3-Phenyloxirane-2-carboxylic acid

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  • Identifiers

    CAS number
    5694-02-0

    Molecular formula
    C9H8O3

    SMILES
    C1=CC=C(C=C1)C2C(O2)C(=O)O

  • Odor profile

    Fragrance
    Sweet 64.2%
    Honey 52.77%
    Fruity 51.31%
    Balsamic 37.29%
    Almond 32.51%
    Caramellic 31.26%
    Floral 30.84%
    Powdery 28.7%
    Bitter 28.47%
    Cocoa 25.75%

     

    Flavor
    Bitter 45.54%
    Sweet 36.63%
    Odorless 33.74%
    Balsam 26.5%
    Mild 25.67%
    Honey 24.69%
    Faint 23.15%
    Sour 22.34%
    Honeysuckle 22.14%
    Urine 21.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    5.26 (weak acid)

    Molecular weight
    164.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    314°C

    Flash point

    • 153.56 ˚C est.

  • Synonyms

    • 3-phenyloxirane-2-carboxylic acid
    • 5694-02-0
    • Oxiranecarboxylic acid, 3-phenyl- (9CI)
    • 3-phenyl-2-oxiranecarboxylic acid
    • 1566-68-3
    • (2R,3S)-rel-3-Phenyl-2-oxiranecarboxylic acid
    • ss-Phenyl-glycidsaure
    • Oxiranecarboxylic acid,3-phenyl-(9CI)
    • NCIOpen2_001180
    • NCIOpen2_004482
    • SCHEMBL2533818
    • CHEBI:177967
    • 2,3-Epoxy-3-phenylpropionic acid
    • Oxiranecarboxylic acid, 3-phenyl-
    • 3-phenyl-oxirane-2-carboxylic acid
    • AKOS015905634
    • PD135985
    • DB-288375

