Irigenin

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  • Identifiers

    CAS number
    548-76-5

    Molecular formula
    C18H16O8

    SMILES
    COC1=CC(=CC(=C1OC)O)C2=COC3=C(C2=O)C(=C(C(=C3)O)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 60.13%
    Spicy 40.61%
    Burnt 39.65%
    Odorless 39.04%
    Smoky 38.76%
    Vanilla 34.23%
    Woody 31.33%
    Balsamic 29.21%
    Medicinal 25.8%
    Dry 23.48%

     

    Flavor
    Bitter 80.32%
    Bland 26.82%
    Odorless 23.25%
    Parsley 21.9%
    Eugenol 21.74%
    Sweet-like 20.83%
    Cedarleaf 20.23%
    Lovage 19.76%
    Ham 19.6%
    Allspice 19.39%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    9.07 (weak base)

    Molecular weight
    360.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    989°C

    Flash point

    • 237.51 ˚C est.

  • Synonyms

    • Irigenin
    • 548-76-5
    • 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
    • 6O4NX37350
    • CHEBI:81409
    • DTXSID90203285
    • 5,7,3'-Trimethoxy-6,4',5'-trimethoxyisoflavone
    • RefChem:148728
    • DTXCID90125776
    • 208-958-3
    • 5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
    • 5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4-benzopyrone
    • 5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
    • 5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone
    • Irigenin?
    • UNII-6O4NX37350
    • EINECS 208-958-3
    • Irigenin (Standard)
    • MFCD00597047
    • IRIGENIN [MI]
    • 3',5,7-Trihydroxy-4',5',6-trimethoxyisoflavone
    • SCHEMBL554864
    • CHEMBL487013
    • orb1303647
    • SCHEMBL30335091
    • HY-N2587R
    • TUGWPJJTQNLKCL-UHFFFAOYSA-N
    • HY-N2587
    • LMPK12050417
    • s9121
    • AKOS030632868
    • CCG-214382
    • EBC-510377
    • FI12116
    • AC-35036
    • BS-17232
    • DA-54377
    • CS-0022931
    • NS00033204
    • C17957
    • SR-05000002617
    • Q2481557
    • SR-05000002617-1
    • 5,7-Di-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
    • 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxy-phenyl)-6-methoxy-chromen-4-one
    • 548-76-5

