Methyl 2,5-dihydroxycinnamate

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  • Identifiers

    CAS number
    63177-57-1

    Molecular formula
    C10H10O4

    SMILES
    COC(=O)/C=C/C1=C(C=CC(=C1)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 49.05%
    Odorless 46.89%
    Vanilla 39.43%
    Spicy 37.82%
    Burnt 32.39%
    Balsamic 31.96%
    Sweet 28.4%
    Aromatic 25.91%
    Smoky 25.1%
    Milky 24.29%

     

    Flavor
    Bitter 61.13%
    Odorless 40.95%
    Mild 25.21%
    Bland 22.98%
    Very mild 21.44%
    Ethyl benzoate 20.49%
    Orange flower 20.33%
    Lovage 19.88%
    Nitrile 19.8%
    Parsley 19.74%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    8.74 (weak base)

    Molecular weight
    194.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    394°C

    Flash point

    • 178.1 ˚C est.

  • Synonyms

    • Methyl 2,5-dihydroxycinnamate
    • 63177-57-1
    • 2,5-Dihydroxycinnamic acid methyl ester
    • 2,4-Dihydroxymethylcinnamate
    • methyl (E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
    • Methyl 3-(2,5-dihydroxyphenyl)-2-propenoate
    • 2-Propenoic acid, 3-(2,5-dihydroxyphenyl)-, methyl ester
    • 6LF2DGK4XM
    • methyl-2,5-dihydroxycinnamate
    • CHEBI:84089
    • methyl 3-(2,5-dihydroxyphenyl)prop-2-enoate
    • RefChem:812957
    • 3-(2,5-dihydroxyphenyl)-2-propenoic acid methyl ester
    • BML-EI146
    • ALX-270-098
    • 636-304-0
    • methyl 3-(2,5-dihydroxyphenyl)acrylate
    • 123064-80-2
    • (E)-methyl 3-(2,5-dihydroxyphenyl)acrylate
    • MFCD00132932
    • 2-Propenoic acid, 3-(2,5-dihydroxyphenyl)-, methyl ester, (2E)-
    • methyl (2E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
    • CHEMBL17329
    • Methyl 2,5-dihydoxycinnamate
    • methyl grevillate
    • BQCNSTFWSKOWMA-GORDUTHDSA-N
    • DTXSID401365019
    • BiomolKI_000061
    • BiomolKI2_000067
    • BMK1-G1
    • SCHEMBL343784
    • orb1305764
    • CHEBI:93543
    • HMS3411G10
    • HMS3675G10
    • BDBM50025624
    • HSCI1_000370
    • AKOS006271583
    • CCG-100665
    • EBC-511213
    • Methyl 2 pound not5-Dihydroxycinnamate
    • SMP2_000107
    • NCGC00024661-02
    • AS-59872
    • BS-14687
    • methyl 3-(2',5'dihydroxyphenyl)acrylate
    • HY-101006
    • (E)-3-(2,5-dihydroxyphenyl)prop-2-enoate
    • CS-0020685
    • CS-0166762
    • F16667
    • K00021
    • Methyl (2E)-3-(2,5-dihydroxyphenyl)acrylate
    • F601081
    • SR-01000597715
    • Methyl (2E)-3-(2,5-dihydroxyphenyl)-2-propenoate
    • SR-01000597715-1
    • BRD-K35573744-001-02-7
    • BRD-K35573744-001-06-8
    • BRD-K88741031-001-01-0
    • Methyl 3-(2,5-dihydroxyphenyl)acrylate(only trans-)
    • Q27157467
    • 2,5-Dihydroxycinnamic acid methyl ester, >=95%, crystalline
    • 63177-57-1

