Dehydrosilybin

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  • Identifiers

    CAS number
    25166-14-7

    Molecular formula
    C25H20O10

    SMILES
    COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 56.71%
    Phenolic 45.18%
    Vanilla 40.25%
    Burnt 31.86%
    Smoky 25.55%
    Spicy 24.87%
    Balsamic 24.58%
    Creamy 24.57%
    Milky 24.21%
    Savory 23.42%

     

    Flavor
    Bitter 90.88%
    Bland 26.97%
    Odorless 24.26%
    Sweet-like 22.91%
    Parsley 20.47%
    Eugenol 20.37%
    Cedarleaf 20.01%
    Lovage 19.74%
    Ham 18.94%
    Ethyl benzoate 18.84%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    10.47 (weak base)

    Molecular weight
    480.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2540°C

    Flash point

    • 288.11 ˚C est.

  • Synonyms

    • 25166-14-7
    • YT9LPK42UU
    • Dehydrosilybin
    • DTXSID60858706
    • RefChem:585663
    • DTXCID70809446
    • 3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)chromen-4-one
    • 2,3-Dehydrosilybin
    • 3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)chromen-4-one
    • 2,3-Dehydrosilybin A
    • 2,3-Dehydrosilybin A
    • CHEMBL315670
    • orb1991552
    • HY-N12360
    • AKOS040735208
    • CS-0898993
    • 2-((2R,3R)-2-(Hydroxymethyl)-3-(3-methoxy-4-oxidanyl-phenyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-3,5,7-tris(oxidanyl)chromen-4-one
    • 2-[(2R,3R)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
    • 3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4H-chromen-4-one
    • 3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-1-benzopyran-4-one
    • 4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-3,5,7-trihydroxy-
    • 25166-14-7

