4-Hydroxybutanoic acid

Overview IFRA Request a quote

  • Identifiers

    CAS number
    591-81-1

    Molecular formula
    C4H8O3

    SMILES
    C(CC(=O)O)CO

  • Odor profile

    Fragrance
    Odorless 58.78%
    Sour 42.63%
    Buttery 29.1%
    Caramellic 27.27%
    Sharp 26.82%
    Cheesy 24.56%
    Milky 24.5%
    Ethereal 21.59%
    Alcoholic 21.08%
    Creamy 20.57%

     

    Flavor
    Odorless 68.75%
    Sour 46.96%
    Acidic 40.74%
    Pungent 35.52%
    Rancid 33.6%
    Sweet 29.81%
    Vinegar 29.31%
    Sweat 29.14%
    Sharp 25.72%
    Soy 24.37%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    7.28 (neutral)

    Molecular weight
    104.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 48-50 °C

    Boiling point

    • 180 °C (dec)

    Flash point

    • 139.29 ˚C est.

    Solubility expt.

    • Very soluble in water, alcohol and ether.

  • Synonyms

    • 4-Hydroxybutanoic acid
    • 4-Hydroxybutyric acid
    • gamma-Hydroxybutyric acid
    • 591-81-1
    • gamma-Hydroxybutyrate
    • Xyrem
    • 4-hydroxy-butyric acid
    • Oxybate
    • Butanoic acid, 4-hydroxy-
    • Gamma Hydroxybutyric Acid
    • 4-hydroxy-butanoic acid
    • GHB
    • oxy-n-butyric acid
    • Butyric acid, 4-hydroxy-
    • Oxybate sodium
    • 3-carboxypropoxy acid
    • 4-Hydroxyalkanoic acid
    • 4-Hydroxycarboxylic acid
    • Somsanit
    • gamma Hydroxybutyrate
    • 4-Hydroxybutyrate sodium
    • .gamma.-hydroxybutyrate
    • Gamma OH
    • Gam-OH
    • CHEMBL1342
    • CHEBI:30830
    • 4-Hydroxybutyric acid monosodium salt
    • Sodium .gamma.-oxybutyrate
    • 30IW36W5B2
    • 4-OHB
    • Sodium .gamma.-hydroxybutyrate
    • 4 HB
    • 4-Hydroxybuttersaeure
    • EB 27
    • .gamma.-OH
    • WY 3478
    • WY-3478
    • gamma-Hydroxybutanoic acid
    • 4-Hydroxyacid
    • .gamma.-Hydroxybutyrate sodium
    • .gamma.-Hydroxy sodium butyrate
    • Hydroxybutyric acid monosodium salt
    • NSC84223
    • gamma-hydroxy butyrate
    • .gamma.-Hydroxybutyric acid, sodium salt
    • NCGC00247714-01
    • SHB
    • .gamma.-Hydroxybutyric acid monosodium salt
    • BRN 1720582
    • Alcover
    • UNII-30IW36W5B2
    • 52352-27-9
    • HSDB 6927
    • Hydroxybutyric acid-
    • Sodium gamma-oxybutyrate
    • .Gamma.-Hydroxy butyrate
    • 4-Hydroxybutanoic acid #
    • SCHEMBL10786
    • 4-03-00-00774 (Beilstein Handbook Reference)
    • GTPL4711
    • DEA No. 2010
    • AA3E2AF0-AB7A-4A1E-A391-199C049D7162
    • DTXSID2074740
    • .GAMMA.-HYDROXYBUTYRIC ACID
    • BDBM50023575
    • LMFA01050006
    • PDSP1_000342
    • PDSP2_000340
    • .GAMMA.-HYDROXYBUTYRATE [MI]
    • GAMMA-HYDROXYBUTYRATE [WHO-DD]
    • DB01440
    • GAMMA-HYDROXYBUTYRIC ACID [HSDB]
    • SBI-0206686.P002
    • NS00002886
    • C00989
    • C01991
    • Q207920
    • BRD-K82166906-236-02-8

