(S)-mandelic acid

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  • Identifiers

    CAS number
    17199-29-0

    Molecular formula
    C8H8O3

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

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 72.67%
    Honey 51.61%
    Caramellic 43.98%
    Balsamic 42.38%
    Almond 40.89%
    Vanilla 37.41%
    Creamy 37.25%
    Spicy 34.39%
    Powdery 33.95%
    Phenolic 33.34%

     

    Flavor
    Odorless 50.01%
    Sweet 45.69%
    Sour 39.06%
    Mild 34.92%
    Faint 27.74%
    Honey 26.86%
    Balsam 26.54%
    Balsamic 25.94%
    Very mild 24.77%
    Fruity 23.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    5.85 (weak acid)

    Molecular weight
    152.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    290°C

    Melting point expt.

    • 119 °C
    • 120 - 122 °C

    Flash point

    • 158.31 ˚C est.

    Solubility expt.

    • 181000 mg/L (at 25 °C)
    • 181.0 mg/mL

  • Synonyms

    • 17199-29-0
    • (S)-Mandelic acid
    • (S)-2-Hydroxy-2-phenylacetic acid
    • Mandelic acid, (S)-
    • Mandelic acid, L-
    • D-2-Hydroxy-2-phenylacetic acid
    • (S)-alpha-hydroxybenzeneacetic acid
    • L0UMW58G3T
    • CHEBI:32800
    • DTXSID301014792
    • RefChem:906467
    • DTXCID601471549
    • 241-240-8
    • (S)-(+)-Mandelic acid
    • L-mandelic acid
    • (2S)-2-hydroxy-2-phenylacetic acid
    • S-(+)-Mandelic acid
    • L-(+)-MANDELIC ACID
    • MFCD00004495
    • Atomoxetine EP Impurity E
    • l(+)-mandelic acid
    • (S)-(+)-Mandelic acid, 98% e.e.
    • CHEMBL58910
    • MLS000069517
    • (2s)-hydroxy(phenyl)ethanoic acid
    • (S)-alpha-Hydroxyphenylacetic acid
    • Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-
    • SMR000058582
    • (2S)-2-Hydroxy-2-phenylacetic Acid (L-Mandelic Acid)
    • SMN
    • (S)-(+)-Mandelic acid, ReagentPlus(R), >=99%
    • alpha-Hydroxy-alpha-toluic acid
    • UNII-L0UMW58G3T
    • 2-Hydroxy-2-phenylethanoic acid
    • alpha-hydroxybenzeneacetate
    • Amygdalate
    • Paramandelate
    • Phenylglycolate
    • DL-Amygdalate
    • (+-)-alpha-Hydroxybenzeneacetic acid
    • (S)-Hydroxy-phenyl-acetic acid
    • DL-Mandelate
    • 2-Phenylglycolate
    • (RS)-Mandelate
    • (S)-Mandelsaeure
    • Phenylhydroxyacetate
    • EINECS 241-240-8
    • a-Hydroxy-a-toluate
    • a-Hydroxyphenylacetate
    • alpha-Hydroxybenzeneacetic acid, (S)-
    • L-(+)mandelic acid
    • (2S)-2-hydroxy-2-phenyl-acetic acid
    • a-Hydroxybenzeneacetate
    • (S)-L-Mandelic acid
    • Opera_ID_622
    • a-Hydroxy-a-toluic acid
    • (s)(+)-mandelic acid
    • alpha-Hydroxyphenylacetate
    • a-Hydroxyphenylacetic acid
    • DL-Hydroxy(phenyl)acetate
    • (+)-(s)-mandelic acid
    • a-Hydroxybenzeneacetic acid
    • 2-Phenyl-2-hydroxyacetate
    • (S)-hydroxyphenylaceticacid
    • alpha-Hydroxy-alpha-toluate
    • Benzeneacetic acid, alpha-hydroxy-, (alphaS)-
    • EC 241-240-8
    • cid_1292
    • (S)-(+)-Amygdalic Acid
    • 2-Hydroxy-2-phenylethanoate
    • (S)--(+)--mandelic acid
    • SCHEMBL255601
    • cid_439616
    • orb2940011
    • (S)-?-Hydroxyphenylacetic acid
    • BDBM16420
    • HMS2233J03
    • BB_NC-02315
    • CS-D1423
    • HY-Y0816
    • STR07719
    • EBC-14286
    • (S)-A-HYDROXYPHENYLACETIC ACID
    • AKOS006343440
    • AKOS007930623
    • AC-2496
    • DB03357
    • FM25008
    • ST075171
    • SY001670
    • Benzeneacetic acid, alpha-hydroxy-, (S)-
    • M0661
    • (+)-.ALPHA.-HYDROXYPHENYLACETIC ACID
    • EN300-97210
    • C01984
    • MLS-0090889.0001
    • SBI-0633447.0002
    • L-(+)-Mandelic acid, purum, >=98.0% (T)
    • F046847
    • Q27096314
    • (S)-(+)-Mandelic acid, Vetec(TM) reagent grade, 99%
    • Z1201618616
    • ATOMOXETINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
    • 17199-29-0

