(R)-2-acetoxy-2-phenylacetic acid

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  • Identifiers

    CAS number
    51019-43-3

    Molecular formula
    C10H10O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Honey 48.93%
    Fruity 42.87%
    Sweet 42.12%
    Floral 39.48%
    Balsamic 38.5%
    Caramellic 32.61%
    Phenolic 31.4%
    Sour 29.82%
    Burnt 28.0%
    Odorless 27.71%

     

    Flavor
    Sweet 55.14%
    Fruity 52.11%
    Odorless 33.59%
    Sour 32.5%
    Mild 31.5%
    Floral 28.91%
    Creamy 28.35%
    Powdery 26.25%
    Honey 24.59%
    Musty 24.28%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    6.07 (neutral)

    Molecular weight
    194.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    311°C

    Flash point

    • 161.04 ˚C est.

  • Synonyms

    • (R)-2-Acetoxy-2-phenylacetic acid
    • RefChem:407188
    • 610-598-0
    • 51019-43-3
    • (-)-O-Acetyl-D-mandelic acid
    • (R)-(-)-O-Acetylmandelic acid
    • (R)-(-)-alpha-Acetoxyphenylacetic acid
    • (2R)-2-acetyloxy-2-phenylacetic acid
    • (2R)-2-(acetyloxy)-2-phenylacetic acid
    • (R)-alpha-Acetoxyphenylacetic acid
    • Benzeneacetic acid, a-(acetyloxy)-, (aR)-
    • MFCD00004249
    • EC 610-598-0
    • (R)-(-)-a-Acetylmandelic acid
    • Mandelic Acid 12
    • SCHEMBL628737
    • orb2940079
    • R-(-)-O-Acetoxyphenylaceticacid
    • (R)-(+)-O-Acetylmandelic acid
    • HY-A0025
    • (R)-(-)-A-Acetoxyphenylacetic acid
    • AKOS015890145
    • (2R)-2-acetoxy-2-phenyl-acetic acid
    • (R)-(-)- alpha -Acetylmandelic acid
    • CS-W018501
    • (R)-(-)-2-Acetoxy-2-phenylacetic acid
    • AC-27043
    • AC-27045
    • AS-15100
    • BP-12918
    • SY008267
    • A1453
    • O10162
    • EN300-7366314
    • F094136
    • (R)-(-)-O-Acetylmandelic acid, 99%, optical purity ee: 98% (GLC)
    • 51019-43-3

