Pinosylvin

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  • Identifiers

    CAS number
    22139-77-1

    Molecular formula
    C14H12O2

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

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Phenolic 48.32%
    Spicy 45.96%
    Fruity 44.1%
    Balsamic 37.11%
    Sweet 32.47%
    Floral 32.08%
    Woody 29.86%
    Medicinal 25.69%
    Animal 25.53%
    Honey 25.21%

     

    Flavor
    Bitter 63.64%
    Nitrile 22.36%
    Balsam 22.35%
    Almond shell 21.05%
    Phenolic 20.85%
    Very strong 20.69%
    Oriental 20.46%
    Indole 20.01%
    Red hots 19.97%
    Cinnamic 19.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    11.08 (strong base)

    Molecular weight
    212.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    440°C

    Flash point

    • 197.04 ˚C est.

  • Synonyms

    • Pinosylvin
    • 22139-77-1
    • Pinosylvine
    • trans-3,5-Dihydroxystilbene
    • trans-pinosylvin
    • (E)-5-(2-Phenylethenyl)-1,3-benzenediol
    • 3,5-Stilbenediol, (E)-
    • 5-[(E)-2-phenylethenyl]benzene-1,3-diol
    • 1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)-
    • 881R434AIB
    • NSC-362430
    • CHEBI:17323
    • CHEBI:36011
    • 5-((E)-2-phenylethenyl)benzene-1,3-diol
    • RefChem:863363
    • 5-(2-phenylethenyl)benzene-1,3-diol
    • (E)-5-Styrylbenzene-1,3-diol
    • 102-61-4
    • 3,5-stilbenediol
    • (E)-3,5-stilbenediol
    • 5-[(1E)-2-phenylethenyl]benzene-1,3-diol
    • 5-[(E)-styryl]benzene-1,3-diol
    • MFCD00210544
    • 3,5-dihydroxy-trans-stilbene
    • CHEMBL101506
    • 1,3-Benzenediol, 5-(2-phenylethenyl)-
    • 5-[(E)-2-phenylvinyl]benzene-1,3-diol
    • 5-[(1E)-2-phenylethenyl]-1,3-benzenediol
    • 5-(2-phenylethenyl)-1,3-benzenediol
    • 1,3-Benzenediol, 5-[(1E)-2-phenylethenyl]-
    • 5-((1E)-2-Phenylethenyl)-1,3-benzenediol
    • 5-styrylbenzene-1,3-diol
    • 1,3-BENZENEDIOL, 5-((1E)-2-PHENYLETHENYL)-
    • NSC 362430
    • BRN 1870942
    • UNII-881R434AIB
    • (E)-pinosylvin
    • DTXSID00895857
    • Stilbene, 1f
    • Pinosylvin (Standard)
    • PINOSYLVIN [MI]
    • Spectrum5_000307
    • (trans)-3,5-stilbenediol
    • C01745
    • BSPBio_001753
    • 3-06-00-05577 (Beilstein Handbook Reference)
    • 5-[(E)-2-PHENYLETHENYL]-1,3-BENZENEDIOL
    • SCHEMBL454262
    • orb1303675
    • SCHEMBL20969215
    • HY-N2387R
    • EX-A3505
    • HY-N2387
    • Pinosylvin, >=97.0% (HPLC)
    • 5-(2-phenylvinyl)benzene-1,3-diol
    • BDBM50045924
    • CCG-38399
    • LMPK13090001
    • NSC362430
    • Stilbene, 3,5-dihydroxy-, trans-
    • AKOS000276828
    • AC-7928
    • EBC-463042
    • FP65132
    • SDCCGMLS-0066433.P001
    • NCGC00179033-01
    • AS-76520
    • DA-56879
    • CS-0022590
    • A11372
    • 5-[(E)-2-Phenylethen-1-yl]benzene-1,3-diol
    • 139P771
    • Q7196412
    • BRD-K94645280-001-02-1
    • D33B05BD-8441-4288-A247-D461C3D1F1CA
    • 22139-77-1

