3-Hydroxy-5-methoxy-6-prenylstilbene-2-carboxylic acid

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  • Identifiers

    CAS number
    87402-83-3

    Molecular formula
    C21H22O4

    SMILES
    CC(=CCC1=C(C=C(C(=C1/C=C/C2=CC=CC=C2)C(=O)O)O)OC)C

    Safety labels

  • Odor profile

    Fragrance
    Floral 63.04%
    Sweet 52.24%
    Balsamic 46.84%
    Fruity 43.19%
    Spicy 42.81%
    Woody 35.65%
    Rose 32.48%
    Fresh 32.21%
    Herbal 31.16%
    Powdery 30.74%

     

    Flavor
    Bitter 66.38%
    Odorless 21.48%
    Heather 19.96%
    Broom 19.86%
    Genet 19.66%
    Lovage 19.47%
    Nitrile 19.19%
    Parsley 19.04%
    Oriental 18.74%
    Ethyl benzoate 18.71%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.8

    pKa est.
    7.6 (neutral)

    Molecular weight
    338.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    688°C

    Melting point expt.

    • 144 - 146 °C

    Flash point

    • 228.46 ˚C est.

  • Synonyms

    • 3-Hydroxy-5-methoxy-6-prenylstilbene-2-carboxylic acid
    • 87402-83-3
    • 6-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-2-[(E)-2-phenylethenyl]benzoic acid
    • 6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylethenyl]benzoic acid
    • SCHEMBL4744171
    • CHEBI:28152
    • DTXSID201131046
    • LMPK13090009
    • 6-Hydroxy-4-methoxy-3-prenyl-2-styrylbenzoic acid
    • Q27103532
    • 6-Hydroxy-4-methoxy-3-(3-methyl-2-buten-1-yl)-2-[(1E)-2-phenylethenyl]benzoic acid
    • 6-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-2-[(E)-2-phenylvinyl]benzoic acid
    • 87402-83-3

