Coumarin

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  • Identifiers

    CAS number
    91-64-5

    Molecular formula
    C9H6O2

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1431.0
    • Carbowax: 2392.4

  • Odor profile

    Sweet 92.56%
    Coumarinic 62.63%
    Coconut 49.22%
    Powdery 48.99%
    Balsamic 45.11%
    Hay 41.12%
    Nutty 40.69%
    Vanilla 37.43%
    Almond 36.91%
    Creamy 36.59%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    Molecular weight
    146.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 154 to 158 °F (NTP, 1992)
    • 71 °C
    • 68-70 °C

    Boiling point

    • 568 °F at 760 mmHg (NTP, 1992)
    • 301.71 °C
    • 297.00 to 301.00 °C. @ 760.00 mm Hg
    • 297-299 °C

    Flash point est.
    120.13 ˚C

    Flash point expt.

    • 304 °F (NTP, 1992)
    • 150 °C

    Solubility expt.

    • less than 0.1 mg/mL at 63.5 °F (NTP, 1992)
    • Soluble in ethanol; very soluble in ether and chloroform
    • Freely soluble in oils
    • Soluble in aqueous alkali, oxygenated and chlorinated solvents
    • In chloroform 49.4 g/100 g @ 25 °C; in pyridine 87.7 g/100 g @ 20-25 °C
    • In water, 1,900 mg/l @ 20 °C
    • 1.9 mg/mL
    • Solubility in water: poor

  • Synonyms

    • coumarin
    • 91-64-5
    • 2H-Chromen-2-one
    • 2H-1-Benzopyran-2-one
    • cumarin
    • 1,2-Benzopyrone
    • chromen-2-one
    • Rattex
    • Coumarinic anhydride
    • Tonka bean camphor
    • Coumarine
    • cis-o-Coumarinic acid lactone
    • Coumarinic lactone
    • o-Hydroxycinnamic acid lactone
    • Benzo-alpha-pyrone
    • o-Hydroxycinnamic lactone
    • 2-Oxo-1,2-benzopyran
    • Kumarin
    • Benzo-a-pyrone
    • 2H-Benzo(b)pyran-2-one
    • 5,6-Benzo-2-pyrone
    • 2H-1-Benzopyran, 2-oxo-
    • Kumarin [Czech]
    • o-Hydroxyzimtsaure-lacton
    • 5,6-Benzo-alpha-pyrone
    • 2H-Benzo[b]pyran-2-one
    • Coumarinum
    • 1-Benzopyran-2-one
    • NCI C07103
    • 103802-83-1
    • Caswell No. 259C
    • o-Coumaric acid lactone
    • NSC 8774
    • CCRIS 181
    • cis-o-Coumaric acid anhydride
    • chromenone
    • EPA Pesticide Chemical Code 127301
    • DTXSID7020348
    • CHEBI:28794
    • BRN 0383644
    • HSDB 1623
    • 2-oxo-2H-1-benzopyran
    • o-Hydroxyzimtsaure-lacton [German]
    • AI3-00753
    • UNII-A4VZ22K1WT
    • NSC-8774
    • EINECS 202-086-7
    • A4VZ22K1WT
    • Nci-c07103
    • MFCD00006850
    • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone
    • 3-(2-Hydroxyphenyl)-2-propenoic delta-lactone
    • Benzo-.alpha.-pyrone
    • Cinnamic acid, o-hydroxy-, delta-lactone
    • Coumarin (prohibited)
    • NSC8774
    • o-hydroxycinnamic acid delta-lactone
    • CHEMBL6466
    • 2-Propenoic acid, 3-(2-hydroxyphenyl)-delta-lactone
    • DTXCID50348
    • MLS000028741
    • EC 202-086-7
    • 5-17-10-00143 (Beilstein Handbook Reference)
    • NCGC00091502-01
    • Coumarin, >=98%
    • SMR000059040
    • COUMARIN (IARC)
    • COUMARIN [IARC]
    • COUMARIN (MART.)
    • COUMARIN [MART.]
    • 2h-chromene-2-one
    • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone
    • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, .delta.-lactone
    • benzopyranone
    • coumarinac lactone
    • CAS-91-64-5
    • Coumarin [NF]
    • COU
    • 2H-Benzopyran-2-one
    • SR-01000721887
    • chromen-one
    • a coumarin
    • coumarin-
    • d-lactone
    • Venalot mono
    • Coumarin Phenolic
    • Rattex Rodenticide
    • benzopyrylium olate
    • Coumarin (DCF)
    • Coumarin1513
    • 1, 2-Benzopyrone
    • a 1,2-benzopyrone
    • Coumarin (Standard)
    • Venalot mono (TN)
    • Spectrum_001336
    • ST023509
    • COUMARIN [HSDB]
    • Opera_ID_268
    • 2H-Chromen-2-one #
    • 3-(2-hydroxyphenyl)-
    • COUMARIN [MI]
    • 2H-1-benzopyran-2-on
    • Spectrum2_000303
    • Spectrum3_001772
    • Spectrum4_001818
    • Spectrum5_000555
    • COUMARINUM [HPUS]
    • bmse000077
    • COUMARIN [WHO-DD]
    • Epitope ID:114082
    • SCHEMBL6252
    • WLN: T66 BOVJ
    • BSPBio_003263
    • KBioGR_002460
    • KBioSS_001816
    • MLS001148422
    • MLS002454395
    • {2H-Benzo[b]pyran-2-one}
    • BIDD:ER0667
    • SPECTRUM1400208
    • SPBio_000266
    • Cinnamic acid, .delta.-lactone
    • Coumarin, >=99% (HPLC)
    • BDBM12342
    • HY-N0709R
    • KBio2_001816
    • KBio2_004384
    • KBio2_006952

