Diethyl 2-hydroxypentanedioate

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  • Identifiers

    CAS number
    69134-53-8

    Molecular formula
    C9H16O5

    SMILES
    CCOC(=O)CCC(C(=O)OCC)O

  • Odor profile

    Fragrance
    Fruity 67.67%
    Winey 55.03%
    Caramellic 54.8%
    Sweet 45.38%
    Buttery 40.57%
    Fatty 34.75%
    Oily 33.82%
    Ethereal 32.39%
    Creamy 30.61%
    Apple 29.47%

     

    Flavor
    Fruity 57.44%
    Mild 42.33%
    Bitter 41.21%
    Odorless 38.18%
    Waxy 34.76%
    Creamy 34.13%
    Wine 32.78%
    Grape 30.21%
    Fruit 29.39%
    Fatty 27.36%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    6.68 (neutral)

    Molecular weight
    204.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    259°C

    Flash point

    • 128.4 ˚C est.

  • Synonyms

    • diethyl 2-hydroxypentanedioate
    • 69134-53-8
    • Diethyl 2-hydroxyglutarate
    • 2-hydroxyglutaric acid diethyl ester
    • Diethyl 2-Hydroxypentanedioate (>90%)
    • MFCD16620610
    • diethyl2-hydroxypentanedioate
    • SCHEMBL8100254
    • CHEBI:87295
    • DTXSID90533579
    • DYLHSDCNOUDICA-UHFFFAOYSA-N
    • AKOS015843401
    • CS-W007118
    • DS-9352
    • DB-074124
    • Pentanedioic acid, 2-hydroxy-1,5-diethyl ester
    • Q27159500
    • Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester
    • PENTANEDIOIC ACID, 2-HYDROXY-, 1,5-DIETHYL ESTER

