Dicoumarol

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  • Identifiers

    CAS number
    66-76-2

    Molecular formula
    C19H12O6

    SMILES
    C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Phenolic 45.72%
    Odorless 41.01%
    Sweet 34.23%
    Burnt 33.13%
    Bitter 26.05%
    Balsamic 25.98%
    Medicinal 22.98%
    Fruity 22.61%
    Spicy 22.6%
    Coconut 20.83%

     

    Flavor
    Bitter 95.1%
    Odorless 20.02%
    Cedarleaf 19.55%
    Very strong 19.24%
    Sweet-like 19.11%
    Nitrile 18.97%
    Lovage 18.96%
    Indole 18.89%
    Parsley 18.41%
    Moth ball 18.4%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    6.65 (neutral)

    Molecular weight
    336.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1453°C

    Melting point expt.

    • 290 °C
    • 287-293 °C

    Flash point

    • 259.77 ˚C est.

    Solubility expt.

    • 128 mg/L
    • Practically insol in water, alc, ether.
    • INSOL IN ACETONE
    • Sol in aq alkaline solns, in pyridine and similar org bases. Slightly sol in benzene and chloroform.
    • 6.62e-02 g/L

  • Synonyms

    • dicumarol
    • dicoumarol
    • 66-76-2
    • Bishydroxycoumarin
    • melitoxin
    • Antitrombosin
    • Baracoumin
    • Dicumarine
    • Acadyl
    • Acavyl
    • Dicuman
    • Dicumol
    • Dicoumal
    • Dufalone
    • Kumoran
    • Temparin
    • Trombosan
    • Cumid
    • Cuma
    • bis-hydroxycoumarin
    • Dicumaol R
    • Dicoumarolum
    • 3,3'-Methylenebis(4-hydroxycoumarin)
    • Anathrombase
    • Apekumarol
    • Dicoumerol
    • Dicumarinum
    • Dicumarolum
    • Bis(4-hydroxycoumarin-3-yl)methane
    • Bis-3,3'-(4-hydroxycoumarinyl)methane
    • Di-(4-hydroxy-3-coumarinyl)methane
    • Dicumarolo
    • Dwukumarol
    • Di-4-hydroxy-3,3'-methylenedicoumarin
    • 3,3'-Methylen-bis(4-hydroxy-cumarin)
    • 3,3'-Methylene-bis(4-hydroxycoumarine)
    • 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
    • 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
    • NC 034
    • 3,3'-Metilen-bis(4-idrossi-cumarina)
    • 3,3'-Methyleen-bis(4-hydroxy-cumarine)
    • 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-
    • DTXSID8021729
    • Coumarin, 3,3'-methylenebis(4-hydroxy-
    • 7QID3E7BG7
    • 4,4'-Dihydroxy-3,3'-methylene bis coumarin
    • NSC-17860
    • NSC-41834
    • 3,3'-Methylenebis[4-hydroxycoumarin]
    • 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-
    • NSC41834
    • NSC-221570
    • 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
    • 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
    • CHEBI:4513
    • DTXCID701729
    • 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-
    • 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone]
    • 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]
    • 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-2H-chromen-2-one
    • 4-hydroxy-3-((4-hydroxy-2-oxochromen-3-yl)methyl)chromen-2-one
    • 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-
    • RefChem:55011
    • B01AA01
    • 200-632-9
    • dicoumarin
    • 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one)
    • Dicumarol [USAN]
    • 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
    • NSC 17860
    • Dicoumarol (INN)
    • Dicoumarol [INN]
    • Dicumarol (USAN)
    • NSC 221570
    • MFCD00006857
    • CHEMBL1466
    • NSC17860
    • 3,2-benzopyrone]
    • CAS-66-76-2
    • Dicumarolo [DCIT]
    • NCGC00016296-01
    • Dwukumarol [Polish]
    • Dikumarol
    • Dicumarol [INN-Spanish]
    • Dicoumarolum [INN-Latin]
    • CHEMBL43154
    • 4-hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)methyl]chromen-2-one
    • Coumarin,3'-methylenebis[4-hydroxy-
    • CCRIS 3713
    • Bis-3,3'-(4-oxycoumarinyl)ethylacetate
    • NSC221570
    • HSDB 3223
    • WLN: T66 BOVJ EQ D1- DT66 BOVJ EQ
    • SR-05000001605
    • Dicumarol [USAN:USP]
    • 2H-1-Benzopyran-2-one,3'-methylenebis[4-hydroxy-
    • EINECS 200-632-9
    • NSC 41834
    • 2H-1-Benzopyran-2-one],3'-methylenebis[4-hydroxy-
    • 3,3'-Methylen-bis(4-hydroxy-cumarin) [German]
    • 3,3'-Methyleen-bis(4-hydroxy-cumarine) [Dutch]
    • 3,3'-Methylene-bis(4-hydroxycoumarine) [French]
    • 3,3'-Metilen-bis(4-idrossi-cumarina) [Italian]
    • UNII-7QID3E7BG7
    • BRN 0335444
    • Dicoumarin;
    • AI3-14546
    • Dicumarol;
    • Dicumarol?
    • Dufalone;
    • Cumid;
    • uncoupler of oxidative respiration
    • Bishydroxycoumarin;
    • Prestwick_90
    • 3,3'-Methylene-bis(4-hydroxycoumarin)
    • Spectrum_000165
    • DICUMAROL [MI]
    • DICUMAROL [HSDB]
    • Prestwick0_000785
    • Prestwick1_000785
    • Prestwick2_000785
    • Prestwick3_000785
    • Spectrum2_000144
    • Spectrum3_000387
    • Spectrum4_000508
    • Spectrum5_000871
    • DICUMAROL [VANDF]
    • 66-76-2