  • Applications

    3-Hydroxy-5-methoxy-6-prenylstilbene-2-carboxylic acid (CAS number: 87402-83-3) is a functionalized stilbene carboxylic acid that is commonly used as an intermediate in organic synthesis, enabling the preparation of substituted stilbene derivatives for pharmaceutical research and agrochemical development; it can be employed as a building block for fragrance and cosmetic ingredient synthesis due to its prenylated phenolic motif; it also serves as a precursor in polymer and coating formulations where its rigid aromatic scaffold and functional groups enable further derivatization; and it may be explored as a precursor to stilbene-derived dyes or chromophores in specialty materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 122.74
    methanol 101.06
    isopropanol 83.71
    water 0.01
    ethyl acetate 99.34
    n-propanol 144.23
    acetone 284.39
    n-butanol 96.8
    acetonitrile 52.09
    DMF 726.64
    toluene 38.06
    isobutanol 86.13
    1,4-dioxane 122.28
    methyl acetate 122.45
    THF 577.76
    2-butanone 211.49
    n-pentanol 62.54
    sec-butanol 94.69
    n-hexane 1.39
    ethylene glycol 25.99
    NMP 512.92
    cyclohexane 1.79
    DMSO 960.62
    n-butyl acetate 53.03
    n-octanol 10.52
    chloroform 235.41
    n-propyl acetate 48.74
    acetic acid 114.14
    dichloromethane 179.46
    cyclohexanone 199.95
    propylene glycol 111.07
    isopropyl acetate 67.82
    DMAc 779.37
    2-ethoxyethanol 127.89
    isopentanol 71.11
    n-heptane 0.81
    ethyl formate 41.16
    1,2-dichloroethane 182.66
    n-hexanol 44.42
    2-methoxyethanol 312.42
    isobutyl acetate 36.23
    tetrachloromethane 12.31
    n-pentyl acetate 27.33
    transcutol 294.47
    n-heptanol 18.51
    ethylbenzene 14.28
    MIBK 81.97
    2-propoxyethanol 152.43
    tert-butanol 102.93
    MTBE 71.93
    2-butoxyethanol 62.09
    propionic acid 89.22
    o-xylene 20.45
    formic acid 40.67
    diethyl ether 69.0
    m-xylene 23.33
    p-xylene 16.59
    chlorobenzene 51.8
    dimethyl carbonate 103.27
    n-octane 0.38
    formamide 96.42
    cyclopentanone 423.89
    2-pentanone 157.61
    anisole 56.7
    cyclopentyl methyl ether 144.39
    gamma-butyrolactone 332.6
    1-methoxy-2-propanol 276.52
    pyridine 132.67
    3-pentanone 114.67
    furfural 156.94
    n-dodecane 0.45
    diethylene glycol 111.49
    diisopropyl ether 14.58
    tert-amyl alcohol 87.06
    acetylacetone 181.4
    n-hexadecane 0.53
    acetophenone 60.71
    methyl propionate 145.98
    isopentyl acetate 54.04
    trichloroethylene 334.12
    n-nonanol 11.7
    cyclohexanol 71.57
    benzyl alcohol 60.52
    2-ethylhexanol 21.98
    isooctanol 16.31
    dipropyl ether 27.02
    1,2-dichlorobenzene 43.96
    ethyl lactate 50.19
    propylene carbonate 112.14
    n-methylformamide 188.66
    2-pentanol 56.25
    n-pentane 1.42
    1-propoxy-2-propanol 98.14
    1-methoxy-2-propyl acetate 108.38
    2-(2-methoxypropoxy) propanol 79.4
    mesitylene 11.38
    ε-caprolactone 148.79
    p-cymene 9.13
    epichlorohydrin 437.19
    1,1,1-trichloroethane 95.97
    2-aminoethanol 90.17
    morpholine-4-carbaldehyde 289.95
    sulfolane 591.2
    2,2,4-trimethylpentane 1.68
    2-methyltetrahydrofuran 203.61
    n-hexyl acetate 33.55
    isooctane 1.21
    2-(2-butoxyethoxy)ethanol 99.03
    sec-butyl acetate 39.07
    tert-butyl acetate 83.0
    decalin 1.77
    glycerin 141.02
    diglyme 168.66
    acrylic acid 81.13
    isopropyl myristate 15.35
    n-butyric acid 98.82
    acetyl acetate 53.69
    di(2-ethylhexyl) phthalate 23.2
    ethyl propionate 55.63
    nitromethane 250.64
    1,2-diethoxyethane 62.72
    benzonitrile 41.64
    trioctyl phosphate 15.46
    1-bromopropane 64.82
    gamma-valerolactone 376.65
    n-decanol 8.97
    triethyl phosphate 27.85
    4-methyl-2-pentanol 32.33
    propionitrile 60.11
    vinylene carbonate 78.3
    1,1,2-trichlorotrifluoroethane 286.6
    DMS 65.31
    cumene 10.04
    2-octanol 9.86
    2-hexanone 64.02
    octyl acetate 20.44
    limonene 14.31
    1,2-dimethoxyethane 157.62
    ethyl orthosilicate 26.16
    tributyl phosphate 19.39
    diacetone alcohol 143.97
    N,N-dimethylaniline 41.17
    acrylonitrile 80.79
    aniline 89.41
    1,3-propanediol 116.27
    bromobenzene 44.97
    dibromomethane 102.68
    1,1,2,2-tetrachloroethane 303.28
    2-methyl-cyclohexyl acetate 40.59
    tetrabutyl urea 29.98
    diisobutyl methanol 14.96
    2-phenylethanol 52.38
    styrene 18.76
    dioctyl adipate 32.39
    dimethyl sulfate 223.71
    ethyl butyrate 39.34
    methyl lactate 128.33
    butyl lactate 40.3
    diethyl carbonate 29.25
    propanediol butyl ether 59.81
    triethyl orthoformate 34.48
    p-tert-butyltoluene 10.09
    methyl 4-tert-butylbenzoate 55.05
    morpholine 254.16
    tert-butylamine 39.27
    n-dodecanol 6.71
    dimethoxymethane 356.82
    ethylene carbonate 67.26
    cyrene 89.64
    2-ethoxyethyl acetate 57.97
    2-ethylhexyl acetate 37.37
    1,2,4-trichlorobenzene 66.86
    4-methylpyridine 132.57
    dibutyl ether 14.39
    2,6-dimethyl-4-heptanol 14.96
    DEF 178.15
    dimethyl isosorbide 139.57
    tetrachloroethylene 121.21
    eugenol 55.25
    triacetin 53.63
    span 80 55.27
    1,4-butanediol 34.02
    1,1-dichloroethane 135.59
    2-methyl-1-pentanol 53.82
    methyl formate 110.15
    2-methyl-1-butanol 78.26
    n-decane 0.74
    butyronitrile 54.69
    3,7-dimethyl-1-octanol 16.52
    1-chlorooctane 6.03
    1-chlorotetradecane 2.55
    n-nonane 0.6
    undecane 0.57
    tert-butylcyclohexane 1.73
    cyclooctane 0.59
    cyclopentanol 112.17
    tetrahydropyran 139.2
    tert-amyl methyl ether 61.79
    2,5,8-trioxanonane 123.23
    1-hexene 10.32
    2-isopropoxyethanol 82.65
    2,2,2-trifluoroethanol 33.53
    methyl butyrate 65.91

    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