Ribonolactone

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  • Identifiers

    CAS number
    5336-08-3

    Molecular formula
    C5H8O5

    SMILES
    C([C@@H]1[C@H]([C@H](C(=O)O1)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 72.7%
    Caramellic 41.93%
    Sweet 33.11%
    Burnt 23.28%
    Buttery 18.91%
    Milky 17.63%
    Clean 17.23%
    Sharp 17.15%
    Malty 14.62%
    Savory 14.58%

     

    Flavor
    Sweet 62.46%
    Bitter 53.15%
    Odorless 46.22%
    Sweet-like 28.9%
    Very mild 26.65%
    Caramel 23.61%
    Very slight 22.12%
    Cauliflower 22.06%
    Fenugreek 22.03%
    Extremely sweet 20.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.4

    pKa est.
    5.38 (weak acid)

    Molecular weight
    148.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    595°C

    Melting point expt.

    • 83 - 85 °C

    Flash point

    • 178.69 ˚C est.

  • Synonyms

    • Ribonolactone
    • (3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
    • D-Ribono-gamma-lactone
    • 64E63NC231
    • Ribonic acid, gamma-lactone, D-
    • NSC-1031
    • RefChem:883599
    • CHEBI:37434
    • 226-256-5
    • D-Ribono-1,4-lactone
    • 5336-08-3
    • D-Ribonolactone
    • D(+)-Ribonic acid gamma-lactone
    • 3327-63-7
    • Ribono-gamma-lactone
    • D-(+)-Ribonic acid gamma-lactone
    • MFCD00063241
    • D-(+)-Ribono-1,4-lactone
    • D-Ribopentono-1,4-lactone
    • (3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
    • D-Ribonic acid-1,4-Lactone
    • gamma-Lactone of ribonic acid
    • ribono-1,4-lactone
    • (3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one
    • NSC 1031
    • Ribonic acid, .gamma.-lactone, D-
    • delta-Ribonolactone
    • gamma-lactone-Ribonate
    • D-(+)-Ribonolactone
    • D-Ribonolactone (VAN)
    • D-ribonic acid g-lactone
    • gamma-Lactone of ribonate
    • ribonic acid-gamma-lactone
    • delta-Ribono-gamma-lactone
    • gamma-lactone-Ribonic acid
    • (+)-RIBONOLACTONE
    • delta-Ribono-1,4-lactone
    • Ribonic acid-1,4-lactone
    • Ribonic acid, gamma-lactone
    • D-(+)-Ribonic-gamma-lactone
    • SCHEMBL625893
    • delta-Ribopentono-1,4-lactone
    • CHEMBL607627
    • orb1309794
    • D-(+)-Ribonic acid g-Lactone
    • D-(+)-Ribonone-1.4-lactone
    • UNII-64E63NC231
    • CHEBI:74168
    • CUOKHACJLGPRHD-BXXZVTAOSA-
    • D-RIBOPENTONO-1,4-LACTON
    • delta-(+)-Ribonone-1.4-lactone
    • DTXSID201347750
    • DTXSID701350100
    • delta-(+)-Ribonic acid g-Lactone
    • BB_NC-00562
    • CS-M1132
    • D-(+)-RIBONIC ACID LACTONE
    • EINECS 226-256-5
    • MSK012765
    • D-(+)-Ribonic gamma-lactone, 97%
    • AKOS015955664
    • delta-(+)-Ribonic acid gamma-lactone
    • EBC-616590
    • AC-15682
    • AS-46673
    • HY-76691
    • SY059506
    • DB-222987
    • ST50307093
    • E10111
    • F050969
    • Q27144478
    • 93B77B8F-39C4-4159-83A4-A05A3F85E8C5
    • D-(+)-Ribonic acid-gamma-lactone, puriss., >=99.0% (T)
    • (3R,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)dihydro-2(3h)-furanone
    • (4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3,4,5-trihydrofuran-2-one
    • Rel-(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
    • InChI=1/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1
    • 5336-08-3

