Isoferulic Acid

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  • Identifiers

    CAS number
    537-73-5

    Molecular formula
    C10H10O4

    SMILES
    COC1=C(C=C(C=C1)/C=C/C(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Vanilla 51.4%
    Balsamic 48.63%
    Spicy 44.22%
    Phenolic 44.04%
    Odorless 43.54%
    Sweet 37.81%
    Creamy 35.25%
    Milky 33.03%
    Burnt 29.66%
    Caramellic 28.65%

     

    Flavor
    Odorless 42.27%
    Phenolic 30.67%
    Sweet 30.49%
    Mild 30.34%
    Faint 29.64%
    Balsam 27.05%
    Balsamic 26.69%
    Powdery 23.48%
    Sour 22.95%
    Nutty 22.42%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    8.18 (weak base)

    Molecular weight
    194.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 228 - 233 °C

    Boiling point

    • 409.00 to 411.00 °C. @ 760.00 mm Hg

    Flash point

    • 180.76 ˚C est.

  • Synonyms

    • Isoferulic acid
    • 3-Hydroxy-4-methoxycinnamic acid
    • 537-73-5
    • Hesperetic acid
    • (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
    • 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid
    • XSQ2K2G7MC
    • (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
    • NSC-51987
    • CHEBI:27794
    • DTXSID80862148
    • RefChem:39780
    • DTXCID50810954
    • 208-676-0
    • 25522-33-2
    • trans-Isoferulic acid
    • 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid
    • (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid
    • 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-
    • MFCD00004391
    • Isoferulate
    • (E)-3'-Hydroxy-4'-methoxycinnamic acid
    • Cinnamic acid, 3-hydroxy-4-methoxy-
    • trans-3-Hydroxy-4-methoxycinnamic acid
    • CHEMBL233295
    • (E)-3-(3-hydroxy-4-methoxy-phenyl)-acrylic acid
    • 3-Hydroxy-4-methoxycinnamic acid (isoferulic acid)
    • cis-Isoferulic acid
    • 3-Hydroxy-4-methoxycinnamate
    • Hesperetinic acid
    • 3-hydroxy-4-methoxy-cinnamic acid
    • UNII-XSQ2K2G7MC
    • Hesperetate
    • Isoferulasaure
    • isoferrulic acid
    • iso-ferulic acid
    • Hesperetic acid;
    • rans-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid; trans-3-Hydroxy-4-methoxycinnamic acid; Hesperetic acid; trans-Isoferulic acid
    • EINECS 208-676-0
    • EINECS 247-071-6
    • NSC 51987
    • BRN 2212760
    • bmse000618
    • 4-10-00-01777 (Beilstein Handbook Reference)
    • MLS000563054
    • SCHEMBL249041
    • 3-hydroxy-4-methoxy-Cinnamate
    • 4-O-METHYLCAFFEIC ACID
    • 3-Hydroxy-4-methoxycinnamic acid, predominantly trans
    • GTPL7980
    • orb1304884
    • SCHEMBL29574481
    • HY-N0761A
    • 3-Hydroxy-4-methoxycinnamic-acid
    • 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, (2E)-
    • DTXSID901314847
    • HMS2268G06
    • ABA52233
    • BB_NC-03267
    • HY-N0761
    • MSK40364
    • NSC51987
    • STR05122
    • BBL036268
    • BDBM50241245
    • EBC-69057
    • s3764
    • SBB042817
    • STL186177
    • AKOS000141174
    • CCG-266533
    • CS-W020120
    • DB07109
    • FH24260
    • 3-Hydroxy-4-Methoxycinnamic Acid,Trans
    • NCGC00247490-01
    • NCGC00247490-02
    • AC-34927
    • LS-13768
    • MS-11465
    • SMR001215828
    • ST098721
    • SY013717
    • SY290434
    • trans-Isoferulic acid, analytical standard
    • 3-(3-hydroxy-4-methoxyphenyl)-2-Propenoate
    • H0524
    • NS00014666
    • EN300-50983
    • (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid
    • EN300-331979
    • G77265
    • 537H735
    • F554593
    • F791625
    • Q27096447
    • (2E)-3-(3-HYDROXY-4-METHOXYPHENYL)ACRYLIC ACID
    • (E)-3-(3-hydroxy-4-methoxy-phenyl)prop-2-enoic acid
    • Z2693271860
    • (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid #
    • 3-Hydroxy-4-methoxycinnamic acid, predominantly trans, 97%
    • ISOFERULIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]
    • 4FE
    • 537-73-5

