Phenprocoumon

Overview IFRA Request a quote

  • Identifiers

    CAS number
    435-97-2

    Molecular formula
    C18H16O3

    SMILES
    CCC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Phenolic 40.76%
    Spicy 35.12%
    Balsamic 32.52%
    Animal 30.14%
    Herbal 27.5%
    Sweet 27.43%
    Odorless 25.33%
    Fruity 23.54%
    Leathery 23.16%
    Medicinal 21.95%

     

    Flavor
    Bitter 77.2%
    Herbal 21.17%
    Cedarleaf 20.09%
    Lovage 19.58%
    Nitrile 18.76%
    Heather 18.59%
    Parsley 18.54%
    Butyric 18.36%
    Green pepper 18.32%
    Genet 18.31%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    7.76 (neutral)

    Molecular weight
    280.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    587°C

    Melting point expt.

    • 179.5 °C
    • 179-180 °C

    Flash point

    • 182.41 ˚C est.

    Solubility expt.

    • 12.9 mg/L
    • PRACTICALLY INSOL IN H2O; SOL IN CHLOROFORM & METHANOL
    • SOL IN SOLN OF ALKALI HYDROXIDES
    • 4.86e-02 g/L

  • Synonyms

    • PHENPROCOUMON
    • 435-97-2
    • Phenprocoumarol
    • Phenprocoumarole
    • 4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
    • Marcumar
    • Fencumar
    • Liquamar
    • Marcoumar
    • Falithrom
    • Phenprocoumone
    • Phenprocumone
    • Fenprocumone
    • Phenprocoumonum
    • Phenprocumonum
    • Fenprocumone [DCIT]
    • 3-(1-Phenylpropyl)-4-hydroxycoumarin
    • fenprocumon
    • Fenprocoumona
    • 4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one
    • 3-(alpha-Ethylbenzyl)-4-hydroxycoumarin
    • 3-(1'-Phenyl-propyl)-4-oxycoumarin
    • Ro 1-4849
    • 3-(alpha-Phenylpropyl)-4-hydroxycoumarin
    • 2H-1-Benzopyran-2-one, 4-hydroxy-3-(1-phenylpropyl)-
    • Fenprocoumona [INN-Spanish]
    • Phenprocoumone [INN-French]
    • Phenprocoumonum [INN-Latin]
    • HSDB 3248
    • 4-hydroxy-3-(1-phenylpropyl)chromen-2-one
    • EINECS 207-108-9
    • UNII-Q08SIO485D
    • BRN 1291115
    • Q08SIO485D
    • CHEBI:50438
    • Coumarin, 3-(alpha-ethylbenzyl)-4-hydroxy-
    • Phenprocoumon (Marcumar)
    • 2-hydroxy-3-(1-phenylpropyl)-4H-chromen-4-one
    • BS-7565
    • (+/-)-PHENPROCOUMON
    • RO-1-4849
    • 70206-44-9
    • Phenprocoumalol
    • DTXSID5023459
    • Phenprocoumon [USAN:USP:INN:BAN]
    • Coumarin, 3-(.alpha.-ethylbenzyl)-4-hydroxy-
    • Fenprocoumona (INN-Spanish)
    • Phenprocoumone (INN-French)
    • Phenprocoumonum (INN-Latin)
    • Phenylpropylhydroxycumarinum
    • CHEMBL16694
    • PHENPROCOUMON (MART.)
    • PHENPROCOUMON [MART.]
    • 4-HYDROXY-2-OXO-3-(1-PHENYLPROPYL)-2H-CHROMENE
    • 2H-1-Benzopyran-2-one, 4-hydroxy-3-[(1R)-1-phenylpropyl]-
    • Phenprocoumon (USAN:USP:INN:BAN)
    • Liquamar (TN)
    • 3-(1'-Phenyl-propyl)-4-oxycoumarin [German]
    • Phenprocoumon (USAN/INN)
    • PHENPROCOUMON [MI]
    • PHENPROCOUMON [INN]
    • U29342
    • CHEMBL1465
    • PHENPROCOUMON [HSDB]
    • PHENPROCOUMON [USAN]
    • Oprea1_002598
    • SCHEMBL43031
    • BDBM768
    • PHENPROCOUMON [VANDF]
    • MLS006010940
    • PHENPROCOUMON [WHO-DD]
    • DTXCID203459
    • GTPL6839
    • SCHEMBL1651720
    • B01AA04
    • PHENPROCOUMON [ORANGE BOOK]
    • AAA43597
    • BCP01576
    • HY-A0145
    • s2188
    • 3-(a-ethyl-benzyl)-4-hydroxycoumarin
    • AKOS002126557
    • AKOS016844146
    • DB00946
    • NCGC00346442-02
    • AS-77043
    • DA-66664
    • SMR004703040
    • 1ST156914
    • 3-(.alpha.-Ethylbenzyl)-4-hydroxycoumarin
    • CS-0017467
    • NS00043894
    • Phenprocoumon 100 microg/mL in Acetonitrile
    • D05457
    • D82043
    • EN300-219939
    • 435-97-2,53621-47-9 (sodium salt)
    • DL-3-(alpha-ETHYLBENZYL)-4-HYDROXYCOUMARIN
    • Q267896
    • 3-(.ALPHA.-PHENYLPROPYL)-4-HYDROXYCOUMARIN
    • 4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one #
    • doi:10.14272/DQDAYGNAKTZFIW-UHFFFAOYSA-N.1
    • BRD-A49838158-001-01-1
    • DL-3-(.ALPHA.-ETHYLBENZYL)-4-HYDROXYCOUMARIN
    • Z2177958148
    • 2H-Pyran-2-one, 4-hydroxy-3-[[2-(1-methylethyl)phenyl]thio]-6-(3-methylphenyl)-
    • 3-(1-Phenylpropyl)-4-hydroxycoumarin; 4-Hydroxy-2-oxo-3-(1-phenylpropyl)-2H-chromene
    • 207-108-9
    • 5999-41-7

