Ethyl 3-Hydroxybutyrate

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    5405-41-4

    Molecular formula
    C6H12O3

    SMILES
    CCOC(=O)CC(C)O

    Safety labels

    Flammable
    Flammable

    Retention indicies (RI)

    • DB5: 935.0
    • Carbowax: 1524.0

  • Odor profile

    Fruity 93.56%
    Green 78.32%
    Apple 63.12%
    Fresh 60.42%
    Sweet 51.5%
    Winey 50.65%
    Tropical 49.57%
    Pineapple 45.2%
    Grape 41.11%
    Ethereal 38.76%

    Scent© AI

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    8.71 (weak base)

    Molecular weight
    132.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 338 °F at 760 mmHg (NTP, 1992)
    • 170.00 to 175.00 °C. @ 760.00 mm Hg

    Flash point est.
    75.92 ˚C

    Flash point expt.

    • 148 °F (NTP, 1992)

    Solubility expt.

    • greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)
    • 100 g in 100 ml water at 23�C

  • Synonyms

    • Ethyl 3-hydroxybutyrate
    • Ethyl 3-hydroxybutanoate
    • 5405-41-4
    • Butanoic acid, 3-hydroxy-, ethyl ester
    • Ethyl beta-hydroxybutyrate
    • 35608-64-1
    • Ethyl dl-3-hydroxybutyrate
    • grape butyrate
    • Ethyl (R)-(-)-3-hydroxybutyrate
    • FEMA No. 3428
    • Butyric acid, 3-hydroxy-, ethyl ester
    • NSC 8115
    • Ethyl (1)-3-hydroxybutyrate
    • NSC 42916
    • Ethyl 3-hydroxybutyrate (natural)
    • EINECS 226-456-2
    • EINECS 252-642-8
    • Ethyl .beta.-hydroxybutyrate
    • DTXSID6025305
    • UNII-52008C87PV
    • AI3-11592
    • NSC-8115
    • DL-3-Hydroxy-n-butyrate ethyl ester
    • NSC-42916
    • 52008C87PV
    • (s)-ethyl 3-hydroxybutyrate
    • (R)-Ethyl 3-hydroxybutyrate
    • DTXCID105305
    • CHEBI:87685
    • FEMA 3428
    • 3-hydroxybutyric acid ethyl ester
    • CH3CH(OH)CH2C(O)OC2H5
    • DL-3-HYDROXY-N-BUTYRIC ACID ETHYL ESTER
    • 3-hydroxybutanoic acid ethyl ester
    • Ethyl-dl-.beta.-hydroxy n-butyrate
    • ETHYL 3-HYDROXYBUTYRATE [FHFI]
    • (+/-)-ETHYL 3-HYDROXYBUTYRATE
    • ETHYL (+/-)-3-HYDROXYBUTANOATE
    • Ethyl3-hydroxybutyrate
    • Butyric acid, .beta.-hydroxy-, ethyl ester
    • dl-.beta.-Hydroxy-n-butyric acid ethyl ester
    • (+/-)-3-HYDROXYBUTANOIC ACID ETHYL ESTER
    • Butanoic acid, 3-hydroxy-, ethyl ester, (.+/-.)-
    • (S)-3-hydroxybutyric acid ethyl ester
    • MFCD00004545
    • Ethyl b-hydroxybutyrate
    • Ethyl I2-hydroxybutyrate
    • ethyl 3-hydroxy-n-butyrate
    • Ethyl b-hydroxybutyric acid
    • Ethyl 3-hydroxybutanoate #
    • Ethyl 3-hydroxybutyric acid
    • Ethyl I2-hydroxybutyric acid
    • SCHEMBL76382
    • Ethyl beta-hydroxybutyric acid
    • ETHYL-3-HYDROXYBUTYRATE
    • Racemic ethyl 3-hydroxybutyrate
    • Ethyl (+/-)-3-hydroxybutyrate
    • Ethyl-dl-beta-hydroxy n-butyrate
    • NSC8115
    • Ethyl 3-hydroxybutyrate, >=98%
    • 3-hydroxy-butyric acid ethyl ester
    • Ethyl 3-hydroxybutyrate (Standard)
    • HY-W012701R
    • NSC42916
    • (R)-(-)-ethyl 3-hydroxybutanoate
    • EINECS 260-393-1
    • Ethyl (A+-)-3-hydroxybutyric acid
    • Tox21_303950
    • Ethyl 3-hydroxybutyrate, natural, FG
    • AKOS009157139
    • DL-3-Hydroxybutyric Acid Ethyl Ester
    • (+-)-ETHYL 3-HYDROXYBUTYRATE
    • AB88672
    • CS-W013417
    • Ethyl 3-hydroxybutyrate, >=97%, FG
    • HY-W012701
    • SB45075
    • ETHYL (+-)-3-HYDROXYBUTANOATE
    • NCGC00357184-01
    • (.+-.)-ETHYL 3-HYDROXYBUTYRATE
    • Butyric acid, beta-hydroxy-, ethyl ester
    • DS-15292
    • SY017544
    • SY017547
    • CAS-5405-41-4
    • dl-beta-Hydroxy-n-butyric acid ethyl ester
    • ETHYL (.+-.)-3-HYDROXYBUTANOATE
    • DB-011716
    • DB-264963
    • Ethyl 3-hydroxybutyrate, analytical standard
    • H0230
    • NS00012409
    • D70263
    • EN300-123226
    • (+-)-3-HYDROXYBUTANOIC ACID ETHYL ESTER
    • Butanoic acid, 3-hydroxy-, ethyl ester, (+/-)-
    • (.+-.)-3-HYDROXYBUTANOIC ACID ETHYL ESTER
    • Q27159827
    • 226-456-2

