Coumarin, 4-hydroxy-3-phenyl-

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  • Identifiers

    CAS number
    1786-05-6

    Molecular formula
    C15H10O3

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 54.21%
    Sweet 42.44%
    Balsamic 36.49%
    Medicinal 31.39%
    Animal 30.28%
    Spicy 30.16%
    Odorless 29.54%
    Burnt 29.09%
    Bitter 28.55%
    Coumarinic 28.06%

     

    Flavor
    Bitter 89.64%
    Very strong 21.0%
    Moth ball 20.63%
    Indole 20.49%
    Naphthelene 20.38%
    Nitrile 20.09%
    Balsam 20.07%
    Tar 19.78%
    Tonka 19.76%
    Cedarleaf 19.74%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    7.95 (neutral)

    Molecular weight
    238.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    503°C

    Flash point

    • 177.35 ˚C est.

  • Synonyms

    • 4-Hydroxy-3-phenylcoumarin
    • 1786-05-6
    • 2H-1-Benzopyran-2-one, 4-hydroxy-3-phenyl-
    • 4-Hydroxy-3-phenyl-2H-1-benzopyran-2-one
    • COUMARIN, 4-HYDROXY-3-PHENYL-
    • BRN 1285893
    • DTXSID40170514
    • 5-18-02-00279 (Beilstein Handbook Reference)
    • RefChem:579314
    • DTXCID0093005
    • 661-500-8
    • 4-Hydroxy-3-phenyl-2H-chromen-2-one
    • 4-hydroxy-3-phenylchromen-2-one
    • NSC 251152
    • 4-Hydroxy-3-phenyl-chromen-2-one
    • 3-Phenyl-4-hydroxycoumarin
    • isoflavonol
    • 3-phenyl-4-hydroxy-coumarin
    • 4-hydroxy-3-phenyl-coumarin
    • Oprea1_855909
    • 3-Phenyl-chroman-2,4-dione
    • CHEMBL64744
    • SCHEMBL669375
    • SCHEMBL2318320
    • SCHEMBL29466790
    • 85LW4K48E8
    • AKOS024325098
    • CCG-249870
    • FH66556
    • 2-Hydroxy-3-phenyl-4H-1-benzopyran-4-one
    • 3-Phenyl-2H-1-benzopyran-2,4(3H)-dione
    • ST50447091
    • G85780
    • AB-337/40897009
    • 1786-05-6