  • Applications

    (S)-mandelic acid, CAS 17199-29-0, is a chiral building block and pharmaceutical intermediate used in the synthesis of active pharmaceutical ingredients and other fine chemicals, and it can also serve as a resolving agent or ligand in asymmetric synthesis. In cosmetics and personal care, it functions as an alpha-hydroxy acid exfoliant to improve skin texture. In fragrance and flavor applications, its almond-like aroma can be used as a fragrance ingredient or precursor for fragrance molecules. Additionally, its mandelate derivatives serve as precursors in polymer synthesis and other polymeric materials research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 143.36
    methanol 233.76
    isopropanol 78.36
    water 23.77
    ethyl acetate 22.54
    n-propanol 75.47
    acetone 42.56
    n-butanol 48.35
    acetonitrile 22.21
    DMF 483.96
    toluene 4.66
    isobutanol 33.22
    1,4-dioxane 45.56
    methyl acetate 23.14
    THF 70.27
    2-butanone 30.18
    n-pentanol 34.24
    sec-butanol 49.33
    n-hexane 0.85
    ethylene glycol 193.39
    NMP 208.93
    cyclohexane 1.21
    DMSO 546.94
    n-butyl acetate 12.35
    n-octanol 33.29
    chloroform 5.09
    n-propyl acetate 11.33
    acetic acid 46.53
    dichloromethane 11.68
    cyclohexanone 27.8
    propylene glycol 97.51
    isopropyl acetate 14.15
    DMAc 321.5
    2-ethoxyethanol 130.75
    isopentanol 32.04
    n-heptane 3.67
    ethyl formate 19.39
    1,2-dichloroethane 16.76
    n-hexanol 36.24
    2-methoxyethanol 240.29
    isobutyl acetate 4.76
    tetrachloromethane 2.0
    n-pentyl acetate 14.34
    transcutol 175.81
    n-heptanol 35.94
    ethylbenzene 5.67
    MIBK 17.9
    2-propoxyethanol 89.16
    tert-butanol 77.59
    MTBE 20.3
    2-butoxyethanol 64.66
    propionic acid 36.76
    o-xylene 9.68
    formic acid 105.17
    diethyl ether 17.78
    m-xylene 8.98
    p-xylene 5.19
    chlorobenzene 5.01
    dimethyl carbonate 27.03
    n-octane 2.11
    formamide 207.97
    cyclopentanone 44.45
    2-pentanone 27.61
    anisole 18.68
    cyclopentyl methyl ether 24.06
    gamma-butyrolactone 65.55
    1-methoxy-2-propanol 150.26
    pyridine 20.51
    3-pentanone 16.69
    furfural 54.44
    n-dodecane 2.21
    diethylene glycol 123.23
    diisopropyl ether 6.34
    tert-amyl alcohol 56.81
    acetylacetone 35.0
    n-hexadecane 2.32
    acetophenone 23.94
    methyl propionate 36.35
    isopentyl acetate 11.87
    trichloroethylene 18.75
    n-nonanol 30.39
    cyclohexanol 24.53
    benzyl alcohol 27.81
    2-ethylhexanol 18.01
    isooctanol 24.34
    dipropyl ether 16.78
    1,2-dichlorobenzene 8.33
    ethyl lactate 23.31
    propylene carbonate 26.23
    n-methylformamide 190.05
    2-pentanol 32.91
    n-pentane 1.21
    1-propoxy-2-propanol 59.97
    1-methoxy-2-propyl acetate 30.56
    2-(2-methoxypropoxy) propanol 56.91