  • Applications

    Phenprocoumon (CAS 435-97-2) is an oral pharmaceutical active ingredient in the vitamin K antagonist class, primarily used as an anticoagulant to prevent thromboembolism in patients at high risk, such as those with atrial fibrillation or prosthetic heart valves. In addition to its main therapeutic use, it may be employed as an active component in related coumarin anticoagulant chemistry and can serve as a reference standard in analytical method development and quality control for anticoagulant APIs based on the coumarin scaffold.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.04
    methanol 20.01
    isopropanol 10.38
    water 0.0
    ethyl acetate 19.27
    n-propanol 19.75
    acetone 55.54
    n-butanol 17.8
    acetonitrile 11.68
    DMF 297.94
    toluene 42.09
    isobutanol 13.9
    1,4-dioxane 73.88
    methyl acetate 27.34
    THF 207.61
    2-butanone 52.12
    n-pentanol 12.87
    sec-butanol 9.6
    n-hexane 0.34
    ethylene glycol 3.34
    NMP 152.54
    cyclohexane 1.04
    DMSO 128.84
    n-butyl acetate 23.11
    n-octanol 5.47
    chloroform 85.96
    n-propyl acetate 19.45
    acetic acid 21.75
    dichloromethane 130.62
    cyclohexanone 118.84
    propylene glycol 3.84
    isopropyl acetate 18.08
    DMAc 176.69
    2-ethoxyethanol 21.51
    isopentanol 18.34
    n-heptane 0.49
    ethyl formate 15.91
    1,2-dichloroethane 147.79
    n-hexanol 15.62
    2-methoxyethanol 53.2
    isobutyl acetate 16.54
    tetrachloromethane 3.37
    n-pentyl acetate 20.07
    transcutol 58.08
    n-heptanol 9.3
    ethylbenzene 10.95
    MIBK 28.58
    2-propoxyethanol 40.56
    tert-butanol 14.74
    MTBE 13.63
    2-butoxyethanol 24.95
    propionic acid 14.5
    o-xylene 14.86
    formic acid 6.45
    diethyl ether 16.25
    m-xylene 16.32
    p-xylene 14.12
    chlorobenzene 51.7
    dimethyl carbonate 25.98
    n-octane 0.34
    formamide 19.07
    cyclopentanone 173.38
    2-pentanone 39.89
    anisole 23.7
    cyclopentyl methyl ether 46.55
    gamma-butyrolactone 121.26
    1-methoxy-2-propanol 33.73
    pyridine 147.63
    3-pentanone 32.02
    furfural 119.06
    n-dodecane 0.46
    diethylene glycol 27.77
    diisopropyl ether 3.95
    tert-amyl alcohol 11.7
    acetylacetone 59.6
    n-hexadecane 0.57
    acetophenone 30.11
    methyl propionate 28.39
    isopentyl acetate 25.93
    trichloroethylene 270.57
    n-nonanol 6.43
    cyclohexanol 18.95
    benzyl alcohol 25.93
    2-ethylhexanol 9.95
    isooctanol 8.64
    dipropyl ether 10.18
    1,2-dichlorobenzene 39.84
    ethyl lactate 10.02
    propylene carbonate 43.91
    n-methylformamide 50.58
    2-pentanol 7.79
    n-pentane 0.35
    1-propoxy-2-propanol 22.52
    1-methoxy-2-propyl acetate 33.47
    2-(2-methoxypropoxy) propanol 21.76
    mesitylene 7.29
    ε-caprolactone 64.58
