Levoglucosenone

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  • Identifiers

    CAS number
    37112-31-5

    Molecular formula
    C6H6O3

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 48.88%
    Sweet 44.23%
    Nutty 39.35%
    Burnt 38.58%
    Roasted 38.35%
    Buttery 28.14%
    Spicy 25.09%
    Popcorn 21.02%
    Coffee 20.84%
    Green 20.54%

     

    Flavor
    Bitter 66.37%
    Shrimp 19.6%
    Fenugreek 19.36%
    Alkaline 19.17%
    Naphthalic 19.02%
    Sweet-like 18.88%
    Maple syrup 18.86%
    Taco 18.85%
    Cauliflower 18.78%
    Seedy 18.68%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    6.55 (neutral)

    Molecular weight
    126.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    240°C

    Flash point

    • 93.63 ˚C est.

  • Synonyms

    • Levoglucosenone
    • 37112-31-5
    • B7N23SN1LB
    • 1,6-Anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
    • 1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose
    • CHEBI:30999
    • 6,8-DIOXABICYCLO(3.2.1)OCT-2-EN-4-ONE, (1S,5R)-
    • DTXSID70880912
    • RefChem:153211
    • DTXCID001022255
    • (1S,5R)-6,8-dioxabicyclo(3.2.1)oct-2-en-4-one;1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose
    • (1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
    • CHEMBL4126941
    • MFCD00191664
    • (1S)-6,8-Dioxabicyclo(3.2.1)oct-2-en-4-one
    • CCRIS 4274
    • (1S)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
    • UNII-B7N23SN1LB
    • BRN 4859778
    • 6,8-Dioxabicyclo(3.2.1)oct-2-en-4-one, (1S)-
    • LEVOGLUCOSENONE [MI]
    • SCHEMBL7155405
    • LEVOGLUCOSENONE, (-)-
    • Levoglucosenone, >=95% (GC)
    • BDBM50276378
    • AKOS006345460
    • FL03963
    • PS-4213
    • HY-21226
    • SY112154
    • CS-0016272
    • L0150
    • T72379
    • 112L315
    • (1S,5R)-6,8-Dioxobicyclo[3.2.1]oct-2-en-4-one
    • Q27114054
    • 1,6-Anhydro-3,4-dideoxy-a-D-glycero-hex-3-enopyranose-2-ulose
    • 1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyran-2-ulose
    • 1,6-ANHYDRO-3,4-DIDEOXY-.BETA.-D-GLYCERO-HEX-3-ENOPYRANOS-2-ULOSE
    • 1,6-ANHYDRO-3,4-DIDEOXY-.DELTA.3-.BETA.-D-PYRANOSEN-2-ONE
    • 37112-31-5