  • Applications

    3-Phenyloxirane-2-carboxylic acid (CAS 5694-02-0) is primarily used as an organic synthesis intermediate and chiral building block in pharmaceutical and agrochemical research, enabling the preparation of functionalized intermediates through epoxide ring opening and related transformations, including routes to beta-hydroxy acid motifs. It also serves as a reactive epoxide building block in polymer chemistry, allowing incorporation of phenyl and carboxyl functionalities into specialty polymers and epoxy networks. In coatings and adhesives, it can act as a reactive monomer or co-monomer to enhance crosslinking and functionalization of epoxy formulations. Additionally, it is commonly evaluated in early-stage R&D as a starting material for the synthesis of more complex intermediates and lead compounds in related specialty chemicals. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 103.32
    methanol 198.68
    isopropanol 58.43
    water 0.75
    ethyl acetate 61.55
    n-propanol 59.83
    acetone 106.26
    n-butanol 43.41
    acetonitrile 39.1
    DMF 234.67
    toluene 6.22
    isobutanol 32.88
    1,4-dioxane 62.19
    methyl acetate 68.63
    THF 136.77
    2-butanone 75.4
    n-pentanol 31.3
    sec-butanol 42.72
    n-hexane 0.15
    ethylene glycol 104.19
    NMP 140.27
    cyclohexane 0.29
    DMSO 350.22
    n-butyl acetate 29.27
    n-octanol 10.04
    chloroform 5.6
    n-propyl acetate 32.06
    acetic acid 64.47
    dichloromethane 13.45
    cyclohexanone 48.95
    propylene glycol 62.04
    isopropyl acetate 36.15
    DMAc 241.32
    2-ethoxyethanol 152.28
    isopentanol 48.56
    n-heptane 0.56
    ethyl formate 30.62
    1,2-dichloroethane 22.52
    n-hexanol 30.01
    2-methoxyethanol 273.53
    isobutyl acetate 15.32
    tetrachloromethane 1.64
    n-pentyl acetate 13.88
    transcutol 318.4
    n-heptanol 13.53
    ethylbenzene 5.79
    MIBK 40.74
    2-propoxyethanol 95.47
    tert-butanol 79.23
    MTBE 32.29
    2-butoxyethanol 49.05
    propionic acid 52.65
    o-xylene 7.84
    formic acid 112.32
    diethyl ether 23.87
    m-xylene 8.06
    p-xylene 6.44
    chlorobenzene 7.89
    dimethyl carbonate 39.51
    n-octane 0.23
    formamide 287.42
    cyclopentanone 101.16
    2-pentanone 62.97
    anisole 29.98
    cyclopentyl methyl ether 37.09
    gamma-butyrolactone 124.51
    1-methoxy-2-propanol 164.93
    pyridine 41.99
    3-pentanone 29.7
    furfural 95.41
    n-dodecane 0.32
    diethylene glycol 129.33
    diisopropyl ether 7.55
    tert-amyl alcohol 57.57
    acetylacetone 83.14
    n-hexadecane 0.36
    acetophenone 37.31
    methyl propionate 64.43
    isopentyl acetate 27.98
    trichloroethylene 37.08
    n-nonanol 10.02
    cyclohexanol 21.87
    benzyl alcohol 35.46
    2-ethylhexanol 15.02
    isooctanol 12.03
    dipropyl ether 11.49
    1,2-dichlorobenzene 10.15
    ethyl lactate 31.09
    propylene carbonate 47.49
    n-methylformamide 143.71
    2-pentanol 29.57
    n-pentane 0.23
    1-propoxy-2-propanol 54.88
    1-methoxy-2-propyl acetate 50.23
    2-(2-methoxypropoxy) propanol 53.53
    mesitylene 5.46
    ε-caprolactone 53.02
    p-cymene 6.08
    epichlorohydrin 142.54
    1,1,1-trichloroethane 8.6
    2-aminoethanol 118.06
    morpholine-4-carbaldehyde 124.31
    sulfolane 143.96
    2,2,4-trimethylpentane 0.59
    2-methyltetrahydrofuran 71.5
    n-hexyl acetate 20.39
    isooctane 0.54
    2-(2-butoxyethoxy)ethanol 78.74
    sec-butyl acetate 23.71
    tert-butyl acetate 43.63
    decalin 0.68
    glycerin 121.86
    diglyme 139.37
    acrylic acid 56.37
    isopropyl myristate 9.0
    n-butyric acid 44.21
    acetyl acetate 29.26
    di(2-ethylhexyl) phthalate 12.01
    ethyl propionate 30.71
    nitromethane 166.61
    1,2-diethoxyethane 37.89
    benzonitrile 22.74
    trioctyl phosphate 8.52
    1-bromopropane 4.53
    gamma-valerolactone 122.91
    n-decanol 7.86
    triethyl phosphate 14.59
    4-methyl-2-pentanol 21.31
    propionitrile 25.29
    vinylene carbonate 35.14
    1,1,2-trichlorotrifluoroethane 102.97
    DMS 28.25
    cumene 5.18
    2-octanol 6.78
    2-hexanone 29.29
    octyl acetate 12.26
    limonene 7.36
    1,2-dimethoxyethane 122.66
    ethyl orthosilicate 12.93
    tributyl phosphate 9.57
    diacetone alcohol 97.56
    N,N-dimethylaniline 22.73
    acrylonitrile 47.74
    aniline 22.65
    1,3-propanediol 126.37
    bromobenzene 5.56
    dibromomethane 5.06
    1,1,2,2-tetrachloroethane 26.88
    2-methyl-cyclohexyl acetate 20.17
    tetrabutyl urea 15.92
    diisobutyl methanol 10.31
    2-phenylethanol 31.29
    styrene 6.06
    dioctyl adipate 15.36
    dimethyl sulfate 70.66
    ethyl butyrate 23.44
    methyl lactate 58.93
    butyl lactate 21.84
    diethyl carbonate 17.96
    propanediol butyl ether 52.9
    triethyl orthoformate 16.28
    p-tert-butyltoluene 5.71
    methyl 4-tert-butylbenzoate 30.64
    morpholine 103.09
    tert-butylamine 21.75
    n-dodecanol 5.81
    dimethoxymethane 130.28
    ethylene carbonate 26.46
    cyrene 53.88
    2-ethoxyethyl acetate 33.91
    2-ethylhexyl acetate 18.86
    1,2,4-trichlorobenzene 15.08
    4-methylpyridine 34.76
    dibutyl ether 7.52
    2,6-dimethyl-4-heptanol 10.31
    DEF 69.34
    dimethyl isosorbide 69.51
    tetrachloroethylene 19.47
    eugenol 34.55
    triacetin 31.78
    span 80 31.33
    1,4-butanediol 53.33
    1,1-dichloroethane 8.95
    2-methyl-1-pentanol 33.16
    methyl formate 83.7
    2-methyl-1-butanol 39.05
    n-decane 0.41
    butyronitrile 21.86
    3,7-dimethyl-1-octanol 13.2
    1-chlorooctane 2.51
    1-chlorotetradecane 1.32
    n-nonane 0.31
    undecane 0.36
    tert-butylcyclohexane 0.69
    cyclooctane 0.23
    cyclopentanol 31.8
    tetrahydropyran 28.17
    tert-amyl methyl ether 28.17
    2,5,8-trioxanonane 90.39
    1-hexene 1.18
    2-isopropoxyethanol 86.97
    2,2,2-trifluoroethanol 36.93
    methyl butyrate 38.86

    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