4-Hydroxy-3-methoxy-mandelic acid

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  • Identifiers

    CAS number
    13244-77-4

    Molecular formula
    C9H10O5

    SMILES
    COC1=C(C=CC(=C1)[C@@H](C(=O)O)O)O

  • Odor profile

    Fragrance
    Vanilla 71.98%
    Sweet 70.73%
    Creamy 52.67%
    Balsamic 43.75%
    Milky 42.49%
    Caramellic 41.92%
    Phenolic 38.9%
    Powdery 37.78%
    Odorless 33.97%
    Dairy 33.87%

     

    Flavor
    Odorless 55.68%
    Mild 34.03%
    Very mild 31.83%
    Bland 29.69%
    Sweet 25.64%
    Faint 24.88%
    Sour 24.01%
    Sweet-like 23.38%
    Creamy 22.9%
    Phenolic 22.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    6.7 (neutral)

    Molecular weight
    198.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    378°C

    Melting point expt.

    • 132 - 134 °C

    Flash point

    • 190.92 ˚C est.

  • Synonyms

    • Vanilmandelic acid, L-(+)-
    • (+)-Vanilmandelic acid
    • 13244-77-4
    • T9EAH8NHTC
    • UNII-T9EAH8NHTC
    • Vanilmandelic acid L-form [MI]
    • (2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
    • (S)-4-Hydroxy-3-methoxymandelic acid
    • L-(+)-3-Methoxy-4-hydroxymandelic acid
    • Lopac-H-0131
    • 4-hydroxy-3-methoxy-Mandelic acid
    • Benzeneacetic acid, alpha,4-dihydroxy-3-methoxy-, (S)-
    • Vanillomandelic acid
    • vanilmandelate
    • Vanillinmandelic Acid
    • 3-methoxy-4-hydroxymandelic acid
    • Vanillomandelate
    • 4'-Hydroxy-3'-methoxymandelic acid
    • Vanillinmandelate
    • 4-Hydroxy-3-methoxymandelate
    • vanylmandelic acid
    • DL-vanillomandelate
    • vanillymandelic acid
    • vanilylmandelic acid
    • vanyl-mandelic acid
    • DL-vanillylmandelate
    • vainillylmandelic acid
    • vanillylmandellic acid
    • vanillyl-mandelic acid
    • L-(+)-vanilmandelic acid
    • 4-hydroxy-3-methoxy-Mandelate
    • SCHEMBL1243722
    • 4'-Hydroxy-3'-methoxymandelate
    • CHEMBL1603851
    • DL-3-Methoxy-4-hydroxymandelate
    • DL-4-Hydroxy-3-methoxymandelate
    • 4-hydroxy 3-methoxymandelic acid
    • 4 Hydroxy 3 Methoxymandelic Acid
    • 3-methoxy-4-hydroxy-mandelic acid
    • 4-Hydroxy-3-methoxy-DL-mandelate
    • (4-Hydroxy-3-methoxyphenyl)glycolate
    • 4-Hydroxy-3-methoxy-DL-mandelic acid
    • AKOS040754340
    • 3-Methoxy-4-hydroxyphenylhydroxyacetate
    • NCGC00015492-01
    • Q27289848
    • BENZENEACETIC ACID, .ALPHA.,4-DIHYDROXY-3-METHOXY-, (S)-

