Prenyl Caffeate

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  • Identifiers

    CAS number
    118971-61-2

    Molecular formula
    C14H16O4

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

    Safety labels

  • Odor profile

    Fragrance
    Spicy 49.3%
    Balsamic 42.17%
    Sweet 32.46%
    Odorless 32.11%
    Fruity 31.89%
    Phenolic 31.34%
    Vanilla 30.87%
    Woody 29.02%
    Warm 27.68%
    Clove 26.31%

     

    Flavor
    Bitter 47.78%
    Odorless 29.26%
    Ethyl benzoate 20.76%
    Broom 20.01%
    Heather 19.99%
    Parsley 19.98%
    Lovage 19.8%
    Mild 19.65%
    Genet 19.61%
    Orange flower 19.41%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    10.33 (weak base)

    Molecular weight
    248.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    418°C

    Flash point

    • 188.66 ˚C est.

  • Synonyms

    • Prenyl caffeate
    • 3-methylbut-2-enyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • RefChem:929962
    • 118971-61-2
    • Caffeic acid 1,1-dimethylallyl ester
    • 3-Methyl-2-butenyl caffeate
    • Isoprenyl caffeate
    • 1,1-Dimethylallyl caffeic acid ester
    • 1,1-Dacae
    • Prenyl cis-caffeate
    • 100884-13-7
    • CHEBI:8393
    • Cinnamic acid, 3,4-dihydroxy-, 3-methyl-2-butenyl ester
    • 3-Methylbut-2-En-1-Yl (2e)-3-(3,4-Dihydroxyphenyl)prop-2-Enoate
    • Prenyl cafeate
    • dimethylallylcaffeate
    • 3-methylbut-2-enyl caffeate
    • CHEMBL471184
    • orb2695057
    • SCHEMBL14461142
    • BDBM50030893
    • SY410704
    • DB-257534
    • Q27108066
    • Caffeic acid 1,1-dimethylallyl ester, analytical standard
    • (E)-2-Methylbut-3-en-2-yl 3-(3,4-Dihydroxyphenyl)acrylate
    • (2E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid 3-methyl-2-buten-1-yl ester
    • 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-,3-methyl-2-buten-1-yl ester,(2E)-
    • 100884-13-7