  • Applications

    Ethyl 3-hydroxybutyrate, CAS 5405-41-4, is a naturally occurring chiral ester whose versatility spans several fields: in flavor and fragrance it imparts a fresh pineapple-caramel note that lifts soft drinks, confectionery, yogurts and wines; in pharmaceuticals it serves as a key synthon for the enantioselective construction of statins, β-lactams, HIV antivirals and diverse 3-hydroxy-γ-butyrolactone derivatives, providing a convenient C4 chiral building block for complex natural-product scaffolds; in agriculture it is incorporated into semi-synthetic insect pheromones and tobacco flavor modifiers; in research it functions as an isotope tracer and a GC-MS reference standard for ketosis metabolism studies, and as a model monomer for biodegradable poly(3-hydroxybutyrate) materials; moreover, owing to its good solvating power and moderate volatility, ethyl 3-hydroxybutyrate is employed as a biocatalytic reaction medium, a fine-tuning co-solvent in aroma formulations and a carrier for natural colorants.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 621.01
    methanol 1234.59
    isopropanol 476.82
    water 103.99
    ethyl acetate 136.64
    n-propanol 401.08
    acetone 394.05
    n-butanol 302.75
    acetonitrile 290.39
    DMF 1048.57
    toluene 26.9
    isobutanol 260.11
    1,4-dioxane 451.15
    methyl acetate 178.05
    THF 582.72
    2-butanone 149.22
    n-pentanol 185.04
    sec-butanol 295.62
    n-hexane 18.52
    ethylene glycol 555.42
    NMP 752.75
    cyclohexane 27.66
    DMSO 785.8
    n-butyl acetate 59.83
    n-octanol 125.61
    chloroform 262.7
    n-propyl acetate 74.24
    acetic acid 1052.95
    dichloromethane 238.62
    cyclohexanone 280.29
    propylene glycol 559.69
    isopropyl acetate 79.24
    DMAc 672.0
    2-ethoxyethanol 317.61
    isopentanol 187.43
    n-heptane 13.78
    ethyl formate 177.78
    1,2-dichloroethane 125.19
    n-hexanol 162.75
    2-methoxyethanol 798.37
    isobutyl acetate 47.86
    tetrachloromethane 31.89
    n-pentyl acetate 58.69
    transcutol 547.59
    n-heptanol 69.99
    ethylbenzene 26.01
    MIBK 82.79
    2-propoxyethanol 327.56
    tert-butanol 491.66
    MTBE 126.22
    2-butoxyethanol 134.76
    propionic acid 441.91
    o-xylene 37.21
    formic acid 514.16
    diethyl ether 116.13
    m-xylene 32.25
    p-xylene 37.02
    chlorobenzene 59.21
    dimethyl carbonate 99.62
    n-octane 6.35
    formamide 395.49
    cyclopentanone 347.88
    2-pentanone 130.08
    anisole 91.49
    cyclopentyl methyl ether 171.45
    gamma-butyrolactone 488.09
    1-methoxy-2-propanol 518.14
    pyridine 145.45
    3-pentanone 92.35
    furfural 427.42
    n-dodecane 8.21
    diethylene glycol 422.26
    diisopropyl ether 31.17
    tert-amyl alcohol 289.38
    acetylacetone 183.31
    n-hexadecane 8.86
    acetophenone 99.04
    methyl propionate 160.38
    isopentyl acetate 55.11
    trichloroethylene 222.14
    n-nonanol 101.09
    cyclohexanol 260.55
    benzyl alcohol 124.36
    2-ethylhexanol 72.51
    isooctanol 54.34
    dipropyl ether 63.41
    1,2-dichlorobenzene 75.7
    ethyl lactate 117.53
    propylene carbonate 251.28
    n-methylformamide 476.61
    2-pentanol 170.69
    n-pentane 18.81
