(S)-(-)-5-Hydroxymethyl-2(5H)-furanone

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  • Identifiers

    CAS number
    78508-96-0

    Molecular formula
    C5H6O3

    SMILES
    C1=CC(=O)O[C@@H]1CO

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 59.14%
    Buttery 39.61%
    Odorless 39.31%
    Burnt 38.12%
    Sweet 36.31%
    Nutty 34.56%
    Roasted 28.4%
    Creamy 22.05%
    Sour 21.79%
    Coconut 20.73%

     

    Flavor
    Caramel 28.85%
    Odorless 27.1%
    Bitter 26.76%
    Very mild 23.92%
    Maple 22.08%
    Buttery 22.02%
    Fenugreek 21.32%
    Cotton candy 21.22%
    Extremely sweet 21.07%
    Seedy 20.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    7.4 (neutral)

    Molecular weight
    114.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    348°C

    Flash point

    • 127.2 ˚C est.

  • Synonyms

    • 78508-96-0
    • (S)-(-)-5-Hydroxymethyl-2(5H)-furanone
    • (S)-5-(Hydroxymethyl)furan-2(5H)-one
    • (2S)-2-(hydroxymethyl)-2H-furan-5-one
    • MFCD00075370
    • (5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-one
    • (S)-5-Hydroxymethyl-2[5H]-furanone
    • 2(5H)-Furanone, 5-(hydroxymethyl)-, (5S)-
    • (5S)-5-(hydroxymethyl)furan-2(5H)-one
    • SCHEMBL2672216
    • (S)-5-hydroxy-2-penten-4-olide
    • GEO-03017
    • AKOS015856117
    • 5-(Hydroxymethyl)-2(5H)-furanone #
    • AS-62948
    • SY037336
    • (25)-2-(hydroxymethyl)-2H-furan-5-one
    • (5s)-5-(hydroxymethyl)-2-(5h)-furanone
    • CS-0319426
    • A51108
    • 508H960
    • F722850
    • (S)-(-)-5-Hydroxymethyl-2(5H)-furanone, 98%
    • 78508-96-0

