11beta,13-Dihydrolactucin

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  • Identifiers

    CAS number
    83117-63-9

    Molecular formula
    C15H18O5

    SMILES
    C[C@H]1[C@@H]2[C@H](CC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=O)CO)C)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 45.94%
    Odorless 44.49%
    Caramellic 41.08%
    Burnt 32.17%
    Nutty 26.96%
    Roasted 26.87%
    Vanilla 23.55%
    Spicy 23.3%
    Milky 19.9%
    Creamy 19.35%

     

    Flavor
    Bitter 83.69%
    Sweet-like 20.71%
    Cedarleaf 20.18%
    Lovage 19.73%
    Odorless 19.61%
    Fenugreek 19.59%
    Leaves 19.39%
    Seedy 19.35%
    Basil 19.25%
    Extremely sweet 19.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    5.88 (weak acid)

    Molecular weight
    278.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1319°C

    Flash point

    • 209.46 ˚C est.

  • Synonyms

    • 11beta,13-Dihydrolactucin
    • 83117-63-9
    • (3S,3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
    • CHEBI:90267
    • DTXSID701019932
    • (3S,3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-3,3a,4,5,9a,9b-hexahydroazuleno(4,5-b)furan-2,7-dione
    • RefChem:78039
    • DTXCID401477791
    • 11,13-dihydrolactucin
    • 11|A,13-Dihydrolactucin
    • 11I(2),13-dihydrolactucin
    • SCHEMBL14215974
    • FS-8500
    • CS-0227128
    • NS00094052
    • Q27105128
    • 83117-63-9

