Levulinic Acid

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  • Identifiers

    CAS number
    123-76-2

    Molecular formula
    C5H8O3

    SMILES
    CC(=O)CCC(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 71.86%
    Sweet 62.8%
    Buttery 59.34%
    Creamy 54.45%
    Sour 48.02%
    Fatty 45.72%
    Milky 40.66%
    Burnt 40.08%
    Fruity 40.03%
    Cheesy 38.31%

     

    Flavor
    Sweet 65.78%
    Acidic 46.32%
    Caramel 46.21%
    Pungent 44.39%
    Butter 43.23%
    Sour 42.17%
    Buttery 41.9%
    Cheese 38.16%
    Sharp 36.2%
    Creamy 34.34%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    7.65 (neutral)

    Molecular weight
    116.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 33 °C
    • 30 - 33 °C

    Boiling point

    • 245.5 °C
    • 245.00 to 246.00 °C. @ 760.00 mm Hg

    Flash point

    • 117.19 ˚C est.

    Solubility expt.

    • soluble in water, alcohol, and oil
    • 1 mL in 1 mL 95% alcohol (in ethanol)

  • Synonyms

    • LEVULINIC ACID
    • 4-Oxopentanoic acid
    • 123-76-2
    • Laevulinic acid
    • Pentanoic acid, 4-oxo-
    • 4-Oxovaleric acid
    • Levulic acid
    • 3-Acetylpropionic acid
    • 4-Ketovaleric acid
    • gamma-Ketovaleric acid
    • Acetopropionic acid
    • Laevulic acid
    • LEVA
    • Levulinsaeure
    • Valeric acid, 4-oxo-
    • beta-Acetylpropionic acid
    • 4-oxo-pentanoic acid
    • USAF CZ-1
    • Propionic acid, 3-acetyl-
    • 4-Oxopentansaeure
    • Acidum laevulinicum
    • FEMA No. 2627
    • 3-Acetylpropionsaeure
    • 3-Ketobutane-1-carboxylic acid
    • .beta.-Acetylpropionic acid
    • NSC 3716
    • Pentanoic acid, 4-oxo
    • g-Ketovalerate
    • .gamma.-Ketovaleric acid
    • UNII-RYX5QG61EI
    • b-Acetylpropionate
    • NSC-3716
    • EINECS 204-649-2
    • g-Ketovaleric acid
    • Acetylpropionic acid
    • BRN 0506796
    • b-Acetylpropionic acid
    • DTXSID8021648
    • CHEBI:45630
    • AI3-03377
    • RYX5QG61EI
    • Valeric acid, 4-oxo-(levulinic acid)
    • LEVULINIC ACID [MI]
    • LEVULINIC ACID [FCC]
    • LEVULINIC ACID [FHFI]
    • DTXCID701648
    • NSC3716
    • laevulinate
    • levulate
    • levulinate
    • 4-03-00-01560 (Beilstein Handbook Reference)
    • 4-ketovalerate
    • 4-oxovalerate
    • gamma-ketovalerate
    • 3-acetylpropionate
    • beta-acetylpropionate
    • CALCIUM LEVULATE
    • Levulinic acid, calcium salt
    • CAS-123-76-2
    • MFCD00002796
    • Laevulinsaeure
    • Diasporal
    • levulenic acid
    • 4Oxopentansaeure
    • 4Oxovaleric acid
    • 4Ketovaleric acid
    • 4oxopentanoic acid
    • 4-Oxopentanoicacid
    • 3Acetylpropionsaeure
    • gammaOxovaleric acid
    • magnesium laevulinate
    • gammaKetovaleric acid
    • 4-ketopentanoic acid
    • Valeric acid, 4oxo
    • 3Acetylpropionic acid
    • gammaOxopentanoic acid
    • Pentanoic acid, 4oxo
    • betaAcetylpropionic acid
    • Levulinic acid, 98%
    • Propionic acid, 3acetyl
    • Levulinic acid (Standard)
    • 3Ketobutane1carboxylic acid
    • 3-Ketobutane-1-carboxylate
    • WLN: QV2V1
    • SCHEMBL20868
    • LEVULINIC ACID [INCI]
    • Levulinic acid, >=97%, FG
    • CHEMBL1235931
    • BDBM82191
    • HY-Y0839R
    • Levulinic acid, analytical standard
    • GYB18552
    • HY-Y0839
    • Levulinic acid, natural, 99%, FG
    • Tox21_201483
    • Tox21_302729
    • BBL027404
    • GEO-04255
    • LMFA01060006
    • s6207
    • STK802043
    • AKOS000119608
    • DB02239
    • FL37560
    • PB48051
    • 4-Oxopentanoic acid, 4-ketovaleric acid
    • NCGC00249052-01
    • NCGC00256314-01
    • NCGC00259034-01
    • 4-Oxovaleric acid;3-Acetylpropionic acid
    • VS-08535
    • PENTANOIC ACID,4-OXO MFC5 H8 O3
    • DB-003710
    • PENTANOIC ACID,4-OXO MFC5 H8 O3
    • CS-0015813
    • L0042
    • NS00012787
    • EN300-20219
    • D70802
    • SBI-0633496.0002
    • Q903322
    • SR-01000944838
    • SR-01000944838-1
    • F2191-0253
    • Z104477318
    • Laevulinic acid; 4-Oxopentanoic acid; 4-Oxovaleric acid; gamma-Ketovaleric acid; Levulic acid; 4-Oxo-pentanoic acid