  • Applications

    4-Hydroxy-3-methoxy-mandelic acid (CAS 13244-77-4) is primarily used as an intermediate and a chiral building block in the synthesis of pharmaceutical compounds and related fine chemicals. It is commonly evaluated as a precursor for active pharmaceutical ingredients and other specialty chemicals. In fragrance and flavor chemistry, it can serve as a starting point for the synthesis of aroma-related derivatives, while in cosmetics and personal care it may underpin chiral scaffolds for cosmetic actives. The compound can also be used as a functionalized aromatic building block in polymer and materials chemistry, and may be explored as an intermediate in the synthesis of agrochemicals, subject to regulatory and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 68.38
    methanol 175.82
    isopropanol 25.81
    water 21.75
    ethyl acetate 5.25
    n-propanol 26.39
    acetone 12.74
    n-butanol 13.46
    acetonitrile 1.74
    DMF 233.35
    toluene 0.67
    isobutanol 9.34
    1,4-dioxane 13.82
    methyl acetate 5.49
    THF 32.09
    2-butanone 7.72
    n-pentanol 5.61
    sec-butanol 16.13
    n-hexane 0.21
    ethylene glycol 182.93
    NMP 209.82
    cyclohexane 0.5
    DMSO 753.65
    n-butyl acetate 2.87
    n-octanol 5.81
    chloroform 0.32
    n-propyl acetate 2.05
    acetic acid 32.66
    dichloromethane 0.83
    cyclohexanone 6.51
    propylene glycol 77.52
    isopropyl acetate 3.53
    DMAc 159.45
    2-ethoxyethanol 83.19
    isopentanol 10.23
    n-heptane 0.73
    ethyl formate 5.51
    1,2-dichloroethane 1.77
    n-hexanol 8.08
    2-methoxyethanol 215.71
    isobutyl acetate 0.45
    tetrachloromethane 0.54
    n-pentyl acetate 3.01
    transcutol 90.82
    n-heptanol 7.2
    ethylbenzene 0.68
    MIBK 5.09
    2-propoxyethanol 43.69
    tert-butanol 45.3
    MTBE 7.0
    2-butoxyethanol 22.41
    propionic acid 17.23
    o-xylene 1.77
    formic acid 252.98
    diethyl ether 5.54
    m-xylene 1.22
    p-xylene 0.58
    chlorobenzene 0.34
    dimethyl carbonate 12.4
    n-octane 0.31
    formamide 387.92
    cyclopentanone 14.81
    2-pentanone 7.25
    anisole 4.1
    cyclopentyl methyl ether 10.98
    gamma-butyrolactone 27.2
    1-methoxy-2-propanol 115.44
    pyridine 4.32
    3-pentanone 5.06
    furfural 28.78
    n-dodecane 0.19
    diethylene glycol 99.03
    diisopropyl ether 1.96
    tert-amyl alcohol 29.86
    acetylacetone 14.1
    n-hexadecane 0.2
    acetophenone 5.9
    methyl propionate 10.51
    isopentyl acetate 2.53
    trichloroethylene 1.87
    n-nonanol 5.27
    cyclohexanol 8.03
    benzyl alcohol 6.39
    2-ethylhexanol 3.84
    isooctanol 4.99
    dipropyl ether 4.21
    1,2-dichlorobenzene 0.79
    ethyl lactate 10.02
    propylene carbonate 8.13
    n-methylformamide 115.35
    2-pentanol 9.84
    n-pentane 0.44
    1-propoxy-2-propanol 24.42
    1-methoxy-2-propyl acetate 11.38
    2-(2-methoxypropoxy) propanol 26.77
    mesitylene 1.27
    ε-caprolactone 9.48
    p-cymene 1.48
    epichlorohydrin 16.23
    1,1,1-trichloroethane 0.51
    2-aminoethanol 163.54
    morpholine-4-carbaldehyde 98.76
    sulfolane 117.04
    2,2,4-trimethylpentane 0.37
    2-methyltetrahydrofuran 12.05
    n-hexyl acetate 4.75
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 34.49
    sec-butyl acetate 1.29
    tert-butyl acetate 7.92
    decalin 0.25
    glycerin 199.74
    diglyme 59.46
    acrylic acid 24.81
    isopropyl myristate 1.99
    n-butyric acid 10.08
    acetyl acetate 3.34
    di(2-ethylhexyl) phthalate 4.02
    ethyl propionate 3.29
    nitromethane 51.46
    1,2-diethoxyethane 7.51
    benzonitrile 1.46
    trioctyl phosphate 3.54
    1-bromopropane 0.63
    gamma-valerolactone 33.5
    n-decanol 3.84
    triethyl phosphate 4.35
    4-methyl-2-pentanol 5.28
    propionitrile 1.68
    vinylene carbonate 5.5
    1,1,2-trichlorotrifluoroethane 45.92
    DMS 5.7
    cumene 0.75
    2-octanol 3.9
    2-hexanone 2.43
    octyl acetate 3.24
    limonene 2.31
    1,2-dimethoxyethane 47.2
    ethyl orthosilicate 3.64
    tributyl phosphate 2.99
    diacetone alcohol 34.64
    N,N-dimethylaniline 6.4
    acrylonitrile 3.75
    aniline 3.45
    1,3-propanediol 99.02
    bromobenzene 0.25
    dibromomethane 0.5
    1,1,2,2-tetrachloroethane 2.3
    2-methyl-cyclohexyl acetate 3.25
    tetrabutyl urea 6.55
    diisobutyl methanol 3.41
    2-phenylethanol 6.26
    styrene 0.57
    dioctyl adipate 4.25
    dimethyl sulfate 47.37
    ethyl butyrate 3.12
    methyl lactate 35.25
    butyl lactate 7.72
    diethyl carbonate 2.57
    propanediol butyl ether 26.93
    triethyl orthoformate 3.77
    p-tert-butyltoluene 1.76
    methyl 4-tert-butylbenzoate 14.72
    morpholine 29.13
    tert-butylamine 13.06
    n-dodecanol 2.6
    dimethoxymethane 81.03
    ethylene carbonate 3.64
    cyrene 35.09
    2-ethoxyethyl acetate 7.29
    2-ethylhexyl acetate 1.66
    1,2,4-trichlorobenzene 1.29
    4-methylpyridine 3.15
    dibutyl ether 2.24
    2,6-dimethyl-4-heptanol 3.41
    DEF 25.94
    dimethyl isosorbide 35.63
    tetrachloroethylene 3.21
    eugenol 15.08
    triacetin 9.9
    span 80 17.59
    1,4-butanediol 32.28
    1,1-dichloroethane 0.38
    2-methyl-1-pentanol 4.73
    methyl formate 50.75
    2-methyl-1-butanol 9.52
    n-decane 0.34
    butyronitrile 1.32
    3,7-dimethyl-1-octanol 4.19
    1-chlorooctane 1.05
    1-chlorotetradecane 0.42
    n-nonane 0.32
    undecane 0.25
    tert-butylcyclohexane 0.23
    cyclooctane 0.36
    cyclopentanol 12.26
    tetrahydropyran 4.4
    tert-amyl methyl ether 9.1
    2,5,8-trioxanonane 46.23
    1-hexene 0.5
    2-isopropoxyethanol 26.94
    2,2,2-trifluoroethanol 25.0
    methyl butyrate 4.02

    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