4-Methylmandelic acid

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  • Identifiers

    CAS number
    18584-20-8

    Molecular formula
    C9H10O3

    SMILES
    CC1=CC=C(C=C1)C(C(=O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 69.75%
    Honey 51.91%
    Floral 42.98%
    Powdery 39.76%
    Vanilla 39.2%
    Almond 39.0%
    Balsamic 37.5%
    Creamy 36.82%
    Phenolic 35.04%
    Fruity 33.9%

     

    Flavor
    Odorless 46.62%
    Sweet 45.11%
    Mild 36.6%
    Sour 32.03%
    Fruity 28.43%
    Faint 26.27%
    Phenolic 26.13%
    Balsamic 25.01%
    Powdery 24.16%
    Balsam 24.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    6.1 (neutral)

    Molecular weight
    166.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    304°C

    Flash point

    • 151.3 ˚C est.

  • Synonyms

    • 18584-20-8
    • 4-Methylmandelic acid
    • 2S2B4H5RL9
    • NSC-126594
    • RefChem:1071175
    • 2-hydroxy-2-(4-methylphenyl)acetic acid
    • hydroxy-p-tolyl-acetic acid
    • 2-hydroxy-2-(p-tolyl)acetic acid
    • MFCD00961860
    • p-methylmandelic acid
    • P-methyl mandelic acid
    • 4-Methyl-D-mandelic acid
    • NSC126594
    • NSC 126594
    • alpha-Hydroxy-4-methylbenzeneacetic acid
    • p-Methyl-mandelic acid
    • Benzeneacetic acid, alpha-hydroxy-4-methyl-
    • UNII-2S2B4H5RL9
    • SCHEMBL245405
    • 4-Methylcarboxy-benzyl alcohol
    • 2-hydroxy-2-(p-tolyl)aceticacid
    • SBB065020
    • AKOS002676241
    • AKOS016046698
    • SS-2000
    • AC-19772
    • SY287845
    • CS-0318386
    • F20952
    • F722401
    • 18584-20-8