  • Applications

    Irigenin (CAS 548-76-5) is a naturally occurring isoflavone used chiefly as a research chemical and analytical standard in natural product studies. It serves as a reference compound and a starting material for the synthesis of flavonoid derivatives in medicinal chemistry, supporting structure–activity explorations. It is commonly evaluated in basic research for potential biological activities such as antioxidant, anti-inflammatory, and antimicrobial effects, without implying clinical efficacy. In cosmetics and personal care research, irigenin is explored as a plant-derived antioxidant ingredient in formulation studies. In analytical laboratories, it is used as a quantitative/qualitative standard for LC–MS and HPLC analyses of isoflavones in botanical extracts. When applicable, it may also serve as an intermediate in organic synthesis to access more advanced flavonoid structures. All uses are subject to local regulations and formulation limitations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.06
    methanol 0.1
    isopropanol 0.07
    water 0.0
    ethyl acetate 0.18
    n-propanol 0.15
    acetone 0.09
    n-butanol 0.13
    acetonitrile 0.07
    DMF 3.46
    toluene 0.02
    isobutanol 0.13
    1,4-dioxane 0.32
    methyl acetate 0.24
    THF 1.39
    2-butanone 0.34
    n-pentanol 0.15
    sec-butanol 0.18
    n-hexane 0.01
    ethylene glycol 0.22
    NMP 9.91
    cyclohexane 0.0
    DMSO 8.22
    n-butyl acetate 0.35
    n-octanol 0.19
    chloroform 0.09
    n-propyl acetate 0.22
    acetic acid 0.35
    dichloromethane 0.15
    cyclohexanone 0.64
    propylene glycol 0.27
    isopropyl acetate 0.14
    DMAc 6.48
    2-ethoxyethanol 1.26
    isopentanol 0.17
    n-heptane 0.02
    ethyl formate 0.14
    1,2-dichloroethane 0.16
    n-hexanol 0.17
    2-methoxyethanol 2.23
    isobutyl acetate 0.14
    tetrachloromethane 0.01
    n-pentyl acetate 0.36
    transcutol 4.02
    n-heptanol 0.24
    ethylbenzene 0.02
    MIBK 0.19
    2-propoxyethanol 2.1
    tert-butanol 0.16
    MTBE 0.12
    2-butoxyethanol 1.34
    propionic acid 0.44
    o-xylene 0.03
    formic acid 0.47
    diethyl ether 0.1
    m-xylene 0.02
    p-xylene 0.03
    chlorobenzene 0.03
    dimethyl carbonate 0.49
    n-octane 0.01
    formamide 0.86
    cyclopentanone 1.29
    2-pentanone 0.21
    anisole 0.11
    cyclopentyl methyl ether 0.4
    gamma-butyrolactone 2.44
    1-methoxy-2-propanol 1.78
    pyridine 0.29
    3-pentanone 0.26
    furfural 1.94
    n-dodecane 0.01
    diethylene glycol 2.33
    diisopropyl ether 0.04
    tert-amyl alcohol 0.29
    acetylacetone 0.38
    n-hexadecane 0.01
    acetophenone 0.27
    methyl propionate 0.48
    isopentyl acetate 0.4
    trichloroethylene 0.32
    n-nonanol 0.23
    cyclohexanol 0.19
    benzyl alcohol 0.18
    2-ethylhexanol 0.2
    isooctanol 0.24
    dipropyl ether 0.31
    1,2-dichlorobenzene 0.06
    ethyl lactate 0.56
    propylene carbonate 0.6
    n-methylformamide 0.89
    2-pentanol 0.11
    n-pentane 0.0
    1-propoxy-2-propanol 1.56
    1-methoxy-2-propyl acetate 1.15
    2-(2-methoxypropoxy) propanol 2.01
    mesitylene 0.02
    ε-caprolactone 0.9
    p-cymene 0.07
    epichlorohydrin 1.89
    1,1,1-trichloroethane 0.05
    2-aminoethanol 0.37
    morpholine-4-carbaldehyde 5.39
    sulfolane 10.96
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.52
    n-hexyl acetate 0.43
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 2.04
    sec-butyl acetate 0.16
    tert-butyl acetate 0.29
    decalin 0.01
    glycerin 1.72
    diglyme 4.32
    acrylic acid 0.64
    isopropyl myristate 0.2
    n-butyric acid 0.31
    acetyl acetate 0.13
    di(2-ethylhexyl) phthalate 0.35
    ethyl propionate 0.3
    nitromethane 1.26
    1,2-diethoxyethane 0.63
    benzonitrile 0.12
    trioctyl phosphate 0.3
    1-bromopropane 0.07
    gamma-valerolactone 3.35
    n-decanol 0.16
    triethyl phosphate 0.57
    4-methyl-2-pentanol 0.09
    propionitrile 0.16
    vinylene carbonate 0.49
    1,1,2-trichlorotrifluoroethane 4.23
    DMS 0.62
    cumene 0.03
    2-octanol 0.16
    2-hexanone 0.28
    octyl acetate 0.28
    limonene 0.12
    1,2-dimethoxyethane 1.82
    ethyl orthosilicate 0.49
    tributyl phosphate 0.34
    diacetone alcohol 1.02
    N,N-dimethylaniline 0.2
    acrylonitrile 0.34
    aniline 0.09
    1,3-propanediol 0.49
    bromobenzene 0.02
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.4
    2-methyl-cyclohexyl acetate 0.46
    tetrabutyl urea 0.68
    diisobutyl methanol 0.16
    2-phenylethanol 0.26
    styrene 0.02
    dioctyl adipate 0.48
    dimethyl sulfate 2.61
    ethyl butyrate 0.42
    methyl lactate 1.18
    butyl lactate 0.74
    diethyl carbonate 0.33
    propanediol butyl ether 1.11
    triethyl orthoformate 0.61
    p-tert-butyltoluene 0.08
    methyl 4-tert-butylbenzoate 1.04
    morpholine 0.86
    tert-butylamine 0.06
    n-dodecanol 0.11
    dimethoxymethane 1.39
    ethylene carbonate 0.32
    cyrene 2.71
    2-ethoxyethyl acetate 0.82
    2-ethylhexyl acetate 0.33
    1,2,4-trichlorobenzene 0.12
    4-methylpyridine 0.18
    dibutyl ether 0.21
    2,6-dimethyl-4-heptanol 0.16
    DEF 0.94
    dimethyl isosorbide 4.34
    tetrachloroethylene 0.2
    eugenol 1.14
    triacetin 1.03
    span 80 1.24
    1,4-butanediol 0.2
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.21
    methyl formate 0.5
    2-methyl-1-butanol 0.21
    n-decane 0.01
    butyronitrile 0.1
    3,7-dimethyl-1-octanol 0.19
    1-chlorooctane 0.07
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 0.31
    tetrahydropyran 0.19
    tert-amyl methyl ether 0.24
    2,5,8-trioxanonane 3.28
    1-hexene 0.03
    2-isopropoxyethanol 0.79
    2,2,2-trifluoroethanol 0.37
    methyl butyrate 0.39

    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