    1-propoxy-2-propanol 195.77
    1-methoxy-2-propyl acetate 105.72
    2-(2-methoxypropoxy) propanol 195.67
    mesitylene 27.31
    ε-caprolactone 253.38
    p-cymene 28.58
    epichlorohydrin 317.8
    1,1,1-trichloroethane 103.97
    2-aminoethanol 611.35
    morpholine-4-carbaldehyde 649.27
    sulfolane 593.41
    2,2,4-trimethylpentane 12.6
    2-methyltetrahydrofuran 253.78
    n-hexyl acetate 125.98
    isooctane 8.89
    2-(2-butoxyethoxy)ethanol 265.61
    sec-butyl acetate 48.09
    tert-butyl acetate 92.13
    decalin 14.54
    glycerin 729.08
    diglyme 338.63
    acrylic acid 437.22
    isopropyl myristate 54.94
    n-butyric acid 373.7
    acetyl acetate 113.96
    di(2-ethylhexyl) phthalate 76.3
    ethyl propionate 84.5
    nitromethane 794.19
    1,2-diethoxyethane 92.79
    benzonitrile 122.46
    trioctyl phosphate 59.06
    1-bromopropane 64.82
    gamma-valerolactone 540.46
    n-decanol 75.38
    triethyl phosphate 50.29
    4-methyl-2-pentanol 83.53
    propionitrile 176.99
    vinylene carbonate 252.84
    1,1,2-trichlorotrifluoroethane 384.52
    DMS 109.6
    cumene 27.98
    2-octanol 57.96
    2-hexanone 81.06
    octyl acetate 78.34
    limonene 43.08
    1,2-dimethoxyethane 391.97
    ethyl orthosilicate 47.1
    tributyl phosphate 64.88
    diacetone alcohol 199.31
    N,N-dimethylaniline 86.55
    acrylonitrile 253.01
    aniline 95.85
    1,3-propanediol 534.3
    bromobenzene 43.5
    dibromomethane 130.26
    1,1,2,2-tetrachloroethane 205.48
    2-methyl-cyclohexyl acetate 69.86
    tetrabutyl urea 96.37
    diisobutyl methanol 47.11
    2-phenylethanol 95.91
    styrene 30.86
    dioctyl adipate 98.67
    dimethyl sulfate 179.75
    ethyl butyrate 67.12
    methyl lactate 227.35
    butyl lactate 92.6
    diethyl carbonate 57.7
    propanediol butyl ether 244.7
    triethyl orthoformate 57.15
    p-tert-butyltoluene 29.55
    methyl 4-tert-butylbenzoate 129.02
    morpholine 508.45
    tert-butylamine 237.93
    n-dodecanol 59.45
    dimethoxymethane 351.88
    ethylene carbonate 188.37
    cyrene 209.56
    2-ethoxyethyl acetate 84.36
    2-ethylhexyl acetate 42.18
    1,2,4-trichlorobenzene 94.99
    4-methylpyridine 145.27
    dibutyl ether 65.31
    2,6-dimethyl-4-heptanol 47.11
    DEF 240.45
    dimethyl isosorbide 268.07
    tetrachloroethylene 127.95
    eugenol 145.12
    triacetin 156.66
    span 80 206.7
    1,4-butanediol 240.47
    1,1-dichloroethane 119.04
    2-methyl-1-pentanol 130.97
    methyl formate 366.44
    2-methyl-1-butanol 188.16
    n-decane 12.56
    butyronitrile 163.23
    3,7-dimethyl-1-octanol 92.1
    1-chlorooctane 45.69
    1-chlorotetradecane 21.63
    n-nonane 12.13
    undecane 9.72
    tert-butylcyclohexane 15.38
    cyclooctane 8.29
    cyclopentanol 341.48
    tetrahydropyran 255.29
    tert-amyl methyl ether 99.61
    2,5,8-trioxanonane 311.17
    1-hexene 47.89
    2-isopropoxyethanol 178.26
    2,2,2-trifluoroethanol 294.28
    methyl butyrate 115.6

    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

Botanical

Name CAS Botanical Proportion
Ambarella fruit Spondias cytherea Sonnerat (Ambarella), fam. Anacardiaceae 0.15%
Ambarella fruit (Brazil) Spondias cytherea Sonnerat, fam. Anarcardiaceae 0.9%