3,4-Dihydrocoumarin

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  • Identifiers

    CAS number
    119-84-6

    Molecular formula
    C9H8O2

    SMILES
    C1CC(=O)OC2=CC=CC=C21

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1377.5
    • Carbowax: 2286.0

  • Odor profile

    Coumarinic 81.06%
    Sweet 76.18%
    Coconut 73.78%
    Spicy 63.62%
    Herbal 57.78%
    Hay 55.42%
    Nutty 54.96%
    Creamy 50.38%
    Cinnamon 49.82%
    Vanilla 49.07%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    7.57 (neutral)

    Molecular weight
    148.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 77 °F (NTP, 1992)
    • 25 °C

    Boiling point

    • 522 °F at 760 mmHg (NTP, 1992)
    • 272 °C
    • 271.00 to 272.00 °C. @ 760.00 mm Hg

    Flash point est.
    122.23 ˚C

    Flash point expt.

    • 266 °F (NTP, 1992)
    • 130 °C

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • Slightly soluble in ether and carbon tetrachloride
    • 1:2.5-3.5 IN 70% ALCOHOL
    • Soluble in chloroform.
    • Soluble in chlorinated solvents
    • In water, 3,000 mg/l at 37 °C
    • 3 mg/mL at 37 °C
    • Slightly soluble in water; soluble in oil
    • soluble (in ethanol)

  • Synonyms

    • dihydrocoumarin
    • 3,4-dihydrocoumarin
    • 119-84-6
    • hydrocoumarin
    • chroman-2-one
    • Benzodihydropyrone
    • melilotin
    • 2-chromanone
    • melilotol
    • 1,2-benzodihydropyrone
    • melilotic lactone
    • 2H-1-Benzopyran-2-one, 3,4-dihydro-
    • Melilotine
    • Melilotic acid lactone
    • 3,4-Dihydro-2H-1-benzopyran-2-one
    • Oxochroman
    • Chroman, 2-oxo-
    • Benzopyranone, dihydro-
    • Dihydrobenzopyrone
    • Coumarin, 3,4-dihydro-
    • Usaf do-12
    • 2-Hydroxydihydrocinnamic acid lactone
    • Meliotine
    • 3,4-Dyhydrocoumarin
    • NCI-C55890
    • 3,4-dihydro-2H-chromen-2-one
    • 3,4-Dihydro-1-benzopyran-2-one
    • 3,4-dihydrochromen-2-one
    • o-hydroxydihydrocinnamic acid lactone
    • FEMA No. 2381
    • CCRIS 5803
    • Hydroxydihydrocinnamic acid lactone, o-
    • HSDB 4333
    • o-hydroxyhydrocinnamic acid delta-lactone
    • 2-Oxochroman
    • 2-oxo-chroman
    • UNII-NM5K1Y1BT2
    • EINECS 204-354-9
    • Hydrocinnamic acid, o-hydroxy-, delta-lactone
    • NSC 10121
    • COUMARIN,3,4-DIHYDRO
    • BRN 0004584
    • Melilotin (coumarin)
    • DTXSID2020474
    • CHEBI:16151
    • AI3-03425
    • o-hydroxyhydrocinnamic acid lactone
    • MELILOTIN [HSDB]
    • MFCD00006881
    • NSC-10121
    • hydrocinnamic acid, o-hydroxy-,lactone
    • NM5K1Y1BT2
    • CHEMBL89306
    • DIHYDROCOUMARIN [FHFI]
    • DTXCID00474
    • 5-17-10-00013 (Beilstein Handbook Reference)
    • NSC10121
    • Hydrocinnamic acid, o-hydroxy-, .delta.-lactone
    • O-HYDROXY-HYDROCINNAMIC ACID-.DELTA.-LACTONE
    • CAS-119-84-6
    • dihydrocumarin
    • dihydrocoumarine
    • 2Chromanone
    • dihydro coumarin
    • Melilotin??
    • Chroman, 2oxo
    • Hydrocoumarin, 8CI
    • Dihydro-Benzopyranone
    • 2,3-dihydrocoumarin
    • 3,4-Dihydrocumarine
    • Coumarin,4-dihydro-
    • 1,2Benzodihydropyrone
    • 3,4-dihydrocoumarine
    • Benzopyranone, dihydro
    • 3,4 -dihydrocoumarin
    • 3,4-Dihydroxycoumarin
    • 3,4-Dihydro-Coumarin
    • Coumarin, 3,4dihydro
    • Dihydrocoumarin, 99%
    • Dihydrocoumarin (Standard)
    • bmse000412
    • SCHEMBL28795
    • 3,4Dihydro2H1benzopyran2one
    • MLS002454372
    • 2-Hydroxyhydrocinnamic lactone
    • DIHYDROCOUMARIN [INCI]
    • COUMARIN,3,4,-DIHYDRO
    • 2H1Benzopyran2one, 3,4dihydro
    • WLN: T66 BOVT & J
    • FEMA 2381
    • HY-N1926R
    • HMS2268K22
    • 2Hydroxydihydrocinnamic acid lactone
    • Dihydrocoumarin, analytical standard
    • HY-N1926
    • Hydrocinnamic acid, .delta.-lactone
    • Tox21_202137
    • Tox21_302745
    • 2H-1-Benzopyran-2-one,4-dihydro-
    • BBL027621
    • BDBM50146070
    • s9379
    • STK801851
    • Dihydrocoumarin, >=99%, FCC, FG
    • Hydroxydihydrocinnamic acid lactone, o
    • 1,2-BENZODIHYDROPYRONE [FCC]
    • AKOS000277415
    • CCG-266187
    • FD31582
    • NCGC00091491-01
    • NCGC00091491-02
    • NCGC00091491-03
    • NCGC00256356-01
    • NCGC00259686-01
    • AC-34197
    • Hydrocinnamic acid, ohydroxy, deltalactone
    • NCI60_000035
    • SMR000112325
    • VS-08570
    • 2H-1-Benzopyran-2-one, 3, 4-dihydro-
    • DB-061667
    • CS-0018237
    • D1223
    • NS00019587
    • Dihydrocoumarin 100 microg/mL in Acetonitrile
    • EN300-49183
    • 2H-1-BENZOPYRAN-2-ONE,3,4-DIHYDRO-
    • C02274