  • Applications

    Ribonolactone is primarily used as a chiral building block and synthetic intermediate in carbohydrate and nucleoside chemistry. In the pharmaceutical industry it serves as a precursor for ribose-based nucleoside and nucleotide analogs and related APIs. It is used in carbohydrate chemistry as a starting material for preparing ribofuranose derivatives and glycosyl derivatives, enabling the construction of sugar-based frameworks common in drug discovery. In industrial and specialty chemicals, ribonolactone is regarded as a versatile intermediate for the synthesis of ribose-based scaffolds and related APIs derived from ribose, with applications typically pursued under controlled conditions and regulatory constraints. In academic R&D, it is often employed to explore stereochemical transformations and to develop sugar-based ligands and catalysts.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 60.15
    methanol 239.36
    isopropanol 21.83
    water 1951.25
    ethyl acetate 6.61
    n-propanol 20.67
    acetone 28.86
    n-butanol 14.39
    acetonitrile 7.24
    DMF 687.53
    toluene 0.86
    isobutanol 8.76
    1,4-dioxane 38.62
    methyl acetate 6.32
    THF 35.96
    2-butanone 8.5
    n-pentanol 7.95
    sec-butanol 12.47
    n-hexane 0.27
    ethylene glycol 606.41
    NMP 260.87
    cyclohexane 0.92
    DMSO 2120.85
    n-butyl acetate 3.16
    n-octanol 6.91
    chloroform 2.86
    n-propyl acetate 3.71
    acetic acid 99.36
    dichloromethane 5.99
    cyclohexanone 15.48
    propylene glycol 147.41
    isopropyl acetate 5.35
    DMAc 255.85
    2-ethoxyethanol 138.1
    isopentanol 10.28
    n-heptane 1.08
    ethyl formate 15.31
    1,2-dichloroethane 7.19
    n-hexanol 8.57
    2-methoxyethanol 390.26
    isobutyl acetate 1.32
    tetrachloromethane 1.91
    n-pentyl acetate 3.56
    transcutol 83.34
    n-heptanol 7.84
    ethylbenzene 0.8
    MIBK 7.42
    2-propoxyethanol 62.33
    tert-butanol 27.86
    MTBE 5.01
    2-butoxyethanol 35.74
    propionic acid 24.12
    o-xylene 2.04
    formic acid 1266.4
    diethyl ether 4.9
    m-xylene 1.89
    p-xylene 0.91
    chlorobenzene 0.84
    dimethyl carbonate 20.5
    n-octane 0.61
    formamide 964.86
    cyclopentanone 25.6
    2-pentanone 10.26
    anisole 4.23
    cyclopentyl methyl ether 9.83
    gamma-butyrolactone 44.14
    1-methoxy-2-propanol 155.05
    pyridine 7.29
    3-pentanone 6.47
    furfural 68.71
    n-dodecane 0.43
    diethylene glycol 220.26
    diisopropyl ether 2.11
    tert-amyl alcohol 18.26
    acetylacetone 28.38
    n-hexadecane 0.46
    acetophenone 7.49
    methyl propionate 12.1
    isopentyl acetate 2.72
    trichloroethylene 8.22
    n-nonanol 6.2
    cyclohexanol 12.17
    benzyl alcohol 10.04
    2-ethylhexanol 4.03
    isooctanol 5.73
    dipropyl ether 4.69
    1,2-dichlorobenzene 1.69
    ethyl lactate 17.59
    propylene carbonate 15.18
    n-methylformamide 315.2
    2-pentanol 8.17
    n-pentane 0.53
    1-propoxy-2-propanol 28.25
    1-methoxy-2-propyl acetate 12.64
    2-(2-methoxypropoxy) propanol 31.68
    mesitylene 2.12
    ε-caprolactone 16.29
    p-cymene 1.87
    epichlorohydrin 32.83
    1,1,1-trichloroethane 2.07
    2-aminoethanol 282.6
    morpholine-4-carbaldehyde 243.09
    sulfolane 199.27
    2,2,4-trimethylpentane 0.42
    2-methyltetrahydrofuran 10.84
    n-hexyl acetate 4.87
    isooctane 0.35
    2-(2-butoxyethoxy)ethanol 42.62
    sec-butyl acetate 2.08
    tert-butyl acetate 7.58
    decalin 0.4
    glycerin 518.24
    diglyme 87.49
    acrylic acid 46.78
    isopropyl myristate 2.5
    n-butyric acid 19.67
    acetyl acetate 6.37
    di(2-ethylhexyl) phthalate 4.64
    ethyl propionate 4.38
    nitromethane 149.8
    1,2-diethoxyethane 7.98
    benzonitrile 3.93
    trioctyl phosphate 4.64
    1-bromopropane 1.29
    gamma-valerolactone 82.32
    n-decanol 4.78
    triethyl phosphate 4.68
    4-methyl-2-pentanol 5.44
    propionitrile 3.65
    vinylene carbonate 14.86
    1,1,2-trichlorotrifluoroethane 123.85
    DMS 6.18
    cumene 0.91
    2-octanol 4.49
    2-hexanone 3.88
    octyl acetate 3.74
    limonene 2.73
    1,2-dimethoxyethane 77.35
    ethyl orthosilicate 3.87
    tributyl phosphate 3.64
    diacetone alcohol 39.93
    N,N-dimethylaniline 6.34
    acrylonitrile 9.98
    aniline 4.25
    1,3-propanediol 207.64
    bromobenzene 0.64
    dibromomethane 2.58
    1,1,2,2-tetrachloroethane 8.96
    2-methyl-cyclohexyl acetate 3.68
    tetrabutyl urea 8.53
    diisobutyl methanol 4.16
    2-phenylethanol 8.71
    styrene 0.71
    dioctyl adipate 4.75
    dimethyl sulfate 87.49
    ethyl butyrate 4.05
    methyl lactate 65.24
    butyl lactate 9.41
    diethyl carbonate 2.8
    propanediol butyl ether 37.66
    triethyl orthoformate 4.41
    p-tert-butyltoluene 2.05
    methyl 4-tert-butylbenzoate 16.07
    morpholine 52.39
    tert-butylamine 7.63
    n-dodecanol 3.79
    dimethoxymethane 121.78
    ethylene carbonate 10.57
    cyrene 55.45
    2-ethoxyethyl acetate 7.19
    2-ethylhexyl acetate 1.9
    1,2,4-trichlorobenzene 2.12
    4-methylpyridine 5.47
    dibutyl ether 2.72
    2,6-dimethyl-4-heptanol 4.16
    DEF 46.62
    dimethyl isosorbide 43.63
    tetrachloroethylene 9.52
    eugenol 22.23
    triacetin 9.9
    span 80 22.43
    1,4-butanediol 90.9
    1,1-dichloroethane 1.93
    2-methyl-1-pentanol 5.65
    methyl formate 154.74
    2-methyl-1-butanol 8.8
    n-decane 0.65
    butyronitrile 3.7
    3,7-dimethyl-1-octanol 5.2
    1-chlorooctane 1.62
    1-chlorotetradecane 0.83
    n-nonane 0.67
    undecane 0.51
    tert-butylcyclohexane 0.31
    cyclooctane 0.72
    cyclopentanol 17.53
    tetrahydropyran 7.35
    tert-amyl methyl ether 6.05
    2,5,8-trioxanonane 69.93
    1-hexene 0.54
    2-isopropoxyethanol 44.33
    2,2,2-trifluoroethanol 139.41
    methyl butyrate 6.73

    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