  • Applications

    11beta,13-Dihydrolactucin (CAS 83117-63-9) is used primarily as an intermediate in the synthesis of sesquiterpene lactones and related scaffolds, enabling access to natural-product chemistries in organic synthesis. It is also the subject of research for potential antifeedant and pest-management properties, informing agrochemical lead development. In analytical workflows, it serves as a reference compound for quality control and quantification in chicory/endive extracts and other plant matrices. In flavor contexts, related lactones contribute to bitterness, and dihydrolactucin may be involved in bitterness profiles of chicory-derived ingredients used in flavor formulations. Additionally, it is evaluated in academic studies on biological activity and as a potential precursor for semi-synthetic routes to related compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.05
    methanol 83.28
    isopropanol 13.97
    water 5.6
    ethyl acetate 18.2
    n-propanol 14.96
    acetone 40.96
    n-butanol 14.09
    acetonitrile 23.11
    DMF 178.91
    toluene 7.33
    isobutanol 10.38
    1,4-dioxane 57.77
    methyl acetate 25.71
    THF 76.83
    2-butanone 29.57
    n-pentanol 12.25
    sec-butanol 7.89
    n-hexane 0.15
    ethylene glycol 32.66
    NMP 150.71
    cyclohexane 0.47
    DMSO 253.32
    n-butyl acetate 18.33
    n-octanol 7.6
    chloroform 41.85
    n-propyl acetate 19.34
    acetic acid 82.33
    dichloromethane 51.83
    cyclohexanone 61.63
    propylene glycol 14.1
    isopropyl acetate 12.92
    DMAc 138.47
    2-ethoxyethanol 58.92
    isopentanol 14.0
    n-heptane 0.18
    ethyl formate 30.76
    1,2-dichloroethane 27.25
    n-hexanol 13.65
    2-methoxyethanol 104.32
    isobutyl acetate 12.15
    tetrachloromethane 5.39
    n-pentyl acetate 17.54
    transcutol 52.5
    n-heptanol 11.6
    ethylbenzene 4.78
    MIBK 15.52
    2-propoxyethanol 58.34
    tert-butanol 13.47
    MTBE 2.98
    2-butoxyethanol 38.19
    propionic acid 30.41
    o-xylene 5.98
    formic acid 141.76
    diethyl ether 4.75
    m-xylene 6.03
    p-xylene 7.56
    chlorobenzene 12.96
    dimethyl carbonate 30.26
    n-octane 0.17
    formamide 166.86
    cyclopentanone 90.45
    2-pentanone 21.2
    anisole 15.38
    cyclopentyl methyl ether 15.86
    gamma-butyrolactone 112.7
    1-methoxy-2-propanol 56.44
    pyridine 51.62
    3-pentanone 14.63
    furfural 116.3
    n-dodecane 0.22
    diethylene glycol 87.19
    diisopropyl ether 1.59
    tert-amyl alcohol 8.64
    acetylacetone 37.95
    n-hexadecane 0.27
    acetophenone 28.95
    methyl propionate 23.42
    isopentyl acetate 17.24
    trichloroethylene 64.83
    n-nonanol 8.09
    cyclohexanol 14.15
    benzyl alcohol 29.95
    2-ethylhexanol 7.63
    isooctanol 9.24
    dipropyl ether 3.98
    1,2-dichlorobenzene 15.35
    ethyl lactate 25.49
    propylene carbonate 56.62
    n-methylformamide 103.08
    2-pentanol 5.87
    n-pentane 0.13
    1-propoxy-2-propanol 29.44
    1-methoxy-2-propyl acetate 29.83
    2-(2-methoxypropoxy) propanol 31.2
    mesitylene 3.66
    ε-caprolactone 55.87
    p-cymene 4.51
    epichlorohydrin 94.02
    1,1,1-trichloroethane 13.39
    2-aminoethanol 29.75
    morpholine-4-carbaldehyde 139.89
    sulfolane 160.17
    2,2,4-trimethylpentane 0.16
    2-methyltetrahydrofuran 25.07
    n-hexyl acetate 18.47
    isooctane 0.14
    2-(2-butoxyethoxy)ethanol 35.63
    sec-butyl acetate 10.73
    tert-butyl acetate 13.37
    decalin 0.53
    glycerin 54.6
    diglyme 64.88
    acrylic acid 44.87
    isopropyl myristate 7.11
    n-butyric acid 34.9
    acetyl acetate 20.98
    di(2-ethylhexyl) phthalate 15.53
    ethyl propionate 15.36
    nitromethane 128.71
    1,2-diethoxyethane 12.83
    benzonitrile 31.32
    trioctyl phosphate 11.56
    1-bromopropane 5.8
    gamma-valerolactone 132.88
    n-decanol 5.63
    triethyl phosphate 12.66
    4-methyl-2-pentanol 5.58
    propionitrile 15.72
    vinylene carbonate 63.71
    1,1,2-trichlorotrifluoroethane 95.06
    DMS 24.48
    cumene 3.81
    2-octanol 5.84
    2-hexanone 17.79
    octyl acetate 10.96
    limonene 4.81
    1,2-dimethoxyethane 69.6
    ethyl orthosilicate 10.46
    tributyl phosphate 11.85
    diacetone alcohol 30.58
    N,N-dimethylaniline 12.64
    acrylonitrile 37.7
    aniline 17.93
    1,3-propanediol 43.51
    bromobenzene 10.37
    dibromomethane 20.8
    1,1,2,2-tetrachloroethane 39.07
    2-methyl-cyclohexyl acetate 17.83
    tetrabutyl urea 18.46
    diisobutyl methanol 4.22
    2-phenylethanol 28.27
    styrene 5.25
    dioctyl adipate 14.73
    dimethyl sulfate 63.74
    ethyl butyrate 14.14
    methyl lactate 40.51
    butyl lactate 23.76
    diethyl carbonate 12.86
    propanediol butyl ether 29.22
    triethyl orthoformate 12.15
    p-tert-butyltoluene 3.61
    methyl 4-tert-butylbenzoate 26.37
    morpholine 56.34
    tert-butylamine 3.25
    n-dodecanol 3.88
    dimethoxymethane 70.78
    ethylene carbonate 50.97
    cyrene 58.87
    2-ethoxyethyl acetate 27.14
    2-ethylhexyl acetate 13.15
    1,2,4-trichlorobenzene 21.08
    4-methylpyridine 38.85
    dibutyl ether 3.9
    2,6-dimethyl-4-heptanol 4.22
    DEF 35.47
    dimethyl isosorbide 51.54
    tetrachloroethylene 30.27
    eugenol 34.5
    triacetin 26.55
    span 80 25.39
    1,4-butanediol 25.64
    1,1-dichloroethane 14.07
    2-methyl-1-pentanol 11.76
    methyl formate 90.19
    2-methyl-1-butanol 10.78
    n-decane 0.37
    butyronitrile 14.85
    3,7-dimethyl-1-octanol 6.57
    1-chlorooctane 2.36
    1-chlorotetradecane 1.03
    n-nonane 0.27
    undecane 0.27
    tert-butylcyclohexane 0.35
    cyclooctane 0.21
    cyclopentanol 20.62
    tetrahydropyran 18.8
    tert-amyl methyl ether 3.7
    2,5,8-trioxanonane 47.1
    1-hexene 0.97
    2-isopropoxyethanol 34.62
    2,2,2-trifluoroethanol 59.13
    methyl butyrate 24.06

    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