1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid

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  • Identifiers

    CAS number
    126-49-8

    Molecular formula
    C10H10O6

    SMILES
    C1=CC(C=CC1O)(CC(=O)C(=O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 47.71%
    Caramellic 39.35%
    Burnt 33.13%
    Roasted 30.25%
    Sweet 28.11%
    Nutty 27.82%
    Savory 24.88%
    Buttery 22.64%
    Cooked 21.52%
    Meaty 19.47%

     

    Flavor
    Odorless 47.55%
    Very mild 36.97%
    Bitter 29.17%
    Yeast 20.89%
    Caramellic 20.85%
    Sweet-like 20.12%
    Faint 19.83%
    Bland 19.77%
    Nutty 19.75%
    Seedy 19.71%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    4.35 (weak acid)

    Molecular weight
    226.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    393°C

    Flash point

    • 237.05 ˚C est.

  • Synonyms

    • prephenate
    • 126-49-8
    • 1-carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
    • RefChem:907541
    • Prephenic acid
    • 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid
    • Prephenic acid, cis
    • cis-prephenic acid
    • 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
    • (1s,4s)-prephenic acid
    • Z66B98Z97I
    • cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
    • 87664-40-2
    • 2,5-Cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-alpha-oxo-
    • (1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
    • PRE
    • cis-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
    • Prephenic acid [MI]
    • UNII-Z66B98Z97I
    • bmse000108
    • SCHEMBL1703157
    • SCHEMBL1703158
    • CHEBI:16666
    • CHEBI:84387
    • DTXSID60894109
    • DTXSID70894110
    • DB08427
    • NS00073261
    • C00254
    • D0CAEB4E-FD01-4AD2-9DC4-AABEBF5AED8A
    • Q2598317
    • 2,5-Cyclohexadiene-1-pyruvic acid, 1-carboxy-4-hydroxy-
    • 2,5-Cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-a-oxo- (9CI)
    • 2,5-Cyclohexadiene-1-pyruvic acid, 1-carboxy-4-hydroxy- (6CI,7CI,8CI)
    • CIS-1-CARBOXY-4-HYDROXY-.ALPHA.-OXO-2,5-CYCLOHEXADIENE-1-PROPANOIC ACID
    • rel-(1r,4r)-1-(2-Carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
    • 126-49-8