  • Applications

    Pinosylvin (CAS 22139-77-1) is primarily used as a natural antifungal and antioxidant in wood protection formulations, helping deter fungal decay in treated timber. It is also evaluated as a bio-based antioxidant and active ingredient for cosmetics and personal care products, contributing to oxidative stability. In industrial coatings and inks, it can serve as a stilbene-derived additive or intermediate for UV-stable formulations, and it is explored as a renewable building block for specialty polymers. Additionally, it is studied as a starting point for synthesizing stilbene derivatives in chemical research. Use in any application remains subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 118.75
    methanol 116.65
    isopropanol 67.42
    water 0.05
    ethyl acetate 110.74
    n-propanol 85.83
    acetone 521.25
    n-butanol 55.85
    acetonitrile 97.62
    DMF 252.91
    toluene 8.83
    isobutanol 41.82
    1,4-dioxane 233.98
    methyl acetate 130.73
    THF 699.95
    2-butanone 208.14
    n-pentanol 42.07
    sec-butanol 52.67
    n-hexane 0.79
    ethylene glycol 52.22
    NMP 116.46
    cyclohexane 0.52
    DMSO 1112.7
    n-butyl acetate 50.43
    n-octanol 18.02
    chloroform 4.56
    n-propyl acetate 56.52
    acetic acid 99.64
    dichloromethane 1.25
    cyclohexanone 105.05
    propylene glycol 139.31
    isopropyl acetate 71.71
    DMAc 261.41
    2-ethoxyethanol 138.29
    isopentanol 49.2
    n-heptane 1.12
    ethyl formate 43.49
    1,2-dichloroethane 9.69
    n-hexanol 39.92
    2-methoxyethanol 281.5
    isobutyl acetate 40.79
    tetrachloromethane 1.62
    n-pentyl acetate 24.7
    transcutol 627.29
    n-heptanol 20.81
    ethylbenzene 6.34
    MIBK 86.37
    2-propoxyethanol 158.84
    tert-butanol 115.52
    MTBE 96.5
    2-butoxyethanol 71.42
    propionic acid 85.26
    o-xylene 6.49
    formic acid 35.63
    diethyl ether 74.28
    m-xylene 8.74
    p-xylene 6.65
    chlorobenzene 7.78
    dimethyl carbonate 71.48
    n-octane 0.47
    formamide 111.07
    cyclopentanone 292.69
    2-pentanone 127.49
    anisole 49.16
    cyclopentyl methyl ether 96.84
    gamma-butyrolactone 243.08
    1-methoxy-2-propanol 249.3
    pyridine 59.75
    3-pentanone 74.42
    furfural 112.57
    n-dodecane 0.99
    diethylene glycol 165.83
    diisopropyl ether 21.31
    tert-amyl alcohol 73.97
    acetylacetone 220.32
    n-hexadecane 1.14
    acetophenone 41.07
    methyl propionate 107.29
    isopentyl acetate 55.43
    trichloroethylene 22.73
    n-nonanol 18.96
    cyclohexanol 32.52
    benzyl alcohol 35.48
    2-ethylhexanol 26.36
    isooctanol 20.48
    dipropyl ether 47.92
    1,2-dichlorobenzene 7.98
    ethyl lactate 52.41
    propylene carbonate 91.46
    n-methylformamide 113.64
    2-pentanol 35.56
    n-pentane 0.52
    1-propoxy-2-propanol 110.04
    1-methoxy-2-propyl acetate 117.6
    2-(2-methoxypropoxy) propanol 112.83
    mesitylene 6.43
    ε-caprolactone 87.12
    p-cymene 7.8
    epichlorohydrin 199.18
    1,1,1-trichloroethane 13.07
    2-aminoethanol 106.4
    morpholine-4-carbaldehyde 168.63
    sulfolane 352.91
    2,2,4-trimethylpentane 1.63
    2-methyltetrahydrofuran 175.74
    n-hexyl acetate 41.41
    isooctane 1.84
    2-(2-butoxyethoxy)ethanol 156.24
    sec-butyl acetate 45.54
    tert-butyl acetate 104.97
    decalin 1.38
    glycerin 171.23
    diglyme 270.25
    acrylic acid 71.52
    isopropyl myristate 23.35
    n-butyric acid 83.44
    acetyl acetate 64.12
    di(2-ethylhexyl) phthalate 22.3
    ethyl propionate 58.99
    nitromethane 264.61
    1,2-diethoxyethane 108.31
    benzonitrile 23.14
    trioctyl phosphate 16.38
    1-bromopropane 4.37
    gamma-valerolactone 250.76
    n-decanol 15.71
    triethyl phosphate 32.72
    4-methyl-2-pentanol 32.93
    propionitrile 55.79
    vinylene carbonate 54.88
    1,1,2-trichlorotrifluoroethane 151.65
    DMS 56.45
    cumene 6.62
    2-octanol 11.97
    2-hexanone 70.54
    octyl acetate 26.9
    limonene 10.81
    1,2-dimethoxyethane 230.24
    ethyl orthosilicate 30.06
    tributyl phosphate 21.74
    diacetone alcohol 164.45
    N,N-dimethylaniline 28.43
    acrylonitrile 65.16
    aniline 27.85
    1,3-propanediol 119.43
    bromobenzene 4.85
    dibromomethane 1.28
    1,1,2,2-tetrachloroethane 29.78
    2-methyl-cyclohexyl acetate 40.17
    tetrabutyl urea 29.7
    diisobutyl methanol 24.63
    2-phenylethanol 39.23
    styrene 6.74
    dioctyl adipate 39.64
    dimethyl sulfate 130.36
    ethyl butyrate 47.42
    methyl lactate 95.7
    butyl lactate 37.52
    diethyl carbonate 38.09
    propanediol butyl ether 81.87
    triethyl orthoformate 44.55
    p-tert-butyltoluene 9.14
    methyl 4-tert-butylbenzoate 52.94
    morpholine 271.96
    tert-butylamine 42.46
    n-dodecanol 12.51
    dimethoxymethane 233.24
    ethylene carbonate 48.19
    cyrene 79.37
    2-ethoxyethyl acetate 61.87
    2-ethylhexyl acetate 36.04
    1,2,4-trichlorobenzene 15.21
    4-methylpyridine 38.4
    dibutyl ether 31.27
    2,6-dimethyl-4-heptanol 24.63
    DEF 75.39
    dimethyl isosorbide 163.69
    tetrachloroethylene 13.93
    eugenol 57.7
    triacetin 66.85
    span 80 72.72
    1,4-butanediol 34.39
    1,1-dichloroethane 7.04
    2-methyl-1-pentanol 40.57
    methyl formate 81.55
    2-methyl-1-butanol 41.12
    n-decane 1.35
    butyronitrile 45.4
    3,7-dimethyl-1-octanol 26.85
    1-chlorooctane 7.29
    1-chlorotetradecane 3.98
    n-nonane 1.05
    undecane 1.15
    tert-butylcyclohexane 2.18
    cyclooctane 0.32
    cyclopentanol 51.7
    tetrahydropyran 133.59
    tert-amyl methyl ether 58.99
    2,5,8-trioxanonane 197.66
    1-hexene 5.52
    2-isopropoxyethanol 90.27
    2,2,2-trifluoroethanol 27.03
    methyl butyrate 63.32

    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