Limonin

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  • Identifiers

    CAS number
    1180-71-8

    Molecular formula
    C26H30O8

    SMILES
    C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 43.44%
    Sweet 33.13%
    Spicy 32.43%
    Odorless 28.6%
    Mint 25.58%
    Tobacco 25.32%
    Coumarinic 25.32%
    Nutty 24.4%
    Lactonic 24.2%
    Herbal 23.47%

     

    Flavor
    Bitter 93.65%
    Cedarleaf 22.08%
    Ripe apricot 19.95%
    Sweet-like 19.94%
    Red fruit 19.63%
    Parsley 19.47%
    Naphthalic 19.42%
    Lovage 19.17%
    Cereal 18.88%
    Patchouli 18.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    5.58 (weak acid)

    Molecular weight
    470.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    795°C

    Flash point

    • 187.34 ˚C est.

  • Synonyms

    • Limonin
    • 1180-71-8
    • Obaculactone
    • Dictamnolactone
    • Citrolimonin
    • Evodin
    • Limonine
    • 7,16-Dioxo-7,16-dideoxylimondiol
    • Limonoic acid, di-delta-lactone
    • DTXSID8045985
    • L0F260866S
    • DTXCID6025985
    • CHEBI:16226
    • NSC-36508
    • (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione
    • 11H,13H-Oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furyl)decahydro-2,2,4a,8a-tetramethyl-
    • 11H,13H-Oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-
    • (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
    • (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo(11.9.0.02,7.02,10.014,16.014,20)docosane-5,12,17-trione
    • (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno(d)pyrano(4',3':3,3a)(2)benzofuro(5,4-f)isochromene-3,8,10(6H,9aH)-trione
    • RefChem:153470
    • 808-129-1
    • MFCD00075922
    • Limoni
    • limonoic acid 3,19:16,17-dilactone
    • Limonoate D-ring-lactone
    • (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
    • (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
    • Limonoic acid 3,19:16,17 dilactone
    • limonoic acid di-delta-lactone
    • C26H30O8
    • 1809582-56-6
    • rel-(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
    • CAS-1180-71-8
    • 3-furyl(tetramethyl)[?]trione
    • Linonin
    • NSC36508
    • CCRIS 4047
    • UNII-L0F260866S
    • NCGC00095714-01
    • Limonoic acid, di-.delta.-lactone
    • Limonin (Standard)
    • NSC 36508
    • AI3-37932
    • LIMONIN [MI]
    • Spectrum2_001728
    • Spectrum3_001012
    • Spectrum4_001140
    • Spectrum5_000935
    • Limonin, analytical standard
    • BSPBio_002763
    • KBioGR_001659
    • SCHEMBL320315
    • SPECTRUM1800018
    • Di-delta-lactone limonoic acid
    • SPBio_001776
    • CHEMBL517449
    • orb1305103
    • ACon1_001996
    • KBio3_001983
    • Limonoic acid di-.delta.-lactone
    • Tox21_111513
    • BDBM50418089
    • CCG-38796
    • EBC-17122
    • HY-17411R
    • MSK157590
    • AKOS015965307
    • Tox21_111513_1
    • AC-8045
    • CS-1237
    • FL09973
    • SDCCGMLS-0066837.P001
    • NCGC00178483-01
    • NCGC00178483-02
    • NCGC00178483-04
    • NCGC00178483-05
    • NCGC00178483-14
    • NCGC00263659-01
    • AS-15249
    • HY-17411
    • SY045111
    • L0258
    • Limonin, from citrus seeds, >90% (HPLC)
    • S2319
    • C03514
    • 180L718
    • Q2398745
    • BRD-K05906022-001-03-6
    • BRD-K05906022-001-05-1
    • Limone; Citrolimonin; Evodine; Dictamnolactone; Obaculactone
    • (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(3-furyl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione
    • (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione
    • (4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
    • (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4 inverted exclamation mark ,3 inverted exclamation mark :3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
    • (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
    • (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione
    • 11H,13H-Oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR-(2aalpha,4abeta,4bR,5aalpha,8alpha,8aalpha,10aalpha,10bR*,14aalpha))-
    • 1180-71-8

