(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

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  • Identifiers

    CAS number
    50-99-7

    Molecular formula
    C6H12O6

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

  • Odor profile

    Fragrance
    Odorless 70.65%
    Sweet 41.06%
    Caramellic 27.77%
    Buttery 21.58%
    Savory 16.91%
    Bitter 16.75%
    Clean 16.2%
    Sharp 16.1%
    Milky 16.01%
    Alcoholic 15.94%

     

    Flavor
    Odorless 66.31%
    Sweet 38.33%
    Sweet-like 30.63%
    Very mild 27.98%
    Very slight 21.17%
    Bland 20.89%
    Yeast 19.9%
    Mild 19.66%
    Acetoin 19.14%
    Caramellic 19.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.9

    pKa est.
    4.02 (weak acid)

    Molecular weight
    180.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • less than 32 °F (USCG, 1999)
    • 146 °C
    • Crystals from water, MP: 83 °C; specific optical rotation = +102.0 deg to 47.9 deg (water) at 25 °C/D. 0.74 times as sweet as sucrose; 1 g dissolves in ca 1 mL water, ca 60 mL alcohol /alpha-Glucose, monohydrate/

    Boiling point

    • greater than 212 °F at 760 mmHg (USCG, 1999)

    Flash point

    • 227.49 ˚C est.

    Solubility expt.

    • In water, 5.46X10+5 mg/L at 30 °C, 4.79X10+5 mg/L at 20 °C
    • Very soluble in water
    • Slightly soluble in ethanol; insoluble in acetone, ethyl acetate; soluble in pyrine

  • Synonyms

    • 50-99-7
    • D(+)-Glucose
    • (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
    • Dextrose Anhydrous
    • aldehydo-D-glucose
    • D-(+)-Glucose
    • Glucose Anhydrous
    • DL-Glucose
    • 58367-01-4
    • Dextrose, anhydrous
    • Glucose [JAN]
    • 5SL0G7R0OK
    • DTXSID4048729
    • DTXSID7022910
    • CHEBI:42758
    • 815-92-9
    • Glucose, liquid
    • 28823-03-2
    • Glucopur
    • GLO
    • (14C)-Glucose
    • (14C)D-Glucose
    • (C13)D-Glucose
    • (U-14C)Glucose
    • Glucose (C-13)
    • Glucose (C-14)
    • D-(U-14C)Glucose
    • Glucose, liquid [NF]
    • 8027-56-3
    • (U-13C)-D-glucose
    • Insta-Glucose
    • D-Glucose, labeled with tritium
    • NSC-406891
    • NCGC00159408-02
    • D-Glucose, labeled with carbon-13
    • D-Glucose, labeled with carbon-14
    • Glucose-40
    • Dextrose (D-glucose)
    • D-Glucose (Standard)
    • D-Glucose - anhydrous
    • D(+)-Glucose;(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal
    • anhydrous dextrose (open form)
    • GLUCOSE [EP MONOGRAPH]
    • CHEMBL448805
    • ANHYDROUS DEXTROSE [II]
    • Dextrosum (Glucosum) anhydricum
    • HY-B0389R
    • MSK3203
    • D-(+)-Glucose pound notanhydrous
    • DTXCID701436386
    • D-Glucose;Grape sugar;Glucopyranose
    • HY-B0389
    • Tox21_113165
    • Tox21_200145
    • MFCD00148912
    • s2123
    • AKOS006239080
    • CCG-266428
    • DB01914
    • MG08747
    • CAS-50-99-7
    • NCGC00257699-01
    • NCGC00386163-02
    • 19030-38-7
    • ANHYDROUS DEXTROSE [USP MONOGRAPH]
    • OM168412
    • Maltodextrin - dextrose equivalent 18-28
    • CAS-58367-01-4
    • DB-230493
    • DB-264747
    • NS00007629
    • NS00081306
    • SW220288-1
    • D85170
    • EN300-109407
    • SBI-0633535.0002
    • AB01274744-01
    • AB01274744_02
    • A828386
    • BRD-K51431759-001-02-9
    • Q21036645
    • rel-(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal
    • (2R,3S,4R,5R)-2,3,4,5,6-pentakis(oxidanyl)hexanal
    • Z1201619321
    • 109427F7-ABCA-4F12-91AE-01BC27C22B31
    • DEXTROSE (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
    • D-GLUCOSE,2-(ACETYLAMINO)-4-O-[2-(ACETYLAMINO)-2-DEOXY-4-O-SULFO-B-D-GALACTOPYRANOSYL]-2-DEOXY-

