Coumestrol

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  • Identifiers

    CAS number
    479-13-0

    Molecular formula
    C15H8O5

    SMILES
    C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 55.03%
    Odorless 44.01%
    Burnt 34.8%
    Nutty 26.1%
    Medicinal 24.1%
    Animal 21.96%
    Balsamic 20.61%
    Bitter 20.45%
    Musty 20.23%
    Sweet 19.88%

     

    Flavor
    Bitter 97.02%
    Odorless 20.37%
    Very strong 19.48%
    Indole 19.07%
    Nitrile 18.83%
    Cedarleaf 18.78%
    Sweet-like 18.71%
    Rotten 18.32%
    Moth ball 18.29%
    Naphthelene 17.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    7.9 (neutral)

    Molecular weight
    268.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    601°C

    Melting point expt.

    • 385 °C

    Flash point

    • 249.97 ˚C est.

  • Synonyms

    • COUMESTROL
    • 479-13-0
    • Cumoestrol
    • Cumostrol
    • 3,9-Dihydroxycoumestan
    • DTXSID6022399
    • V7NW98OB34
    • 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
    • 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one
    • 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-
    • NSC-22842
    • CHEBI:3908
    • DTXCID102399
    • 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-
    • 3,9-dihydroxy-(1)benzofuro(3,2-c)chromen-6-one
    • RefChem:33625
    • 207-525-6
    • Cumoesterol
    • 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
    • NSC 22842
    • Cumestrol
    • MFCD00016885
    • 3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one
    • NSC22842
    • CHEMBL30707
    • MLS000738006
    • 3,9-dihydroxybenzofuro[3,2-c]chromen-6-one
    • Coumesterol
    • SMR000059001
    • CCRIS 7311
    • EINECS 207-525-6
    • BRN 0266702
    • UNII-V7NW98OB34
    • Coumestrol?
    • Coumestrol (COU)
    • Coumestrol (Standard)
    • COUMESTROL [MI]
    • NCIMech_000078
    • Oprea1_222511
    • SCHEMBL22012
    • 5-19-06-00405 (Beilstein Handbook Reference)
    • MLS000069446
    • BIDD:ER0114
    • orb1296071
    • SCHEMBL29453366
    • BDBM23451
    • GTPL12437
    • HY-N2335R
    • HMS2235B05
    • HMS3374A07
    • 6H-Benzofuro[3, 3,9-dihydroxy-
    • Coumestrol, >=95.0% (HPLC)
    • HY-N2335
    • Tox21_200032
    • CCG-35536
    • CCG-36200
    • LMPK12090018
    • MSK159856
    • AKOS028111776
    • CS-6343
    • EBC-436047
    • FC20578
    • 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone
    • SMP2_000163
    • NCGC00018124-01
    • NCGC00018124-02
    • NCGC00018124-03
    • NCGC00018124-04
    • NCGC00018124-05
    • NCGC00018124-06
    • NCGC00023462-03
    • NCGC00023462-04
    • NCGC00257586-01
    • AS-81377
    • CAS-479-13-0
    • NCI60_001863
    • DB-051484
    • NS00004410
    • ST50320052
    • D85092
    • S00280
    • US8552057, 3
    • 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
    • 3,9-dihydroxybenzo[d]chromeno[4,3-b]furan-6-one
    • Q908865
    • A1-00298
    • BRD-K97509413-001-01-8
    • 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one #
    • 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihdyroxy-
    • 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one
    • Coumestrol, BioReagent, suitable for fluorescence, >=97.5% (HPLC)
    • 3-Benzofurancarboxylic acid,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone
    • 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone
    • CoumestrolCumoesterol; Cumostrol; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
    • 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
    • 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one
    • Coumestrol