  • Applications

    Dihydrocoumarin (CAS 119-84-6) is a sweet tonka-, vanilla- and hay-scented aroma chemical employed widely as a flavoring agent in confectionery, baked goods, beverages, dairy analogues and flavored tobacco at FEMA/JECFA-approved levels, as a perfumery material in cosmetics, fine fragrances, creams, soaps, detergents and deodorants to add warmth, smooth rough top notes or mask off-odors, and as an odor stabilizer in paints, polymers and other industrial products; it also serves as an intermediate for higher-value aroma compounds, and while generally recognized as safe by the FDA, its use must respect regulatory concentration limits to minimize potential skin sensitization.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 95.75
    methanol 180.41
    isopropanol 65.62
    water 1.53
    ethyl acetate 316.75
    n-propanol 69.32
    acetone 571.17
    n-butanol 58.25
    acetonitrile 484.49
    DMF 966.01
    toluene 115.43
    isobutanol 51.85
    1,4-dioxane 875.42
    methyl acetate 449.29
    THF 549.08
    2-butanone 362.05
    n-pentanol 65.54
    sec-butanol 59.25
    n-hexane 6.57
    ethylene glycol 59.53
    NMP 742.61
    cyclohexane 7.43
    DMSO 1221.37
    n-butyl acetate 181.08
    n-octanol 61.67
    chloroform 729.73
    n-propyl acetate 220.43
    acetic acid 218.66
    dichloromethane 1077.14
    cyclohexanone 439.77
    propylene glycol 34.29
    isopropyl acetate 156.11
    DMAc 647.63
    2-ethoxyethanol 210.44
    isopentanol 65.74
    n-heptane 8.02
    ethyl formate 221.68
    1,2-dichloroethane 675.83
    n-hexanol 67.66
    2-methoxyethanol 312.87
    isobutyl acetate 119.48
    tetrachloromethane 54.74
    n-pentyl acetate 128.45
    transcutol 1383.41
    n-heptanol 45.23
    ethylbenzene 75.14
    MIBK 136.54
    2-propoxyethanol 210.12
    tert-butanol 105.68
    MTBE 132.84
    2-butoxyethanol 134.3
    propionic acid 168.32
    o-xylene 88.06
    formic acid 101.9
    diethyl ether 156.14
    m-xylene 85.35
    p-xylene 104.65
    chlorobenzene 238.83
    dimethyl carbonate 218.74
    n-octane 5.68
    formamide 308.91
    cyclopentanone 640.14
    2-pentanone 226.51
    anisole 254.41
    cyclopentyl methyl ether 190.07
    gamma-butyrolactone 830.11
    1-methoxy-2-propanol 191.42
    pyridine 477.4
    3-pentanone 206.75
    furfural 688.11
    n-dodecane 7.81
    diethylene glycol 219.31
    diisopropyl ether 49.35
    tert-amyl alcohol 84.92
    acetylacetone 423.92
    n-hexadecane 9.22
    acetophenone 240.32
    methyl propionate 288.01
    isopentyl acetate 145.13
    trichloroethylene 1163.64
    n-nonanol 57.97
    cyclohexanol 72.14
    benzyl alcohol 143.34
    2-ethylhexanol 53.06
    isooctanol 43.53
    dipropyl ether 81.49
    1,2-dichlorobenzene 237.0
    ethyl lactate 94.75
    propylene carbonate 334.96
    n-methylformamide 430.36
    2-pentanol 44.99
    n-pentane 4.67
    1-propoxy-2-propanol 126.34
    1-methoxy-2-propyl acetate 198.97
    2-(2-methoxypropoxy) propanol 193.74
    mesitylene 57.64
    ε-caprolactone 372.35
    p-cymene 46.27
    epichlorohydrin 976.45
    1,1,1-trichloroethane 338.71
    2-aminoethanol 71.58
    morpholine-4-carbaldehyde 887.6
    sulfolane 862.24
    2,2,4-trimethylpentane 6.44
    2-methyltetrahydrofuran 314.83
    n-hexyl acetate 198.33
    isooctane 5.82
    2-(2-butoxyethoxy)ethanol 301.17
    sec-butyl acetate 132.94
    tert-butyl acetate 172.35
    decalin 12.71
    glycerin 83.33
    diglyme 643.39
    acrylic acid 186.12
    isopropyl myristate 80.78
    n-butyric acid 149.39
    acetyl acetate 243.99
    di(2-ethylhexyl) phthalate 74.43
    ethyl propionate 188.49
    nitromethane 969.65
    1,2-diethoxyethane 319.9
