Isosilybin

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  • Identifiers

    CAS number
    72581-71-6

    Molecular formula
    C25H22O10

    SMILES
    COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 60.02%
    Vanilla 50.18%
    Phenolic 38.12%
    Sweet 34.71%
    Creamy 28.68%
    Spicy 26.9%
    Milky 26.08%
    Balsamic 25.81%
    Burnt 24.2%
    Smoky 23.46%

     

    Flavor
    Bitter 89.34%
    Bland 30.0%
    Sweet-like 23.78%
    Odorless 23.55%
    Parsley 20.21%
    Cedarleaf 20.07%
    Lovage 19.79%
    Eugenol 19.61%
    Ethyl benzoate 18.7%
    Ripe apricot 18.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    9.46 (weak base)

    Molecular weight
    482.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1973°C

    Flash point

    • 270.44 ˚C est.

  • Synonyms

    • Isosilybin
    • 72581-71-6
    • CHEBI:80744
    • RefChem:792332
    • 3,5,7-trihydroxy-2-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one
    • 3,5,7-trihydroxy-2-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-3,4-dihydro-2H-1-benzopyran-4-one
    • Isosilybinin
    • CHEMBL5204643
    • (2R,3R)-3,5,7-Trihydroxy-2-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
    • (2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
    • Isosilibinin
    • (2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-4-one
    • isosilybine
    • DTXSID10858695
    • MFCD09842608
    • Isosilybin (Standard)
    • SCHEMBL4653986
    • EX-A8002P
    • HY-N0779R
    • HY-N0779
    • BDBM50595721
    • MSK158716
    • s9250
    • Isosilybin (Mixture of Diastereomers)
    • AKOS030573651
    • CCG-269565
    • CS-6233
    • EBC-609489
    • FI24728
    • (2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
    • AC-34989
    • DA-54460
    • SY232020
    • Isosilybin (isomeric mixture of isosilybin A&B)
    • Q27149797
    • Z3247556409
    • (2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxy-phenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
    • 2-[2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4- one
    • Isosilybin(2R,3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one; Isosilibinin
    • 72581-71-6