  • Applications

    (R)-2-acetoxy-2-phenylacetic acid, CAS number: 51019-43-3, is a protected mandelate-type alpha-hydroxy acid derivative that serves as a valuable chiral building block and intermediate in pharmaceutical and fine chemical synthesis. The acetoxy group acts as a protecting group for the alpha-hydroxy functionality, enabling multi-step sequences while preserving stereochemistry. It is commonly converted into esters, amides, or salts, expanding its use in medicinal chemistry and chemical manufacturing. In asymmetric synthesis, it can serve as a chiral auxiliary to direct enantioselective transformations. Additionally, it may be evaluated for cosmetic or fragrance ingredient development as a masked mandelate intermediate, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 138.07
    methanol 270.78
    isopropanol 83.55
    water 4.73
    ethyl acetate 20.88
    n-propanol 86.65
    acetone 99.02
    n-butanol 69.65
    acetonitrile 27.18
    DMF 609.67
    toluene 13.36
    isobutanol 45.33
    1,4-dioxane 104.21
    methyl acetate 39.96
    THF 165.0
    2-butanone 50.86
    n-pentanol 51.37
    sec-butanol 59.56
    n-hexane 0.95
    ethylene glycol 110.49
    NMP 182.91
    cyclohexane 1.2
    DMSO 537.84
    n-butyl acetate 17.81
    n-octanol 26.66
    chloroform 17.45
    n-propyl acetate 16.18
    acetic acid 42.61
    dichloromethane 29.58
    cyclohexanone 53.78
    propylene glycol 60.59
    isopropyl acetate 12.85
    DMAc 430.18
    2-ethoxyethanol 125.5
    isopentanol 51.43
    n-heptane 1.04
    ethyl formate 41.65
    1,2-dichloroethane 36.31
    n-hexanol 40.98
    2-methoxyethanol 243.68
    isobutyl acetate 9.39
    tetrachloromethane 2.64
    n-pentyl acetate 13.08
    transcutol 79.33
    n-heptanol 24.01
    ethylbenzene 14.52
    MIBK 23.24
    2-propoxyethanol 85.66
    tert-butanol 104.29
    MTBE 26.31
    2-butoxyethanol 49.75
    propionic acid 31.95
    o-xylene 16.66
    formic acid 85.64
    diethyl ether 21.38
    m-xylene 13.31
    p-xylene 14.2
    chlorobenzene 12.99
    dimethyl carbonate 28.89
    n-octane 1.02
    formamide 133.87
    cyclopentanone 88.2
    2-pentanone 36.38
    anisole 41.45
    cyclopentyl methyl ether 32.28
    gamma-butyrolactone 73.98
    1-methoxy-2-propanol 112.89
    pyridine 49.12
    3-pentanone 25.09
    furfural 86.4
    n-dodecane 1.78
    diethylene glycol 123.52
    diisopropyl ether 4.71
    tert-amyl alcohol 68.16
    acetylacetone 39.38
    n-hexadecane 1.93
    acetophenone 39.17
    methyl propionate 35.06
    isopentyl acetate 17.65
    trichloroethylene 37.98
    n-nonanol 24.24
    cyclohexanol 38.26
    benzyl alcohol 47.03
    2-ethylhexanol 20.69
    isooctanol 18.43
    dipropyl ether 13.53
    1,2-dichlorobenzene 15.74
    ethyl lactate 25.58
    propylene carbonate 35.57
    n-methylformamide 164.61
    2-pentanol 30.31
    n-pentane 0.77
    1-propoxy-2-propanol 43.95
    1-methoxy-2-propyl acetate 28.37
    2-(2-methoxypropoxy) propanol 47.36
    mesitylene 8.07
    ε-caprolactone 41.06
    p-cymene 9.93
    epichlorohydrin 93.67
    1,1,1-trichloroethane 9.66
    2-aminoethanol 125.82
    morpholine-4-carbaldehyde 150.38
    sulfolane 134.71
    2,2,4-trimethylpentane 1.06
    2-methyltetrahydrofuran 58.36
    n-hexyl acetate 21.6
    isooctane 0.73
    2-(2-butoxyethoxy)ethanol 57.16
    sec-butyl acetate 10.43
    tert-butyl acetate 19.04
    decalin 2.22
    glycerin 100.0
    diglyme 99.03
    acrylic acid 33.22
    isopropyl myristate 12.24
    n-butyric acid 31.85
    acetyl acetate 11.77
    di(2-ethylhexyl) phthalate 16.92
    ethyl propionate 18.72
    nitromethane 77.86
    1,2-diethoxyethane 23.86
    benzonitrile 29.0
    trioctyl phosphate 14.13
    1-bromopropane 15.07
    gamma-valerolactone 100.43
    n-decanol 19.93
    triethyl phosphate 16.0
    4-methyl-2-pentanol 18.4
    propionitrile 30.53
    vinylene carbonate 35.13
    1,1,2-trichlorotrifluoroethane 75.99
    DMS 22.45
    cumene 11.24
    2-octanol 15.36
    2-hexanone 24.3
    octyl acetate 16.94
    limonene 12.02
    1,2-dimethoxyethane 162.37
    ethyl orthosilicate 14.71
    tributyl phosphate 13.47
    diacetone alcohol 50.82
    N,N-dimethylaniline 38.82
    acrylonitrile 44.38
    aniline 30.69
    1,3-propanediol 124.86
    bromobenzene 10.26
    dibromomethane 17.06
    1,1,2,2-tetrachloroethane 38.46
    2-methyl-cyclohexyl acetate 19.3
    tetrabutyl urea 26.15
    diisobutyl methanol 13.11
    2-phenylethanol 36.45
    styrene 14.5
    dioctyl adipate 19.1
    dimethyl sulfate 67.2
    ethyl butyrate 15.93
    methyl lactate 43.41
    butyl lactate 19.5
    diethyl carbonate 14.23
    propanediol butyl ether 42.01
    triethyl orthoformate 14.74
    p-tert-butyltoluene 9.21
    methyl 4-tert-butylbenzoate 35.98
    morpholine 114.88
    tert-butylamine 39.42
    n-dodecanol 15.88
    dimethoxymethane 157.91
    ethylene carbonate 27.73
    cyrene 55.34
    2-ethoxyethyl acetate 18.99
    2-ethylhexyl acetate 13.54
    1,2,4-trichlorobenzene 19.63
    4-methylpyridine 52.63
    dibutyl ether 14.08
    2,6-dimethyl-4-heptanol 13.11
    DEF 72.14
    dimethyl isosorbide 64.0
    tetrachloroethylene 22.99
    eugenol 43.89
    triacetin 21.83
    span 80 34.08
    1,4-butanediol 64.19
    1,1-dichloroethane 14.28
    2-methyl-1-pentanol 39.33
    methyl formate 118.77
    2-methyl-1-butanol 47.04
    n-decane 2.29
    butyronitrile 31.22
    3,7-dimethyl-1-octanol 20.17
    1-chlorooctane 10.07
    1-chlorotetradecane 5.4
    n-nonane 1.9
    undecane 2.0
    tert-butylcyclohexane 1.91
    cyclooctane 0.63
    cyclopentanol 43.54
    tetrahydropyran 45.54
    tert-amyl methyl ether 27.09
    2,5,8-trioxanonane 84.77
    1-hexene 6.37
    2-isopropoxyethanol 61.41
    2,2,2-trifluoroethanol 26.53
    methyl butyrate 29.36

    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