Caffeic Acid

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  • Identifiers

    CAS number
    331-39-5

    Molecular formula
    C9H8O4

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

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 63.79%
    Phenolic 45.7%
    Balsamic 35.68%
    Burnt 35.39%
    Spicy 30.33%
    Vanilla 28.3%
    Savory 24.54%
    Milky 23.08%
    Bitter 21.75%
    Sour 21.37%

     

    Flavor
    Odorless 51.69%
    Phenolic 40.89%
    Mild 40.1%
    Nutty 34.45%
    Faint 29.78%
    Bitter 28.05%
    Balsamic 26.98%
    Very mild 26.27%
    Balsam 26.01%
    Sour 25.73%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    9.05 (weak base)

    Molecular weight
    180.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    394°C

    Melting point expt.

    • 433 to 437 °F (decomposes) (NTP, 1992)
    • 225 dec °C
    • Decomposes at 223-225 °C (Softens at 194 °C).
    • 225 °C

    Flash point

    • 201.91 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 72 °F (NTP, 1992)
    • Sparingly soluble in cold water. Freely soluble in hot water, cold alcohol.

  • Synonyms

    • caffeic acid
    • 3,4-Dihydroxycinnamic acid
    • 331-39-5
    • 3,4-Dihydroxybenzeneacrylic acid
    • (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
    • Cinnamic acid, 3,4-dihydroxy-
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-
    • 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene
    • 3-(3,4-Dihydroxyphenyl)propenoic acid
    • 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene
    • NSC 57197
    • U2S3A33KVM
    • NSC-57197
    • NSC-623438
    • DTXSID5020231
    • trans-3,4-Dihydroxycinnamic Acid
    • NSC57197
    • DTXCID10231
    • CHEBI:16433
    • CHEBI:36281
    • NSC623438
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-
    • CHEBI:17395
    • Caffeic Acid 1507
    • caffeic acid, (E)-
    • RefChem:6400
    • Trans 3,4-Dihydroxycinnamic acid
    • 206-361-2
    • (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • cis-Caffeic acid
    • trans-caffeic acid
    • 501-16-6
    • 3-(3,4-dihydroxyphenyl)acrylic acid
    • (E)-3-(3,4-dihydroxyphenyl)acrylic acid
    • (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • Caffeicacid
    • 3,4-Dihydroxy-trans-cinnamate
    • (E)-3,4-dihydroxycinnamic acid
    • 71693-97-5
    • MFCD00004392
    • Caffeate
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-
    • 3-(3,4-Dihydroxy phenyl)-2-propenoic acid
    • CHEMBL145
    • AI3-63211
    • MLS000069738
    • 331-89-5
    • SMR000058214
    • CCRIS 847
    • HSDB 7088
    • 3,4-Dihydroxycinnamic acid, predominantly trans
    • SR-01000000203
    • EINECS 206-361-2
    • UNII-U2S3A33KVM
    • caffeic-acid
    • e-caffeic acid
    • Caffeic acid pure
    • (e)-caffeic acid
    • Caffeic acid, 1
    • Caffeic acid 1000 microg/mL in Acetone
    • 3,4-dihydroxycinnamic acid (caffeic acid)
    • Caffeic acid, trans-
    • 3,4-dihydroxycinnamate
    • CAFFEIC ACID natural
    • (2E)-3-(3,4-dihydroxyphenyl)acrylic acid
    • Opera_ID_1700
    • CAFFEIC ACID [MI]
    • CAFFEIC ACID [DSC]
    • Cinnamic acid,4-dihydroxy-
    • CAFFEIC ACID [HSDB]
    • CAFFEIC ACID [IARC]
    • 3,4-Dihydroxybenzeneacrylate
    • SCHEMBL23358
    • MLS001076493
    • MLS002207132
    • MLS002222302
    • MLS006011849
    • BIDD:ER0456
    • SPECTRUM1503987
    • CAFFEIC ACID [WHO-DD]
    • 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, (2E)-
    • 3,4-Dihydroxycinnamate, XVII
    • BDBM4375
    • cid_689043
    • E-3,4-dihydroxy cinnamic acid
    • GTPL5155
    • orb1685080
    • SCHEMBL4859286
    • SCHEMBL29353048
    • DTXSID901316055
    • HMS2235G09
    • HMS3260J17
    • HMS3649O17
    • HMS5080F04
    • AAA50116
    • BB_NC-02102
    • HY-N0172
    • MSK10401
    • Tox21_200648
    • Tox21_500208
    • BBL012113
    • Caffeic Acid - CAS 331-39-5
    • CCG-38895
    • EBC-11077
    • EBC-44189
    • s2277
    • SBB006475
    • STK397812
    • Caffeic acid, >=98.0% (HPLC)
    • 2-Propenoic acid,4-dihydroxyphenyl)-
    • AKOS000144463
    • AC-8006
    • CS-8205
    • DB01880
    • FC19625
    • LP00208
    • SDCCGMLS-0002982.P003
    • SDCCGSBI-0050196.P004
    • NCGC00017364-04
    • NCGC00017364-05
    • NCGC00017364-06
    • NCGC00017364-07
    • NCGC00017364-08
    • NCGC00017364-09
    • NCGC00017364-10
    • NCGC00017364-11
    • 331-39-5