  • Applications

    Coumarin (CAS 91-64-5) is a fragrant compound with broad applications: widely used as a sweet hay/vanilla-like perfumery material in perfumes, soaps, detergents, fabric softeners, candles and personal care products; formerly employed as a flavoring in foods and tobacco but now prohibited or strictly limited in many jurisdictions because of hepatotoxicity and allergen concerns; serves as a versatile scaffold/intermediate to make coumarin derivatives such as anticoagulant drugs and rodenticides (e.g., warfarin), laser dyes and fluorescent emitters, UV absorbers/optical brighteners for plastics and coatings; heavily used in research as fluorescent probes, FRET donors, enzyme substrates (umbelliferone/4-MU), photoresponsive protecting groups and UV-reversible polymer crosslinking motifs; acts as a nickel electroplating brightener; and functions as an analytical standard and probe substrate to phenotype CYP2A6 and assess liver function; use should comply with fragrance-allergen labeling and exposure limits under GHS/EU rules.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 145.51
    methanol 289.21
    isopropanol 71.72
    water 0.94
    ethyl acetate 405.48
    n-propanol 89.11
    acetone 847.6
    n-butanol 71.95
    acetonitrile 528.64
    DMF 1335.53
    toluene 111.76
    isobutanol 61.05
    1,4-dioxane 879.06
    methyl acetate 580.86
    THF 870.45
    2-butanone 559.68
    n-pentanol 59.27
    sec-butanol 71.91
    n-hexane 4.71
    ethylene glycol 43.28
    NMP 666.14
    cyclohexane 6.31
    DMSO 1228.54
    n-butyl acetate 190.26
    n-octanol 53.42
    chloroform 291.89
    n-propyl acetate 224.67
    acetic acid 213.2
    dichloromethane 708.18
    cyclohexanone 412.47
    propylene glycol 23.56
    isopropyl acetate 151.22
    DMAc 674.31
    2-ethoxyethanol 206.69
    isopentanol 77.16
    n-heptane 9.11
    ethyl formate 224.64
    1,2-dichloroethane 655.66
    n-hexanol 68.2
    2-methoxyethanol 415.32
    isobutyl acetate 108.79
    tetrachloromethane 22.1
    n-pentyl acetate 128.12
    transcutol 1172.05
    n-heptanol 44.05
    ethylbenzene 58.52
    MIBK 137.81
    2-propoxyethanol 200.65
    tert-butanol 101.62
    MTBE 149.37
    2-butoxyethanol 126.25
    propionic acid 157.41
    o-xylene 70.64
    formic acid 81.94
    diethyl ether 244.49
    m-xylene 71.72
    p-xylene 78.97
    chlorobenzene 133.67
    dimethyl carbonate 196.88
    n-octane 5.45
    formamide 374.23
    cyclopentanone 730.61
    2-pentanone 319.7
    anisole 193.14
    cyclopentyl methyl ether 234.79
    gamma-butyrolactone 845.47
    1-methoxy-2-propanol 201.15
    pyridine 566.08
    3-pentanone 258.2
    furfural 551.95
    n-dodecane 6.62
    diethylene glycol 164.54
    diisopropyl ether 49.37
    tert-amyl alcohol 91.75
    acetylacetone 423.81
    n-hexadecane 7.72
    acetophenone 187.11
    methyl propionate 361.8
    isopentyl acetate 143.06
    trichloroethylene 856.17
    n-nonanol 51.65
    cyclohexanol 69.26
    benzyl alcohol 108.78
    2-ethylhexanol 49.67
    isooctanol 40.82
    dipropyl ether 87.42
    1,2-dichlorobenzene 132.96
