(S)-Warfarin

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  • Identifiers

    CAS number
    5543-57-7

    Molecular formula
    C19H16O4

    SMILES
    CC(=O)C[C@@H](C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 47.79%
    Sweet 47.78%
    Fruity 46.29%
    Balsamic 39.4%
    Powdery 31.54%
    Honey 31.22%
    Berry 30.56%
    Vanilla 29.71%
    Spicy 29.32%
    Phenolic 26.53%

     

    Flavor
    Bitter 76.89%
    Odorless 21.95%
    Mild 19.99%
    Heather 19.24%
    Broom 19.24%
    Orange flower 19.07%
    Cedarleaf 19.03%
    Lovage 19.01%
    Ethyl benzoate 18.93%
    Orange blossom 18.85%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    7.74 (neutral)

    Molecular weight
    308.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    792°C

    Flash point

    • 206.51 ˚C est.

  • Synonyms

    • (S)-Warfarin
    • (-)-Warfarin
    • S-WARFARIN
    • levrowarfarin
    • Warfarin, (S)-
    • UNII-HP31W7FNP4
    • 4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]chromen-2-one
    • 4-HYDROXY-3-[(1S)-3-OXO-1-PHENYLBUTYL]-2H-CHROMEN-2-ONE
    • (S)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone
    • WARFARIN, L-
    • EINECS 226-907-3
    • CHEBI:87738
    • DTXSID50873382
    • Coumarin, 3-(.alpha.-acetonylbenzyl)-4-hydroxy-, (S)-(-)-
    • 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1S)-3-OXO-1-PHENYLBUTYL)-
    • 4-hydroxy-3-((1S)-3-oxo-1-phenylbutyl)chromen-2-one
    • 4-hydroxy-3-((1S)-3-oxo-1-phenylbutyl)-2H-chromen-2-one
    • RefChem:70524
    • DTXCID30820899
    • COUMARIN, 3-(ALPHA-ACETONYLBENZYL)-4-HYDROXY-, (S)-(-)-
    • 5543-57-7
    • (S)-(-)-Warfarin
    • s-(-)-warfarin
    • (S)-4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
    • HP31W7FNP4
    • 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, (S)-
    • 2-hydroxy-3-[(1S)-3-oxo-1-phenyl-butyl]chromen-4-one
    • 4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one
    • SWF
    • MFCD00006854
    • 4-HYDROXY-3-((1S)-3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE
    • s(-)-warfarin
    • 2H-1-Benzopyran-2-one, 4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-; 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, (S)-; Coumarin, 3-(a-acetonylbenzyl)-4-hydroxy-, (S)-(-)- (8CI); 4-Hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one; (-)-Warfarin; (S)-Warfarin
    • 1ha2
    • BIDD:PXR0197
    • SCHEMBL20806
    • SCHEMBL662875
    • CHEMBL251074
    • orb1705998
    • MFCD00272381
    • AKOS027320629
    • AKOS037653253
    • DB02507
    • DB14055
    • GS-6170
    • NCGC00165934-01
    • (S)-(-)-Warfarin, >=97% (HPLC)
    • NS00099248
    • Warfarin Sodium Impurity 23 ((S)-Warfarin)
    • BIM-0061758.0001
    • C20129
    • A840201
    • BRD-K25991148-001-01-7
    • Q27093493
    • 4-hydroxy-3-[(1S)-3-oxo-1-phenyl-butyl]chromen-2-one
    • 2-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-4H-chromen-4-one
    • 5543-57-7