  • Applications

    Dehydrosilybin is a flavonolignan derivative related to silybin, isolated from milk thistle. In industry it is primarily investigated as an antioxidant and polymer stabilizer, with potential use in cosmetic and personal care formulations as a bioactive antioxidant, and as a stabilizing additive in coatings, inks, and plastics to improve oxidative stability. It is commonly evaluated as a chemical intermediate or building block in the synthesis of flavonolignan-related compounds for pharmaceutical or nutraceutical research. The compound is also explored as a research reagent in formulation science and as a starting material for related synthetic routes, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.67
    methanol 2.76
    isopropanol 1.19
    water 0.01
    ethyl acetate 0.4
    n-propanol 2.68
    acetone 0.98
    n-butanol 1.41
    acetonitrile 0.2
    DMF 24.83
    toluene 0.04
    isobutanol 0.82
    1,4-dioxane 3.92
    methyl acetate 0.78
    THF 9.61
    2-butanone 2.05
    n-pentanol 0.57
    sec-butanol 1.47
    n-hexane 0.0
    ethylene glycol 5.27
    NMP 16.43
    cyclohexane 0.0
    DMSO 44.61
    n-butyl acetate 0.22
    n-octanol 0.53
    chloroform 0.06
    n-propyl acetate 0.3
    acetic acid 3.94
    dichloromethane 0.1
    cyclohexanone 1.99
    propylene glycol 5.74
    isopropyl acetate 0.23
    DMAc 23.31
    2-ethoxyethanol 11.02
    isopentanol 0.57
    n-heptane 0.01
    ethyl formate 0.76
    1,2-dichloroethane 0.13
    n-hexanol 0.24
    2-methoxyethanol 33.09
    isobutyl acetate 0.1
    tetrachloromethane 0.01
    n-pentyl acetate 0.53
    transcutol 10.26
    n-heptanol 0.51
    ethylbenzene 0.02
    MIBK 0.26
    2-propoxyethanol 6.5
    tert-butanol 0.58
    MTBE 0.24
    2-butoxyethanol 3.95
    propionic acid 2.02
    o-xylene 0.04
    formic acid 6.32
    diethyl ether 0.37
    m-xylene 0.02
    p-xylene 0.02
    chlorobenzene 0.02
    dimethyl carbonate 0.97
    n-octane 0.01
    formamide 8.74
    cyclopentanone 4.76
    2-pentanone 0.84
    anisole 0.16
    cyclopentyl methyl ether 0.66
    gamma-butyrolactone 5.53
    1-methoxy-2-propanol 15.04
    pyridine 1.25
    3-pentanone 0.54
    furfural 4.29
    n-dodecane 0.01
    diethylene glycol 8.81
    diisopropyl ether 0.04
    tert-amyl alcohol 0.76
    acetylacetone 1.08
    n-hexadecane 0.01
    acetophenone 0.27
    methyl propionate 1.12
    isopentyl acetate 0.2
    trichloroethylene 0.26
    n-nonanol 0.6
    cyclohexanol 0.62
    benzyl alcohol 0.43
    2-ethylhexanol 0.14
    isooctanol 0.32
    dipropyl ether 0.31
    1,2-dichlorobenzene 0.02
    ethyl lactate 1.0
    propylene carbonate 0.89
    n-methylformamide 8.74
    2-pentanol 0.48
    n-pentane 0.01
    1-propoxy-2-propanol 3.36
    1-methoxy-2-propyl acetate 1.12
    2-(2-methoxypropoxy) propanol 3.32
    mesitylene 0.01
    ε-caprolactone 2.26
    p-cymene 0.02
    epichlorohydrin 4.95
    1,1,1-trichloroethane 0.02
    2-aminoethanol 7.87
    morpholine-4-carbaldehyde 19.79
    sulfolane 15.02
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.6
    n-hexyl acetate 0.69
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 4.93
    sec-butyl acetate 0.14
    tert-butyl acetate 0.27
    decalin 0.0
    glycerin 19.01
    diglyme 9.38
    acrylic acid 2.7
    isopropyl myristate 0.2
    n-butyric acid 1.51
    acetyl acetate 0.18
    di(2-ethylhexyl) phthalate 0.33
    ethyl propionate 0.3
    nitromethane 6.47
    1,2-diethoxyethane 1.12
    benzonitrile 0.13
    trioctyl phosphate 0.3
    1-bromopropane 0.06
    gamma-valerolactone 19.43
    n-decanol 0.36
    triethyl phosphate 0.23
    4-methyl-2-pentanol 0.13
    propionitrile 0.36
    vinylene carbonate 0.8
    1,1,2-trichlorotrifluoroethane 9.88
    DMS 0.48
    cumene 0.01
    2-octanol 0.31
    2-hexanone 0.43
    octyl acetate 0.39
    limonene 0.04
    1,2-dimethoxyethane 8.46
    ethyl orthosilicate 0.21
    tributyl phosphate 0.27
    diacetone alcohol 1.89
    N,N-dimethylaniline 0.14
    acrylonitrile 0.73
    aniline 0.27
    1,3-propanediol 9.79
    bromobenzene 0.01
    dibromomethane 0.04
    1,1,2,2-tetrachloroethane 0.27
    2-methyl-cyclohexyl acetate 0.21
    tetrabutyl urea 0.61
    diisobutyl methanol 0.08
    2-phenylethanol 0.29
    styrene 0.02
    dioctyl adipate 0.51
    dimethyl sulfate 2.62
    ethyl butyrate 0.28
    methyl lactate 3.95
    butyl lactate 1.17
    diethyl carbonate 0.16
    propanediol butyl ether 4.35
    triethyl orthoformate 0.42
    p-tert-butyltoluene 0.02
    methyl 4-tert-butylbenzoate 0.87
    morpholine 10.6
    tert-butylamine 0.11
    n-dodecanol 0.21
    dimethoxymethane 8.82
    ethylene carbonate 0.61
    cyrene 3.75
    2-ethoxyethyl acetate 1.43
    2-ethylhexyl acetate 0.14
    1,2,4-trichlorobenzene 0.05
    4-methylpyridine 0.48
    dibutyl ether 0.31
    2,6-dimethyl-4-heptanol 0.08
    DEF 2.57
    dimethyl isosorbide 3.57
    tetrachloroethylene 0.16
    eugenol 1.22
    triacetin 1.15
    span 80 2.63
    1,4-butanediol 2.06
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.31
    methyl formate 4.27
    2-methyl-1-butanol 0.8
    n-decane 0.01
    butyronitrile 0.26
    3,7-dimethyl-1-octanol 0.24
    1-chlorooctane 0.07
    1-chlorotetradecane 0.02
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 1.31
    tetrahydropyran 1.14
    tert-amyl methyl ether 0.32
    2,5,8-trioxanonane 5.85
    1-hexene 0.02
    2-isopropoxyethanol 3.32
    2,2,2-trifluoroethanol 1.42
    methyl butyrate 0.55

    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