    p-cymene 7.21
    epichlorohydrin 248.8
    1,1,1-trichloroethane 37.69
    2-aminoethanol 8.73
    morpholine-4-carbaldehyde 123.26
    sulfolane 168.74
    2,2,4-trimethylpentane 0.51
    2-methyltetrahydrofuran 68.91
    n-hexyl acetate 20.8
    isooctane 0.4
    2-(2-butoxyethoxy)ethanol 29.62
    sec-butyl acetate 13.69
    tert-butyl acetate 22.41
    decalin 1.02
    glycerin 9.14
    diglyme 71.5
    acrylic acid 17.87
    isopropyl myristate 9.22
    n-butyric acid 24.51
    acetyl acetate 15.95
    di(2-ethylhexyl) phthalate 12.62
    ethyl propionate 15.71
    nitromethane 59.42
    1,2-diethoxyethane 24.41
    benzonitrile 34.94
    trioctyl phosphate 7.84
    1-bromopropane 32.13
    gamma-valerolactone 195.37
    n-decanol 5.12
    triethyl phosphate 10.6
    4-methyl-2-pentanol 6.84
    propionitrile 19.32
    vinylene carbonate 48.84
    1,1,2-trichlorotrifluoroethane 78.83
    DMS 29.81
    cumene 6.47
    2-octanol 5.67
    2-hexanone 28.48
    octyl acetate 11.42
    limonene 9.03
    1,2-dimethoxyethane 66.82
    ethyl orthosilicate 10.06
    tributyl phosphate 8.98
    diacetone alcohol 35.67
    N,N-dimethylaniline 16.4
    acrylonitrile 35.15
    aniline 44.29
    1,3-propanediol 18.39
    bromobenzene 51.24
    dibromomethane 63.9
    1,1,2,2-tetrachloroethane 149.48
    2-methyl-cyclohexyl acetate 18.88
    tetrabutyl urea 15.86
    diisobutyl methanol 7.28
    2-phenylethanol 29.96
    styrene 14.88
    dioctyl adipate 14.26
    dimethyl sulfate 48.9
    ethyl butyrate 14.64
    methyl lactate 16.69
    butyl lactate 15.36
    diethyl carbonate 10.01
    propanediol butyl ether 14.2
    triethyl orthoformate 12.13
    p-tert-butyltoluene 6.7
    methyl 4-tert-butylbenzoate 26.47
    morpholine 97.95
    tert-butylamine 6.72
    n-dodecanol 4.12
    dimethoxymethane 96.51
    ethylene carbonate 34.83
    cyrene 31.49
    2-ethoxyethyl acetate 32.71
    2-ethylhexyl acetate 19.87
    1,2,4-trichlorobenzene 51.81
    4-methylpyridine 102.11
    dibutyl ether 8.95
    2,6-dimethyl-4-heptanol 7.28
    DEF 56.95
    dimethyl isosorbide 54.8
    tetrachloroethylene 75.65
    eugenol 28.93
    triacetin 20.4
    span 80 18.04
    1,4-butanediol 5.49
    1,1-dichloroethane 53.12
    2-methyl-1-pentanol 14.82
    methyl formate 37.14
    2-methyl-1-butanol 15.68
    n-decane 0.65
    butyronitrile 19.57
    3,7-dimethyl-1-octanol 7.41
    1-chlorooctane 5.06
    1-chlorotetradecane 2.41
    n-nonane 0.47
    undecane 0.54
    tert-butylcyclohexane 0.85
    cyclooctane 0.31
    cyclopentanol 23.92
    tetrahydropyran 70.01
    tert-amyl methyl ether 11.17
    2,5,8-trioxanonane 45.15
    1-hexene 3.94
    2-isopropoxyethanol 16.19
    2,2,2-trifluoroethanol 6.49
    methyl butyrate 24.97

    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