  • Applications

    Methyl 2,5-dihydroxycinnamate (CAS 63177-57-1) is used as a synthetic building block and intermediate for hydroxycinnamate derivatives in pharmaceutical and fine-chemical synthesis. In polymers, coatings, and adhesives, it often serves as an antioxidant and light stabilizer to improve oxidative and photostability of materials. In cosmetics and personal care, hydroxycinnamate esters may be used as antioxidants and can act as fragrance precursors or formulation stabilizers. In fragrance and perfumery applications, it can serve as an aroma-active constituent or a precursor for scent-related compounds, contributing to fragrance profiles.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 31.26
    methanol 39.07
    isopropanol 23.68
    water 0.39
    ethyl acetate 18.04
    n-propanol 24.62
    acetone 29.32
    n-butanol 16.89
    acetonitrile 12.22
    DMF 143.98
    toluene 1.14
    isobutanol 11.44
    1,4-dioxane 43.82
    methyl acetate 34.06
    THF 119.45
    2-butanone 39.17
    n-pentanol 11.44
    sec-butanol 28.76
    n-hexane 0.11
    ethylene glycol 17.3
    NMP 82.05
    cyclohexane 0.1
    DMSO 216.08
    n-butyl acetate 8.87
    n-octanol 3.58
    chloroform 3.75
    n-propyl acetate 10.63
    acetic acid 29.63
    dichloromethane 4.64
    cyclohexanone 19.71
    propylene glycol 20.09
    isopropyl acetate 11.11
    DMAc 236.41
    2-ethoxyethanol 75.39
    isopentanol 17.5
    n-heptane 0.16
    ethyl formate 11.41
    1,2-dichloroethane 5.51
    n-hexanol 8.87
    2-methoxyethanol 107.33
    isobutyl acetate 3.88
    tetrachloromethane 0.83
    n-pentyl acetate 4.81
    transcutol 126.19
    n-heptanol 4.7
    ethylbenzene 1.52
    MIBK 12.8
    2-propoxyethanol 41.9
    tert-butanol 61.75
    MTBE 30.85
    2-butoxyethanol 18.87
    propionic acid 21.95
    o-xylene 2.51
    formic acid 48.8
    diethyl ether 17.2
    m-xylene 1.25
    p-xylene 1.88
    chlorobenzene 1.63
    dimethyl carbonate 19.63
    n-octane 0.08
    formamide 139.99
    cyclopentanone 42.95
    2-pentanone 18.23
    anisole 19.63
    cyclopentyl methyl ether 16.16
    gamma-butyrolactone 54.37
    1-methoxy-2-propanol 67.75
    pyridine 15.8
    3-pentanone 15.41
    furfural 49.32
    n-dodecane 0.1
    diethylene glycol 52.4
    diisopropyl ether 3.39
    tert-amyl alcohol 59.54
    acetylacetone 24.58
    n-hexadecane 0.12
    acetophenone 18.29
    methyl propionate 24.17
    isopentyl acetate 9.59
    trichloroethylene 11.17
    n-nonanol 3.86
    cyclohexanol 9.05
    benzyl alcohol 15.63
    2-ethylhexanol 5.56
    isooctanol 4.23
    dipropyl ether 6.05
    1,2-dichlorobenzene 3.17
    ethyl lactate 13.87
    propylene carbonate 19.07
    n-methylformamide 59.16
    2-pentanol 12.14
    n-pentane 0.09
    1-propoxy-2-propanol 25.32
    1-methoxy-2-propyl acetate 21.78
    2-(2-methoxypropoxy) propanol 35.81
    mesitylene 1.14
    ε-caprolactone 22.01
    p-cymene 1.99
    epichlorohydrin 60.78
    1,1,1-trichloroethane 3.2
    2-aminoethanol 33.2
    morpholine-4-carbaldehyde 85.65
    sulfolane 84.77
    2,2,4-trimethylpentane 0.35
    2-methyltetrahydrofuran 42.67
    n-hexyl acetate 8.16
    isooctane 0.16
    2-(2-butoxyethoxy)ethanol 38.72
    sec-butyl acetate 7.72
    tert-butyl acetate 20.33
    decalin 0.26
    glycerin 47.1
    diglyme 74.61
    acrylic acid 22.49
    isopropyl myristate 3.85
    n-butyric acid 15.23
    acetyl acetate 9.81
    di(2-ethylhexyl) phthalate 6.54
    ethyl propionate 13.3
    nitromethane 81.66
    1,2-diethoxyethane 19.77
    benzonitrile 6.71
    trioctyl phosphate 3.91
    1-bromopropane 2.1
    gamma-valerolactone 55.09
    n-decanol 2.87
    triethyl phosphate 10.25
    4-methyl-2-pentanol 7.74
    propionitrile 11.12
    vinylene carbonate 14.88
    1,1,2-trichlorotrifluoroethane 53.0
    DMS 13.73
    cumene 1.66
    2-octanol 2.71
    2-hexanone 12.68
    octyl acetate 5.09
    limonene 2.71
    1,2-dimethoxyethane 85.86
    ethyl orthosilicate 8.87
    tributyl phosphate 5.31
    diacetone alcohol 43.48
    N,N-dimethylaniline 14.32
    acrylonitrile 16.05
    aniline 8.58
    1,3-propanediol 39.46
    bromobenzene 1.08
    dibromomethane 2.07
    1,1,2,2-tetrachloroethane 11.16
    2-methyl-cyclohexyl acetate 10.44
    tetrabutyl urea 8.97
    diisobutyl methanol 4.13
    2-phenylethanol 11.77
    styrene 1.88
    dioctyl adipate 8.68
    dimethyl sulfate 48.51
    ethyl butyrate 9.72
    methyl lactate 25.98
    butyl lactate 8.88
    diethyl carbonate 9.14
    propanediol butyl ether 19.24
    triethyl orthoformate 10.16
    p-tert-butyltoluene 2.1
    methyl 4-tert-butylbenzoate 18.0
    morpholine 74.56
    tert-butylamine 16.16
    n-dodecanol 2.1
    dimethoxymethane 71.46
    ethylene carbonate 11.41
    cyrene 34.09
    2-ethoxyethyl acetate 13.17
    2-ethylhexyl acetate 6.54
    1,2,4-trichlorobenzene 5.23
    4-methylpyridine 13.52
    dibutyl ether 4.39
    2,6-dimethyl-4-heptanol 4.13
    DEF 35.88
    dimethyl isosorbide 47.78
    tetrachloroethylene 6.98
    eugenol 19.65
    triacetin 16.43
    span 80 17.33
    1,4-butanediol 14.1
    1,1-dichloroethane 2.5
    2-methyl-1-pentanol 13.51
    methyl formate 33.85
    2-methyl-1-butanol 16.73
    n-decane 0.17
    butyronitrile 7.19
    3,7-dimethyl-1-octanol 5.01
    1-chlorooctane 1.1
    1-chlorotetradecane 0.49
    n-nonane 0.13
    undecane 0.13
    tert-butylcyclohexane 0.3
    cyclooctane 0.07
    cyclopentanol 12.88
    tetrahydropyran 17.93
    tert-amyl methyl ether 26.77
    2,5,8-trioxanonane 57.86
    1-hexene 0.83
    2-isopropoxyethanol 39.83
    2,2,2-trifluoroethanol 17.98
    methyl butyrate 16.03

    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