Lactucin

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  • Identifiers

    CAS number
    1891-29-8

    Molecular formula
    C15H16O5

    SMILES
    CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 46.82%
    Odorless 43.23%
    Caramellic 40.87%
    Burnt 34.71%
    Nutty 28.57%
    Roasted 25.69%
    Spicy 23.62%
    Mint 18.37%
    Vanilla 17.21%
    Savory 17.17%

     

    Flavor
    Bitter 86.86%
    Sweet-like 19.69%
    Odorless 19.62%
    Cedarleaf 19.45%
    Lovage 19.43%
    Fenugreek 18.98%
    Basil 18.98%
    Leaves 18.65%
    Nitrile 18.63%
    Seedy 18.57%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    6.35 (neutral)

    Molecular weight
    276.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1580°C

    Flash point

    • 212.82 ˚C est.

  • Synonyms

    • Lactucin
    • 1891-29-8
    • Lactucine
    • CHEBI:6358
    • R6E2918904
    • DTXSID70894751
    • (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
    • (3AR,4S,9AS,9BR)-3,3A,4,5,9A,9B-HEXAHYDRO-4-HYDROXY-9-(HYDROXYMETHYL)-6-METHYL-3-METHYLENEAZULENO(4,5-B)FURAN-2,7-DIONE
    • (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno(4,5-b)furan-2,7-dione
    • (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
    • (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno(4,5-b)furan-2,7-dione
    • RefChem:798386
    • DTXCID001324308
    • 112-288-6
    • VJQAFLAZRVKAKM-VZLIPTOUSA-
    • (3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-3,3a,4,5-tetrahydroazuleno[4,5-b]furan-2,7(9aH,9bH)-dione
    • (3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
    • AC1L9CIQ
    • UNII-R6E2918904
    • LACTUCIN [MI]
    • orb1679991
    • SCHEMBL14215975
    • HY-N9438
    • AKOS040763768
    • FS-7317
    • DA-64848
    • CS-0169537
    • NS00094051
    • C09489
    • Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR-(3aalpha,4beta,9aalpha,9bbeta))-
    • InChI=1/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
    • 1891-29-8

