Rhapontigenin

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  • Identifiers

    CAS number
    500-65-2

    Molecular formula
    C15H14O4

    SMILES
    COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 60.2%
    Spicy 50.93%
    Woody 35.21%
    Odorless 33.23%
    Smoky 32.86%
    Fruity 32.03%
    Vanilla 31.31%
    Balsamic 31.24%
    Sweet 30.21%
    Burnt 29.78%

     

    Flavor
    Bitter 85.16%
    Odorless 21.17%
    Parsley 20.87%
    Nitrile 20.71%
    Cedarleaf 20.67%
    Curry 20.66%
    Eugenol 20.62%
    Flat 20.27%
    Very strong 20.2%
    Lovage 20.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    11.5 (strong base)

    Molecular weight
    258.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    537°C

    Flash point

    • 218.6 ˚C est.

  • Synonyms

    • Rhapontigenin
    • 500-65-2
    • Protigenin
    • Pontigenin
    • Rhapontin genin
    • 22BG4NNH6W
    • DTXSID501023634
    • 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
    • 5-((E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)BENZENE-1,3-DIOL
    • RefChem:179124
    • DTXCID701508969
    • (E)-5-(3-Hydroxy-4-methoxystyryl)benzene-1,3-diol
    • PRONTIGENIN
    • RHAPONTIN AGLYCONE
    • MFCD00017718
    • 5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
    • 5-[(1E)-2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
    • 3,3',5-trihydroxy-4'-methoxystilbene
    • 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-1,3-BENZENEDIOL
    • 4'-Methoxy-3,3',5-trihydroxystilbene
    • (E)-rhapontigenin
    • Rhapontigenin (Standard)
    • UNII-22BG4NNH6W
    • piceatannol 4'-methyl ether
    • CHEMBL113029
    • orb1303764
    • SCHEMBL1486816
    • SCHEMBL30940360
    • HY-N2229R
    • CHEBI:174376
    • PHMHDRYYFAYWEG-NSCUHMNNSA-N
    • HMS3648K18
    • 5-[(E)-2-(3-hydroxy-4-methoxy-phenyl)vinyl]benzene-1,3-diol
    • HY-N2229
    • s9163
    • trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene
    • AKOS015915122
    • AC-7022
    • CCG-267039
    • EBC-470074
    • FR74524
    • NCGC00344112-02
    • AS-68092
    • (E)-3,3',5-trihydroxy-4'-methoxystibene
    • CS-0019552
    • R0089
    • 3,3',5-Trihydroxy-4'-methoxy-trans-stilbene
    • 500R652
    • SR-01000946385
    • 3,3,5-STILBENETRIOL, 4-METHOXY-, (E)-
    • Q7320232
    • SR-01000946385-1
    • Rhapontigenin is known as a natural analog of resveratrol.
    • 1,3-BENZENEDIOL, 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-
    • 1,3-BENZENEDIOL, 5-(2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-, (E)-
    • 500-65-2