  • Applications

    4-Methylmandelic acid (CAS 18584-20-8) is primarily used as an organic synthesis intermediate, providing a substituted mandelic acid framework that enables the preparation of more complex molecules in pharmaceutical and agrochemical development. It is employed as a chiral building block or resolving agent in asymmetric synthesis due to its aromatic alpha-hydroxy acid structure. The compound also serves as a precursor in fragrance chemistry, enabling the synthesis of substituted aroma compounds. Through functionalization, it may be used as a starting material for dyes, polymers, or other specialty chemicals. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 96.19
    methanol 182.79
    isopropanol 53.88
    water 6.97
    ethyl acetate 42.7
    n-propanol 53.12
    acetone 38.27
    n-butanol 35.44
    acetonitrile 7.21
    DMF 89.26
    toluene 7.67
    isobutanol 34.89
    1,4-dioxane 26.05
    methyl acetate 25.61
    THF 80.95
    2-butanone 35.89
    n-pentanol 23.36
    sec-butanol 50.58
    n-hexane 1.08
    ethylene glycol 112.12
    NMP 258.27
    cyclohexane 1.08
    DMSO 287.25
    n-butyl acetate 25.37
    n-octanol 16.86
    chloroform 2.85
    n-propyl acetate 16.16
    acetic acid 83.25
    dichloromethane 3.54
    cyclohexanone 36.13
    propylene glycol 77.72
    isopropyl acetate 26.86
    DMAc 204.0
    2-ethoxyethanol 128.88
    isopentanol 47.53
    n-heptane 1.93
    ethyl formate 16.23
    1,2-dichloroethane 7.97
    n-hexanol 51.92
    2-methoxyethanol 235.54
    isobutyl acetate 5.91
    tetrachloromethane 3.52
    n-pentyl acetate 14.55
    transcutol 252.83
    n-heptanol 26.05
    ethylbenzene 7.26
    MIBK 33.86
    2-propoxyethanol 124.73
    tert-butanol 127.65
    MTBE 32.32
    2-butoxyethanol 64.42
    propionic acid 68.25
    o-xylene 13.59
    formic acid 179.96
    diethyl ether 14.06
    m-xylene 13.85
    p-xylene 6.58
    chlorobenzene 4.97
    dimethyl carbonate 29.51
    n-octane 0.75
    formamide 305.31
    cyclopentanone 72.16
    2-pentanone 44.84
    anisole 23.46
    cyclopentyl methyl ether 50.16
    gamma-butyrolactone 110.83
    1-methoxy-2-propanol 155.87
    pyridine 18.08
    3-pentanone 25.34
    furfural 76.64
    n-dodecane 0.53
    diethylene glycol 157.18
    diisopropyl ether 9.79
    tert-amyl alcohol 115.65
    acetylacetone 55.76
    n-hexadecane 0.59
    acetophenone 32.51
    methyl propionate 47.72
    isopentyl acetate 25.12
    trichloroethylene 15.56
    n-nonanol 15.47
    cyclohexanol 27.56
    benzyl alcohol 29.33
    2-ethylhexanol 26.16
    isooctanol 21.65
    dipropyl ether 15.13
    1,2-dichlorobenzene 8.62
    ethyl lactate 30.39
    propylene carbonate 45.43
    n-methylformamide 94.61
    2-pentanol 38.69
    n-pentane 1.14
    1-propoxy-2-propanol 79.37
    1-methoxy-2-propyl acetate 54.69
    2-(2-methoxypropoxy) propanol 65.4
    mesitylene 10.19
    ε-caprolactone 49.76
    p-cymene 8.59
    epichlorohydrin 70.75
    1,1,1-trichloroethane 6.33
    2-aminoethanol 149.34
    morpholine-4-carbaldehyde 137.18
    sulfolane 211.11
    2,2,4-trimethylpentane 2.04
    2-methyltetrahydrofuran 61.01
    n-hexyl acetate 22.16
    isooctane 1.72
    2-(2-butoxyethoxy)ethanol 96.97
    sec-butyl acetate 13.67
    tert-butyl acetate 46.38
    decalin 1.6
    glycerin 157.43
    diglyme 141.61
    acrylic acid 72.18
    isopropyl myristate 8.68
    n-butyric acid 52.6
    acetyl acetate 19.19
    di(2-ethylhexyl) phthalate 14.12
    ethyl propionate 20.19
    nitromethane 99.86
    1,2-diethoxyethane 27.21
    benzonitrile 10.69
    trioctyl phosphate 11.5
    1-bromopropane 2.89
    gamma-valerolactone 88.97
    n-decanol 11.91
    triethyl phosphate 15.4
    4-methyl-2-pentanol 30.09
    propionitrile 7.65
    vinylene carbonate 25.39
    1,1,2-trichlorotrifluoroethane 104.02
    DMS 24.18
    cumene 7.43
    2-octanol 13.14
    2-hexanone 17.49
    octyl acetate 12.92
    limonene 11.87
    1,2-dimethoxyethane 69.16
    ethyl orthosilicate 14.16
    tributyl phosphate 11.14
    diacetone alcohol 121.44
    N,N-dimethylaniline 27.29
    acrylonitrile 13.38
    aniline 20.2
    1,3-propanediol 142.85
    bromobenzene 3.71
    dibromomethane 2.57
    1,1,2,2-tetrachloroethane 16.46
    2-methyl-cyclohexyl acetate 21.34
    tetrabutyl urea 18.92
    diisobutyl methanol 17.18
    2-phenylethanol 39.32
    styrene 5.73
    dioctyl adipate 15.27
    dimethyl sulfate 77.48
    ethyl butyrate 19.5
    methyl lactate 64.94
    butyl lactate 27.12
    diethyl carbonate 13.19
    propanediol butyl ether 66.1
    triethyl orthoformate 14.99
    p-tert-butyltoluene 9.66
    methyl 4-tert-butylbenzoate 42.25
    morpholine 47.69
    tert-butylamine 43.67
    n-dodecanol 8.18
    dimethoxymethane 75.94
    ethylene carbonate 19.28
    cyrene 72.15
    2-ethoxyethyl acetate 29.51
    2-ethylhexyl acetate 16.08
    1,2,4-trichlorobenzene 13.0
    4-methylpyridine 17.64
    dibutyl ether 6.94
    2,6-dimethyl-4-heptanol 17.18
    DEF 69.76
    dimethyl isosorbide 101.64
    tetrachloroethylene 18.65
    eugenol 43.86
    triacetin 30.73
    span 80 47.28
    1,4-butanediol 54.19
    1,1-dichloroethane 3.75
    2-methyl-1-pentanol 31.79
    methyl formate 57.52
    2-methyl-1-butanol 46.25
    n-decane 0.85
    butyronitrile 6.64
    3,7-dimethyl-1-octanol 20.76
    1-chlorooctane 3.72
    1-chlorotetradecane 1.71
    n-nonane 0.75
    undecane 0.67
    tert-butylcyclohexane 1.83
    cyclooctane 0.9
    cyclopentanol 42.85
    tetrahydropyran 13.46
    tert-amyl methyl ether 42.94
    2,5,8-trioxanonane 105.15
    1-hexene 3.33
    2-isopropoxyethanol 76.21
    2,2,2-trifluoroethanol 50.24
    methyl butyrate 24.23

    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