  • Applications

    Levoglucosenone (CAS 37112-31-5) is a biomass-derived platform chemical widely used as a chiral building block and intermediate in organic synthesis. It enables the synthesis of cyclic lactones and other enantioenriched intermediates via Michael-type additions and cyclizations, and serves as a precursor for fragrance and flavor compounds in perfumery and taste chemistry. It is commonly evaluated as a versatile starting point for pharmaceutical and agrochemical synthesis, and as a building block in polymer and materials chemistry for specialty polymers and resins. It is also explored for applications in cosmetics/personal care as a source of chiral functional groups, and in coatings and inks as a reactive platform for functionalization.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.76
    methanol 54.0
    isopropanol 10.08
    water 40.9
    ethyl acetate 14.23
    n-propanol 13.57
    acetone 26.53
    n-butanol 11.94
    acetonitrile 35.08
    DMF 126.17
    toluene 2.12
    isobutanol 8.92
    1,4-dioxane 27.88
    methyl acetate 20.51
    THF 21.89
    2-butanone 16.07
    n-pentanol 10.17
    sec-butanol 10.06
    n-hexane 0.29
    ethylene glycol 46.22
    NMP 86.02
    cyclohexane 0.61
    DMSO 160.51
    n-butyl acetate 9.18
    n-octanol 9.24
    chloroform 25.61
    n-propyl acetate 10.46
    acetic acid 110.96
    dichloromethane 34.64
    cyclohexanone 22.87
    propylene glycol 22.04
    isopropyl acetate 7.95
    DMAc 97.28
    2-ethoxyethanol 51.87
    isopentanol 11.37
    n-heptane 0.79
    ethyl formate 21.07
    1,2-dichloroethane 18.46
    n-hexanol 9.12
    2-methoxyethanol 90.04
    isobutyl acetate 5.91
    tetrachloromethane 2.86
    n-pentyl acetate 7.98
    transcutol 202.33
    n-heptanol 7.36
    ethylbenzene 1.97
    MIBK 10.96
    2-propoxyethanol 36.61
    tert-butanol 11.95
    MTBE 4.32
    2-butoxyethanol 28.16
    propionic acid 33.01
    o-xylene 3.5
    formic acid 184.58
    diethyl ether 5.22
    m-xylene 3.32
    p-xylene 3.35
    chlorobenzene 6.92
    dimethyl carbonate 14.86
    n-octane 0.48
    formamide 230.86
    cyclopentanone 27.62
    2-pentanone 12.8
    anisole 10.03
    cyclopentyl methyl ether 8.57
    gamma-butyrolactone 46.57
    1-methoxy-2-propanol 49.58
    pyridine 25.65
    3-pentanone 9.75
    furfural 77.76
    n-dodecane 0.61
    diethylene glycol 67.47
    diisopropyl ether 2.1
    tert-amyl alcohol 10.64
    acetylacetone 24.88
    n-hexadecane 0.67
    acetophenone 17.08
    methyl propionate 17.1
    isopentyl acetate 8.79
    trichloroethylene 40.7
    n-nonanol 8.73
    cyclohexanol 9.56
    benzyl alcohol 16.24
    2-ethylhexanol 6.51
    isooctanol 6.55
    dipropyl ether 5.16
    1,2-dichlorobenzene 9.73
    ethyl lactate 17.45
    propylene carbonate 24.17
    n-methylformamide 84.92
    2-pentanol 7.27
    n-pentane 0.38
    1-propoxy-2-propanol 21.92
    1-methoxy-2-propyl acetate 16.76
    2-(2-methoxypropoxy) propanol 40.75
    mesitylene 2.88
    ε-caprolactone 24.84
    p-cymene 3.52
    epichlorohydrin 41.01
    1,1,1-trichloroethane 8.2
    2-aminoethanol 43.11
    morpholine-4-carbaldehyde 94.11
    sulfolane 64.44
    2,2,4-trimethylpentane 0.4
    2-methyltetrahydrofuran 12.46
    n-hexyl acetate 12.97
    isooctane 0.35
    2-(2-butoxyethoxy)ethanol 52.21
    sec-butyl acetate 6.35
    tert-butyl acetate 9.15
    decalin 0.58
    glycerin 67.44
    diglyme 92.28
    acrylic acid 51.54
    isopropyl myristate 6.35
    n-butyric acid 27.82
    acetyl acetate 15.05
    di(2-ethylhexyl) phthalate 10.38
    ethyl propionate 10.17
    nitromethane 161.41
    1,2-diethoxyethane 18.85
    benzonitrile 17.4
    trioctyl phosphate 7.37
    1-bromopropane 4.42
    gamma-valerolactone 58.06
    n-decanol 6.78
    triethyl phosphate 9.29
    4-methyl-2-pentanol 6.02
    propionitrile 16.42
    vinylene carbonate 29.11
    1,1,2-trichlorotrifluoroethane 74.04
    DMS 15.87
    cumene 2.57
    2-octanol 4.74
    2-hexanone 9.68
    octyl acetate 8.71
    limonene 4.26
    1,2-dimethoxyethane 50.34
    ethyl orthosilicate 7.77
    tributyl phosphate 9.31
    diacetone alcohol 23.17
    N,N-dimethylaniline 10.24
    acrylonitrile 35.12
    aniline 9.49
    1,3-propanediol 41.24
    bromobenzene 5.14
    dibromomethane 14.1
    1,1,2,2-tetrachloroethane 27.1
    2-methyl-cyclohexyl acetate 9.8
    tetrabutyl urea 14.63
    diisobutyl methanol 4.87
    2-phenylethanol 13.74
    styrene 2.54
    dioctyl adipate 11.93
    dimethyl sulfate 34.75
    ethyl butyrate 10.03
    methyl lactate 28.6
    butyl lactate 13.98
    diethyl carbonate 9.27
    propanediol butyl ether 36.14
    triethyl orthoformate 9.13
    p-tert-butyltoluene 3.1
    methyl 4-tert-butylbenzoate 20.44
    morpholine 33.76
    tert-butylamine 4.98
    n-dodecanol 5.3
    dimethoxymethane 39.99
    ethylene carbonate 19.88
    cyrene 37.13
    2-ethoxyethyl acetate 16.42
    2-ethylhexyl acetate 6.76
    1,2,4-trichlorobenzene 13.79
    4-methylpyridine 16.08
    dibutyl ether 6.61
    2,6-dimethyl-4-heptanol 4.87
    DEF 32.53
    dimethyl isosorbide 47.17
    tetrachloroethylene 18.71
    eugenol 27.85
    triacetin 25.11
    span 80 25.84
    1,4-butanediol 23.83
    1,1-dichloroethane 9.43
    2-methyl-1-pentanol 9.67
    methyl formate 57.68
    2-methyl-1-butanol 10.04
    n-decane 0.83
    butyronitrile 13.55
    3,7-dimethyl-1-octanol 9.67
    1-chlorooctane 3.41
    1-chlorotetradecane 1.79
    n-nonane 0.71
    undecane 0.71
    tert-butylcyclohexane 0.49
    cyclooctane 0.4
    cyclopentanol 11.69
    tetrahydropyran 9.24
    tert-amyl methyl ether 5.2
    2,5,8-trioxanonane 73.04
    1-hexene 1.12
    2-isopropoxyethanol 27.2
    2,2,2-trifluoroethanol 72.58
    methyl butyrate 14.52

    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