    mesitylene 8.17
    ε-caprolactone 30.64
    p-cymene 9.48
    epichlorohydrin 59.29
    1,1,1-trichloroethane 5.03
    2-aminoethanol 193.85
    morpholine-4-carbaldehyde 149.85
    sulfolane 135.65
    2,2,4-trimethylpentane 1.42
    2-methyltetrahydrofuran 30.93
    n-hexyl acetate 20.91
    isooctane 1.42
    2-(2-butoxyethoxy)ethanol 89.43
    sec-butyl acetate 7.57
    tert-butyl acetate 19.19
    decalin 1.69
    glycerin 153.33
    diglyme 124.51
    acrylic acid 37.87
    isopropyl myristate 12.21
    n-butyric acid 31.56
    acetyl acetate 11.57
    di(2-ethylhexyl) phthalate 16.03
    ethyl propionate 14.03
    nitromethane 85.35
    1,2-diethoxyethane 29.3
    benzonitrile 13.64
    trioctyl phosphate 15.91
    1-bromopropane 5.56
    gamma-valerolactone 73.55
    n-decanol 25.27
    triethyl phosphate 11.19
    4-methyl-2-pentanol 15.86
    propionitrile 15.94
    vinylene carbonate 21.9
    1,1,2-trichlorotrifluoroethane 70.64
    DMS 16.36
    cumene 6.5
    2-octanol 20.35
    2-hexanone 13.19
    octyl acetate 17.71
    limonene 12.32
    1,2-dimethoxyethane 87.8
    ethyl orthosilicate 10.68
    tributyl phosphate 11.97
    diacetone alcohol 57.2
    N,N-dimethylaniline 25.85
    acrylonitrile 30.37
    aniline 13.98
    1,3-propanediol 147.8
    bromobenzene 4.03
    dibromomethane 6.16
    1,1,2,2-tetrachloroethane 20.6
    2-methyl-cyclohexyl acetate 13.52
    tetrabutyl urea 27.01
    diisobutyl methanol 14.56
    2-phenylethanol 30.32
    styrene 5.08
    dioctyl adipate 19.59
    dimethyl sulfate 60.21
    ethyl butyrate 13.37
    methyl lactate 58.61
    butyl lactate 22.06
    diethyl carbonate 8.92
    propanediol butyl ether 66.44
    triethyl orthoformate 11.14
    p-tert-butyltoluene 10.0
    methyl 4-tert-butylbenzoate 42.55
    morpholine 75.91
    tert-butylamine 29.14
    n-dodecanol 20.03
    dimethoxymethane 135.16
    ethylene carbonate 16.31
    cyrene 61.72
    2-ethoxyethyl acetate 23.1
    2-ethylhexyl acetate 7.95
    1,2,4-trichlorobenzene 11.03
    4-methylpyridine 16.52
    dibutyl ether 12.49
    2,6-dimethyl-4-heptanol 14.56
    DEF 75.64
    dimethyl isosorbide 70.39
    tetrachloroethylene 15.1
    eugenol 46.79
    triacetin 24.88
    span 80 48.54
    1,4-butanediol 76.56
    1,1-dichloroethane 6.27
    2-methyl-1-pentanol 21.65
    methyl formate 86.69
    2-methyl-1-butanol 29.68
    n-decane 2.89
    butyronitrile 14.07
    3,7-dimethyl-1-octanol 21.46
    1-chlorooctane 9.92
    1-chlorotetradecane 5.22
    n-nonane 2.59
    undecane 2.53
    tert-butylcyclohexane 1.56
    cyclooctane 1.17
    cyclopentanol 32.5
    tetrahydropyran 18.53
    tert-amyl methyl ether 21.71
    2,5,8-trioxanonane 107.79
    1-hexene 2.85
    2-isopropoxyethanol 63.48
    2,2,2-trifluoroethanol 32.91
    methyl butyrate 17.18

    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