    ethyl lactate 67.54
    propylene carbonate 272.42
    n-methylformamide 579.44
    2-pentanol 48.86
    n-pentane 4.08
    1-propoxy-2-propanol 117.46
    1-methoxy-2-propyl acetate 188.39
    2-(2-methoxypropoxy) propanol 155.48
    mesitylene 42.59
    ε-caprolactone 362.48
    p-cymene 39.17
    epichlorohydrin 1110.7
    1,1,1-trichloroethane 206.9
    2-aminoethanol 60.43
    morpholine-4-carbaldehyde 724.28
    sulfolane 728.77
    2,2,4-trimethylpentane 5.46
    2-methyltetrahydrofuran 455.64
    n-hexyl acetate 187.19
    isooctane 4.62
    2-(2-butoxyethoxy)ethanol 233.7
    sec-butyl acetate 115.85
    tert-butyl acetate 150.76
    decalin 9.82
    glycerin 54.65
    diglyme 565.78
    acrylic acid 152.62
    isopropyl myristate 66.03
    n-butyric acid 162.62
    acetyl acetate 204.39
    di(2-ethylhexyl) phthalate 53.89
    ethyl propionate 178.46
    nitromethane 995.32
    1,2-diethoxyethane 297.02
    benzonitrile 182.21
    trioctyl phosphate 41.84
    1-bromopropane 151.6
    gamma-valerolactone 775.81
    n-decanol 41.19
    triethyl phosphate 61.46
    4-methyl-2-pentanol 37.16
    propionitrile 240.62
    vinylene carbonate 259.37
    1,1,2-trichlorotrifluoroethane 256.38
    DMS 229.75
    cumene 40.96
    2-octanol 36.39
    2-hexanone 196.27
    octyl acetate 87.9
    limonene 50.36
    1,2-dimethoxyethane 510.56
    ethyl orthosilicate 53.8
    tributyl phosphate 55.24
    diacetone alcohol 185.67
    N,N-dimethylaniline 108.43
    acrylonitrile 408.16
    aniline 116.3
    1,3-propanediol 108.35
    bromobenzene 136.82
    dibromomethane 277.51
    1,1,2,2-tetrachloroethane 418.77
    2-methyl-cyclohexyl acetate 87.6
    tetrabutyl urea 78.45
    diisobutyl methanol 35.93
    2-phenylethanol 106.97
    styrene 80.18
    dioctyl adipate 96.86
    dimethyl sulfate 282.16
    ethyl butyrate 125.35
    methyl lactate 95.62
    butyl lactate 82.71
    diethyl carbonate 90.88
    propanediol butyl ether 112.91
    triethyl orthoformate 72.99
    p-tert-butyltoluene 36.01
    methyl 4-tert-butylbenzoate 135.09
    morpholine 720.19
    tert-butylamine 48.02
    n-dodecanol 32.3
    dimethoxymethane 603.39
    ethylene carbonate 207.52
    cyrene 133.63
    2-ethoxyethyl acetate 253.86
    2-ethylhexyl acetate 116.59
    1,2,4-trichlorobenzene 156.69
    4-methylpyridine 411.15
    dibutyl ether 99.23
    2,6-dimethyl-4-heptanol 35.93
    DEF 419.28
    dimethyl isosorbide 270.82
    tetrachloroethylene 243.25
    eugenol 134.02
    triacetin 196.58
    span 80 99.13
    1,4-butanediol 39.94
    1,1-dichloroethane 300.46
    2-methyl-1-pentanol 66.22
    methyl formate 473.92
    2-methyl-1-butanol 68.99
    n-decane 9.25
    butyronitrile 164.57
    3,7-dimethyl-1-octanol 57.1
    1-chlorooctane 43.14
    1-chlorotetradecane 20.17
    n-nonane 8.19
    undecane 7.8
    tert-butylcyclohexane 9.3
    cyclooctane 3.23
    cyclopentanol 99.38
    tetrahydropyran 394.25
    tert-amyl methyl ether 116.75
    2,5,8-trioxanonane 330.9
    1-hexene 29.57
    2-isopropoxyethanol 130.81
    2,2,2-trifluoroethanol 82.62
    methyl butyrate 237.09