  • Applications

    Isoferulic Acid (CAS 537-73-5) has multiple practical roles in industry: it is commonly used as an intermediate in the synthesis of other cinnamic acid derivatives and related compounds for fragrance and aroma applications in perfumery; it can function as a fragrance material or aroma precursor; it may serve as an antioxidant or stabilizer in cosmetics and personal care formulations. In polymer and coating applications, it can act as an antioxidant additive or stabilizer to improve material longevity. In pharmaceutical research, it is used as a building block for cinnamic derivatives and related compounds. In flavor science, it is evaluated as a precursor for flavor-active phenolic compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 88.29
    methanol 121.8
    isopropanol 54.26
    water 0.68
    ethyl acetate 26.37
    n-propanol 53.69
    acetone 91.89
    n-butanol 38.01
    acetonitrile 17.46
    DMF 177.11
    toluene 5.54
    isobutanol 25.84
    1,4-dioxane 85.08
    methyl acetate 37.68
    THF 313.65
    2-butanone 48.88
    n-pentanol 31.98
    sec-butanol 42.24
    n-hexane 0.47
    ethylene glycol 62.15
    NMP 68.64
    cyclohexane 0.45
    DMSO 287.91
    n-butyl acetate 15.03
    n-octanol 12.54
    chloroform 4.04
    n-propyl acetate 18.22
    acetic acid 40.65
    dichloromethane 6.16
    cyclohexanone 32.19
    propylene glycol 48.51
    isopropyl acetate 15.64
    DMAc 171.86
    2-ethoxyethanol 141.17
    isopentanol 33.94
    n-heptane 1.06
    ethyl formate 19.7
    1,2-dichloroethane 9.77
    n-hexanol 27.43
    2-methoxyethanol 204.57
    isobutyl acetate 7.64
    tetrachloromethane 1.07
    n-pentyl acetate 10.21
    transcutol 108.34
    n-heptanol 14.44
    ethylbenzene 4.08
    MIBK 25.26
    2-propoxyethanol 81.83
    tert-butanol 166.29
    MTBE 37.57
    2-butoxyethanol 35.6
    propionic acid 28.04
    o-xylene 6.54
    formic acid 73.94
    diethyl ether 27.53
    m-xylene 5.74
    p-xylene 4.55
    chlorobenzene 3.39
    dimethyl carbonate 23.14
    n-octane 0.71
    formamide 152.65
    cyclopentanone 69.29
    2-pentanone 36.99
    anisole 24.17
    cyclopentyl methyl ether 38.37
    gamma-butyrolactone 80.3
    1-methoxy-2-propanol 118.67
    pyridine 21.84
    3-pentanone 20.36
    furfural 48.66
    n-dodecane 0.76
    diethylene glycol 102.08
    diisopropyl ether 6.95
    tert-amyl alcohol 79.3
    acetylacetone 37.56
    n-hexadecane 0.83
    acetophenone 21.36
    methyl propionate 34.09
    isopentyl acetate 15.65
    trichloroethylene 13.19
    n-nonanol 12.85
    cyclohexanol 23.79
    benzyl alcohol 25.15
    2-ethylhexanol 13.69
    isooctanol 11.76
    dipropyl ether 14.08
    1,2-dichlorobenzene 4.62
    ethyl lactate 21.35
    propylene carbonate 22.57
    n-methylformamide 94.91
    2-pentanol 26.31
    n-pentane 0.42
    1-propoxy-2-propanol 45.26
    1-methoxy-2-propyl acetate 29.45