  • Applications

    Known as (S)-(-)-5-Hydroxymethyl-2(5H)-furanone, this chiral gamma-hydroxymethyl lactone is primarily used as a chiral intermediate in the synthesis of pharmaceuticals and agrochemicals; it also serves as a building block for fragrance and flavor compounds or as a precursor to aroma molecules in perfumery and flavor applications; in cosmetics and personal care it can be used as a fragrance intermediate or functional building block; it can function as a lactone-bearing building block for polymer and materials development; and it is considered an intermediate in the production of specialty chemicals for industrial manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 163.42
    methanol 404.15
    isopropanol 97.49
    water 180.62
    ethyl acetate 39.15
    n-propanol 90.05
    acetone 110.33
    n-butanol 72.1
    acetonitrile 100.73
    DMF 722.92
    toluene 7.17
    isobutanol 56.15
    1,4-dioxane 113.36
    methyl acetate 67.01
    THF 124.91
    2-butanone 48.45
    n-pentanol 52.11
    sec-butanol 60.45
    n-hexane 0.77
    ethylene glycol 214.07
    NMP 254.32
    cyclohexane 1.26
    DMSO 720.36
    n-butyl acetate 21.23
    n-octanol 24.38
    chloroform 23.18
    n-propyl acetate 25.82
    acetic acid 203.07
    dichloromethane 46.44
    cyclohexanone 49.44
    propylene glycol 89.55
    isopropyl acetate 22.41
    DMAc 413.83
    2-ethoxyethanol 201.17
    isopentanol 63.16
    n-heptane 1.49
    ethyl formate 70.5
    1,2-dichloroethane 36.65
    n-hexanol 30.64
    2-methoxyethanol 382.78
    isobutyl acetate 13.41
    tetrachloromethane 4.8
    n-pentyl acetate 16.31
    transcutol 325.69
    n-heptanol 18.94
    ethylbenzene 5.76
    MIBK 31.11
    2-propoxyethanol 88.87
    tert-butanol 127.46
    MTBE 34.87
    2-butoxyethanol 56.43
    propionic acid 79.06
    o-xylene 9.89
    formic acid 452.74
    diethyl ether 27.07
    m-xylene 9.33
    p-xylene 7.72
    chlorobenzene 12.25
    dimethyl carbonate 45.37
    n-octane 0.96
    formamide 539.57
    cyclopentanone 77.25
    2-pentanone 39.63
    anisole 38.03
    cyclopentyl methyl ether 32.6
    gamma-butyrolactone 127.22
    1-methoxy-2-propanol 177.84
    pyridine 54.9
    3-pentanone 23.9
    furfural 157.37
    n-dodecane 1.3
    diethylene glycol 167.82
    diisopropyl ether 7.73
    tert-amyl alcohol 78.37
    acetylacetone 60.15
    n-hexadecane 1.38
    acetophenone 39.01
    methyl propionate 46.07
    isopentyl acetate 20.32
    trichloroethylene 50.34
    n-nonanol 21.61
    cyclohexanol 33.78
    benzyl alcohol 47.93
    2-ethylhexanol 17.45
    isooctanol 16.47
    dipropyl ether 13.92
    1,2-dichlorobenzene 15.85
    ethyl lactate 33.92
    propylene carbonate 51.88
    n-methylformamide 332.26
    2-pentanol 38.26
    n-pentane 1.21
    1-propoxy-2-propanol 52.16
    1-methoxy-2-propyl acetate 34.35
    2-(2-methoxypropoxy) propanol 75.89
    mesitylene 7.06
    ε-caprolactone 49.96
    p-cymene 6.95
    epichlorohydrin 115.05
    1,1,1-trichloroethane 13.65
    2-aminoethanol 204.34
    morpholine-4-carbaldehyde 265.82
    sulfolane 164.49
    2,2,4-trimethylpentane 1.24
    2-methyltetrahydrofuran 56.82
    n-hexyl acetate 25.79
    isooctane 1.15
    2-(2-butoxyethoxy)ethanol 98.33
    sec-butyl acetate 15.68
    tert-butyl acetate 29.05
    decalin 1.3
    glycerin 202.8
    diglyme 176.39
    acrylic acid 101.85
    isopropyl myristate 13.29
    n-butyric acid 66.51
    acetyl acetate 27.61
    di(2-ethylhexyl) phthalate 19.02
    ethyl propionate 26.02
    nitromethane 340.78
    1,2-diethoxyethane 45.51
    benzonitrile 36.34
    trioctyl phosphate 13.81
    1-bromopropane 11.73
    gamma-valerolactone 142.23
    n-decanol 17.25
    triethyl phosphate 17.46
    4-methyl-2-pentanol 25.36
    propionitrile 52.1
    vinylene carbonate 58.42
    1,1,2-trichlorotrifluoroethane 124.27
    DMS 29.74
    cumene 5.97
    2-octanol 13.26
    2-hexanone 25.2
    octyl acetate 18.09
    limonene 8.92
    1,2-dimethoxyethane 213.03
    ethyl orthosilicate 15.57
    tributyl phosphate 16.27
    diacetone alcohol 72.41
    N,N-dimethylaniline 33.2
    acrylonitrile 89.49
    aniline 30.02
    1,3-propanediol 196.49
    bromobenzene 8.75
    dibromomethane 20.39
    1,1,2,2-tetrachloroethane 36.45
    2-methyl-cyclohexyl acetate 19.04
    tetrabutyl urea 27.38
    diisobutyl methanol 12.96
    2-phenylethanol 31.34
    styrene 7.62
    dioctyl adipate 22.61
    dimethyl sulfate 100.76
    ethyl butyrate 21.45
    methyl lactate 63.81
    butyl lactate 23.97
    diethyl carbonate 18.22
    propanediol butyl ether 66.22
    triethyl orthoformate 18.86
    p-tert-butyltoluene 6.95
    methyl 4-tert-butylbenzoate 40.49
    morpholine 134.58
    tert-butylamine 43.99
    n-dodecanol 13.62
    dimethoxymethane 193.47
    ethylene carbonate 42.62
    cyrene 71.8
    2-ethoxyethyl acetate 30.4
    2-ethylhexyl acetate 14.19
    1,2,4-trichlorobenzene 20.2
    4-methylpyridine 50.39
    dibutyl ether 16.28
    2,6-dimethyl-4-heptanol 12.96
    DEF 102.57
    dimethyl isosorbide 90.67
    tetrachloroethylene 26.57
    eugenol 51.42
    triacetin 37.18
    span 80 46.1
    1,4-butanediol 101.84
    1,1-dichloroethane 18.54
    2-methyl-1-pentanol 43.45
    methyl formate 221.87
    2-methyl-1-butanol 52.18
    n-decane 1.77
    butyronitrile 46.78
    3,7-dimethyl-1-octanol 23.89
    1-chlorooctane 7.49
    1-chlorotetradecane 4.02
    n-nonane 1.53
    undecane 1.46
    tert-butylcyclohexane 1.32
    cyclooctane 0.76
    cyclopentanol 44.88
    tetrahydropyran 38.09
    tert-amyl methyl ether 28.61
    2,5,8-trioxanonane 142.4
    1-hexene 3.73
    2-isopropoxyethanol 94.79
    2,2,2-trifluoroethanol 116.46
    methyl butyrate 40.1

    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