  • Applications

    Prenyl caffeate (CAS 118971-61-2) is used primarily as an antioxidant and stabilizer in cosmetic and personal care formulations, helping to improve the oxidative stability and longevity of polyphenol-containing ingredients; it also serves as an intermediate for the synthesis of polyphenolic compounds and polymeric/resin materials in the coatings and plastics sector; it is considered an intermediate in pharmaceutical and agrochemical synthesis; in industrial manufacturing, prenyl caffeate can function as a building block for other organic synthesis workflows.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 960.97
    methanol 1089.41
    isopropanol 463.13
    water 0.11
    ethyl acetate 429.56
    n-propanol 567.01
    acetone 439.95
    n-butanol 316.6
    acetonitrile 239.53
    DMF 153.76
    toluene 25.91
    isobutanol 184.25
    1,4-dioxane 450.47
    methyl acetate 354.81
    THF 1124.87
    2-butanone 484.13
    n-pentanol 181.9
    sec-butanol 413.03
    n-hexane 0.75
    ethylene glycol 53.96
    NMP 38.46
    cyclohexane 1.42
    DMSO 543.43
    n-butyl acetate 61.21
    n-octanol 31.14
    chloroform 77.18
    n-propyl acetate 89.69
    acetic acid 227.01
    dichloromethane 77.15
    cyclohexanone 122.38
    propylene glycol 204.66
    isopropyl acetate 133.37
    DMAc 290.76
    2-ethoxyethanol 490.76
    isopentanol 170.64
    n-heptane 1.35
    ethyl formate 104.3
    1,2-dichloroethane 75.12
    n-hexanol 96.38
    2-methoxyethanol 989.76
    isobutyl acetate 39.71
    tetrachloromethane 3.81
    n-pentyl acetate 31.35
    transcutol 535.22
    n-heptanol 36.92
    ethylbenzene 16.07
    MIBK 102.29
    2-propoxyethanol 239.97
    tert-butanol 521.84
    MTBE 201.43
    2-butoxyethanol 98.16
    propionic acid 147.68
    o-xylene 16.44
    formic acid 96.26
    diethyl ether 232.72
    m-xylene 15.79
    p-xylene 18.64
    chlorobenzene 19.36
    dimethyl carbonate 63.85
    n-octane 1.06
    formamide 310.59
    cyclopentanone 169.39
    2-pentanone 242.59
    anisole 81.73
    cyclopentyl methyl ether 105.1
    gamma-butyrolactone 184.93
    1-methoxy-2-propanol 522.83
    pyridine 156.68
    3-pentanone 117.42
    furfural 106.98
    n-dodecane 1.51
    diethylene glycol 199.72
    diisopropyl ether 23.9
    tert-amyl alcohol 355.67
    acetylacetone 205.98
    n-hexadecane 1.65
    acetophenone 58.57
    methyl propionate 222.94
    isopentyl acetate 61.08
    trichloroethylene 114.12
    n-nonanol 30.2
    cyclohexanol 94.2
    benzyl alcohol 75.54
    2-ethylhexanol 36.22
    isooctanol 29.57
    dipropyl ether 39.29
    1,2-dichlorobenzene 16.85
    ethyl lactate 52.19
    propylene carbonate 69.87
    n-methylformamide 169.35
    2-pentanol 171.96
    n-pentane 0.97
    1-propoxy-2-propanol 130.64
    1-methoxy-2-propyl acetate 104.27
    2-(2-methoxypropoxy) propanol 102.02
    mesitylene 9.31
    ε-caprolactone 111.46
    p-cymene 10.55
    epichlorohydrin 347.67
    1,1,1-trichloroethane 43.28
    2-aminoethanol 253.27
    morpholine-4-carbaldehyde 138.11
    sulfolane 115.33
    2,2,4-trimethylpentane 1.98
    2-methyltetrahydrofuran 346.46
    n-hexyl acetate 45.13
    isooctane 1.43
    2-(2-butoxyethoxy)ethanol 161.13
    sec-butyl acetate 65.17
    tert-butyl acetate 135.19
    decalin 1.63
    glycerin 169.51
    diglyme 267.89
    acrylic acid 84.05
    isopropyl myristate 22.37
    n-butyric acid 196.1
    acetyl acetate 90.35
    di(2-ethylhexyl) phthalate 22.21
    ethyl propionate 86.78
    nitromethane 404.39
    1,2-diethoxyethane 129.01
    benzonitrile 40.18
    trioctyl phosphate 16.2
    1-bromopropane 37.19
    gamma-valerolactone 223.19
    n-decanol 23.79
    triethyl phosphate 26.5
    4-methyl-2-pentanol 69.39
    propionitrile 158.39
    vinylene carbonate 48.55
    1,1,2-trichlorotrifluoroethane 129.64
    DMS 46.64
    cumene 11.51
    2-octanol 22.66
    2-hexanone 98.9
    octyl acetate 28.32
    limonene 14.23
    1,2-dimethoxyethane 420.22
    ethyl orthosilicate 26.44
    tributyl phosphate 20.6
    diacetone alcohol 244.6
    N,N-dimethylaniline 41.59
    acrylonitrile 139.19
    aniline 65.49
    1,3-propanediol 389.88
    bromobenzene 14.26
    dibromomethane 40.67
    1,1,2,2-tetrachloroethane 100.48
    2-methyl-cyclohexyl acetate 40.83
    tetrabutyl urea 29.82
    diisobutyl methanol 25.71
    2-phenylethanol 63.78
    styrene 19.57
    dioctyl adipate 35.73
    dimethyl sulfate 58.93
    ethyl butyrate 50.64
    methyl lactate 90.59
    butyl lactate 36.77
    diethyl carbonate 35.08
    propanediol butyl ether 87.68
    triethyl orthoformate 35.54
    p-tert-butyltoluene 11.14
    methyl 4-tert-butylbenzoate 52.65
    morpholine 708.24
    tert-butylamine 140.66
    n-dodecanol 17.98
    dimethoxymethane 377.75
    ethylene carbonate 46.42
    cyrene 72.49
    2-ethoxyethyl acetate 75.06
    2-ethylhexyl acetate 37.77
    1,2,4-trichlorobenzene 24.01
    4-methylpyridine 84.59
    dibutyl ether 32.78
    2,6-dimethyl-4-heptanol 25.71
    DEF 118.58
    dimethyl isosorbide 138.46
    tetrachloroethylene 40.71
    eugenol 59.98
    triacetin 55.02
    span 80 69.96
    1,4-butanediol 98.13
    1,1-dichloroethane 69.48
    2-methyl-1-pentanol 112.01
    methyl formate 109.97
    2-methyl-1-butanol 165.97
    n-decane 2.09
    butyronitrile 124.56
    3,7-dimethyl-1-octanol 35.21
    1-chlorooctane 10.79
    1-chlorotetradecane 5.21
    n-nonane 1.59
    undecane 1.77
    tert-butylcyclohexane 1.89
    cyclooctane 0.63
    cyclopentanol 111.88
    tetrahydropyran 332.8
    tert-amyl methyl ether 135.94
    2,5,8-trioxanonane 195.86
    1-hexene 9.22
    2-isopropoxyethanol 238.23
    2,2,2-trifluoroethanol 40.2
    methyl butyrate 101.34

    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