Avenanthramide A

Overview IFRA Request a quote

  • Identifiers

    CAS number
    108605-70-5

    Molecular formula
    C16H13NO5

    SMILES
    C1=CC(=CC=C1/C=C/C(=O)NC2=C(C=C(C=C2)O)C(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 53.88%
    Fruity 36.89%
    Savory 31.62%
    Meaty 28.05%
    Cooked 27.26%
    Bitter 26.17%
    Burnt 25.75%
    Grape 24.62%
    Balsamic 22.29%
    Phenolic 22.28%

     

    Flavor
    Bitter 66.68%
    Odorless 52.17%
    Mild 33.49%
    Very mild 25.07%
    Bland 22.89%
    Nitrile 22.02%
    Faint 20.72%
    Yeast 20.71%
    Sweet-like 20.69%
    Urine 20.67%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    8.78 (weak base)

    Molecular weight
    299.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    594°C

    Melting point expt.

    • 277 °C

    Flash point

    • 279.97 ˚C est.

  • Synonyms

    • Avenanthramide A
    • 108605-70-5
    • Avenanthramide 2P
    • Avenanthramide BP
    • G1I8LE060C
    • Benzoic acid, 5-hydroxy-2-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)amino)-
    • Benzoic acid, 5-hydroxy-2-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]amino]-
    • DTXSID801316626
    • 5-hydroxy-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]benzoic acid
    • 5-hydroxy-2-(((E)-3-(4-hydroxyphenyl)prop-2-enoyl)amino)benzoic acid
    • RefChem:560397
    • DTXCID501746464
    • UNII-G1I8LE060C
    • (E)-5-Hydroxy-2-(3-(4-hydroxyphenyl)acrylamido)benzoic acid
    • (Z)-N-Coumaroyl-5-hydroxyanthranilic acid
    • Avenalumin I
    • 5-Hydroxy-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]benzoic Acid; Avenanthramide 2p; Avenanthramide Bp
    • C08472
    • CHEBI:2939
    • orb1698267
    • SCHEMBL4670083
    • 5-hydroxy-2-[3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
    • 5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
    • Avenanthramide A, analytical standard
    • AKOS040750647
    • EBC-618313
    • HY-114977
    • CS-0064722
    • G83417
    • 5-Hydroxy-N-(4-hydroxycinnamoyl)anthranilic acid
    • F554565
    • Q27105894
    • N-(4'-hydroxy-(e)-cinnamoyl)-5-hydroxyanthranilic acid
    • 5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoate
    • 5-hydroxy-2-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]amino}benzoic acid
    • 917224-54-5
    • 108605-70-5