    2-(2-methoxypropoxy) propanol 44.7
    mesitylene 4.41
    ε-caprolactone 29.9
    p-cymene 5.09
    epichlorohydrin 84.85
    1,1,1-trichloroethane 4.77
    2-aminoethanol 81.47
    morpholine-4-carbaldehyde 87.44
    sulfolane 104.11
    2,2,4-trimethylpentane 0.84
    2-methyltetrahydrofuran 80.58
    n-hexyl acetate 14.78
    isooctane 0.66
    2-(2-butoxyethoxy)ethanol 53.74
    sec-butyl acetate 11.36
    tert-butyl acetate 28.04
    decalin 0.82
    glycerin 86.88
    diglyme 84.84
    acrylic acid 25.11
    isopropyl myristate 8.59
    n-butyric acid 26.02
    acetyl acetate 11.44
    di(2-ethylhexyl) phthalate 10.92
    ethyl propionate 18.39
    nitromethane 82.42
    1,2-diethoxyethane 27.9
    benzonitrile 11.65
    trioctyl phosphate 8.74
    1-bromopropane 4.95
    gamma-valerolactone 74.98
    n-decanol 10.73
    triethyl phosphate 13.53
    4-methyl-2-pentanol 16.76
    propionitrile 18.97
    vinylene carbonate 18.39
    1,1,2-trichlorotrifluoroethane 51.94
    DMS 17.04
    cumene 4.01
    2-octanol 9.06
    2-hexanone 22.24
    octyl acetate 11.25
    limonene 7.11
    1,2-dimethoxyethane 133.73
    ethyl orthosilicate 12.64
    tributyl phosphate 9.7
    diacetone alcohol 62.47
    N,N-dimethylaniline 19.13
    acrylonitrile 23.87
    aniline 16.77
    1,3-propanediol 92.3
    bromobenzene 2.37
    dibromomethane 3.78
    1,1,2,2-tetrachloroethane 12.94
    2-methyl-cyclohexyl acetate 15.62
    tetrabutyl urea 16.22
    diisobutyl methanol 10.24
    2-phenylethanol 21.71
    styrene 4.41
    dioctyl adipate 14.25
    dimethyl sulfate 46.76
    ethyl butyrate 14.53
    methyl lactate 35.19
    butyl lactate 14.76
    diethyl carbonate 11.87
    propanediol butyl ether 30.67
    triethyl orthoformate 14.03
    p-tert-butyltoluene 5.31
    methyl 4-tert-butylbenzoate 25.46
    morpholine 129.4
    tert-butylamine 42.49
    n-dodecanol 8.71
    dimethoxymethane 128.63
    ethylene carbonate 15.21
    cyrene 42.24
    2-ethoxyethyl acetate 20.19
    2-ethylhexyl acetate 10.85
    1,2,4-trichlorobenzene 6.36
    4-methylpyridine 19.75
    dibutyl ether 10.65
    2,6-dimethyl-4-heptanol 10.24
    DEF 38.34
    dimethyl isosorbide 61.65
    tetrachloroethylene 8.27
    eugenol 28.31
    triacetin 20.03
    span 80 26.32
    1,4-butanediol 40.7
    1,1-dichloroethane 5.06
    2-methyl-1-pentanol 24.65
    methyl formate 62.75
    2-methyl-1-butanol 27.59
    n-decane 1.1
    butyronitrile 16.39
    3,7-dimethyl-1-octanol 12.62
    1-chlorooctane 4.54
    1-chlorotetradecane 2.45
    n-nonane 0.92
    undecane 0.91
    tert-butylcyclohexane 0.92
    cyclooctane 0.4
    cyclopentanol 34.27
    tetrahydropyran 40.59
    tert-amyl methyl ether 31.28
    2,5,8-trioxanonane 75.96
    1-hexene 3.07
    2-isopropoxyethanol 68.71
    2,2,2-trifluoroethanol 21.25
    methyl butyrate 22.45

    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