  • Applications

    Caffeic Acid (CAS 331-39-5) is a natural hydroxycinnamic acid used primarily as an intermediate in the synthesis of pharmaceuticals and specialty chemicals; it is also employed as an antioxidant and stabilizer in cosmetics and personal care formulations; it may be used as a natural antioxidant in food applications and packaging, subject to local regulations; it serves as a building block for bio-based polymers, coatings, and UV-curable resins; it is a precursor for dyes and colorants in polymer and textile applications; and it is explored as a feedstock for agricultural research and plant-protection compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 64.98
    methanol 85.68
    isopropanol 33.84
    water 1.88
    ethyl acetate 3.99
    n-propanol 29.85
    acetone 96.29
    n-butanol 22.05
    acetonitrile 4.29
    DMF 71.81
    toluene 1.76
    isobutanol 12.72
    1,4-dioxane 15.41
    methyl acetate 10.78
    THF 161.5
    2-butanone 27.17
    n-pentanol 17.89
    sec-butanol 24.34
    n-hexane 0.23
    ethylene glycol 37.61
    NMP 45.49
    cyclohexane 0.12
    DMSO 82.17
    n-butyl acetate 9.03
    n-octanol 9.81
    chloroform 0.08
    n-propyl acetate 7.42
    acetic acid 13.07
    dichloromethane 0.1
    cyclohexanone 11.28
    propylene glycol 24.8
    isopropyl acetate 7.26
    DMAc 119.29
    2-ethoxyethanol 88.79
    isopentanol 26.41
    n-heptane 0.79
    ethyl formate 6.85
    1,2-dichloroethane 0.41
    n-hexanol 20.8
    2-methoxyethanol 111.27
    isobutyl acetate 2.69
    tetrachloromethane 0.19
    n-pentyl acetate 7.26
    transcutol 47.44
    n-heptanol 15.22
    ethylbenzene 2.15
    MIBK 17.68
    2-propoxyethanol 59.26
    tert-butanol 90.07
    MTBE 23.66
    2-butoxyethanol 34.99
    propionic acid 9.19
    o-xylene 3.06
    formic acid 38.42
    diethyl ether 7.47
    m-xylene 2.86
    p-xylene 1.92
    chlorobenzene 0.38
    dimethyl carbonate 7.87
    n-octane 0.45
    formamide 85.48
    cyclopentanone 36.77
    2-pentanone 21.41
    anisole 9.81
    cyclopentyl methyl ether 16.96
    gamma-butyrolactone 33.96
    1-methoxy-2-propanol 67.2
    pyridine 5.08
    3-pentanone 7.2
    furfural 16.67
    n-dodecane 0.45
    diethylene glycol 65.56
    diisopropyl ether 4.51
    tert-amyl alcohol 60.45
    acetylacetone 20.94
    n-hexadecane 0.48
    acetophenone 10.65
    methyl propionate 7.78
    isopentyl acetate 9.56
    trichloroethylene 0.6
    n-nonanol 10.13
    cyclohexanol 8.68
    benzyl alcohol 10.78
    2-ethylhexanol 10.72
    isooctanol 11.53
    dipropyl ether 9.43
    1,2-dichlorobenzene 0.63
    ethyl lactate 12.15
    propylene carbonate 9.18
    n-methylformamide 41.09
    2-pentanol 16.93
    n-pentane 0.2
    1-propoxy-2-propanol 37.38
    1-methoxy-2-propyl acetate 17.82
    2-(2-methoxypropoxy) propanol 32.01