  • Applications

    Isosilybin (CAS 72581-71-6) is a natural flavonolignan commonly found in the silymarin extract from milk thistle (Silybum marianum). In industry, it is primarily treated as a phytochemical for pharmaceutical research and development and is used as a reference standard for analytical characterization of plant-derived products; in cosmetics and personal care, it is evaluated for antioxidant activity and considered for potential inclusion in plant-based formulations; in the functional food and dietary supplement space, it may appear in silymarin-based products and is studied for stability and related analytical considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 12.03
    methanol 26.8
    isopropanol 5.19
    water 0.04
    ethyl acetate 3.65
    n-propanol 12.14
    acetone 14.75
    n-butanol 7.13
    acetonitrile 3.01
    DMF 129.42
    toluene 0.34
    isobutanol 3.08
    1,4-dioxane 22.94
    methyl acetate 5.18
    THF 57.13
    2-butanone 12.84
    n-pentanol 2.11
    sec-butanol 4.12
    n-hexane 0.01
    ethylene glycol 21.45
    NMP 57.13
    cyclohexane 0.02
    DMSO 264.08
    n-butyl acetate 0.85
    n-octanol 1.57
    chloroform 0.8
    n-propyl acetate 1.32
    acetic acid 29.66
    dichloromethane 1.17
    cyclohexanone 13.7
    propylene glycol 21.57
    isopropyl acetate 1.57
    DMAc 89.68
    2-ethoxyethanol 41.86
    isopentanol 2.23
    n-heptane 0.03
    ethyl formate 7.31
    1,2-dichloroethane 1.41
    n-hexanol 0.79
    2-methoxyethanol 141.01
    isobutyl acetate 0.39
    tetrachloromethane 0.09
    n-pentyl acetate 1.6
    transcutol 25.82
    n-heptanol 1.45
    ethylbenzene 0.1
    MIBK 1.8
    2-propoxyethanol 21.47
    tert-butanol 2.26
    MTBE 0.95
    2-butoxyethanol 10.47
    propionic acid 8.92
    o-xylene 0.19
    formic acid 43.16
    diethyl ether 2.34
    m-xylene 0.16
    p-xylene 0.1
    chlorobenzene 0.23
    dimethyl carbonate 6.95
    n-octane 0.02
    formamide 57.1
    cyclopentanone 29.72
    2-pentanone 7.23
    anisole 1.05
    cyclopentyl methyl ether 3.65
    gamma-butyrolactone 31.06
    1-methoxy-2-propanol 56.52
    pyridine 7.86
    3-pentanone 3.83
    furfural 22.94
    n-dodecane 0.03
    diethylene glycol 30.49
    diisopropyl ether 0.18
    tert-amyl alcohol 1.97
    acetylacetone 11.39
    n-hexadecane 0.03
    acetophenone 1.51
    methyl propionate 7.53
    isopentyl acetate 0.64
    trichloroethylene 2.9
    n-nonanol 1.64
    cyclohexanol 2.38
    benzyl alcohol 2.15
    2-ethylhexanol 0.42
    isooctanol 0.86
    dipropyl ether 1.21
    1,2-dichlorobenzene 0.2
    ethyl lactate 4.01
    propylene carbonate 5.41
    n-methylformamide 56.51
    2-pentanol 1.79
    n-pentane 0.02
    1-propoxy-2-propanol 9.54
    1-methoxy-2-propyl acetate 4.43
    2-(2-methoxypropoxy) propanol 8.16
    mesitylene 0.08
    ε-caprolactone 11.04
    p-cymene 0.09
    epichlorohydrin 29.39
    1,1,1-trichloroethane 0.25
    2-aminoethanol 29.1
    morpholine-4-carbaldehyde 68.82
    sulfolane 64.69
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 7.17
    n-hexyl acetate 2.12
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 12.92
    sec-butyl acetate 0.56
    tert-butyl acetate 1.49
    decalin 0.01
    glycerin 58.64
    diglyme 26.5
    acrylic acid 12.71
    isopropyl myristate 0.73
    n-butyric acid 9.09
    acetyl acetate 2.03
    di(2-ethylhexyl) phthalate 1.08
    ethyl propionate 1.59
    nitromethane 59.68
    1,2-diethoxyethane 3.94
    benzonitrile 0.95
    trioctyl phosphate 1.03
    1-bromopropane 0.47
    gamma-valerolactone 86.28
    n-decanol 1.05
    triethyl phosphate 0.87
    4-methyl-2-pentanol 0.49
    propionitrile 2.89
    vinylene carbonate 5.91
    1,1,2-trichlorotrifluoroethane 37.9
    DMS 2.09
    cumene 0.05
    2-octanol 0.75
    2-hexanone 1.89
    octyl acetate 1.38
    limonene 0.18
    1,2-dimethoxyethane 34.7
    ethyl orthosilicate 0.73
    tributyl phosphate 0.87
    diacetone alcohol 7.78
    N,N-dimethylaniline 0.66
    acrylonitrile 5.77
    aniline 1.71
    1,3-propanediol 40.23
    bromobenzene 0.13
    dibromomethane 0.44
    1,1,2,2-tetrachloroethane 2.19
    2-methyl-cyclohexyl acetate 0.76
    tetrabutyl urea 2.02
    diisobutyl methanol 0.26
    2-phenylethanol 1.17
    styrene 0.12
    dioctyl adipate 1.84
    dimethyl sulfate 15.59
    ethyl butyrate 1.25
    methyl lactate 18.4
    butyl lactate 3.24
    diethyl carbonate 0.74
    propanediol butyl ether 11.24
    triethyl orthoformate 1.39
    p-tert-butyltoluene 0.09
    methyl 4-tert-butylbenzoate 2.94
    morpholine 45.6
    tert-butylamine 0.43
    n-dodecanol 0.65
    dimethoxymethane 55.73
    ethylene carbonate 4.43
    cyrene 11.82
    2-ethoxyethyl acetate 4.55
    2-ethylhexyl acetate 0.42
    1,2,4-trichlorobenzene 0.38
    4-methylpyridine 3.56
    dibutyl ether 1.02
    2,6-dimethyl-4-heptanol 0.26
    DEF 14.82
    dimethyl isosorbide 10.89
    tetrachloroethylene 1.33
    eugenol 3.68
    triacetin 4.27
    span 80 6.51
    1,4-butanediol 8.26
    1,1-dichloroethane 0.48
    2-methyl-1-pentanol 0.92
    methyl formate 35.21
    2-methyl-1-butanol 2.71
    n-decane 0.05
    butyronitrile 2.26
    3,7-dimethyl-1-octanol 0.74
    1-chlorooctane 0.3
    1-chlorotetradecane 0.11
    n-nonane 0.04
    undecane 0.04
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 5.12
    tetrahydropyran 7.09
    tert-amyl methyl ether 1.04
    2,5,8-trioxanonane 16.9
    1-hexene 0.06
    2-isopropoxyethanol 10.82
    2,2,2-trifluoroethanol 9.57
    methyl butyrate 2.78

    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