  • Applications

    Levulinic acid (CAS 123-76-2) is a biomass-derived platform chemical whose versatility underpins numerous applications: in green chemistry it serves as a precursor for γ-valerolactone, diphenolic acid, biopolymer capsules and various bio-based solvents; in biofuel production the acid and its esters are blended with gasoline and diesel to raise octane, cut soot and enhance biodegradability; in agriculture it is converted into mild plant growth regulators, herbicides and pesticides; in pharmaceuticals and cosmetics it works as a preservative, pH adjuster and antimicrobial agent, while levulinate amine derivatives act as topical anesthetics; in food and flavor industry it contributes caramel notes, smoky nuances and product stability; additionally levulinic acid is employed as a bio-plasticizer for cellulose plastics, a cross-linker for epoxy resins, a solvent in electroplating and a metal surface treatment agent, making it a key building block in the renewable-to-chemicals value chain.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 306.31
    methanol 559.53
    isopropanol 188.99
    water 1749.14
    ethyl acetate 24.05
    n-propanol 154.61
    acetone 71.88
    n-butanol 116.42
    acetonitrile 34.82
    DMF 641.47
    toluene 4.3
    isobutanol 93.26
    1,4-dioxane 53.11
    methyl acetate 50.71
    THF 132.05
    2-butanone 46.19
    n-pentanol 70.41
    sec-butanol 108.55
    n-hexane 2.73
    ethylene glycol 328.62
    NMP 224.33
    cyclohexane 0.9
    DMSO 365.18
    n-butyl acetate 19.01
    n-octanol 36.49
    chloroform 28.33
    n-propyl acetate 19.79
    acetic acid 136.37
    dichloromethane 33.4
    cyclohexanone 43.11
    propylene glycol 308.81
    isopropyl acetate 14.4
    DMAc 379.87
    2-ethoxyethanol 212.7
    isopentanol 88.66
    n-heptane 1.71
    ethyl formate 172.99
    1,2-dichloroethane 21.0
    n-hexanol 49.23
    2-methoxyethanol 476.75
    isobutyl acetate 12.11
    tetrachloromethane 9.58
    n-pentyl acetate 17.17
    transcutol 153.35
    n-heptanol 32.98
    ethylbenzene 6.25
    MIBK 21.69
    2-propoxyethanol 147.83
    tert-butanol 166.2
    MTBE 36.09
    2-butoxyethanol 94.1
    propionic acid 103.37
    o-xylene 6.69
    formic acid 441.66
    diethyl ether 16.05
    m-xylene 5.94
    p-xylene 7.98
    chlorobenzene 7.28
    dimethyl carbonate 34.53
    n-octane 1.16
    formamide 384.67
    cyclopentanone 80.38
    2-pentanone 28.07
    anisole 30.71
    cyclopentyl methyl ether 25.64
    gamma-butyrolactone 118.04
    1-methoxy-2-propanol 252.33
    pyridine 27.13
    3-pentanone 13.94
    furfural 175.98
    n-dodecane 1.35
    diethylene glycol 221.99
    diisopropyl ether 4.35
    tert-amyl alcohol 115.46
    acetylacetone 35.35
    n-hexadecane 1.37
    acetophenone 30.8
    methyl propionate 34.04
    isopentyl acetate 20.74
    trichloroethylene 29.07
    n-nonanol 29.69
    cyclohexanol 37.6
    benzyl alcohol 55.43
    2-ethylhexanol 21.6
    isooctanol 24.12
    dipropyl ether 11.07
    1,2-dichlorobenzene 10.42
    ethyl lactate 42.12