    mesitylene 2.52
    ε-caprolactone 12.12
    p-cymene 3.6
    epichlorohydrin 22.01
    1,1,1-trichloroethane 0.48
    2-aminoethanol 51.87
    morpholine-4-carbaldehyde 37.45
    sulfolane 41.47
    2,2,4-trimethylpentane 0.46
    2-methyltetrahydrofuran 37.27
    n-hexyl acetate 8.84
    isooctane 0.49
    2-(2-butoxyethoxy)ethanol 38.15
    sec-butyl acetate 6.08
    tert-butyl acetate 18.9
    decalin 0.34
    glycerin 50.84
    diglyme 53.55
    acrylic acid 8.55
    isopropyl myristate 6.05
    n-butyric acid 8.91
    acetyl acetate 2.93
    di(2-ethylhexyl) phthalate 6.85
    ethyl propionate 7.0
    nitromethane 24.85
    1,2-diethoxyethane 12.88
    benzonitrile 2.79
    trioctyl phosphate 6.1
    1-bromopropane 0.33
    gamma-valerolactone 33.74
    n-decanol 8.55
    triethyl phosphate 6.74
    4-methyl-2-pentanol 14.69
    propionitrile 4.14
    vinylene carbonate 4.72
    1,1,2-trichlorotrifluoroethane 18.34
    DMS 5.75
    cumene 2.34
    2-octanol 8.86
    2-hexanone 12.64
    octyl acetate 7.92
    limonene 4.35
    1,2-dimethoxyethane 68.9
    ethyl orthosilicate 6.86
    tributyl phosphate 5.31
    diacetone alcohol 48.91
    N,N-dimethylaniline 10.81
    acrylonitrile 5.25
    aniline 4.03
    1,3-propanediol 53.13
    bromobenzene 0.26
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.93
    2-methyl-cyclohexyl acetate 8.64
    tetrabutyl urea 11.06
    diisobutyl methanol 9.2
    2-phenylethanol 13.05
    styrene 1.65
    dioctyl adipate 8.41
    dimethyl sulfate 17.08
    ethyl butyrate 8.06
    methyl lactate 17.26
    butyl lactate 9.69
    diethyl carbonate 5.16
    propanediol butyl ether 23.64
    triethyl orthoformate 7.42
    p-tert-butyltoluene 3.85
    methyl 4-tert-butylbenzoate 18.12
    morpholine 29.12
    tert-butylamine 24.44
    n-dodecanol 6.51
    dimethoxymethane 51.12
    ethylene carbonate 3.74
    cyrene 30.66
    2-ethoxyethyl acetate 10.96
    2-ethylhexyl acetate 5.87
    1,2,4-trichlorobenzene 1.02
    4-methylpyridine 5.72
    dibutyl ether 5.61
    2,6-dimethyl-4-heptanol 9.2
    DEF 19.17
    dimethyl isosorbide 45.96
    tetrachloroethylene 0.9
    eugenol 19.24
    triacetin 9.33
    span 80 17.87
    1,4-butanediol 28.6
    1,1-dichloroethane 0.25
    2-methyl-1-pentanol 18.94
    methyl formate 24.84
    2-methyl-1-butanol 19.24
    n-decane 0.64
    butyronitrile 4.94
    3,7-dimethyl-1-octanol 9.37
    1-chlorooctane 1.96
    1-chlorotetradecane 1.11
    n-nonane 0.53
    undecane 0.53
    tert-butylcyclohexane 0.47
    cyclooctane 0.16
    cyclopentanol 15.58
    tetrahydropyran 7.84
    tert-amyl methyl ether 21.75
    2,5,8-trioxanonane 49.24
    1-hexene 1.08
    2-isopropoxyethanol 46.68
    2,2,2-trifluoroethanol 7.99
    methyl butyrate 10.07

    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