Levoglucosan

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  • Identifiers

    CAS number
    498-07-7

    Molecular formula
    C6H10O5

    SMILES
    C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.08%
    Sweet 37.61%
    Woody 28.94%
    Caramellic 24.24%
    Smoky 17.92%
    Burnt 17.5%
    Alcoholic 16.8%
    Clean 15.89%
    Phenolic 15.8%
    Vanilla 15.43%

     

    Flavor
    Sweet 74.08%
    Bitter 46.98%
    Odorless 41.58%
    Sweet-like 29.01%
    Fatty 25.13%
    Cauliflower 21.85%
    Alkaline 20.44%
    Very slight 20.44%
    Naphthalic 19.75%
    Soup 19.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.1

    pKa est.
    6.29 (neutral)

    Molecular weight
    162.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    451°C

    Melting point expt.

    • 183 °C

    Flash point

    • 167.64 ˚C est.

    Solubility expt.

    • 62.3 mg/mL

  • Synonyms

    • Levoglucosan
    • 498-07-7
    • 1,6-Anhydro-beta-D-glucopyranose
    • Leucoglucosan
    • (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
    • 1,6-Anhydro-beta-glucopyranose
    • 5132N17FSD
    • CHEBI:30997
    • beta-D-Glucopyranose, 1,6-anhydro-
    • NSC-46243
    • DTXSID90904321
    • (1R,2S,3S,4R,5R)-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol
    • RefChem:153210
    • DTXCID301474706
    • 207-855-0
    • 1,6-Anhydro-beta-D-glucose
    • 1,6-Anhydroglucose
    • Glucosan
    • 1,6-Anhydro-b-D-glucopyranose
    • 1,6-Anhydro-D-glucose
    • MFCD00063248
    • 1,6-Anhydro-|A-D-glucose
    • .beta.-D-Glucopyranose, 1,6-anhydro-
    • 1,6-Anhydro-|A-D-glucopyranose
    • Anhydro-d-mannosan
    • NSC 46243
    • UNII-5132N17FSD
    • 1,6-Anhydro-D-glucopyranoside
    • CCRIS 4273
    • L-glucosan
    • 4PW
    • EINECS 207-855-0
    • Anhydro-delta-mannosan
    • Levoglucosan (Standard)
    • AI3-61731
    • 1,6-Anhydro--D-glucose
    • bmse000569
    • 1,6-Anhydro-b-D-glucose
    • 1,6-Anhydro-delta-glucose
    • SCHEMBL195289
    • orb1301956
    • orb3025402
    • 1,6-Anhydro-beta-delta-glucose
    • CHEMBL3138649
    • (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (non-preferred name)
    • D-GLUCOSE, 1,6-ANHYDRO-
    • 644-76-8
    • BB_NC-00553
    • HY-W050145R
    • 1,6-Anhydro- beta -D-glucopyranose
    • 1,6-Anhydro-beta-D-glucose, 99%
    • EBC-12040
    • GEO-00235
    • 1,6-Anhydro-beta-delta-glucopyranose
    • AKOS006281170
    • AKOS015924837
    • CS-W023160
    • FS-4431
    • HY-W050145
    • ML06636
    • 1,6-ANHYDRO-D-GLUCOSE [USP-RS]
    • SY048722
    • DB-010113
    • A1074
    • NS00043551
    • T70965
    • EN300-7375411
    • 644A768
    • Q6535767
    • 6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.
    • Z1198149756
    • 6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.
    • 1,6-Anhydro-D-glucose, United States Pharmacopeia (USP) Reference Standard
    • 498-07-7