    benzonitrile 278.0
    trioctyl phosphate 53.07
    1-bromopropane 163.47
    gamma-valerolactone 853.73
    n-decanol 47.45
    triethyl phosphate 84.72
    4-methyl-2-pentanol 40.61
    propionitrile 232.69
    vinylene carbonate 369.75
    1,1,2-trichlorotrifluoroethane 341.47
    DMS 291.98
    cumene 54.02
    2-octanol 39.41
    2-hexanone 187.94
    octyl acetate 100.95
    limonene 55.84
    1,2-dimethoxyethane 495.11
    ethyl orthosilicate 74.94
    tributyl phosphate 79.02
    diacetone alcohol 177.48
    N,N-dimethylaniline 141.34
    acrylonitrile 419.19
    aniline 142.74
    1,3-propanediol 100.79
    bromobenzene 265.78
    dibromomethane 476.21
    1,1,2,2-tetrachloroethane 643.67
    2-methyl-cyclohexyl acetate 107.87
    tetrabutyl urea 102.37
    diisobutyl methanol 39.88
    2-phenylethanol 124.63
    styrene 107.21
    dioctyl adipate 120.45
    dimethyl sulfate 378.58
    ethyl butyrate 139.11
    methyl lactate 120.11
    butyl lactate 98.29
    diethyl carbonate 114.26
    propanediol butyl ether 143.44
    triethyl orthoformate 94.35
    p-tert-butyltoluene 44.09
    methyl 4-tert-butylbenzoate 166.3
    morpholine 616.88
    tert-butylamine 55.22
    n-dodecanol 38.2
    dimethoxymethane 432.9
    ethylene carbonate 291.3
    cyrene 182.84
    2-ethoxyethyl acetate 265.55
    2-ethylhexyl acetate 117.72
    1,2,4-trichlorobenzene 272.93
    4-methylpyridine 404.92
    dibutyl ether 110.14
    2,6-dimethyl-4-heptanol 39.88
    DEF 316.98
    dimethyl isosorbide 333.08
    tetrachloroethylene 364.08
    eugenol 171.81
    triacetin 264.57
    span 80 133.12
    1,4-butanediol 55.7
    1,1-dichloroethane 427.38
    2-methyl-1-pentanol 69.14
    methyl formate 410.93
    2-methyl-1-butanol 55.75
    n-decane 10.56
    butyronitrile 150.5
    3,7-dimethyl-1-octanol 66.49
    1-chlorooctane 50.68
    1-chlorotetradecane 25.17
    n-nonane 9.18
    undecane 8.99
    tert-butylcyclohexane 12.3
    cyclooctane 4.16
    cyclopentanol 91.43
    tetrahydropyran 326.66
    tert-amyl methyl ether 99.2
    2,5,8-trioxanonane 410.26
    1-hexene 33.92
    2-isopropoxyethanol 152.84
    2,2,2-trifluoroethanol 116.79
    methyl butyrate 235.17

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.038 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.43 %
Category 2
Products applied to the axillae
 0.011 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.43 %
Category 3
Products applied to the face/body using fingertips
 0.23 % Category 8
Products with significant anogenital exposure
 0.018 %
Category 4
Products related to fine fragrance
 0.21 % Category 9
Products with body and hand exposure, primarily rinse off
 0.41 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.053 % Category 10A
Household care products with mostly hand contact
 1.5 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.053 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 1.5 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.053 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0.018 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.018 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.018 %
Category 6
Products with oral and lip exposure
 0.12 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Narcissus tazetta absolute 2 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 0.1%
Spike lavender (Spain) 2 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.05%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.01%
Anthoxanthum odoratum (Italy) 1a fresh leaf Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.01%
Anthoxanthum odoratum (Italy) 1b hay Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.4%