  • Applications

    (S)-Warfarin (CAS 5543-57-7) is primarily used as a pharmaceutical anticoagulant in human and veterinary medicine; in addition, it has been utilized as a rodenticide in pest-control programs, taking advantage of its vitamin K–dependent anticoagulant mechanism. It also serves as an intermediate in the synthesis of coumarin derivatives and is encountered in research on the vitamin K cycle and related pharmacophores; in some cases it may be evaluated for use as an analytical standard or for laboratory synthesis of related compounds. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.77
    methanol 7.27
    isopropanol 2.46
    water 0.01
    ethyl acetate 4.3
    n-propanol 4.45
    acetone 15.31
    n-butanol 3.29
    acetonitrile 5.79
    DMF 192.9
    toluene 2.91
    isobutanol 3.29
    1,4-dioxane 34.62
    methyl acetate 10.35
    THF 120.09
    2-butanone 15.26
    n-pentanol 3.77
    sec-butanol 2.49
    n-hexane 0.01
    ethylene glycol 5.31
    NMP 141.5
    cyclohexane 0.02
    DMSO 184.87
    n-butyl acetate 6.36
    n-octanol 2.04
    chloroform 4.21
    n-propyl acetate 7.25
    acetic acid 17.83
    dichloromethane 9.81
    cyclohexanone 35.53
    propylene glycol 6.46
    isopropyl acetate 4.25
    DMAc 167.21
    2-ethoxyethanol 18.06
    isopentanol 4.16
    n-heptane 0.03
    ethyl formate 5.53
    1,2-dichloroethane 12.92
    n-hexanol 2.67
    2-methoxyethanol 46.2
    isobutyl acetate 5.36
    tetrachloromethane 0.18
    n-pentyl acetate 6.02
    transcutol 92.01
    n-heptanol 3.01
    ethylbenzene 1.41
    MIBK 6.9
    2-propoxyethanol 24.89
    tert-butanol 3.73
    MTBE 1.89
    2-butoxyethanol 13.75
    propionic acid 9.35
    o-xylene 1.66
    formic acid 10.59
    diethyl ether 1.24
    m-xylene 1.74
    p-xylene 2.28
    chlorobenzene 5.85
    dimethyl carbonate 14.16
    n-octane 0.02
    formamide 25.39
    cyclopentanone 81.36
    2-pentanone 7.89
    anisole 8.01
    cyclopentyl methyl ether 12.65
    gamma-butyrolactone 90.98
    1-methoxy-2-propanol 27.77
    pyridine 42.69
    3-pentanone 5.99
    furfural 66.54
    n-dodecane 0.07
    diethylene glycol 28.44
    diisopropyl ether 0.42
    tert-amyl alcohol 3.15
    acetylacetone 23.13
    n-hexadecane 0.09
    acetophenone 13.83
    methyl propionate 9.79
    isopentyl acetate 7.75
    trichloroethylene 34.66
    n-nonanol 2.52
    cyclohexanol 4.11
    benzyl alcohol 12.23
    2-ethylhexanol 2.51
    isooctanol 3.07
    dipropyl ether 2.64
    1,2-dichlorobenzene 5.66
    ethyl lactate 8.6
    propylene carbonate 23.5
    n-methylformamide 37.18
    2-pentanol 1.3
    n-pentane 0.01
    1-propoxy-2-propanol 14.86
    1-methoxy-2-propyl acetate 17.34
    2-(2-methoxypropoxy) propanol 20.04
    mesitylene 0.8
    ε-caprolactone 30.1
    p-cymene 1.71
    epichlorohydrin 129.58
    1,1,1-trichloroethane 2.7
    2-aminoethanol 8.45
    morpholine-4-carbaldehyde 117.96
    sulfolane 150.84
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 23.41
    n-hexyl acetate 6.94
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 24.99
    sec-butyl acetate 4.67
    tert-butyl acetate 6.91
    decalin 0.08
    glycerin 21.41
    diglyme 56.7
    acrylic acid 16.33
    isopropyl myristate 3.46
    n-butyric acid 8.57
    acetyl acetate 5.79
    di(2-ethylhexyl) phthalate 7.12
    ethyl propionate 6.06
    nitromethane 51.56
    1,2-diethoxyethane 13.4
    benzonitrile 12.13
    trioctyl phosphate 3.98
    1-bromopropane 1.36
    gamma-valerolactone 127.13
    n-decanol 1.96
    triethyl phosphate 5.96
    4-methyl-2-pentanol 1.62
    propionitrile 5.56
    vinylene carbonate 23.73
    1,1,2-trichlorotrifluoroethane 58.23
    DMS 16.28
    cumene 1.15
    2-octanol 1.61
    2-hexanone 8.72
    octyl acetate 4.5
    limonene 1.87
    1,2-dimethoxyethane 40.47
    ethyl orthosilicate 5.19
    tributyl phosphate 4.8
    diacetone alcohol 17.67
    N,N-dimethylaniline 6.47
    acrylonitrile 14.94
    aniline 9.93
    1,3-propanediol 11.9
    bromobenzene 4.25
    dibromomethane 2.56
    1,1,2,2-tetrachloroethane 21.68
    2-methyl-cyclohexyl acetate 8.65
    tetrabutyl urea 8.27
    diisobutyl methanol 2.18
    2-phenylethanol 11.13
    styrene 1.83
    dioctyl adipate 8.38
    dimethyl sulfate 39.08
    ethyl butyrate 6.1
    methyl lactate 17.0
    butyl lactate 9.08
    diethyl carbonate 5.11
    propanediol butyl ether 12.01
    triethyl orthoformate 6.84
    p-tert-butyltoluene 1.49
    methyl 4-tert-butylbenzoate 16.09
    morpholine 54.93
    tert-butylamine 1.05
    n-dodecanol 1.51
    dimethoxymethane 49.27
    ethylene carbonate 16.08
    cyrene 30.47
    2-ethoxyethyl acetate 14.05
    2-ethylhexyl acetate 5.84
    1,2,4-trichlorobenzene 10.4
    4-methylpyridine 28.6
    dibutyl ether 2.66
    2,6-dimethyl-4-heptanol 2.18
    DEF 20.51
    dimethyl isosorbide 45.9
    tetrachloroethylene 8.67
    eugenol 18.14
    triacetin 15.1
    span 80 14.16
    1,4-butanediol 4.74
    1,1-dichloroethane 2.96
    2-methyl-1-pentanol 4.6
    methyl formate 27.98
    2-methyl-1-butanol 3.79
    n-decane 0.09
    butyronitrile 4.35
    3,7-dimethyl-1-octanol 2.82
    1-chlorooctane 0.84
    1-chlorotetradecane 0.47
    n-nonane 0.05
    undecane 0.08
    tert-butylcyclohexane 0.08
    cyclooctane 0.01
    cyclopentanol 8.31
    tetrahydropyran 11.58
    tert-amyl methyl ether 2.12
    2,5,8-trioxanonane 39.08
    1-hexene 0.17
    2-isopropoxyethanol 12.2
    2,2,2-trifluoroethanol 6.96
    methyl butyrate 9.13

    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