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.089 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.18 %
Category 2
Products applied to the axillae
 0.08 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.18 %
Category 3
Products applied to the face/body using fingertips
 0.089 % Category 8
Products with significant anogenital exposure
 0.035 %
Category 4
Products related to fine fragrance
 1.5 % Category 9
Products with body and hand exposure, primarily rinse off
 0.52 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.38 % Category 10A
Household care products with mostly hand contact
 0.52 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.11 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 1.6 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.16 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0.035 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.035 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.035 %
Category 6
Products with oral and lip exposure
 0.0024 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 33 %

Botanical

Name CAS Botanical Proportion
Boldo leaf Boldea fragrans Juss. (Peumus boldus Mol.) 0.5%
Cassia, branch & leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 15.3%
Cassia, bark (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.28%
Cassia, leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 8.06%
Spike lavender (Spain) 3 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 2.4%
Narcissus tazetta absolute 2 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 1.2%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.02%
Spike lavender (Spain) 2 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.1%
Narcissus poeticus absolute 8023-75-4 Narcissus poeticus L., fam. Amaryllidaceae 6.9%
Thyme (Italy) 3 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.3%
Spike lavender (Spain) 4 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.6%
Lavender 2a hydrodiffusion 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 1.0%
Lavender 2b microwave 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 0.3%
Cassia, branch & leaf 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.3%
Cassia, bark 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.4%
Cassia, branch & leaf (China) 1a 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.16%
Cassia, bark (China) 1 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 2.45%
Cassia, bark (China) 2 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 8.73%
Cinnamon bark 4 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.5%
Artemisia aksaiensis (China) Artemisia aksaiensis Y.R. Ling, fam. Asteraceae (Compositae) 1.2%
Artemisia pubescens (China) Artemisia pubescens Ledeb., fam. Asteraceae (Labiatae) 0.7%
Cassia, branch & leaf (China) 1b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.16%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.01%
Ageratum conyzoides (China) Ageratum conyzoides L., fam. Asteraceae (Compositae) 0.93%
Lavandin (Hungary) 1a 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiseleur), Lamiaceae 2.1%
Lavandin (Hungary) 1b 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiseleur), Lamiaceae 0.7%
Clover, white flower (Austria) Trifolium repens L., fam Liguminosae (Papilionaceae) 1.4%
Clover, red flower (Austria) 85085-25-2 Trifolium pratense L., fam. Leguminosae (Papilionaceae) 1.3%
Acacia confusa flower (China) Acacia confusa Merr., fam. Mimosaceae (Leguminosae) 0.11%
Cinnamomum loureirii bark Cinnamomum loureirii, fam. Lauraceae 0.6%
Datura flower headspace (Japan) Datura candida (Pers.), fam. Solanaceae 0.1%
Psidium cattleianum fruit (R‚union Island) Psidium cattleianum Sabine, fam. Myrtaceae 0.3%
Cassia, bark (China) 4a 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.23%
Cassia, leaf (China) 4b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.05%
Cassia, bark (China) 3b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.85%
Anthoxanthum odoratum (Italy) 1a fresh leaf Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 96.3%
Anthoxanthum odoratum (Italy) 1b hay Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 46.8%
Lavender (France) 8 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.03%