  • Applications

    Dicoumarol (CAS 66-76-2) is a dimeric 4-hydroxycoumarin compound with historical use as a vitamin K antagonist anticoagulant; in practice today its applications are mainly in pharmaceutical research and as a reference compound rather than a primary therapeutic agent. It may be used as a precursor or building block in the synthesis of related 4-hydroxycoumarin anticoagulants, and as an analytical standard or internal reference in laboratory methods evaluating anticoagulant activity. It has been employed as an active ingredient in anticoagulant rodenticide formulations in certain regions under appropriate regulatory controls. It is also encountered in toxicology and agricultural research related to moldy clover crops where dicoumarol is formed, informing risk assessment. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.31
    methanol 0.38
    isopropanol 0.33
    water 0.0
    ethyl acetate 0.56
    n-propanol 0.46
    acetone 0.34
    n-butanol 0.4
    acetonitrile 0.19
    DMF 13.46
    toluene 0.15
    isobutanol 0.33
    1,4-dioxane 2.74
    methyl acetate 0.75
    THF 8.83
    2-butanone 1.33
    n-pentanol 0.38
    sec-butanol 0.56
    n-hexane 0.01
    ethylene glycol 0.77
    NMP 16.81
    cyclohexane 0.0
    DMSO 16.28
    n-butyl acetate 0.73
    n-octanol 0.34
    chloroform 0.05
    n-propyl acetate 0.57
    acetic acid 0.73
    dichloromethane 0.12
    cyclohexanone 1.98
    propylene glycol 0.78
    isopropyl acetate 0.54
    DMAc 19.31
    2-ethoxyethanol 3.41
    isopentanol 0.42
    n-heptane 0.02
    ethyl formate 0.4
    1,2-dichloroethane 0.19
    n-hexanol 0.26
    2-methoxyethanol 6.99
    isobutyl acetate 0.27
    tetrachloromethane 0.01
    n-pentyl acetate 0.99
    transcutol 15.0
    n-heptanol 0.47
    ethylbenzene 0.11
    MIBK 0.63
    2-propoxyethanol 4.45
    tert-butanol 0.48
    MTBE 0.45
    2-butoxyethanol 3.09
    propionic acid 1.1
    o-xylene 0.18
    formic acid 1.19
    diethyl ether 0.37
    m-xylene 0.13
    p-xylene 0.13
    chlorobenzene 0.1
    dimethyl carbonate 1.43
    n-octane 0.01
    formamide 3.01
    cyclopentanone 4.57
    2-pentanone 0.77
    anisole 0.51
    cyclopentyl methyl ether 1.29
    gamma-butyrolactone 6.92
    1-methoxy-2-propanol 5.79
    pyridine 2.14
    3-pentanone 0.8
    furfural 6.44
    n-dodecane 0.02
    diethylene glycol 5.07
    diisopropyl ether 0.13
    tert-amyl alcohol 0.74
    acetylacetone 1.67
    n-hexadecane 0.02
    acetophenone 0.95
    methyl propionate 1.22
    isopentyl acetate 0.82
    trichloroethylene 0.4
    n-nonanol 0.44
    cyclohexanol 0.46
    benzyl alcohol 0.79
    2-ethylhexanol 0.32
    isooctanol 0.49
    dipropyl ether 0.77
    1,2-dichlorobenzene 0.13
    ethyl lactate 1.22
    propylene carbonate 1.53
    n-methylformamide 2.85
    2-pentanol 0.35
    n-pentane 0.01