  • Applications

    1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid (CAS 126-49-8) is a functionalized cyclohexadienone carboxylic acid that serves as a versatile building block in organic synthesis. In pharmaceutical and fine chemical production, it is used as an intermediate for the preparation of active compounds and related derivatives. In cosmetics and personal care, it may be employed as a precursor or intermediate for fragrance-related ingredients and specialty formulations. In polymers and plastics, it can function as a reactive intermediate or monomer precursor enabling functionalization of resins and specialty polymers. In coatings, paints and adhesives, it may participate in resin formulations as an intermediate or crosslinking moiety. In flavor and fragrance chemistry, it may be evaluated as a precursor to aroma compounds due to its hydroxyl and carboxyl functionalities. Use and handling are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 37.37
    methanol 74.52
    isopropanol 14.86
    water 9.95
    ethyl acetate 7.33
    n-propanol 14.52
    acetone 23.37
    n-butanol 9.03
    acetonitrile 5.83
    DMF 191.24
    toluene 4.78
    isobutanol 5.96
    1,4-dioxane 23.33
    methyl acetate 6.97
    THF 43.9
    2-butanone 11.28
    n-pentanol 6.03
    sec-butanol 8.62
    n-hexane 0.62
    ethylene glycol 53.26
    NMP 155.7
    cyclohexane 0.75
    DMSO 168.51
    n-butyl acetate 3.04
    n-octanol 5.36
    chloroform 0.41
    n-propyl acetate 2.77
    acetic acid 11.83
    dichloromethane 1.13
    cyclohexanone 10.14
    propylene glycol 31.74
    isopropyl acetate 4.75
    DMAc 205.03
    2-ethoxyethanol 58.45
    isopentanol 6.91
    n-heptane 1.75
    ethyl formate 4.59
    1,2-dichloroethane 2.3
    n-hexanol 6.65
    2-methoxyethanol 126.57
    isobutyl acetate 0.81
    tetrachloromethane 0.2
    n-pentyl acetate 3.89
    transcutol 49.39
    n-heptanol 8.29
    ethylbenzene 2.77
    MIBK 5.77
    2-propoxyethanol 37.85
    tert-butanol 16.72
    MTBE 6.31
    2-butoxyethanol 25.2
    propionic acid 8.18
    o-xylene 5.74
    formic acid 71.59
    diethyl ether 10.98
    m-xylene 4.55
    p-xylene 2.3
    chlorobenzene 0.81
    dimethyl carbonate 14.96
    n-octane 0.96
    formamide 123.56
    cyclopentanone 21.24
    2-pentanone 11.34
    anisole 7.13
    cyclopentyl methyl ether 15.36
    gamma-butyrolactone 29.42
    1-methoxy-2-propanol 72.58
    pyridine 13.36
    3-pentanone 9.23
    furfural 22.23
    n-dodecane 0.52
    diethylene glycol 56.47
    diisopropyl ether 2.79
    tert-amyl alcohol 12.76
    acetylacetone 14.11
    n-hexadecane 0.58
    acetophenone 8.24
    methyl propionate 15.08
    isopentyl acetate 2.4
    trichloroethylene 2.22
    n-nonanol 5.44
    cyclohexanol 6.43
    benzyl alcohol 8.99
    2-ethylhexanol 3.27
    isooctanol 5.25
    dipropyl ether 8.53
    1,2-dichlorobenzene 1.06
    ethyl lactate 7.81
    propylene carbonate 6.83
    n-methylformamide 66.39
    2-pentanol 6.81
    n-pentane 0.75
    1-propoxy-2-propanol 20.3
    1-methoxy-2-propyl acetate 10.26
    2-(2-methoxypropoxy) propanol 21.85
    mesitylene 3.14
    ε-caprolactone 11.07
    p-cymene 2.54
    epichlorohydrin 20.07
    1,1,1-trichloroethane 0.55
    2-aminoethanol 58.59
    morpholine-4-carbaldehyde 87.7
    sulfolane 56.82
    2,2,4-trimethylpentane 0.4
    2-methyltetrahydrofuran 15.13
    n-hexyl acetate 5.02
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 32.37
    sec-butyl acetate 1.9
    tert-butyl acetate 6.09
    decalin 0.51
    glycerin 74.0
    diglyme 40.77
    acrylic acid 11.65
    isopropyl myristate 2.53
    n-butyric acid 5.97
    acetyl acetate 3.21
    di(2-ethylhexyl) phthalate 3.78
    ethyl propionate 4.61
    nitromethane 27.71
    1,2-diethoxyethane 9.58
    benzonitrile 2.66
    trioctyl phosphate 3.27
    1-bromopropane 1.15
    gamma-valerolactone 37.72
    n-decanol 4.49
    triethyl phosphate 3.18
    4-methyl-2-pentanol 3.6
    propionitrile 3.75
    vinylene carbonate 5.74
    1,1,2-trichlorotrifluoroethane 20.91
    DMS 5.9
    cumene 1.88
    2-octanol 4.08
    2-hexanone 3.8
    octyl acetate 3.93
    limonene 3.33
    1,2-dimethoxyethane 38.98
    ethyl orthosilicate 3.07
    tributyl phosphate 2.33
    diacetone alcohol 19.61
    N,N-dimethylaniline 9.38
    acrylonitrile 7.2
    aniline 8.34
    1,3-propanediol 41.65
    bromobenzene 0.66
    dibromomethane 0.65
    1,1,2,2-tetrachloroethane 2.54
    2-methyl-cyclohexyl acetate 3.17
    tetrabutyl urea 7.17
    diisobutyl methanol 2.78
    2-phenylethanol 7.38
    styrene 2.49
    dioctyl adipate 4.18
    dimethyl sulfate 31.31
    ethyl butyrate 3.52
    methyl lactate 26.42
    butyl lactate 6.34
    diethyl carbonate 2.33
    propanediol butyl ether 19.99
    triethyl orthoformate 3.74
    p-tert-butyltoluene 2.53
    methyl 4-tert-butylbenzoate 13.73
    morpholine 40.09
    tert-butylamine 6.4
    n-dodecanol 3.38
    dimethoxymethane 89.11
    ethylene carbonate 4.41
    cyrene 29.71
    2-ethoxyethyl acetate 7.64
    2-ethylhexyl acetate 1.93
    1,2,4-trichlorobenzene 1.79
    4-methylpyridine 10.76
    dibutyl ether 3.66
    2,6-dimethyl-4-heptanol 2.78
    DEF 30.75
    dimethyl isosorbide 29.99
    tetrachloroethylene 2.2
    eugenol 15.02
    triacetin 7.66
    span 80 15.33
    1,4-butanediol 18.54
    1,1-dichloroethane 0.7
    2-methyl-1-pentanol 4.07
    methyl formate 32.54
    2-methyl-1-butanol 6.04
    n-decane 0.91
    butyronitrile 2.8
    3,7-dimethyl-1-octanol 3.2
    1-chlorooctane 1.66
    1-chlorotetradecane 0.85
    n-nonane 0.9
    undecane 0.68
    tert-butylcyclohexane 0.36
    cyclooctane 0.72
    cyclopentanol 9.51
    tetrahydropyran 9.1
    tert-amyl methyl ether 8.34
    2,5,8-trioxanonane 39.78
    1-hexene 1.66
    2-isopropoxyethanol 23.24
    2,2,2-trifluoroethanol 8.83
    methyl butyrate 4.69

    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