  • Applications

    Diethyl 2-hydroxypentanedioate (CAS 69134-53-8) can be used as an organic synthesis intermediate in pharmaceutical and agrochemical production; it can also act as a chiral building block and may serve as a ligand in asymmetric catalysis to access enantioenriched compounds. In the polymer industry, it can function as a diol component for the synthesis of polyesters and polyurethanes, supporting coatings, adhesives, and plastic materials. It is also a precursor for the synthesis of functionalized malonates used in fine chemicals and materials R&D.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 206.6
    methanol 544.53
    isopropanol 152.45
    water 17.69
    ethyl acetate 317.54
    n-propanol 151.68
    acetone 968.37
    n-butanol 118.89
    acetonitrile 581.69
    DMF 2716.9
    toluene 93.75
    isobutanol 109.06
    1,4-dioxane 410.05
    methyl acetate 397.54
    THF 574.72
    2-butanone 409.87
    n-pentanol 120.1
    sec-butanol 135.73
    n-hexane 16.59
    ethylene glycol 141.05
    NMP 1984.42
    cyclohexane 18.37
    DMSO 4660.58
    n-butyl acetate 172.06
    n-octanol 53.13
    chloroform 450.48
    n-propyl acetate 199.31
    acetic acid 1204.86
    dichloromethane 784.14
    cyclohexanone 552.91
    propylene glycol 120.67
    isopropyl acetate 179.81
    DMAc 2002.84
    2-ethoxyethanol 412.55
    isopentanol 110.81
    n-heptane 7.43
    ethyl formate 305.35
    1,2-dichloroethane 605.67
    n-hexanol 66.94
    2-methoxyethanol 612.26
    isobutyl acetate 89.42
    tetrachloromethane 53.07
    n-pentyl acetate 105.25
    transcutol 843.69
    n-heptanol 38.43
    ethylbenzene 75.43
    MIBK 152.68
    2-propoxyethanol 218.56
    tert-butanol 276.92
    MTBE 225.52
    2-butoxyethanol 111.55
    propionic acid 433.33
    o-xylene 112.58
    formic acid 842.34
    diethyl ether 171.11
    m-xylene 75.54
    p-xylene 104.57
    chlorobenzene 226.8
    dimethyl carbonate 259.14
    n-octane 4.53
    formamide 1344.4
    cyclopentanone 853.31
    2-pentanone 283.86
    anisole 259.61
    cyclopentyl methyl ether 238.89
    gamma-butyrolactone 1236.63
    1-methoxy-2-propanol 379.06
    pyridine 507.31
    3-pentanone 276.2
    furfural 1116.59
    n-dodecane 4.23
    diethylene glycol 251.7
    diisopropyl ether 45.54
    tert-amyl alcohol 252.11
    acetylacetone 555.98
    n-hexadecane 4.94
    acetophenone 326.38
    methyl propionate 361.82
    isopentyl acetate 137.23
    trichloroethylene 1018.8
    n-nonanol 48.4
    cyclohexanol 143.15
    benzyl alcohol 225.46
    2-ethylhexanol 49.17
    isooctanol 34.4
    dipropyl ether 72.54
    1,2-dichlorobenzene 264.26
    ethyl lactate 143.75
    propylene carbonate 499.49
    n-methylformamide 1102.72
    2-pentanol 85.63
    n-pentane 11.46
    1-propoxy-2-propanol 150.65
    1-methoxy-2-propyl acetate 198.67
    2-(2-methoxypropoxy) propanol 188.0
    mesitylene 50.28
    ε-caprolactone 515.57
    p-cymene 41.12
    epichlorohydrin 914.75
    1,1,1-trichloroethane 272.84
    2-aminoethanol 200.95
    morpholine-4-carbaldehyde 1184.29
    sulfolane 2184.92
    2,2,4-trimethylpentane 12.08
    2-methyltetrahydrofuran 353.36
    n-hexyl acetate 148.28
    isooctane 5.69
    2-(2-butoxyethoxy)ethanol 215.11
    sec-butyl acetate 111.81
    tert-butyl acetate 214.91
    decalin 17.2
    glycerin 278.12
    diglyme 492.16
    acrylic acid 599.28
    isopropyl myristate 54.8
    n-butyric acid 374.43
    acetyl acetate 305.13
    di(2-ethylhexyl) phthalate 77.17
    ethyl propionate 206.6
    nitromethane 2531.62
    1,2-diethoxyethane 204.65
    benzonitrile 289.21
    trioctyl phosphate 51.24
    1-bromopropane 176.01
    gamma-valerolactone 1122.35
    n-decanol 35.63
    triethyl phosphate 100.43
    4-methyl-2-pentanol 51.59
    propionitrile 275.76
    vinylene carbonate 538.16
    1,1,2-trichlorotrifluoroethane 742.54
    DMS 228.6
    cumene 53.89
    2-octanol 32.69
    2-hexanone 193.98
    octyl acetate 74.32
    limonene 61.0
    1,2-dimethoxyethane 676.23
    ethyl orthosilicate 83.05
    tributyl phosphate 80.17
    diacetone alcohol 272.53
    N,N-dimethylaniline 204.82
    acrylonitrile 557.94
    aniline 218.66
    1,3-propanediol 230.79
    bromobenzene 201.54
    dibromomethane 402.71
    1,1,2,2-tetrachloroethane 701.03
    2-methyl-cyclohexyl acetate 121.17
    tetrabutyl urea 118.7
    diisobutyl methanol 34.83
    2-phenylethanol 119.6
    styrene 114.14
    dioctyl adipate 115.91
    dimethyl sulfate 761.44
    ethyl butyrate 131.77
    methyl lactate 248.44
    butyl lactate 122.28
    diethyl carbonate 112.99
    propanediol butyl ether 149.95
    triethyl orthoformate 100.39
    p-tert-butyltoluene 37.47
    methyl 4-tert-butylbenzoate 203.53
    morpholine 503.85
    tert-butylamine 139.25
    n-dodecanol 27.62
    dimethoxymethane 632.86
    ethylene carbonate 392.23
    cyrene 277.78
    2-ethoxyethyl acetate 184.89
    2-ethylhexyl acetate 105.56
    1,2,4-trichlorobenzene 322.2
    4-methylpyridine 511.98
    dibutyl ether 71.18
    2,6-dimethyl-4-heptanol 34.83
    DEF 596.39
    dimethyl isosorbide 341.39
    tetrachloroethylene 442.38
    eugenol 179.61
    triacetin 260.77
    span 80 140.47
    1,4-butanediol 136.36
    1,1-dichloroethane 328.12
    2-methyl-1-pentanol 116.54
    methyl formate 810.64
    2-methyl-1-butanol 115.94
    n-decane 7.19
    butyronitrile 211.72
    3,7-dimethyl-1-octanol 57.8
    1-chlorooctane 36.39
    1-chlorotetradecane 15.28
    n-nonane 6.72
    undecane 5.35
    tert-butylcyclohexane 13.1
    cyclooctane 7.2
    cyclopentanol 191.79
    tetrahydropyran 242.81
    tert-amyl methyl ether 197.87
    2,5,8-trioxanonane 355.63
    1-hexene 56.38
    2-isopropoxyethanol 211.73
    2,2,2-trifluoroethanol 521.49
    methyl butyrate 285.64

    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