  • Applications

    Limonin (CAS 1180-71-8) is a natural limonoid isolated from citrus peels and seeds. In industry it is mainly used as a starting material or intermediate for the synthesis of limonoid derivatives used in chemical research and development. It is routinely evaluated for potential applications in flavor and fragrance development as a bitter note or odor-active constituent, and may be used as a botanical ingredient or fragrance component in cosmetics and personal care research. The compound is also studied in agricultural chemistry for possible bioactivities within the limonoid family, including antifeedant or insect-deterrent effects. In analytical and product development contexts, limonin can serve as a reference material or natural product source for developing derivatives used in coatings, inks, or cleaning formulations, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.25
    methanol 1.15
    isopropanol 0.09
    water 0.02
    ethyl acetate 3.81
    n-propanol 0.19
    acetone 15.31
    n-butanol 0.13
    acetonitrile 32.55
    DMF 25.39
    toluene 1.69
    isobutanol 0.14
    1,4-dioxane 9.3
    methyl acetate 8.53
    THF 13.79
    2-butanone 5.29
    n-pentanol 0.23
    sec-butanol 0.07
    n-hexane 0.01
    ethylene glycol 0.79
    NMP 49.14
    cyclohexane 0.03
    DMSO 27.62
    n-butyl acetate 1.75
    n-octanol 0.27
    chloroform 23.23
    n-propyl acetate 3.1
    acetic acid 14.15
    dichloromethane 22.39
    cyclohexanone 9.83
    propylene glycol 0.26
    isopropyl acetate 2.24
    DMAc 31.04
    2-ethoxyethanol 2.86
    isopentanol 0.18
    n-heptane 0.01
    ethyl formate 4.53
    1,2-dichloroethane 8.47
    n-hexanol 0.24
    2-methoxyethanol 3.56
    isobutyl acetate 2.18
    tetrachloromethane 1.3
    n-pentyl acetate 1.81
    transcutol 4.87
    n-heptanol 0.32
    ethylbenzene 0.59
    MIBK 2.04
    2-propoxyethanol 4.47
    tert-butanol 0.17
    MTBE 0.27
    2-butoxyethanol 2.95
    propionic acid 2.6
    o-xylene 0.85
    formic acid 9.43
    diethyl ether 0.45
    m-xylene 0.9
    p-xylene 1.22
    chlorobenzene 5.28
    dimethyl carbonate 10.45
    n-octane 0.01
    formamide 16.01
    cyclopentanone 23.48
    2-pentanone 2.52
    anisole 2.85
    cyclopentyl methyl ether 1.64
    gamma-butyrolactone 35.37
    1-methoxy-2-propanol 1.93
    pyridine 17.59
    3-pentanone 2.93
    furfural 36.59
    n-dodecane 0.01
    diethylene glycol 6.26
    diisopropyl ether 0.16
    tert-amyl alcohol 0.12
    acetylacetone 14.05
    n-hexadecane 0.01
    acetophenone 6.79
    methyl propionate 5.14
    isopentyl acetate 1.86
    trichloroethylene 34.86
    n-nonanol 0.36
    cyclohexanol 0.25
    benzyl alcohol 2.82
    2-ethylhexanol 0.24
    isooctanol 0.33
    dipropyl ether 0.41
    1,2-dichlorobenzene 5.71
    ethyl lactate 2.77
    propylene carbonate 12.06
    n-methylformamide 13.54
    2-pentanol 0.06
    n-pentane 0.01
    1-propoxy-2-propanol 1.88
    1-methoxy-2-propyl acetate 4.9
    2-(2-methoxypropoxy) propanol 4.09
    mesitylene 0.47
    ε-caprolactone 8.06
    p-cymene 0.45
    epichlorohydrin 27.85
    1,1,1-trichloroethane 7.27
    2-aminoethanol 0.7
    morpholine-4-carbaldehyde 31.15
    sulfolane 40.25
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.56
    n-hexyl acetate 1.81
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 3.8
    sec-butyl acetate 1.52
    tert-butyl acetate 2.33
    decalin 0.03
    glycerin 1.76
    diglyme 9.1
    acrylic acid 7.47
    isopropyl myristate 0.72
    n-butyric acid 2.05
    acetyl acetate 9.64
    di(2-ethylhexyl) phthalate 2.36
    ethyl propionate 2.79
    nitromethane 91.12
    1,2-diethoxyethane 1.4
    benzonitrile 9.61
    trioctyl phosphate 1.06
    1-bromopropane 0.74
    gamma-valerolactone 39.56
    n-decanol 0.24
    triethyl phosphate 1.86
    4-methyl-2-pentanol 0.12
    propionitrile 6.01
    vinylene carbonate 19.07
    1,1,2-trichlorotrifluoroethane 23.36
    DMS 5.02
    cumene 0.38
    2-octanol 0.14
    2-hexanone 2.79
    octyl acetate 1.12
    limonene 0.39
    1,2-dimethoxyethane 6.71
    ethyl orthosilicate 1.34
    tributyl phosphate 1.14
    diacetone alcohol 3.26
    N,N-dimethylaniline 1.71
    acrylonitrile 20.86
    aniline 2.3
    1,3-propanediol 0.74
    bromobenzene 5.71
    dibromomethane 7.09
    1,1,2,2-tetrachloroethane 14.41
    2-methyl-cyclohexyl acetate 2.65
    tetrabutyl urea 2.01
    diisobutyl methanol 0.18
    2-phenylethanol 3.37
    styrene 0.96
    dioctyl adipate 2.13
    dimethyl sulfate 20.62
    ethyl butyrate 1.82
    methyl lactate 5.06
    butyl lactate 2.06
    diethyl carbonate 2.11
    propanediol butyl ether 1.79
    triethyl orthoformate 1.54
    p-tert-butyltoluene 0.36
    methyl 4-tert-butylbenzoate 4.76
    morpholine 5.7
    tert-butylamine 0.06
    n-dodecanol 0.16
    dimethoxymethane 9.58
    ethylene carbonate 11.99
    cyrene 12.62
    2-ethoxyethyl acetate 4.59
    2-ethylhexyl acetate 1.46
    1,2,4-trichlorobenzene 9.06
    4-methylpyridine 9.29
    dibutyl ether 0.27
    2,6-dimethyl-4-heptanol 0.18
    DEF 4.17
    dimethyl isosorbide 11.11
    tetrachloroethylene 9.48
    eugenol 5.82
    triacetin 5.89
    span 80 2.85
    1,4-butanediol 0.57
    1,1-dichloroethane 4.48
    2-methyl-1-pentanol 0.27
    methyl formate 15.84
    2-methyl-1-butanol 0.13
    n-decane 0.02
    butyronitrile 2.13
    3,7-dimethyl-1-octanol 0.31
    1-chlorooctane 0.15
    1-chlorotetradecane 0.07
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.02
    cyclooctane 0.02
    cyclopentanol 0.52
    tetrahydropyran 1.58
    tert-amyl methyl ether 0.25
    2,5,8-trioxanonane 7.41
    1-hexene 0.07
    2-isopropoxyethanol 2.0
    2,2,2-trifluoroethanol 10.62
    methyl butyrate 3.27

    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