    propylene carbonate 65.51
    n-methylformamide 403.54
    2-pentanol 45.67
    n-pentane 2.09
    1-propoxy-2-propanol 77.76
    1-methoxy-2-propyl acetate 30.82
    2-(2-methoxypropoxy) propanol 76.2
    mesitylene 4.42
    ε-caprolactone 55.9
    p-cymene 5.74
    epichlorohydrin 108.0
    1,1,1-trichloroethane 12.75
    2-aminoethanol 389.14
    morpholine-4-carbaldehyde 248.19
    sulfolane 134.42
    2,2,4-trimethylpentane 1.66
    2-methyltetrahydrofuran 58.98
    n-hexyl acetate 27.61
    isooctane 1.3
    2-(2-butoxyethoxy)ethanol 90.86
    sec-butyl acetate 11.26
    tert-butyl acetate 18.36
    decalin 1.56
    glycerin 444.31
    diglyme 152.03
    acrylic acid 100.3
    isopropyl myristate 11.32
    n-butyric acid 92.47
    acetyl acetate 15.22
    di(2-ethylhexyl) phthalate 20.21
    ethyl propionate 19.45
    nitromethane 188.01
    1,2-diethoxyethane 23.28
    benzonitrile 29.3
    trioctyl phosphate 15.91
    1-bromopropane 12.25
    gamma-valerolactone 175.38
    n-decanol 21.09
    triethyl phosphate 15.56
    4-methyl-2-pentanol 28.26
    propionitrile 35.17
    vinylene carbonate 71.33
    1,1,2-trichlorotrifluoroethane 138.8
    DMS 19.21
    cumene 7.15
    2-octanol 21.37
    2-hexanone 23.44
    octyl acetate 16.16
    limonene 6.99
    1,2-dimethoxyethane 242.5
    ethyl orthosilicate 14.52
    tributyl phosphate 16.46
    diacetone alcohol 69.92
    N,N-dimethylaniline 33.1
    acrylonitrile 58.88
    aniline 22.47
    1,3-propanediol 339.57
    bromobenzene 4.7
    dibromomethane 17.25
    1,1,2,2-tetrachloroethane 28.47
    2-methyl-cyclohexyl acetate 16.98
    tetrabutyl urea 26.95
    diisobutyl methanol 13.44
    2-phenylethanol 36.25
    styrene 6.35
    dioctyl adipate 18.69
    dimethyl sulfate 74.53
    ethyl butyrate 15.24
    methyl lactate 85.66
    butyl lactate 33.28
    diethyl carbonate 14.05
    propanediol butyl ether 123.97
    triethyl orthoformate 15.3
    p-tert-butyltoluene 5.89
    methyl 4-tert-butylbenzoate 39.54
    morpholine 108.07
    tert-butylamine 67.8
    n-dodecanol 14.77
    dimethoxymethane 152.21
    ethylene carbonate 51.52
    cyrene 73.32
    2-ethoxyethyl acetate 24.55
    2-ethylhexyl acetate 13.57
    1,2,4-trichlorobenzene 12.82
    4-methylpyridine 43.63
    dibutyl ether 13.65
    2,6-dimethyl-4-heptanol 13.44
    DEF 75.17
    dimethyl isosorbide 78.62
    tetrachloroethylene 22.37
    eugenol 60.58
    triacetin 25.74
    span 80 51.98
    1,4-butanediol 153.12
    1,1-dichloroethane 17.75
    2-methyl-1-pentanol 56.87
    methyl formate 306.87
    2-methyl-1-butanol 77.51
    n-decane 1.99
    butyronitrile 44.55
    3,7-dimethyl-1-octanol 27.54
    1-chlorooctane 8.12
    1-chlorotetradecane 3.61
    n-nonane 1.88
    undecane 1.6
    tert-butylcyclohexane 2.34
    cyclooctane 0.55
    cyclopentanol 74.46
    tetrahydropyran 25.45
    tert-amyl methyl ether 27.37
    2,5,8-trioxanonane 109.08
    1-hexene 8.56
    2-isopropoxyethanol 96.91
    2,2,2-trifluoroethanol 98.81
    methyl butyrate 39.33

    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