alpha-Hydroxy-gamma-butyrolactone

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  • Identifiers

    CAS number
    19444-84-9

    Molecular formula
    C4H6O3

    SMILES
    C1COC(=O)C1O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 72.82%
    Sweet 59.44%
    Burnt 44.75%
    Buttery 41.64%
    Nutty 31.27%
    Creamy 28.99%
    Odorless 28.89%
    Coconut 28.52%
    Coumarinic 27.52%
    Lactonic 26.94%

     

    Flavor
    Sweet 78.78%
    Caramel 53.91%
    Coconut 36.53%
    Creamy 33.65%
    Buttery 32.49%
    Tonka 31.35%
    Fatty 31.2%
    Bread 31.17%
    Bitter 30.06%
    Candy 28.56%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    6.41 (neutral)

    Molecular weight
    102.09 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    301°C

    Flash point

    • 108.45 ˚C est.

  • Synonyms

    • 19444-84-9
    • alpha-Hydroxy-gamma-butyrolactone
    • 2-Hydroxy-gamma-butyrolactone
    • L5D4QZ05QR
    • 2(3H)-Furanone, dihydro-3-hydroxy-
    • RefChem:87481
    • 692-561-9
    • 3-Hydroxydihydrofuran-2(3H)-one
    • 3-hydroxyoxolan-2-one
    • 3-Hydroxytetrahydrofuran-2-one
    • 2(3H)-Furanone, dihydrohydroxy-
    • MFCD00134268
    • a-Hydroxy-?-butyrolactone
    • 2-hydroxybutyrolactone
    • ?-Hydroxy-?-butyrolactone
    • UNII-L5D4QZ05QR
    • 3-Hydroxydihydro-2(3H)-furanone
    • hydroxybutyrolactone
    • S-(-)-Alpha-hydroxy-gamma-butyrolactone
    • Dihydro-3-hydroxy-2(3H)-furanone
    • 2-hydroxy-butyrolactone
    • alpha-hydroxybutyrolactone
    • EC 692-561-9
    • 3-hydroxydihydrofuran-2-one
    • SCHEMBL107295
    • orb3023542
    • SCHEMBL1457003
    • SCHEMBL7099601
    • 2-HYDROXY-4-BUTANOLIDE
    • DTXSID00941181
    • 2-OXOTETRAHYDROFURAN-3-OL
    • 3-hydroxydihydrofuran-2-(3H)-one
    • 3-Hydroxydihydrofuran-2(3H);-one
    • (R)-(+)-a-Hydroxy-g-butyrolactone
    • (S)-(-)-a-Hydroxy-g-butyrolactone
    • 3-Hydroxydihydro-2(3H)-furanone #
    • alpha -Hydroxy- gamma -butyrolactone
    • AKOS000277381
    • AKOS016843445
    • CS-W013699
    • MB00930
    • 2-HYDROXY-.GAMMA.-BUTYROLACTONE
    • r-(+)-alpha-hydroxy-gamma-butyrolactone
    • racemic alpha-hydroxy-gamma-butyrolactone
    • AS-60521
    • FH172337
    • SY052569
    • DB-002630
    • DB-071477
    • DB-072211
    • H0788
    • NS00004626
    • .ALPHA.-HYDROXY-.GAMMA.-BUTYROLACTONE
    • A12215
    • 2,4-DIHYDROXYBUTYRIC ACID .GAMMA.-LACTONE
    • 2-HYDROXY-.GAMMA.-BUTYROLACTONE, (2RS)-
    • alpha-Hydroxy-gamma-butyrolactone, technical grade
    • F234086
    • 2-HYDROXY-.GAMMA.-BUTYROLACTONE, (+/-)-
    • Q27282736
    • 19444-84-9

