diethylene glycol 94.06
    diisopropyl ether 10.18
    tert-amyl alcohol 67.46
    acetylacetone 108.95
    n-hexadecane 1.76
    acetophenone 65.0
    methyl propionate 86.01
    isopentyl acetate 37.17
    trichloroethylene 184.77
    n-nonanol 14.79
    cyclohexanol 50.23
    benzyl alcohol 47.07
    2-ethylhexanol 18.29
    isooctanol 11.78
    dipropyl ether 19.83
    1,2-dichlorobenzene 49.3
    ethyl lactate 40.15
    propylene carbonate 150.76
    n-methylformamide 244.42
    2-pentanol 22.01
    n-pentane 4.24
    1-propoxy-2-propanol 46.62
    1-methoxy-2-propyl acetate 57.32
    2-(2-methoxypropoxy) propanol 55.76
    mesitylene 12.39
    ε-caprolactone 153.24
    p-cymene 14.51
    epichlorohydrin 235.31
    1,1,1-trichloroethane 54.91
    2-aminoethanol 64.14
    morpholine-4-carbaldehyde 347.96
    sulfolane 746.03
    2,2,4-trimethylpentane 3.65
    2-methyltetrahydrofuran 106.19
    n-hexyl acetate 35.22
    isooctane 1.57
    2-(2-butoxyethoxy)ethanol 56.01
    sec-butyl acetate 20.79
    tert-butyl acetate 44.43
    decalin 5.99
    glycerin 106.2
    diglyme 131.53
    acrylic acid 148.0
    isopropyl myristate 13.29
    n-butyric acid 80.93
    acetyl acetate 59.28
    di(2-ethylhexyl) phthalate 22.38
    ethyl propionate 39.54
    nitromethane 442.99
    1,2-diethoxyethane 40.33
    benzonitrile 54.74
    trioctyl phosphate 17.44
    1-bromopropane 39.58
    gamma-valerolactone 285.05
    n-decanol 11.09
    triethyl phosphate 37.26
    4-methyl-2-pentanol 13.09
    propionitrile 44.12
    vinylene carbonate 136.14
    1,1,2-trichlorotrifluoroethane 258.25
    DMS 67.32
    cumene 12.57
    2-octanol 10.41
    2-hexanone 31.66
    octyl acetate 19.79
    limonene 23.33
    1,2-dimethoxyethane 142.18
    ethyl orthosilicate 29.43
    tributyl phosphate 22.59
    diacetone alcohol 71.57
    N,N-dimethylaniline 43.23
    acrylonitrile 89.5
    aniline 43.87
    1,3-propanediol 73.66
    bromobenzene 31.8
    dibromomethane 92.65
    1,1,2,2-tetrachloroethane 164.91
    2-methyl-cyclohexyl acetate 37.25
    tetrabutyl urea 36.01
    diisobutyl methanol 13.5
    2-phenylethanol 39.23
    styrene 19.13
    dioctyl adipate 30.39
    dimethyl sulfate 219.24
    ethyl butyrate 37.4
    methyl lactate 82.73
    butyl lactate 34.78
    diethyl carbonate 34.45
    propanediol butyl ether 43.91
    triethyl orthoformate 31.31
    p-tert-butyltoluene 13.9
    methyl 4-tert-butylbenzoate 59.38
    morpholine 139.1
    tert-butylamine 33.29
    n-dodecanol 8.62
    dimethoxymethane 131.8
    ethylene carbonate 102.49
    cyrene 94.58
    2-ethoxyethyl acetate 45.09
    2-ethylhexyl acetate 30.2
    1,2,4-trichlorobenzene 65.46
    4-methylpyridine 93.57
    dibutyl ether 15.48
    2,6-dimethyl-4-heptanol 13.5
    DEF 146.61
    dimethyl isosorbide 116.31
    tetrachloroethylene 130.94
    eugenol 48.72
    triacetin 59.74
    span 80 40.78
    1,4-butanediol 38.53
    1,1-dichloroethane 54.26
    2-methyl-1-pentanol 26.21
    methyl formate 188.45
    2-methyl-1-butanol 32.21
    n-decane 2.6
    butyronitrile 34.13
    3,7-dimethyl-1-octanol 16.82
    1-chlorooctane 11.15
    1-chlorotetradecane 4.64
    n-nonane 2.52
    undecane 1.94
    tert-butylcyclohexane 3.69
    cyclooctane 3.83
    cyclopentanol 68.3
    tetrahydropyran 65.28
    tert-amyl methyl ether 46.22
    2,5,8-trioxanonane 97.69
    1-hexene 9.84
    2-isopropoxyethanol 48.54
    2,2,2-trifluoroethanol 142.63
    methyl butyrate 58.99

    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