4-Hydroxycoumarins

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  • Identifiers

    CAS number
    1076-38-6

    Molecular formula
    C9H6O3

    SMILES
    C1=CC=C2C(=C1)C(=CC(=O)O2)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 50.44%
    Sweet 44.9%
    Odorless 37.11%
    Coconut 33.62%
    Nutty 32.42%
    Burnt 32.37%
    Balsamic 31.99%
    Coumarinic 30.39%
    Creamy 27.27%
    Vanilla 26.53%

     

    Flavor
    Bitter 71.19%
    Sweet 41.09%
    Tonka 32.33%
    Almond 29.49%
    Green 28.67%
    Balsam 27.94%
    Phenolic 24.41%
    Nutty 23.58%
    Creamy 22.47%
    Balsamic 22.43%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    7.8 (neutral)

    Molecular weight
    162.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    312°C

    Melting point expt.

    • 213.5 °C

    Flash point

    • 140.15 ˚C est.

  • Synonyms

    • 4-Hydroxycoumarin
    • 1076-38-6
    • 4-Coumarinol
    • Benzotetronic acid
    • 4-Hydroxy-2H-chromen-2-one
    • Coumarin, 4-hydroxy-
    • 4-hydroxychromen-2-one
    • 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-
    • 4-Hydroxy-2H-1-benzopyran-2-one
    • 4-Hydroxy coumarin
    • 4-Hydroxy-chromen-2-one
    • 4-hydroxy-2-chromenone
    • 4-Hydroxycoumarine
    • MFCD00006856
    • 4-hydroxy-2H-benzo[b]pyran-2-one
    • EINECS 214-060-2
    • X954ZLL2RD
    • NSC 11889
    • 4-HYDROXY-1-BENZOPYRAN-2-ONE
    • BRN 0129768
    • CHEBI:40070
    • AI3-52393
    • NSC-11889
    • 22105-09-5
    • CHEMBL301141
    • 5-18-01-00378 (Beilstein Handbook Reference)
    • NSC11889
    • 4-HYDROXYCOUMARIN [USP IMPURITY]
    • WARFARIN SODIUM IMPURITY B [EP IMPURITY]
    • 4-Hydroxy-2H-1-benzopyran-2-one (4-Hydroxycoumarin)
    • 4-hydroxy-2H-benzo(b)pyran-2-one
    • 4-HYDROXYCOUMARINS
    • 2-Hydroxychromone
    • 4 Hydroxycoumarins
    • 4-OH coumarin
    • 4-HYDROXYCOUMARIN (USP IMPURITY)
    • 4-hydroxy-coumarin
    • 4HC
    • WARFARIN SODIUM IMPURITY B (EP IMPURITY)
    • 4H-1-Benzopyran-4-one, 2-hydroxy-
    • UNII-X954ZLL2RD
    • hydroxychromone
    • 4Coumarinol
    • 4hydroxycoumarin
    • 4-hyroxycoumarin
    • Coumarin, 4hydroxy
    • 4-hydroxyl coumarin
    • 4-Monohydroxycoumarin
    • 4-Hydroxycoumarin, 98%
    • CBiol_000838
    • WLN: T66 BOVJ EQ
    • 2H1Benzopyran2one, 4hydroxy
    • MLS004491719
    • Coumarin, 4-hydroxy-(8CI)
    • SCHEMBL131312
    • MEGxm0_000452
    • SCHEMBL1961365
    • DTXSID8061472
    • ACon1_001952
    • 4-Hydroxy-2H-chromen-2-one #
    • DTXSID50944748
    • HMS1607G02
    • 4-hydroxy-2-oxo-2H-1-benzopyran
    • 2-Hydroxy-4H-1-benzopyran-4-one
    • BCP31120
    • HY-N6856
    • STR01861
    • BBL027616
    • BDBM50055710
    • ICCB4_000134
    • STK801816
    • AKOS000119142
    • AKOS037515220
    • DB03410
    • FH07793
    • NCGC00179970-01
    • AC-13227
    • NCI60_000453
    • PD016118
    • SMR000112320
    • SY001614
    • DB-014485
    • CS-0015925
    • EU-0066799
    • H0235
    • NS00014742
    • EN300-17333
    • C20414
    • D71127
    • 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98%
    • AH-034/32464035
    • SR-01000389319
    • 4-Hydroxy-1-benzopyran-2-one; 4-Coumarinyl alcohol
    • SR-01000389319-1
    • BRD-K48844111-001-01-4
    • Q25323691
    • Z56922074
    • 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-HYDROXYCOUMARIN
    • F0266-2972
    • 4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one
    • InChI=1/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10
    • 214-060-2