  • Applications

    alpha-Hydroxy-gamma-butyrolactone (CAS 19444-84-9) is commonly used as a chiral building block and reactive intermediate in chemical synthesis, with applications in pharmaceutical and agrochemical manufacturing. It also serves as a precursor for beta-hydroxy esters and other chiral building blocks, and can be employed in the synthesis of specialty polymers and polyesters via ring-opening or functionalization of the lactone. In industrial formulations, it may act as a solvent or co-solvent for niche processes, and it is sometimes explored as a fragrance-related intermediate in perfumery and cosmetic ingredient development. Additionally, it can function as a processing aid or reactive intermediate in coatings, inks, and cleaning formulations, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 154.84
    methanol 461.05
    isopropanol 58.15
    water 1075.85
    ethyl acetate 17.32
    n-propanol 62.19
    acetone 43.31
    n-butanol 50.64
    acetonitrile 40.11
    DMF 301.87
    toluene 3.32
    isobutanol 43.26
    1,4-dioxane 39.81
    methyl acetate 24.26
    THF 38.75
    2-butanone 19.36
    n-pentanol 34.07
    sec-butanol 41.6
    n-hexane 1.01
    ethylene glycol 187.73
    NMP 123.16
    cyclohexane 1.83
    DMSO 318.78
    n-butyl acetate 5.77
    n-octanol 14.42
    chloroform 17.65
    n-propyl acetate 9.54
    acetic acid 414.41
    dichloromethane 25.91
    cyclohexanone 22.89
    propylene glycol 92.37
    isopropyl acetate 11.19
    DMAc 181.59
    2-ethoxyethanol 143.85
    isopentanol 47.12
    n-heptane 1.28
    ethyl formate 44.64
    1,2-dichloroethane 15.97
    n-hexanol 13.72
    2-methoxyethanol 270.76
    isobutyl acetate 4.82
    tetrachloromethane 6.25
    n-pentyl acetate 10.37
    transcutol 226.32
    n-heptanol 16.59
    ethylbenzene 3.05
    MIBK 15.51
    2-propoxyethanol 45.42
    tert-butanol 64.37
    MTBE 17.76
    2-butoxyethanol 54.53
    propionic acid 71.17
    o-xylene 5.4
    formic acid 1134.03
    diethyl ether 11.68
    m-xylene 4.27
    p-xylene 4.33
    chlorobenzene 3.98
    dimethyl carbonate 20.65
    n-octane 1.02
    formamide 1200.61
    cyclopentanone 31.78
    2-pentanone 16.72
    anisole 13.86
    cyclopentyl methyl ether 13.49
    gamma-butyrolactone 52.0
    1-methoxy-2-propanol 113.22
    pyridine 26.33
    3-pentanone 10.14
    furfural 102.67
    n-dodecane 0.84
    diethylene glycol 103.9
    diisopropyl ether 4.41
    tert-amyl alcohol 57.33
    acetylacetone 30.91
    n-hexadecane 0.85
    acetophenone 18.43
    methyl propionate 18.11
    isopentyl acetate 6.65
    trichloroethylene 28.94
    n-nonanol 12.9
    cyclohexanol 21.61
    benzyl alcohol 28.47
    2-ethylhexanol 7.85
    isooctanol 14.89
    dipropyl ether 4.76
    1,2-dichlorobenzene 5.85
    ethyl lactate 17.18
    propylene carbonate 27.95
    n-methylformamide 243.21
    2-pentanol 24.94
    n-pentane 1.62
    1-propoxy-2-propanol 23.01
    1-methoxy-2-propyl acetate 12.2
    2-(2-methoxypropoxy) propanol 53.08
    mesitylene 4.0
    ε-caprolactone 27.56
    p-cymene 3.18
    epichlorohydrin 45.88
    1,1,1-trichloroethane 7.85
    2-aminoethanol 204.61
    morpholine-4-carbaldehyde 149.72
    sulfolane 90.07
    2,2,4-trimethylpentane 1.5
    2-methyltetrahydrofuran 22.68
    n-hexyl acetate 13.41
    isooctane 1.02
    2-(2-butoxyethoxy)ethanol 77.24
    sec-butyl acetate 6.12
    tert-butyl acetate 14.37
    decalin 1.08
    glycerin 207.29
    diglyme 135.11
    acrylic acid 109.45
    isopropyl myristate 5.31
    n-butyric acid 64.95
    acetyl acetate 17.82
    di(2-ethylhexyl) phthalate 12.24
    ethyl propionate 7.81
    nitromethane 355.9
    1,2-diethoxyethane 19.83
    benzonitrile 14.57
    trioctyl phosphate 7.82
    1-bromopropane 5.23
    gamma-valerolactone 81.05
    n-decanol 9.24
    triethyl phosphate 5.9
    4-methyl-2-pentanol 19.0
    propionitrile 16.56
    vinylene carbonate 33.34
    1,1,2-trichlorotrifluoroethane 95.58
    DMS 11.47
    cumene 3.45
    2-octanol 10.24
    2-hexanone 9.77
    octyl acetate 8.32
    limonene 3.83
    1,2-dimethoxyethane 87.49
    ethyl orthosilicate 6.0
    tributyl phosphate 7.87
    diacetone alcohol 47.28
    N,N-dimethylaniline 16.52
    acrylonitrile 33.42
    aniline 15.98
    1,3-propanediol 182.05
    bromobenzene 3.03
    dibromomethane 12.49
    1,1,2,2-tetrachloroethane 20.98
    2-methyl-cyclohexyl acetate 6.79
    tetrabutyl urea 13.52
    diisobutyl methanol 7.04
    2-phenylethanol 14.07
    styrene 3.61
    dioctyl adipate 10.18
    dimethyl sulfate 46.88
    ethyl butyrate 6.64
    methyl lactate 39.27
    butyl lactate 17.39
    diethyl carbonate 5.1
    propanediol butyl ether 62.62
    triethyl orthoformate 6.42
    p-tert-butyltoluene 3.1
    methyl 4-tert-butylbenzoate 29.11
    morpholine 60.34
    tert-butylamine 27.75
    n-dodecanol 6.75
    dimethoxymethane 68.97
    ethylene carbonate 21.65
    cyrene 50.44
    2-ethoxyethyl acetate 19.47
    2-ethylhexyl acetate 4.34
    1,2,4-trichlorobenzene 7.48
    4-methylpyridine 20.29
    dibutyl ether 7.19
    2,6-dimethyl-4-heptanol 7.04
    DEF 54.16
    dimethyl isosorbide 46.89
    tetrachloroethylene 24.7
    eugenol 36.32
    triacetin 23.1
    span 80 35.1
    1,4-butanediol 92.47
    1,1-dichloroethane 7.94
    2-methyl-1-pentanol 33.72
    methyl formate 153.58
    2-methyl-1-butanol 44.98
    n-decane 1.23
    butyronitrile 19.68
    3,7-dimethyl-1-octanol 14.5
    1-chlorooctane 3.38
    1-chlorotetradecane 1.68
    n-nonane 1.15
    undecane 0.98
    tert-butylcyclohexane 0.99
    cyclooctane 1.05
    cyclopentanol 28.27
    tetrahydropyran 14.6
    tert-amyl methyl ether 15.94
    2,5,8-trioxanonane 98.54
    1-hexene 2.71
    2-isopropoxyethanol 61.79
    2,2,2-trifluoroethanol 216.58
    methyl butyrate 15.79

    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