  • Applications

    4-Hydroxybutanoic acid (CAS 591-81-1) is primarily used as an industrial intermediate. It is commonly converted to gamma-butyrolactone (GBL), a widely used solvent and processing aid in coatings, paints, and cleaners. The compound also serves as a versatile building block for the synthesis of pharmaceuticals and agrochemicals, and it is employed as a precursor to various lactone- and ester-based derivatives. In polymer chemistry, it can function as a di-functional building block for specialty polyesters and resins. Additionally, it is evaluated for fragrance and flavor chemistry as a hydroxyacid building block. The use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 165.17
    methanol 313.72
    isopropanol 92.96
    water 1514.4
    ethyl acetate 22.61
    n-propanol 92.94
    acetone 87.58
    n-butanol 66.47
    acetonitrile 35.43
    DMF 824.29
    toluene 3.48
    isobutanol 57.03
    1,4-dioxane 92.6
    methyl acetate 25.9
    THF 129.95
    2-butanone 29.68
    n-pentanol 43.46
    sec-butanol 54.14
    n-hexane 2.4
    ethylene glycol 482.49
    NMP 314.75
    cyclohexane 1.71
    DMSO 575.82
    n-butyl acetate 17.86
    n-octanol 25.01
    chloroform 10.23
    n-propyl acetate 17.45
    acetic acid 225.08
    dichloromethane 14.56
    cyclohexanone 52.24
    propylene glycol 261.74
    isopropyl acetate 16.17
    DMAc 369.47
    2-ethoxyethanol 186.65
    isopentanol 57.06
    n-heptane 2.62
    ethyl formate 83.45
    1,2-dichloroethane 15.41
    n-hexanol 44.72
    2-methoxyethanol 402.55
    isobutyl acetate 9.49
    tetrachloromethane 6.22
    n-pentyl acetate 14.83
    transcutol 149.27
    n-heptanol 28.04
    ethylbenzene 4.94
    MIBK 23.8
    2-propoxyethanol 127.12
    tert-butanol 132.3
    MTBE 24.06
    2-butoxyethanol 77.19
    propionic acid 114.99
    o-xylene 7.12
    formic acid 587.18
    diethyl ether 13.58
    m-xylene 6.96
    p-xylene 6.08
    chlorobenzene 5.49
    dimethyl carbonate 26.74
    n-octane 1.38
    formamide 417.21
    cyclopentanone 91.43
    2-pentanone 31.89
    anisole 21.54
    cyclopentyl methyl ether 31.18
    gamma-butyrolactone 133.19
    1-methoxy-2-propanol 196.42
    pyridine 24.23
    3-pentanone 15.86
    furfural 160.24
    n-dodecane 1.38
    diethylene glycol 228.91
    diisopropyl ether 5.79
    tert-amyl alcohol 82.76
    acetylacetone 52.37
    n-hexadecane 1.44
    acetophenone 27.25
    methyl propionate 27.79
    isopentyl acetate 16.56
    trichloroethylene 21.14
    n-nonanol 21.99
    cyclohexanol 40.25
    benzyl alcohol 38.75
    2-ethylhexanol 20.84
    isooctanol 21.54
    dipropyl ether 12.84
    1,2-dichlorobenzene 8.74
    ethyl lactate 39.09
    propylene carbonate 62.14
    n-methylformamide 364.02
    2-pentanol 33.57
    n-pentane 1.81
    1-propoxy-2-propanol 72.73
    1-methoxy-2-propyl acetate 29.38
    2-(2-methoxypropoxy) propanol 72.61
    mesitylene 6.67
    ε-caprolactone 58.25
    p-cymene 6.26
    epichlorohydrin 80.38
    1,1,1-trichloroethane 8.76
    2-aminoethanol 406.24
    morpholine-4-carbaldehyde 291.61
    sulfolane 211.65
    2,2,4-trimethylpentane 1.74
    2-methyltetrahydrofuran 48.4
    n-hexyl acetate 22.88
    isooctane 1.61
    2-(2-butoxyethoxy)ethanol 92.43
    sec-butyl acetate 10.47
    tert-butyl acetate 22.12
    decalin 1.99
    glycerin 477.17
    diglyme 150.0
    acrylic acid 143.57
    isopropyl myristate 10.54
    n-butyric acid 95.9
    acetyl acetate 19.31
    di(2-ethylhexyl) phthalate 19.7
    ethyl propionate 16.97
    nitromethane 242.5
    1,2-diethoxyethane 22.32
    benzonitrile 21.09
    trioctyl phosphate 17.02
    1-bromopropane 5.3
    gamma-valerolactone 175.42
    n-decanol 16.73
    triethyl phosphate 15.53
    4-methyl-2-pentanol 23.75
    propionitrile 21.26
    vinylene carbonate 63.15
    1,1,2-trichlorotrifluoroethane 154.32
    DMS 18.32
    cumene 5.98
    2-octanol 16.38
    2-hexanone 19.98
    octyl acetate 15.74
    limonene 8.19
    1,2-dimethoxyethane 193.51
    ethyl orthosilicate 14.02
    tributyl phosphate 16.05
    diacetone alcohol 78.03
    N,N-dimethylaniline 25.83
    acrylonitrile 44.27
    aniline 17.13
    1,3-propanediol 307.02
    bromobenzene 3.71
    dibromomethane 7.92
    1,1,2,2-tetrachloroethane 21.91
    2-methyl-cyclohexyl acetate 17.54
    tetrabutyl urea 29.24
    diisobutyl methanol 13.63
    2-phenylethanol 29.8
    styrene 4.89
    dioctyl adipate 18.52
    dimethyl sulfate 76.6
    ethyl butyrate 17.09
    methyl lactate 81.76
    butyl lactate 31.59
    diethyl carbonate 12.62
    propanediol butyl ether 89.85
    triethyl orthoformate 15.1
    p-tert-butyltoluene 6.45
    methyl 4-tert-butylbenzoate 39.24
    morpholine 121.17
    tert-butylamine 47.8
    n-dodecanol 13.05
    dimethoxymethane 144.7
    ethylene carbonate 47.67
    cyrene 83.83
    2-ethoxyethyl acetate 21.1
    2-ethylhexyl acetate 11.33
    1,2,4-trichlorobenzene 9.5
    4-methylpyridine 27.52
    dibutyl ether 9.88
    2,6-dimethyl-4-heptanol 13.63
    DEF 87.93
    dimethyl isosorbide 87.32
    tetrachloroethylene 21.07
    eugenol 57.47
    triacetin 26.38
    span 80 60.29
    1,4-butanediol 155.73
    1,1-dichloroethane 8.16
    2-methyl-1-pentanol 38.05
    methyl formate 246.66
    2-methyl-1-butanol 49.06
    n-decane 1.88
    butyronitrile 26.03
    3,7-dimethyl-1-octanol 20.64
    1-chlorooctane 5.82
    1-chlorotetradecane 3.14
    n-nonane 1.73
    undecane 1.56
    tert-butylcyclohexane 2.21
    cyclooctane 1.1
    cyclopentanol 78.36
    tetrahydropyran 29.78
    tert-amyl methyl ether 20.76
    2,5,8-trioxanonane 124.33
    1-hexene 5.22
    2-isopropoxyethanol 88.49
    2,2,2-trifluoroethanol 159.64
    methyl butyrate 34.34

    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