  • Applications

    4-Hydroxycoumarins (CAS 1076-38-6) are widely used as building blocks in the synthesis of coumarin-based pharmaceuticals, notably as precursors to anticoagulants such as warfarin and related derivatives. They are commonly employed as starting materials to prepare 4-Hydroxycoumarin derivatives for pharmaceutical and agricultural applications. Derivatives of 4-Hydroxycoumarin are also explored for dye and fluorescent probe chemistries, leveraging the coumarin chromophore. In materials chemistry, they serve as precursors for functionalized coumarin monomers or crosslinkable systems in specialty polymers. Additionally, 4-Hydroxycoumarins are studied as scaffolds for fragrance compounds in the fragrance industry, with use subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 38.94
    methanol 54.55
    isopropanol 29.96
    water 0.31
    ethyl acetate 58.39
    n-propanol 30.5
    acetone 187.65
    n-butanol 28.35
    acetonitrile 68.6
    DMF 430.94
    toluene 6.26
    isobutanol 23.92
    1,4-dioxane 188.08
    methyl acetate 82.61
    THF 503.86
    2-butanone 98.81
    n-pentanol 27.62
    sec-butanol 25.69
    n-hexane 0.9
    ethylene glycol 27.67
    NMP 230.6
    cyclohexane 0.44
    DMSO 979.86
    n-butyl acetate 42.13
    n-octanol 26.19
    chloroform 10.87
    n-propyl acetate 51.34
    acetic acid 52.32
    dichloromethane 23.15
    cyclohexanone 93.91
    propylene glycol 18.36
    isopropyl acetate 36.24
    DMAc 225.56
    2-ethoxyethanol 86.75
    isopentanol 31.15
    n-heptane 2.1
    ethyl formate 42.01
    1,2-dichloroethane 43.08
    n-hexanol 31.84
    2-methoxyethanol 167.93
    isobutyl acetate 30.15
    tetrachloromethane 2.3
    n-pentyl acetate 35.8
    transcutol 233.38
    n-heptanol 22.98
    ethylbenzene 7.48
    MIBK 51.96
    2-propoxyethanol 102.81
    tert-butanol 49.97
    MTBE 34.98
    2-butoxyethanol 59.8
    propionic acid 39.7
    o-xylene 8.01
    formic acid 25.26
    diethyl ether 35.52
    m-xylene 8.96
    p-xylene 12.01
    chlorobenzene 12.34
    dimethyl carbonate 57.61
    n-octane 1.3
    formamide 79.81
    cyclopentanone 216.01
    2-pentanone 78.47
    anisole 37.75
    cyclopentyl methyl ether 75.94
    gamma-butyrolactone 233.26
    1-methoxy-2-propanol 116.74
    pyridine 51.97
    3-pentanone 52.65
    furfural 127.02
    n-dodecane 2.2
    diethylene glycol 112.57
    diisopropyl ether 12.41
    tert-amyl alcohol 37.74
    acetylacetone 119.72
    n-hexadecane 2.56
    acetophenone 41.47
    methyl propionate 68.74
    isopentyl acetate 38.82
    trichloroethylene 52.14
    n-nonanol 24.9
    cyclohexanol 23.59
    benzyl alcohol 29.68
    2-ethylhexanol 22.24
    isooctanol 20.68
    dipropyl ether 29.8
    1,2-dichlorobenzene 14.39
    ethyl lactate 35.81
    propylene carbonate 76.35
    n-methylformamide 134.65
    2-pentanol 20.9
    n-pentane 0.6
    1-propoxy-2-propanol 66.6
    1-methoxy-2-propyl acetate 62.48