  • Applications

    Avenanthramide A (CAS 108605-70-5) is a naturally occurring oat polyphenol. In practical applications it is used as a natural antioxidant in cosmetic and personal-care formulations, where it can contribute to formulation stability and provide mild skin-conditioning effects; it is also investigated as a component of oat-derived extracts in foods and nutraceuticals to support shelf life; it is explored as an antioxidant stabilizer in polymer formulations and coatings to mitigate oxidative degradation; and it serves as a model bioactive compound in pharmaceutical research for antioxidant studies. Use is typically formulation- and regulation-dependent.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.87
    methanol 24.8
    isopropanol 11.91
    water 0.06
    ethyl acetate 3.47
    n-propanol 15.51
    acetone 33.27
    n-butanol 8.74
    acetonitrile 4.27
    DMF 104.64
    toluene 0.12
    isobutanol 4.8
    1,4-dioxane 13.68
    methyl acetate 9.14
    THF 177.06
    2-butanone 28.85
    n-pentanol 5.15
    sec-butanol 10.24
    n-hexane 0.01
    ethylene glycol 11.23
    NMP 20.93
    cyclohexane 0.01
    DMSO 268.61
    n-butyl acetate 2.17
    n-octanol 1.48
    chloroform 0.05
    n-propyl acetate 3.1
    acetic acid 13.1
    dichloromethane 0.03
    cyclohexanone 8.85
    propylene glycol 21.63
    isopropyl acetate 2.45
    DMAc 183.43
    2-ethoxyethanol 60.75
    isopentanol 6.03
    n-heptane 0.02
    ethyl formate 4.35
    1,2-dichloroethane 0.12
    n-hexanol 2.06
    2-methoxyethanol 130.85
    isobutyl acetate 1.03
    tetrachloromethane 0.03
    n-pentyl acetate 1.35
    transcutol 26.86
    n-heptanol 1.85
    ethylbenzene 0.16
    MIBK 4.15
    2-propoxyethanol 34.28
    tert-butanol 13.81
    MTBE 3.25
    2-butoxyethanol 12.85
    propionic acid 7.41
    o-xylene 0.16
    formic acid 15.71
    diethyl ether 1.71
    m-xylene 0.12
    p-xylene 0.23
    chlorobenzene 0.07
    dimethyl carbonate 5.09
    n-octane 0.02
    formamide 46.96
    cyclopentanone 32.87
    2-pentanone 8.87
    anisole 2.74
    cyclopentyl methyl ether 3.19
    gamma-butyrolactone 23.97
    1-methoxy-2-propanol 63.81
    pyridine 4.26
    3-pentanone 3.7
    furfural 11.85
    n-dodecane 0.03
    diethylene glycol 33.85
    diisopropyl ether 0.31
    tert-amyl alcohol 11.09
    acetylacetone 12.32
    n-hexadecane 0.03
    acetophenone 3.4
    methyl propionate 6.3
    isopentyl acetate 2.32
    trichloroethylene 0.3
    n-nonanol 1.72
    cyclohexanol 1.81
    benzyl alcohol 3.64
    2-ethylhexanol 1.03
    isooctanol 1.47
    dipropyl ether 1.94
    1,2-dichlorobenzene 0.11
    ethyl lactate 5.78
    propylene carbonate 4.16
    n-methylformamide 39.76
    2-pentanol 2.79
    n-pentane 0.01
    1-propoxy-2-propanol 15.94
    1-methoxy-2-propyl acetate 6.88
    2-(2-methoxypropoxy) propanol 14.4
    mesitylene 0.11
    ε-caprolactone 7.59
    p-cymene 0.22
    epichlorohydrin 21.11
    1,1,1-trichloroethane 0.1
    2-aminoethanol 26.37
    morpholine-4-carbaldehyde 34.21
    sulfolane 35.45
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 11.85
    n-hexyl acetate 2.0
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 18.67
    sec-butyl acetate 1.77
    tert-butyl acetate 4.25
    decalin 0.01
    glycerin 40.93
    diglyme 32.52
    acrylic acid 6.45
    isopropyl myristate 1.27
    n-butyric acid 6.37
    acetyl acetate 1.63
    di(2-ethylhexyl) phthalate 1.86
    ethyl propionate 3.53
    nitromethane 43.71
    1,2-diethoxyethane 5.28
    benzonitrile 1.04
    trioctyl phosphate 1.42
    1-bromopropane 0.09
    gamma-valerolactone 45.86
    n-decanol 1.38
    triethyl phosphate 2.26
    4-methyl-2-pentanol 1.55
    propionitrile 3.75
    vinylene carbonate 2.76
    1,1,2-trichlorotrifluoroethane 14.89
    DMS 2.28
    cumene 0.16
    2-octanol 0.91
    2-hexanone 6.54
    octyl acetate 1.79
    limonene 0.24
    1,2-dimethoxyethane 69.42
    ethyl orthosilicate 2.1
    tributyl phosphate 1.71
    diacetone alcohol 17.34
    N,N-dimethylaniline 1.95
    acrylonitrile 5.88
    aniline 0.96
    1,3-propanediol 38.04
    bromobenzene 0.04
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.45
    2-methyl-cyclohexyl acetate 2.38
    tetrabutyl urea 3.92
    diisobutyl methanol 0.9
    2-phenylethanol 2.94
    styrene 0.16
    dioctyl adipate 2.74
    dimethyl sulfate 10.79
    ethyl butyrate 2.59
    methyl lactate 12.88
    butyl lactate 3.35
    diethyl carbonate 1.94
    propanediol butyl ether 8.78
    triethyl orthoformate 3.0
    p-tert-butyltoluene 0.24
    methyl 4-tert-butylbenzoate 5.4
    morpholine 31.63
    tert-butylamine 1.85
    n-dodecanol 1.0
    dimethoxymethane 51.9
    ethylene carbonate 2.32
    cyrene 14.93
    2-ethoxyethyl acetate 3.51
    2-ethylhexyl acetate 1.25
    1,2,4-trichlorobenzene 0.24
    4-methylpyridine 2.17
    dibutyl ether 1.44
    2,6-dimethyl-4-heptanol 0.9
    DEF 11.19
    dimethyl isosorbide 20.78
    tetrachloroethylene 0.25
    eugenol 6.79
    triacetin 3.56
    span 80 6.67
    1,4-butanediol 11.61
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 4.0
    methyl formate 19.79
    2-methyl-1-butanol 5.52
    n-decane 0.04
    butyronitrile 3.18
    3,7-dimethyl-1-octanol 1.42
    1-chlorooctane 0.2
    1-chlorotetradecane 0.13
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 5.27
    tetrahydropyran 4.21
    tert-amyl methyl ether 3.02
    2,5,8-trioxanonane 28.02
    1-hexene 0.11
    2-isopropoxyethanol 21.66
    2,2,2-trifluoroethanol 3.54
    methyl butyrate 5.62

    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