  • Applications

    Rhapontigenin (CAS 500-65-2) is a natural stilbene with various applications in cosmetics and pharmaceuticals. In cosmetic and personal care formulations, it is typically considered as an antioxidant and a stabilizing component that can help protect formulations from oxidative degradation. In pharmaceutical and biochemical research, it is used as a lead compound or scaffold for structure-activity relationship (SAR) studies related to stilbene chemistry and can serve as a reference in related analyses. In organic synthesis, rhapontigenin can be used as an intermediate for the preparation of stilbene derivatives and related fine chemicals, enabling the development of analogs for further study.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 46.62
    methanol 51.63
    isopropanol 38.7
    water 0.01
    ethyl acetate 46.44
    n-propanol 48.59
    acetone 120.84
    n-butanol 30.4
    acetonitrile 27.79
    DMF 89.98
    toluene 3.12
    isobutanol 19.15
    1,4-dioxane 102.6
    methyl acetate 46.7
    THF 729.14
    2-butanone 89.27
    n-pentanol 20.56
    sec-butanol 41.63
    n-hexane 0.37
    ethylene glycol 19.59
    NMP 34.51
    cyclohexane 0.29
    DMSO 881.46
    n-butyl acetate 15.57
    n-octanol 7.18
    chloroform 4.2
    n-propyl acetate 17.03
    acetic acid 39.87
    dichloromethane 1.91
    cyclohexanone 40.12
    propylene glycol 59.11
    isopropyl acetate 28.63
    DMAc 131.75
    2-ethoxyethanol 101.16
    isopentanol 25.1
    n-heptane 0.69
    ethyl formate 16.11
    1,2-dichloroethane 6.45
    n-hexanol 18.07
    2-methoxyethanol 210.99
    isobutyl acetate 9.68
    tetrachloromethane 0.79
    n-pentyl acetate 8.67
    transcutol 224.5
    n-heptanol 8.6
    ethylbenzene 2.06
    MIBK 31.82
    2-propoxyethanol 87.21
    tert-butanol 77.08
    MTBE 49.71
    2-butoxyethanol 30.35
    propionic acid 27.51
    o-xylene 2.58
    formic acid 19.93
    diethyl ether 48.46
    m-xylene 2.75
    p-xylene 1.92
    chlorobenzene 2.45
    dimethyl carbonate 27.26
    n-octane 0.29
    formamide 62.75
    cyclopentanone 117.18
    2-pentanone 55.6
    anisole 18.14
    cyclopentyl methyl ether 60.35
    gamma-butyrolactone 97.4
    1-methoxy-2-propanol 178.98
    pyridine 21.7
    3-pentanone 35.46
    furfural 43.5
    n-dodecane 0.46
    diethylene glycol 87.15
    diisopropyl ether 9.1
    tert-amyl alcohol 53.26
    acetylacetone 79.25
    n-hexadecane 0.55
    acetophenone 14.87
    methyl propionate 45.93
    isopentyl acetate 17.88
    trichloroethylene 13.75
    n-nonanol 7.94
    cyclohexanol 21.62
    benzyl alcohol 14.14
    2-ethylhexanol 10.88
    isooctanol 7.8
    dipropyl ether 20.99
    1,2-dichlorobenzene 3.0
    ethyl lactate 22.71
    propylene carbonate 24.42
    n-methylformamide 47.79
    2-pentanol 24.23
    n-pentane 0.32
    1-propoxy-2-propanol 61.77
    1-methoxy-2-propyl acetate 49.6
    2-(2-methoxypropoxy) propanol 48.58
    mesitylene 2.09
    ε-caprolactone 33.23
    p-cymene 3.09
    epichlorohydrin 115.67
    1,1,1-trichloroethane 5.21
    2-aminoethanol 49.89
    morpholine-4-carbaldehyde 71.34
    sulfolane 154.38
    2,2,4-trimethylpentane 0.76
    2-methyltetrahydrofuran 110.21
    n-hexyl acetate 13.84
    isooctane 0.58
    2-(2-butoxyethoxy)ethanol 62.01
    sec-butyl acetate 14.9
    tert-butyl acetate 44.88
    decalin 0.53
    glycerin 94.78
    diglyme 109.0
    acrylic acid 23.87
    isopropyl myristate 8.9
    n-butyric acid 29.73
    acetyl acetate 22.37
    di(2-ethylhexyl) phthalate 8.1
    ethyl propionate 22.76
    nitromethane 116.97
    1,2-diethoxyethane 48.44
    benzonitrile 7.24
    trioctyl phosphate 6.46
    1-bromopropane 3.96
    gamma-valerolactone 106.88
    n-decanol 6.35
    triethyl phosphate 14.97
    4-methyl-2-pentanol 14.84
    propionitrile 22.74
    vinylene carbonate 16.53
    1,1,2-trichlorotrifluoroethane 72.05
    DMS 19.45
    cumene 1.97
    2-octanol 5.13
    2-hexanone 22.82
    octyl acetate 9.71
    limonene 4.95
    1,2-dimethoxyethane 134.7
    ethyl orthosilicate 14.72
    tributyl phosphate 8.6
    diacetone alcohol 76.7
    N,N-dimethylaniline 10.75
    acrylonitrile 26.32
    aniline 11.83
    1,3-propanediol 72.55
    bromobenzene 1.78
    dibromomethane 1.57
    1,1,2,2-tetrachloroethane 16.76
    2-methyl-cyclohexyl acetate 16.14
    tetrabutyl urea 12.29
    diisobutyl methanol 10.19
    2-phenylethanol 15.51
    styrene 2.24
    dioctyl adipate 14.98
    dimethyl sulfate 53.04
    ethyl butyrate 19.17
    methyl lactate 48.01
    butyl lactate 14.85
    diethyl carbonate 14.58
    propanediol butyl ether 28.81
    triethyl orthoformate 21.4
    p-tert-butyltoluene 3.54
    methyl 4-tert-butylbenzoate 21.64
    morpholine 171.55
    tert-butylamine 22.19
    n-dodecanol 5.14
    dimethoxymethane 156.2
    ethylene carbonate 15.01
    cyrene 36.09
    2-ethoxyethyl acetate 22.74
    2-ethylhexyl acetate 11.35
    1,2,4-trichlorobenzene 5.12
    4-methylpyridine 12.81
    dibutyl ether 12.07
    2,6-dimethyl-4-heptanol 10.19
    DEF 34.09
    dimethyl isosorbide 73.01
    tetrachloroethylene 7.71
    eugenol 22.66
    triacetin 24.81
    span 80 27.27
    1,4-butanediol 17.94
    1,1-dichloroethane 3.95
    2-methyl-1-pentanol 17.64
    methyl formate 30.31
    2-methyl-1-butanol 22.37
    n-decane 0.71
    butyronitrile 17.08
    3,7-dimethyl-1-octanol 9.64
    1-chlorooctane 3.36
    1-chlorotetradecane 1.64
    n-nonane 0.55
    undecane 0.57
    tert-butylcyclohexane 0.66
    cyclooctane 0.21
    cyclopentanol 33.87
    tetrahydropyran 76.81
    tert-amyl methyl ether 36.98
    2,5,8-trioxanonane 89.11
    1-hexene 2.3
    2-isopropoxyethanol 53.72
    2,2,2-trifluoroethanol 10.9
    methyl butyrate 22.22

    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