    2-(2-methoxypropoxy) propanol 72.78
    mesitylene 7.65
    ε-caprolactone 78.03
    p-cymene 11.21
    epichlorohydrin 243.39
    1,1,1-trichloroethane 21.71
    2-aminoethanol 32.96
    morpholine-4-carbaldehyde 192.12
    sulfolane 334.63
    2,2,4-trimethylpentane 1.35
    2-methyltetrahydrofuran 135.14
    n-hexyl acetate 50.49
    isooctane 1.37
    2-(2-butoxyethoxy)ethanol 96.37
    sec-butyl acetate 30.9
    tert-butyl acetate 47.71
    decalin 1.88
    glycerin 47.59
    diglyme 164.49
    acrylic acid 40.02
    isopropyl myristate 26.69
    n-butyric acid 41.88
    acetyl acetate 39.44
    di(2-ethylhexyl) phthalate 22.21
    ethyl propionate 45.92
    nitromethane 203.45
    1,2-diethoxyethane 62.29
    benzonitrile 31.39
    trioctyl phosphate 21.49
    1-bromopropane 14.22
    gamma-valerolactone 216.79
    n-decanol 20.71
    triethyl phosphate 24.33
    4-methyl-2-pentanol 18.51
    propionitrile 41.73
    vinylene carbonate 58.27
    1,1,2-trichlorotrifluoroethane 87.72
    DMS 54.38
    cumene 8.52
    2-octanol 17.83
    2-hexanone 58.35
    octyl acetate 32.15
    limonene 14.27
    1,2-dimethoxyethane 161.41
    ethyl orthosilicate 21.32
    tributyl phosphate 23.15
    diacetone alcohol 85.56
    N,N-dimethylaniline 29.27
    acrylonitrile 62.77
    aniline 17.8
    1,3-propanediol 57.12
    bromobenzene 9.33
    dibromomethane 11.58
    1,1,2,2-tetrachloroethane 40.45
    2-methyl-cyclohexyl acetate 31.0
    tetrabutyl urea 34.32
    diisobutyl methanol 16.67
    2-phenylethanol 34.76
    styrene 7.4
    dioctyl adipate 36.26
    dimethyl sulfate 131.35
    ethyl butyrate 33.95
    methyl lactate 54.71
    butyl lactate 33.85
    diethyl carbonate 24.58
    propanediol butyl ether 60.33
    triethyl orthoformate 26.57
    p-tert-butyltoluene 10.83
    methyl 4-tert-butylbenzoate 51.94
    morpholine 164.33
    tert-butylamine 19.36
    n-dodecanol 16.74
    dimethoxymethane 203.85
    ethylene carbonate 48.82
    cyrene 65.8
    2-ethoxyethyl acetate 55.84
    2-ethylhexyl acetate 29.55
    1,2,4-trichlorobenzene 21.2
    4-methylpyridine 46.62
    dibutyl ether 29.26
    2,6-dimethyl-4-heptanol 16.67
    DEF 88.15
    dimethyl isosorbide 113.9
    tetrachloroethylene 19.16
    eugenol 55.24
    triacetin 52.02
    span 80 48.68
    1,4-butanediol 25.98
    1,1-dichloroethane 22.76
    2-methyl-1-pentanol 26.43
    methyl formate 109.88
    2-methyl-1-butanol 25.31
    n-decane 2.97
    butyronitrile 37.97
    3,7-dimethyl-1-octanol 25.45
    1-chlorooctane 14.0
    1-chlorotetradecane 7.41
    n-nonane 2.44
    undecane 2.56
    tert-butylcyclohexane 2.19
    cyclooctane 0.39
    cyclopentanol 43.81
    tetrahydropyran 75.44
    tert-amyl methyl ether 30.28
    2,5,8-trioxanonane 121.86
    1-hexene 5.75
    2-isopropoxyethanol 59.35
    2,2,2-trifluoroethanol 27.85
    methyl butyrate 58.12

    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