  • Applications

    Coumarin, 4-hydroxy-3-phenyl- (CAS 1786-05-6) is used primarily as an intermediate and fragrance ingredient across several industries: in perfumery, it provides a vanilla-like note and serves as a fragrance ingredient and odor fixative; in pharmaceutical and medicinal chemistry, it acts as a building block for coumarin-derived drugs and as a precursor for anticoagulants and other bioactive compounds; in organic synthesis, it serves as a starting material for constructing more complex heterocycles; in colorants and coatings, it can function as a precursor for coumarin-based dyes and specialty inks and coatings; in analytical chemistry and life sciences, coumarin cores are employed as fluorescent scaffolds and optical probes, with derivatives like this one used in fluorescence-based assays or as reference standards in research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.79
    methanol 4.14
    isopropanol 3.55
    water 0.0
    ethyl acetate 6.03
    n-propanol 4.47
    acetone 24.61
    n-butanol 4.32
    acetonitrile 5.17
    DMF 139.65
    toluene 6.36
    isobutanol 3.37
    1,4-dioxane 35.05
    methyl acetate 10.88
    THF 109.12
    2-butanone 19.69
    n-pentanol 4.73
    sec-butanol 3.04
    n-hexane 0.09
    ethylene glycol 1.85
    NMP 75.75
    cyclohexane 0.23
    DMSO 106.65
    n-butyl acetate 11.72
    n-octanol 4.46
    chloroform 5.39
    n-propyl acetate 9.05
    acetic acid 9.21
    dichloromethane 9.8
    cyclohexanone 41.02
    propylene glycol 2.22
    isopropyl acetate 7.04
    DMAc 91.59
    2-ethoxyethanol 10.39
    isopentanol 5.44
    n-heptane 0.28
    ethyl formate 7.15
    1,2-dichloroethane 20.41
    n-hexanol 6.69
    2-methoxyethanol 26.48
    isobutyl acetate 7.76
    tetrachloromethane 0.37
    n-pentyl acetate 9.97
    transcutol 59.11
    n-heptanol 5.24
    ethylbenzene 3.34
    MIBK 12.29
    2-propoxyethanol 21.11
    tert-butanol 6.29
    MTBE 4.68
    2-butoxyethanol 14.06
    propionic acid 5.28
    o-xylene 3.66
    formic acid 2.83
    diethyl ether 4.03
    m-xylene 3.53
    p-xylene 4.84
    chlorobenzene 8.12
    dimethyl carbonate 10.69
    n-octane 0.21
    formamide 9.66
    cyclopentanone 69.92
    2-pentanone 14.43
    anisole 10.04
    cyclopentyl methyl ether 17.13
    gamma-butyrolactone 55.06
    1-methoxy-2-propanol 19.02
    pyridine 41.77
    3-pentanone 9.44
    furfural 51.91
    n-dodecane 0.45
    diethylene glycol 17.59
    diisopropyl ether 1.66
    tert-amyl alcohol 4.89
    acetylacetone 27.07
    n-hexadecane 0.55
    acetophenone 14.76
    methyl propionate 8.92
    isopentyl acetate 13.68
    trichloroethylene 37.62
    n-nonanol 5.19
    cyclohexanol 5.87
    benzyl alcohol 9.86
    2-ethylhexanol 5.47
    isooctanol 5.11
    dipropyl ether 6.23
    1,2-dichlorobenzene 7.65
    ethyl lactate 6.45
    propylene carbonate 21.03
    n-methylformamide 20.77
    2-pentanol 2.49
    n-pentane 0.08
    1-propoxy-2-propanol 14.53
    1-methoxy-2-propyl acetate 19.17
    2-(2-methoxypropoxy) propanol 18.58
    mesitylene 2.34
    ε-caprolactone 27.17
    p-cymene 3.86
    epichlorohydrin 79.2
    1,1,1-trichloroethane 5.24
    2-aminoethanol 3.79
    morpholine-4-carbaldehyde 59.97
    sulfolane 82.0
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 27.34
    n-hexyl acetate 12.18
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 24.12
    sec-butyl acetate 6.63
    tert-butyl acetate 11.2
    decalin 0.46
    glycerin 6.58
    diglyme 54.9
    acrylic acid 7.23
    isopropyl myristate 6.57
    n-butyric acid 8.34
    acetyl acetate 6.96
    di(2-ethylhexyl) phthalate 7.46
    ethyl propionate 7.14
    nitromethane 28.05
    1,2-diethoxyethane 17.1
    benzonitrile 14.04
    trioctyl phosphate 5.48
    1-bromopropane 4.36
    gamma-valerolactone 82.98
    n-decanol 4.12
    triethyl phosphate 7.07
    4-methyl-2-pentanol 3.16
    propionitrile 6.66
    vinylene carbonate 19.52
    1,1,2-trichlorotrifluoroethane 32.19
    DMS 15.57
    cumene 2.88
    2-octanol 3.58
    2-hexanone 13.65
    octyl acetate 7.57
    limonene 4.64
    1,2-dimethoxyethane 38.26
    ethyl orthosilicate 6.34
    tributyl phosphate 6.45
    diacetone alcohol 21.19
    N,N-dimethylaniline 8.12
    acrylonitrile 13.0
    aniline 9.16
    1,3-propanediol 8.09
    bromobenzene 6.68
    dibromomethane 4.69
    1,1,2,2-tetrachloroethane 24.08
    2-methyl-cyclohexyl acetate 10.6
    tetrabutyl urea 11.86
    diisobutyl methanol 4.8
    2-phenylethanol 13.17
    styrene 3.95
    dioctyl adipate 10.77
    dimethyl sulfate 23.87
    ethyl butyrate 8.45
    methyl lactate 10.04
    butyl lactate 9.48
    diethyl carbonate 6.2
    propanediol butyl ether 10.75
    triethyl orthoformate 7.88
    p-tert-butyltoluene 3.69
    methyl 4-tert-butylbenzoate 15.37
    morpholine 40.18
    tert-butylamine 2.81
    n-dodecanol 3.35
    dimethoxymethane 39.93
    ethylene carbonate 13.92
    cyrene 20.4
    2-ethoxyethyl acetate 15.91
    2-ethylhexyl acetate 10.42
    1,2,4-trichlorobenzene 11.52
    4-methylpyridine 27.48
    dibutyl ether 7.38
    2,6-dimethyl-4-heptanol 4.8
    DEF 23.35
    dimethyl isosorbide 38.54
    tetrachloroethylene 11.67
    eugenol 17.65
    triacetin 13.79
    span 80 13.62
    1,4-butanediol 2.45
    1,1-dichloroethane 5.79
    2-methyl-1-pentanol 6.02
    methyl formate 16.45
    2-methyl-1-butanol 4.32
    n-decane 0.6
    butyronitrile 6.58
    3,7-dimethyl-1-octanol 5.32
    1-chlorooctane 3.29
    1-chlorotetradecane 1.76
    n-nonane 0.41
    undecane 0.51
    tert-butylcyclohexane 0.44
    cyclooctane 0.1
    cyclopentanol 9.02
    tetrahydropyran 21.66
    tert-amyl methyl ether 4.58
    2,5,8-trioxanonane 38.03
    1-hexene 1.05
    2-isopropoxyethanol 8.49
    2,2,2-trifluoroethanol 3.19
    methyl butyrate 11.75

    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