  • Applications

    Coumestrol (CAS 479-13-0) is primarily used as an analytical reference standard and research material in plant chemistry and natural product analysis, notably for developing and validating HPLC/LC-MS methods to quantify coumestans in leguminous sources. It is studied as a phytoestrogen in interdisciplinary research on estrogenic activity and safety. Antioxidant activity assessments of coumestrol are conducted to evaluate its potential in nutraceutical and cosmetic formulations at the research stage. In plant science and agricultural chemistry, it serves for profiling coumestan-related metabolites in crops and for quality control of botanical extracts. Additionally, it may be encountered as a reference compound in method development and analytical quality control in industrial laboratories.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.04
    methanol 6.8
    isopropanol 7.06
    water 0.05
    ethyl acetate 9.88
    n-propanol 7.27
    acetone 20.67
    n-butanol 7.84
    acetonitrile 4.95
    DMF 156.71
    toluene 0.67
    isobutanol 5.27
    1,4-dioxane 25.59
    methyl acetate 14.09
    THF 101.44
    2-butanone 26.84
    n-pentanol 5.01
    sec-butanol 7.57
    n-hexane 0.02
    ethylene glycol 13.49
    NMP 91.15
    cyclohexane 0.03
    DMSO 473.9
    n-butyl acetate 10.96
    n-octanol 3.49
    chloroform 0.14
    n-propyl acetate 11.24
    acetic acid 11.79
    dichloromethane 0.23
    cyclohexanone 31.46
    propylene glycol 13.05
    isopropyl acetate 8.24
    DMAc 174.83
    2-ethoxyethanol 35.32
    isopentanol 8.04
    n-heptane 0.05
    ethyl formate 8.38
    1,2-dichloroethane 0.85
    n-hexanol 3.89
    2-methoxyethanol 108.11
    isobutyl acetate 5.4
    tetrachloromethane 0.04
    n-pentyl acetate 8.1
    transcutol 103.24
    n-heptanol 3.5
    ethylbenzene 0.58
    MIBK 9.85
    2-propoxyethanol 47.09
    tert-butanol 8.56
    MTBE 3.25
    2-butoxyethanol 21.26
    propionic acid 13.21
    o-xylene 0.74
    formic acid 10.24
    diethyl ether 2.88
    m-xylene 0.56
    p-xylene 0.86
    chlorobenzene 0.51
    dimethyl carbonate 15.12
    n-octane 0.03
    formamide 33.75
    cyclopentanone 57.73
    2-pentanone 18.17
    anisole 5.35
    cyclopentyl methyl ether 10.26
    gamma-butyrolactone 56.02
    1-methoxy-2-propanol 77.94
    pyridine 13.66
    3-pentanone 9.72
    furfural 35.15
    n-dodecane 0.11
    diethylene glycol 58.96
    diisopropyl ether 0.79
    tert-amyl alcohol 8.46
    acetylacetone 25.82
    n-hexadecane 0.13
    acetophenone 10.87
    methyl propionate 16.63
    isopentyl acetate 10.01
    trichloroethylene 1.47
    n-nonanol 4.16
    cyclohexanol 7.54
    benzyl alcohol 8.96
    2-ethylhexanol 3.39
    isooctanol 3.32
    dipropyl ether 3.83
    1,2-dichlorobenzene 0.73
    ethyl lactate 17.77
    propylene carbonate 17.63
    n-methylformamide 44.01
    2-pentanol 4.77
    n-pentane 0.02
    1-propoxy-2-propanol 34.34
    1-methoxy-2-propyl acetate 27.38
    2-(2-methoxypropoxy) propanol 30.4
    mesitylene 0.41
    ε-caprolactone 32.53
    p-cymene 1.12
    epichlorohydrin 41.44
    1,1,1-trichloroethane 0.32
    2-aminoethanol 16.32
    morpholine-4-carbaldehyde 94.07
    sulfolane 106.05
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 21.75
    n-hexyl acetate 9.13
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 39.43
    sec-butyl acetate 7.18
    tert-butyl acetate 9.23
    decalin 0.06
    glycerin 46.33
    diglyme 60.98
    acrylic acid 15.06
    isopropyl myristate 5.34
    n-butyric acid 14.04
    acetyl acetate 5.19
    di(2-ethylhexyl) phthalate 6.89
    ethyl propionate 10.36
    nitromethane 37.61
    1,2-diethoxyethane 18.04
    benzonitrile 6.09
    trioctyl phosphate 5.57
    1-bromopropane 0.4
    gamma-valerolactone 102.82
    n-decanol 3.6
    triethyl phosphate 7.15
    4-methyl-2-pentanol 3.31
    propionitrile 6.75
    vinylene carbonate 13.84
    1,1,2-trichlorotrifluoroethane 36.43
    DMS 15.11
    cumene 0.55
    2-octanol 2.69
    2-hexanone 14.63
    octyl acetate 6.99
    limonene 1.4
    1,2-dimethoxyethane 62.62
    ethyl orthosilicate 5.95
    tributyl phosphate 6.69
    diacetone alcohol 34.24
    N,N-dimethylaniline 4.46
    acrylonitrile 12.36
    aniline 4.81
    1,3-propanediol 31.4
    bromobenzene 0.29
    dibromomethane 0.13
    1,1,2,2-tetrachloroethane 2.06
    2-methyl-cyclohexyl acetate 8.25
    tetrabutyl urea 11.07
    diisobutyl methanol 2.74
    2-phenylethanol 8.57
    styrene 0.59
    dioctyl adipate 9.48
    dimethyl sulfate 33.5
    ethyl butyrate 8.62
    methyl lactate 39.47
    butyl lactate 15.58
    diethyl carbonate 6.35
    propanediol butyl ether 23.93
    triethyl orthoformate 8.96
    p-tert-butyltoluene 1.04
    methyl 4-tert-butylbenzoate 12.9
    morpholine 52.35
    tert-butylamine 1.93
    n-dodecanol 2.93
    dimethoxymethane 62.96
    ethylene carbonate 12.4
    cyrene 31.25
    2-ethoxyethyl acetate 17.11
    2-ethylhexyl acetate 7.36
    1,2,4-trichlorobenzene 1.64
    4-methylpyridine 10.64
    dibutyl ether 4.51
    2,6-dimethyl-4-heptanol 2.74
    DEF 34.32
    dimethyl isosorbide 40.48
    tetrachloroethylene 0.93
    eugenol 16.29
    triacetin 16.21
    span 80 19.07
    1,4-butanediol 8.76
    1,1-dichloroethane 0.3
    2-methyl-1-pentanol 5.35
    methyl formate 25.22
    2-methyl-1-butanol 6.97
    n-decane 0.12
    butyronitrile 6.24
    3,7-dimethyl-1-octanol 4.24
    1-chlorooctane 0.7
    1-chlorotetradecane 0.53
    n-nonane 0.08
    undecane 0.12
    tert-butylcyclohexane 0.05
    cyclooctane 0.02
    cyclopentanol 10.3
    tetrahydropyran 10.42
    tert-amyl methyl ether 4.33
    2,5,8-trioxanonane 49.3
    1-hexene 0.18
    2-isopropoxyethanol 21.26
    2,2,2-trifluoroethanol 7.2
    methyl butyrate 15.42

    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