(+)-Vitisin C

Overview IFRA Request a quote

  • Identifiers

    CAS number
    180580-73-8

    Molecular formula
    C56H42O12

    SMILES
    C1=CC(=CC=C1[C@@H]2[C@H](C3=C(C=C(C=C3O2)O)/C=C/C4=CC5=C(C=C4)O[C@H]([C@H]5C6=C7[C@@H]([C@H](OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 48.93%
    Odorless 40.6%
    Fruity 36.9%
    Spicy 27.75%
    Burnt 23.99%
    Animal 23.1%
    Medicinal 22.17%
    Balsamic 20.97%
    Smoky 19.84%
    Bitter 18.88%

     

    Flavor
    Bitter 97.29%
    Odorless 19.01%
    Cedarleaf 18.95%
    Sweet-like 18.84%
    Bland 18.77%
    Very strong 18.6%
    Indole 18.19%
    Nitrile 18.18%
    Lovage 17.54%
    Parsley 17.44%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    10.0

    pKa est.
    10.01 (weak base)

    Molecular weight
    906.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    5512°C

    Flash point

    • 314.03 ˚C est.

  • Synonyms

    • Vitisin C
    • (+)-vitisin C
    • 180580-73-8
    • M2HXT5SWE2
    • DTXSID10583213
    • 5-[(2S,3S)-4-[(E)-2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
    • 5-((2S,3S)-4-((E)-2-((2R,3S)-3-((2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl)ethenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl)benzene-1,3-diol
    • RefChem:67561
    • DTXCID90533978
    • 5-((2S,3S)-4-((E)-2-((3S)-3-((3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl)ethenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl)benzene-1,3-diol
    • 1,3-Benzenediol, 5-((2R,2S,3S,3S)-5-((1E)-2-((2S,3S)-3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-
    • 5-((2R,2S,3S,3S)-5-((1E)-2-((2S,3S)-3-(3,5-Dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-1,3-benzenediol
    • UNII-M2HXT5SWE2
    • CHEMBL442911
    • CHEBI:192464
    • Q7937134
    • 1,3-BENZENEDIOL, 5-(5-(2-(3-(3,5-DIHYDROXYPHENYL)-2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-BENZOFURANYL)ETHENYL)-2,2,3,3-TETRAHYDRO-6-HYDROXY-2,2-BIS(4-HYDROXYPHENYL)(3,4-BIBENZOFURAN)-3-YL)-, (2S-(2.ALPHA.,3.BETA.,4(E(2S*,3R*(2R*,3R*)))))-
    • 1,3-Benzenediol, 5-(5-(2-(3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl)ethenyl)-2,2,3,3-tetrahydro-6-hydroxy-2,2-bis(4-hydroxyphenyl)(3,4-bibenzofuran)-3-yl)-, (2S-(2alpha,3beta,4(E(2S*,3R*(2R*,3R*)))))-
    • 5-[(2S,3S)-4-[(E)-2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzouran-3-yl]benzene-1,3-diol
    • 5-[(2S,3S)-4-{(E)-2-[(2R,2'S,3S,3'S)-3'-(3,5-Dihydroxyphenyl)-6'-hydroxy-2,2'-bis(4-hydroxyphenyl)-2,2',3,3'-tetrahydro[3,4'-bi-1-benzofuran]-5-yl]ethenyl}-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
    • 180580-73-8