  • Applications

    Lactucin (CAS 1891-29-8) is a natural sesquiterpene lactone found in lettuce and some members of the Asteraceae family; practical applications are primarily in natural products and pharmaceutical research, where it is considered a lead compound for bioactivity-guided studies and for the synthesis of terpene derivatives; it can also be used as an analytical reference standard to quantify sesquiterpene lactones in plant extracts; in agriculture and plant biology, it is studied for its role in plant defense and has potential as a natural lead for pest deterrence exploration; and in organic synthesis, lactucin can serve as a scaffold or precursor for the preparation of more complex terpene-lactone derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.46
    methanol 44.88
    isopropanol 9.24
    water 1.27
    ethyl acetate 14.41
    n-propanol 10.65
    acetone 33.33
    n-butanol 10.74
    acetonitrile 15.42
    DMF 140.74
    toluene 5.71
    isobutanol 7.06
    1,4-dioxane 40.89
    methyl acetate 20.64
    THF 71.6
    2-butanone 26.18
    n-pentanol 8.98
    sec-butanol 5.94
    n-hexane 0.11
    ethylene glycol 17.81
    NMP 127.31
    cyclohexane 0.3
    DMSO 197.55
    n-butyl acetate 15.66
    n-octanol 6.43
    chloroform 20.11
    n-propyl acetate 14.93
    acetic acid 45.04
    dichloromethane 26.59
    cyclohexanone 53.04
    propylene glycol 8.35
    isopropyl acetate 10.5
    DMAc 117.92
    2-ethoxyethanol 44.37
    isopentanol 11.32
    n-heptane 0.16
    ethyl formate 21.12
    1,2-dichloroethane 16.95
    n-hexanol 11.46
    2-methoxyethanol 80.99
    isobutyl acetate 8.66
    tetrachloromethane 2.85
    n-pentyl acetate 14.68
    transcutol 44.32
    n-heptanol 9.75
    ethylbenzene 3.53
    MIBK 13.92
    2-propoxyethanol 48.46
    tert-butanol 9.85
    MTBE 2.42
    2-butoxyethanol 31.52
    propionic acid 19.37
    o-xylene 4.63
    formic acid 71.14
    diethyl ether 3.95
    m-xylene 4.66
    p-xylene 5.28
    chlorobenzene 8.58
    dimethyl carbonate 24.41
    n-octane 0.13
    formamide 99.74
    cyclopentanone 75.91
    2-pentanone 19.37
    anisole 12.13
    cyclopentyl methyl ether 13.8
    gamma-butyrolactone 85.25
    1-methoxy-2-propanol 47.06
    pyridine 37.19
    3-pentanone 13.02
    furfural 81.8
    n-dodecane 0.19
    diethylene glycol 63.74
    diisopropyl ether 1.28
    tert-amyl alcohol 6.72
    acetylacetone 32.52
    n-hexadecane 0.23
    acetophenone 22.92
    methyl propionate 20.19
    isopentyl acetate 14.59
    trichloroethylene 38.6
    n-nonanol 6.89
    cyclohexanol 10.52
    benzyl alcohol 22.22
    2-ethylhexanol 6.8
    isooctanol 7.75
    dipropyl ether 3.79
    1,2-dichlorobenzene 9.83
    ethyl lactate 19.16
    propylene carbonate 41.78
    n-methylformamide 72.43
    2-pentanol 4.52
    n-pentane 0.09
    1-propoxy-2-propanol 25.37
    1-methoxy-2-propyl acetate 25.55
    2-(2-methoxypropoxy) propanol 26.64
    mesitylene 2.81
    ε-caprolactone 46.06
    p-cymene 3.66
    epichlorohydrin 72.9
    1,1,1-trichloroethane 8.12
    2-aminoethanol 18.12
    morpholine-4-carbaldehyde 108.27
    sulfolane 130.78
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 22.12
    n-hexyl acetate 15.43
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 31.19
    sec-butyl acetate 8.37
    tert-butyl acetate 11.65
    decalin 0.36
    glycerin 34.11
    diglyme 55.29
    acrylic acid 28.28
    isopropyl myristate 6.08
    n-butyric acid 24.17
    acetyl acetate 14.5
    di(2-ethylhexyl) phthalate 12.37
    ethyl propionate 12.36
    nitromethane 83.82
    1,2-diethoxyethane 11.11
    benzonitrile 21.33
    trioctyl phosphate 9.33
    1-bromopropane 4.12
    gamma-valerolactone 107.58
    n-decanol 4.93
    triethyl phosphate 10.52
    4-methyl-2-pentanol 4.44
    propionitrile 11.69
    vinylene carbonate 44.1
    1,1,2-trichlorotrifluoroethane 68.33
    DMS 18.96
    cumene 2.86
    2-octanol 4.82
    2-hexanone 15.4
    octyl acetate 9.14
    limonene 4.08
    1,2-dimethoxyethane 57.12
    ethyl orthosilicate 8.82
    tributyl phosphate 9.25
    diacetone alcohol 27.32
    N,N-dimethylaniline 9.95
    acrylonitrile 26.54
    aniline 13.67
    1,3-propanediol 29.64
    bromobenzene 6.77
    dibromomethane 11.26
    1,1,2,2-tetrachloroethane 24.53
    2-methyl-cyclohexyl acetate 14.73
    tetrabutyl urea 15.96
    diisobutyl methanol 3.67
    2-phenylethanol 23.14
    styrene 3.82
    dioctyl adipate 12.23
    dimethyl sulfate 49.96
    ethyl butyrate 11.92
    methyl lactate 30.21
    butyl lactate 18.73
    diethyl carbonate 10.17
    propanediol butyl ether 23.59
    triethyl orthoformate 10.29
    p-tert-butyltoluene 2.98
    methyl 4-tert-butylbenzoate 22.61
    morpholine 44.77
    tert-butylamine 2.35
    n-dodecanol 3.41
    dimethoxymethane 61.79
    ethylene carbonate 35.67
    cyrene 47.54
    2-ethoxyethyl acetate 22.14
    2-ethylhexyl acetate 11.14
    1,2,4-trichlorobenzene 14.37
    4-methylpyridine 29.91
    dibutyl ether 3.53
    2,6-dimethyl-4-heptanol 3.67
    DEF 30.7
    dimethyl isosorbide 44.97
    tetrachloroethylene 19.05
    eugenol 28.71
    triacetin 21.15
    span 80 21.27
    1,4-butanediol 16.32
    1,1-dichloroethane 8.26
    2-methyl-1-pentanol 9.22
    methyl formate 61.6
    2-methyl-1-butanol 8.38
    n-decane 0.3
    butyronitrile 11.42
    3,7-dimethyl-1-octanol 5.72
    1-chlorooctane 2.05
    1-chlorotetradecane 0.87
    n-nonane 0.21
    undecane 0.23
    tert-butylcyclohexane 0.25
    cyclooctane 0.15
    cyclopentanol 15.09
    tetrahydropyran 15.28
    tert-amyl methyl ether 3.23
    2,5,8-trioxanonane 40.84
    1-hexene 0.76
    2-isopropoxyethanol 26.09
    2,2,2-trifluoroethanol 32.29
    methyl butyrate 19.4

    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