  • Applications

    Levoglucosan (CAS 498-07-7) is a biomass-derived sugar anhydride that serves as an intermediate in chemical synthesis and as a renewable building block for materials. In polymers and plastics, it is used as a diol-like building block for polyols and polyurethanes and as a precursor for carbohydrate-derived derivatives. In coatings and inks, it can function as a reactive diol component to modify resin properties. In pharmaceuticals, it is explored as a carbohydrate-based scaffold for medicinal chemistry intermediates. In green chemistry and biorefinery contexts, levoglucosan is evaluated as a renewable feedstock for conversion to value-added chemicals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.39
    methanol 38.94
    isopropanol 2.89
    water 616.7
    ethyl acetate 1.66
    n-propanol 3.4
    acetone 3.52
    n-butanol 3.38
    acetonitrile 1.91
    DMF 102.34
    toluene 0.24
    isobutanol 1.73
    1,4-dioxane 6.15
    methyl acetate 0.98
    THF 9.76
    2-butanone 1.36
    n-pentanol 1.39
    sec-butanol 1.83
    n-hexane 0.07
    ethylene glycol 86.51
    NMP 83.69
    cyclohexane 0.31
    DMSO 297.25
    n-butyl acetate 1.27
    n-octanol 2.36
    chloroform 0.64
    n-propyl acetate 0.91
    acetic acid 54.33
    dichloromethane 1.03
    cyclohexanone 5.03
    propylene glycol 25.3
    isopropyl acetate 1.56
    DMAc 40.91
    2-ethoxyethanol 25.22
    isopentanol 2.5
    n-heptane 0.44
    ethyl formate 2.85
    1,2-dichloroethane 0.94
    n-hexanol 1.99
    2-methoxyethanol 78.1
    isobutyl acetate 0.56
    tetrachloromethane 0.39
    n-pentyl acetate 1.62
    transcutol 51.76
    n-heptanol 2.78
    ethylbenzene 0.17
    MIBK 2.49
    2-propoxyethanol 18.25
    tert-butanol 3.24
    MTBE 0.69
    2-butoxyethanol 13.21
    propionic acid 7.03
    o-xylene 0.5
    formic acid 465.71
    diethyl ether 1.08
    m-xylene 0.57
    p-xylene 0.22
    chlorobenzene 0.27
    dimethyl carbonate 3.85
    n-octane 0.23
    formamide 318.87
    cyclopentanone 8.55
    2-pentanone 2.5
    anisole 0.77
    cyclopentyl methyl ether 3.48
    gamma-butyrolactone 15.16
    1-methoxy-2-propanol 39.33
    pyridine 2.15
    3-pentanone 1.53
    furfural 22.3
    n-dodecane 0.16
    diethylene glycol 55.57
    diisopropyl ether 0.62
    tert-amyl alcohol 2.26
    acetylacetone 7.54
    n-hexadecane 0.18
    acetophenone 1.82
    methyl propionate 2.81
    isopentyl acetate 1.3
    trichloroethylene 1.51
    n-nonanol 2.29
    cyclohexanol 3.37
    benzyl alcohol 1.96
    2-ethylhexanol 1.47
    isooctanol 2.26
    dipropyl ether 1.85
    1,2-dichlorobenzene 0.48
    ethyl lactate 5.15
    propylene carbonate 5.95
    n-methylformamide 46.85
    2-pentanol 1.92
    n-pentane 0.15
    1-propoxy-2-propanol 11.22
    1-methoxy-2-propyl acetate 5.0
    2-(2-methoxypropoxy) propanol 13.61
    mesitylene 0.67
    ε-caprolactone 6.1
    p-cymene 0.72
    epichlorohydrin 7.28
    1,1,1-trichloroethane 0.35
    2-aminoethanol 46.35
    morpholine-4-carbaldehyde 66.96
    sulfolane 58.55
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 3.06
    n-hexyl acetate 2.12
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 20.43
    sec-butyl acetate 0.64
    tert-butyl acetate 2.33
    decalin 0.11
    glycerin 121.96
    diglyme 35.81
    acrylic acid 15.45
    isopropyl myristate 1.19
    n-butyric acid 7.56
    acetyl acetate 2.2
    di(2-ethylhexyl) phthalate 2.11
    ethyl propionate 1.1
    nitromethane 44.05
    1,2-diethoxyethane 3.5
    benzonitrile 1.11
    trioctyl phosphate 2.07
    1-bromopropane 0.3
    gamma-valerolactone 28.67
    n-decanol 1.69
    triethyl phosphate 2.01
    4-methyl-2-pentanol 1.7
    propionitrile 0.86
    vinylene carbonate 5.36
    1,1,2-trichlorotrifluoroethane 29.48
    DMS 2.05
    cumene 0.23
    2-octanol 1.57
    2-hexanone 0.87
    octyl acetate 1.64
    limonene 1.05
    1,2-dimethoxyethane 13.13
    ethyl orthosilicate 1.74
    tributyl phosphate 1.9
    diacetone alcohol 10.95
    N,N-dimethylaniline 1.24
    acrylonitrile 2.04
    aniline 1.26
    1,3-propanediol 41.36
    bromobenzene 0.2
    dibromomethane 0.51
    1,1,2,2-tetrachloroethane 1.43
    2-methyl-cyclohexyl acetate 1.74
    tetrabutyl urea 3.56
    diisobutyl methanol 1.7
    2-phenylethanol 2.34
    styrene 0.16
    dioctyl adipate 2.24
    dimethyl sulfate 15.99
    ethyl butyrate 1.79
    methyl lactate 15.32
    butyl lactate 4.48
    diethyl carbonate 1.2
    propanediol butyl ether 16.84
    triethyl orthoformate 2.17
    p-tert-butyltoluene 0.74
    methyl 4-tert-butylbenzoate 6.07
    morpholine 10.97
    tert-butylamine 1.16
    n-dodecanol 1.26
    dimethoxymethane 20.64
    ethylene carbonate 3.66
    cyrene 20.59
    2-ethoxyethyl acetate 3.25
    2-ethylhexyl acetate 0.95
    1,2,4-trichlorobenzene 0.69
    4-methylpyridine 1.38
    dibutyl ether 1.22
    2,6-dimethyl-4-heptanol 1.7
    DEF 9.9
    dimethyl isosorbide 20.18
    tetrachloroethylene 1.7
    eugenol 8.36
    triacetin 4.94
    span 80 10.78
    1,4-butanediol 14.37
    1,1-dichloroethane 0.31
    2-methyl-1-pentanol 1.14
    methyl formate 22.29
    2-methyl-1-butanol 1.94
    n-decane 0.27
    butyronitrile 1.09
    3,7-dimethyl-1-octanol 2.08
    1-chlorooctane 0.59
    1-chlorotetradecane 0.3
    n-nonane 0.26
    undecane 0.2
    tert-butylcyclohexane 0.08
    cyclooctane 0.23
    cyclopentanol 4.58
    tetrahydropyran 2.09
    tert-amyl methyl ether 1.05
    2,5,8-trioxanonane 29.29
    1-hexene 0.12
    2-isopropoxyethanol 9.11
    2,2,2-trifluoroethanol 49.13
    methyl butyrate 1.61

    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