  • Applications

    Applications of (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal (CAS 50-99-7) largely center on several real-world use-cases: as a carbon source for fermentation to produce bio-based chemicals such as organic acids, ethanol, and amino acids; as a carbon source for plant tissue culture media and biotechnological cultivation in agriculture; as a humectant in cosmetics and personal care formulations; as a precursor to sorbitol and other sugar polyols used in cosmetics and plastics; and as a feedstock in food processing and fermentation-based industries.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.02
    methanol 66.02
    isopropanol 3.74
    water 2316.14
    ethyl acetate 0.98
    n-propanol 4.52
    acetone 2.56
    n-butanol 2.41
    acetonitrile 1.82
    DMF 256.64
    toluene 0.23
    isobutanol 1.86
    1,4-dioxane 6.8
    methyl acetate 1.05
    THF 3.68
    2-butanone 1.63
    n-pentanol 0.9
    sec-butanol 2.96
    n-hexane 0.07
    ethylene glycol 336.43
    NMP 176.16
    cyclohexane 0.7
    DMSO 843.09
    n-butyl acetate 0.52
    n-octanol 0.71
    chloroform 0.17
    n-propyl acetate 0.4
    acetic acid 21.99
    dichloromethane 0.4
    cyclohexanone 3.76
    propylene glycol 85.95
    isopropyl acetate 0.62
    DMAc 107.22
    2-ethoxyethanol 16.8
    isopentanol 1.41
    n-heptane 0.51
    ethyl formate 1.46
    1,2-dichloroethane 0.7
    n-hexanol 1.36
    2-methoxyethanol 80.84
    isobutyl acetate 0.15
    tetrachloromethane 0.22
    n-pentyl acetate 0.37
    transcutol 12.95
    n-heptanol 1.08
    ethylbenzene 0.16
    MIBK 0.8
    2-propoxyethanol 9.44
    tert-butanol 3.48
    MTBE 0.75
    2-butoxyethanol 4.41
    propionic acid 8.61
    o-xylene 0.58
    formic acid 606.42
    diethyl ether 0.78
    m-xylene 0.37
    p-xylene 0.19
    chlorobenzene 0.1
    dimethyl carbonate 4.95
    n-octane 0.18
    formamide 402.53
    cyclopentanone 5.18
    2-pentanone 1.38
    anisole 0.51
    cyclopentyl methyl ether 2.4
    gamma-butyrolactone 7.92
    1-methoxy-2-propanol 32.33
    pyridine 1.64
    3-pentanone 1.53
    furfural 10.73
    n-dodecane 0.09
    diethylene glycol 48.43
    diisopropyl ether 0.32
    tert-amyl alcohol 3.29
    acetylacetone 3.04
    n-hexadecane 0.09
    acetophenone 1.08
    methyl propionate 3.01
    isopentyl acetate 0.4
    trichloroethylene 0.64
    n-nonanol 0.65
    cyclohexanol 4.18
    benzyl alcohol 1.53
    2-ethylhexanol 0.79
    isooctanol 0.77
    dipropyl ether 1.02
    1,2-dichlorobenzene 0.2
    ethyl lactate 3.2
    propylene carbonate 2.49
    n-methylformamide 86.96
    2-pentanol 1.46
    n-pentane 0.17
    1-propoxy-2-propanol 5.57
    1-methoxy-2-propyl acetate 2.42
    2-(2-methoxypropoxy) propanol 4.96
    mesitylene 0.43