  • Applications

    (+)-Vitisin C, CAS number: 180580-73-8, is a stilbene-derived polyphenol natural product isolated from Vitis species. In practice, it is mainly encountered as a synthetic intermediate and a research reference compound in organic synthesis, particularly for exploring stilbene-based frameworks. Potential applications span cosmetics/personal care as a bioactive antioxidant ingredient in formulations; pharmaceuticals/medicinal chemistry research as a scaffold for SAR studies and lead-like compounds; polymers/plastics and coatings as an antioxidant stabilizer or functional additive; and food processing or packaging research to evaluate antioxidant performance in food-contact materials. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.12
    methanol 3.63
    isopropanol 0.37
    water 0.01
    ethyl acetate 0.8
    n-propanol 1.1
    acetone 1.53
    n-butanol 0.65
    acetonitrile 0.51
    DMF 27.01
    toluene 0.1
    isobutanol 0.36
    1,4-dioxane 2.72
    methyl acetate 1.34
    THF 9.58
    2-butanone 2.04
    n-pentanol 0.33
    sec-butanol 0.44
    n-hexane 0.0
    ethylene glycol 1.71
    NMP 18.75
    cyclohexane 0.0
    DMSO 21.9
    n-butyl acetate 0.53
    n-octanol 0.32
    chloroform 1.32
    n-propyl acetate 0.49
    acetic acid 8.49
    dichloromethane 0.93
    cyclohexanone 2.03
    propylene glycol 4.21
    isopropyl acetate 0.44
    DMAc 22.66
    2-ethoxyethanol 6.11
    isopentanol 0.27
    n-heptane 0.01
    ethyl formate 1.89
    1,2-dichloroethane 0.43
    n-hexanol 0.2
    2-methoxyethanol 19.23
    isobutyl acetate 0.21
    tetrachloromethane 0.07
    n-pentyl acetate 0.7
    transcutol 13.88
    n-heptanol 0.32
    ethylbenzene 0.03
    MIBK 0.43
    2-propoxyethanol 7.03
    tert-butanol 0.21
    MTBE 0.19
    2-butoxyethanol 4.61
    propionic acid 2.84
    o-xylene 0.05
    formic acid 8.99
    diethyl ether 0.32
    m-xylene 0.05
    p-xylene 0.03
    chlorobenzene 0.15
    dimethyl carbonate 2.34
    n-octane 0.0
    formamide 9.04
    cyclopentanone 6.48
    2-pentanone 1.09
    anisole 0.42
    cyclopentyl methyl ether 0.81
    gamma-butyrolactone 9.91
    1-methoxy-2-propanol 12.46
    pyridine 2.59
    3-pentanone 0.73
    furfural 11.24
    n-dodecane 0.0
    diethylene glycol 5.99
    diisopropyl ether 0.03
    tert-amyl alcohol 0.3
    acetylacetone 2.38
    n-hexadecane 0.0
    acetophenone 0.59
    methyl propionate 1.8
    isopentyl acetate 0.38
    trichloroethylene 2.26
    n-nonanol 0.37
    cyclohexanol 0.26
    benzyl alcohol 0.64
    2-ethylhexanol 0.12
    isooctanol 0.19
    dipropyl ether 0.4
    1,2-dichlorobenzene 0.16
    ethyl lactate 1.58
    propylene carbonate 2.87
    n-methylformamide 11.11
    2-pentanol 0.22
    n-pentane 0.01
    1-propoxy-2-propanol 4.65
    1-methoxy-2-propyl acetate 2.57
    2-(2-methoxypropoxy) propanol 4.64
    mesitylene 0.02
    ε-caprolactone 2.82
    p-cymene 0.04
    epichlorohydrin 8.73
    1,1,1-trichloroethane 0.19
    2-aminoethanol 3.32
    morpholine-4-carbaldehyde 22.73
    sulfolane 22.64
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.29
    n-hexyl acetate 0.87
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 6.56
    sec-butyl acetate 0.23
    tert-butyl acetate 0.47
    decalin 0.0
    glycerin 14.58
    diglyme 11.48
    acrylic acid 5.0
    isopropyl myristate 0.28
    n-butyric acid 2.64
    acetyl acetate 0.7
    di(2-ethylhexyl) phthalate 0.55
    ethyl propionate 0.55
    nitromethane 16.9
    1,2-diethoxyethane 1.22
    benzonitrile 0.38
    trioctyl phosphate 0.41
    1-bromopropane 0.13
    gamma-valerolactone 28.94
    n-decanol 0.22
    triethyl phosphate 0.38
    4-methyl-2-pentanol 0.1
    propionitrile 0.57
    vinylene carbonate 3.58
    1,1,2-trichlorotrifluoroethane 21.68
    DMS 0.91
    cumene 0.02
    2-octanol 0.16
    2-hexanone 0.48
    octyl acetate 0.52
    limonene 0.05
    1,2-dimethoxyethane 6.79
    ethyl orthosilicate 0.32
    tributyl phosphate 0.44
    diacetone alcohol 2.19
    N,N-dimethylaniline 0.25
    acrylonitrile 1.62
    aniline 0.44
    1,3-propanediol 3.74
    bromobenzene 0.1
    dibromomethane 0.29
    1,1,2,2-tetrachloroethane 1.63
    2-methyl-cyclohexyl acetate 0.36
    tetrabutyl urea 0.84
    diisobutyl methanol 0.07
    2-phenylethanol 0.45
    styrene 0.04
    dioctyl adipate 0.77
    dimethyl sulfate 6.06
    ethyl butyrate 0.6
    methyl lactate 6.77
    butyl lactate 2.35
    diethyl carbonate 0.38
    propanediol butyl ether 5.78
    triethyl orthoformate 0.73
    p-tert-butyltoluene 0.04
    methyl 4-tert-butylbenzoate 1.58
    morpholine 5.57
    tert-butylamine 0.05
    n-dodecanol 0.13
    dimethoxymethane 8.9
    ethylene carbonate 1.86
    cyrene 5.69
    2-ethoxyethyl acetate 2.29
    2-ethylhexyl acetate 0.25
    1,2,4-trichlorobenzene 0.3
    4-methylpyridine 1.05
    dibutyl ether 0.29
    2,6-dimethyl-4-heptanol 0.07
    DEF 2.61
    dimethyl isosorbide 7.58
    tetrachloroethylene 0.73
    eugenol 2.29
    triacetin 2.41
    span 80 3.91
    1,4-butanediol 0.92
    1,1-dichloroethane 0.24
    2-methyl-1-pentanol 0.18
    methyl formate 7.97
    2-methyl-1-butanol 0.37
    n-decane 0.01
    butyronitrile 0.43
    3,7-dimethyl-1-octanol 0.2
    1-chlorooctane 0.07
    1-chlorotetradecane 0.02
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.66
    tetrahydropyran 0.92
    tert-amyl methyl ether 0.24
    2,5,8-trioxanonane 7.43
    1-hexene 0.02
    2-isopropoxyethanol 1.86
    2,2,2-trifluoroethanol 2.97
    methyl butyrate 0.92

    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