    1-propoxy-2-propanol 3.74
    1-methoxy-2-propyl acetate 2.95
    2-(2-methoxypropoxy) propanol 4.6
    mesitylene 0.08
    ε-caprolactone 2.48
    p-cymene 0.19
    epichlorohydrin 6.19
    1,1,1-trichloroethane 0.05
    2-aminoethanol 1.06
    morpholine-4-carbaldehyde 18.02
    sulfolane 16.59
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.1
    n-hexyl acetate 0.99
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.07
    sec-butyl acetate 0.44
    tert-butyl acetate 0.86
    decalin 0.01
    glycerin 3.9
    diglyme 11.78
    acrylic acid 1.59
    isopropyl myristate 0.55
    n-butyric acid 0.83
    acetyl acetate 0.42
    di(2-ethylhexyl) phthalate 0.84
    ethyl propionate 0.66
    nitromethane 2.47
    1,2-diethoxyethane 2.78
    benzonitrile 0.49
    trioctyl phosphate 0.55
    1-bromopropane 0.1
    gamma-valerolactone 12.2
    n-decanol 0.34
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.26
    propionitrile 0.35
    vinylene carbonate 1.34
    1,1,2-trichlorotrifluoroethane 5.92
    DMS 1.69
    cumene 0.1
    2-octanol 0.32
    2-hexanone 0.72
    octyl acetate 0.68
    limonene 0.24
    1,2-dimethoxyethane 5.66
    ethyl orthosilicate 0.89
    tributyl phosphate 0.64
    diacetone alcohol 2.52
    N,N-dimethylaniline 0.57
    acrylonitrile 0.84
    aniline 0.59
    1,3-propanediol 1.62
    bromobenzene 0.07
    dibromomethane 0.06
    1,1,2,2-tetrachloroethane 0.43
    2-methyl-cyclohexyl acetate 0.84
    tetrabutyl urea 1.28
    diisobutyl methanol 0.35
    2-phenylethanol 0.84
    styrene 0.09
    dioctyl adipate 1.23
    dimethyl sulfate 4.97
    ethyl butyrate 0.82
    methyl lactate 3.03
    butyl lactate 1.74
    diethyl carbonate 0.62
    propanediol butyl ether 2.64
    triethyl orthoformate 1.26
    p-tert-butyltoluene 0.19
    methyl 4-tert-butylbenzoate 2.57
    morpholine 5.01
    tert-butylamine 0.17
    n-dodecanol 0.25
    dimethoxymethane 5.53
    ethylene carbonate 0.85
    cyrene 5.22
    2-ethoxyethyl acetate 2.8
    2-ethylhexyl acetate 0.67
    1,2,4-trichlorobenzene 0.29
    4-methylpyridine 1.24
    dibutyl ether 0.63
    2,6-dimethyl-4-heptanol 0.35
    DEF 2.79
    dimethyl isosorbide 9.46
    tetrachloroethylene 0.23
    eugenol 2.92
    triacetin 2.69
    span 80 3.03
    1,4-butanediol 0.65
    1,1-dichloroethane 0.05
    2-methyl-1-pentanol 0.44
    methyl formate 1.66
    2-methyl-1-butanol 0.47
    n-decane 0.03
    butyronitrile 0.26
    3,7-dimethyl-1-octanol 0.42
    1-chlorooctane 0.13
    1-chlorotetradecane 0.07
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 0.81
    tetrahydropyran 0.85
    tert-amyl methyl ether 0.67
    2,5,8-trioxanonane 8.55
    1-hexene 0.05
    2-isopropoxyethanol 2.2
    2,2,2-trifluoroethanol 0.67
    methyl butyrate 0.82

    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