    ε-caprolactone 3.82
    p-cymene 0.44
    epichlorohydrin 2.83
    1,1,1-trichloroethane 0.15
    2-aminoethanol 127.21
    morpholine-4-carbaldehyde 96.32
    sulfolane 76.18
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 1.94
    n-hexyl acetate 0.47
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 5.88
    sec-butyl acetate 0.25
    tert-butyl acetate 0.89
    decalin 0.15
    glycerin 354.42
    diglyme 11.95
    acrylic acid 18.91
    isopropyl myristate 0.23
    n-butyric acid 3.82
    acetyl acetate 0.91
    di(2-ethylhexyl) phthalate 0.55
    ethyl propionate 0.62
    nitromethane 25.39
    1,2-diethoxyethane 0.97
    benzonitrile 0.45
    trioctyl phosphate 0.54
    1-bromopropane 0.19
    gamma-valerolactone 16.69
    n-decanol 0.51
    triethyl phosphate 1.0
    4-methyl-2-pentanol 0.7
    propionitrile 0.83
    vinylene carbonate 2.42
    1,1,2-trichlorotrifluoroethane 27.15
    DMS 1.07
    cumene 0.18
    2-octanol 0.59
    2-hexanone 0.42
    octyl acetate 0.35
    limonene 0.8
    1,2-dimethoxyethane 7.72
    ethyl orthosilicate 0.86
    tributyl phosphate 0.44
    diacetone alcohol 5.95
    N,N-dimethylaniline 1.17
    acrylonitrile 2.13
    aniline 1.06
    1,3-propanediol 55.1
    bromobenzene 0.08
    dibromomethane 0.22
    1,1,2,2-tetrachloroethane 0.96
    2-methyl-cyclohexyl acetate 0.61
    tetrabutyl urea 1.25
    diisobutyl methanol 0.75
    2-phenylethanol 1.26
    styrene 0.13
    dioctyl adipate 0.53
    dimethyl sulfate 23.48
    ethyl butyrate 0.71
    methyl lactate 20.79
    butyl lactate 1.49
    diethyl carbonate 0.49
    propanediol butyl ether 6.82
    triethyl orthoformate 0.89
    p-tert-butyltoluene 0.5
    methyl 4-tert-butylbenzoate 2.2
    morpholine 12.49
    tert-butylamine 1.17
    n-dodecanol 0.42
    dimethoxymethane 20.13
    ethylene carbonate 1.82
    cyrene 16.97
    2-ethoxyethyl acetate 0.77
    2-ethylhexyl acetate 0.33
    1,2,4-trichlorobenzene 0.31
    4-methylpyridine 1.0
    dibutyl ether 0.34
    2,6-dimethyl-4-heptanol 0.75
    DEF 12.48
    dimethyl isosorbide 7.48
    tetrachloroethylene 1.13
    eugenol 2.83
    triacetin 1.42
    span 80 4.57
    1,4-butanediol 16.28
    1,1-dichloroethane 0.16
    2-methyl-1-pentanol 0.62
    methyl formate 25.74
    2-methyl-1-butanol 1.66
    n-decane 0.14
    butyronitrile 0.56
    3,7-dimethyl-1-octanol 0.52
    1-chlorooctane 0.21
    1-chlorotetradecane 0.11
    n-nonane 0.16
    undecane 0.11
    tert-butylcyclohexane 0.08
    cyclooctane 0.43
    cyclopentanol 5.19
    tetrahydropyran 1.83
    tert-amyl methyl ether 1.15
    2,5,8-trioxanonane 10.94
    1-hexene 0.09
    2-isopropoxyethanol 5.12
    2,2,2-trifluoroethanol 39.87
    methyl butyrate 0.89

    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