Obacunone

Overview IFRA Request a quote

  • Identifiers

    CAS number
    751-03-1

    Molecular formula
    C26H30O7

    SMILES
    C[C@@]12CC[C@@H]3[C@]4(C=CC(=O)OC([C@@H]4CC(=O)[C@]3([C@@]15[C@H](O5)C(=O)O[C@H]2C6=COC=C6)C)(C)C)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 46.47%
    Spicy 36.12%
    Sweet 30.47%
    Tobacco 29.37%
    Mint 27.64%
    Herbal 24.5%
    Odorless 24.12%
    Coumarinic 23.74%
    Cedar 22.9%
    Nutty 22.4%

     

    Flavor
    Bitter 91.79%
    Cedarleaf 21.9%
    Ripe apricot 20.84%
    Red fruit 20.45%
    Parsley 19.73%
    Lovage 19.63%
    Sweet-like 19.13%
    Naphthalic 18.57%
    Fenugreek 18.54%
    Patchouli 18.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    4.93 (weak acid)

    Molecular weight
    454.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    348°C

    Flash point

    • 182.65 ˚C est.

  • Synonyms

    • Obacunone
    • 751-03-1
    • (1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
    • (1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo(9.9.0.02,4.02,8.012,18)icos-13-ene-5,15,20-trione
    • RefChem:167333
    • OBACUNON
    • MFCD00075888
    • Obacunoic acid, eta-lactone
    • AI3-37934
    • (1S,3aS,4aR,4bR,6aR,11aR,11bR,13aS)-1-(furan-3-yl)-4b,7,7,11a,13a-pentamethyl-1,6a,7,11a,11b,12,13,13a-octahydrooxepino[4',3':3,4]benzo[1,2-f]oxireno[2,3-d]isochromene-3,5,9(3aH,4bH,6H)-trione
    • Casimirolide
    • Obakunone
    • CCRIS 8657
    • DTXSID20996592
    • Obacunone (Standard)
    • MLS002473187
    • Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)-
    • SCHEMBL564187
    • CHEBI:7713
    • CHEMBL404140
    • orb1304247
    • HY-N0428R
    • HMS2198M14
    • EX-A4868
    • HY-N0428
    • s3784
    • AKOS015897086
    • CCG-269280
    • EBC-157223
    • FO65314
    • NCGC00247493-01
    • AC-34270
    • AS-56011
    • SMR001397279
    • SY077229
    • CS-0008951
    • C08775
    • 751O031
    • Q27107562
    • Z3234884793
    • (1R,2R,4S,7S,8S,11R,12R,18R)-7-(3-furyl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
    • (5aR,5bR,7aS,8S,10aS,11aR,11bR,13aR)-8-(Furan-3-yl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4',5']pyrano[4',3':5,6]naphtho[2,1-c]oxepine-3,10,12(1H,5aH,10aH)-trione
    • 8-(Furan-3-yl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4',5']pyrano[4',3':5,6]naphtho[2,1-c]oxepine-3,10,12(1H,5aH,10aH)-trione
    • 751-03-1

  • Applications

    Obacunone (CAS 751-03-1) is a limonoid natural product derived from citrus that is primarily discussed as a bioactive compound for research and development. In agriculture, it is studied as a natural antifeedant and crop-protection agent against pests. In pharmaceutical and biomedical research, it is evaluated as a bioactive scaffold with antimicrobial and antifungal activities, as well as potential anti-inflammatory effects, guiding medicinal chemistry exploration. In chemical manufacturing and formulation development, it can serve as an intermediate or building block for the synthesis of limonoid-derived compounds and related materials. In cosmetics and personal care, it may be evaluated as a natural-origin bioactive ingredient, subject to regulatory and formulation considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.6
    methanol 3.25
    isopropanol 0.7
    water 0.02
    ethyl acetate 6.23
    n-propanol 1.59
    acetone 15.6
    n-butanol 0.97
    acetonitrile 18.27
    DMF 25.07
    toluene 3.7
    isobutanol 1.09
    1,4-dioxane 13.64
    methyl acetate 11.01
    THF 23.19
    2-butanone 11.3
    n-pentanol 1.37
    sec-butanol 0.65
    n-hexane 0.05
    ethylene glycol 1.61
    NMP 53.19
    cyclohexane 0.15
    DMSO 34.13
    n-butyl acetate 3.96
    n-octanol 0.74
    chloroform 25.16
    n-propyl acetate 5.29
    acetic acid 16.77
    dichloromethane 22.8
    cyclohexanone 18.69
    propylene glycol 0.98
    isopropyl acetate 3.98
    DMAc 36.8
    2-ethoxyethanol 6.69
    isopentanol 1.03
    n-heptane 0.05
    ethyl formate 6.04
    1,2-dichloroethane 11.01
    n-hexanol 1.45
    2-methoxyethanol 7.88
    isobutyl acetate 3.66
    tetrachloromethane 2.27
    n-pentyl acetate 3.62
    transcutol 6.14
    n-heptanol 1.26
    ethylbenzene 1.45
    MIBK 4.43
    2-propoxyethanol 10.11
    tert-butanol 0.91
    MTBE 1.11
    2-butoxyethanol 6.11
    propionic acid 6.23
    o-xylene 1.91
    formic acid 9.55
    diethyl ether 1.73
    m-xylene 1.82
    p-xylene 2.28
    chlorobenzene 7.13
    dimethyl carbonate 10.25
    n-octane 0.02
    formamide 14.2
    cyclopentanone 31.63
    2-pentanone 6.18
    anisole 4.78
    cyclopentyl methyl ether 4.39
    gamma-butyrolactone 36.08
    1-methoxy-2-propanol 4.99
    pyridine 21.71
    3-pentanone 6.76
    furfural 31.63
    n-dodecane 0.03
    diethylene glycol 9.17
    diisopropyl ether 0.48
    tert-amyl alcohol 0.83
    acetylacetone 14.05
    n-hexadecane 0.04
    acetophenone 8.96
    methyl propionate 8.55
    isopentyl acetate 3.99
    trichloroethylene 30.97
    n-nonanol 0.97
    cyclohexanol 1.28
    benzyl alcohol 5.52
    2-ethylhexanol 1.02
    isooctanol 1.15
    dipropyl ether 1.17
    1,2-dichlorobenzene 6.82
    ethyl lactate 4.46
    propylene carbonate 13.54
    n-methylformamide 13.26
    2-pentanol 0.43
    n-pentane 0.04
    1-propoxy-2-propanol 4.65
    1-methoxy-2-propyl acetate 8.03
    2-(2-methoxypropoxy) propanol 6.56
    mesitylene 0.92
    ε-caprolactone 14.21
    p-cymene 1.05
    epichlorohydrin 30.55
    1,1,1-trichloroethane 8.53
    2-aminoethanol 2.35
    morpholine-4-carbaldehyde 32.02
    sulfolane 43.35
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 7.62
    n-hexyl acetate 3.52
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 6.15
    sec-butyl acetate 3.11
    tert-butyl acetate 4.11
    decalin 0.12
    glycerin 3.43
    diglyme 11.75
    acrylic acid 10.88
    isopropyl myristate 1.42
    n-butyric acid 5.45
    acetyl acetate 9.05
    di(2-ethylhexyl) phthalate 4.16
    ethyl propionate 4.99
    nitromethane 45.16
    1,2-diethoxyethane 2.43
    benzonitrile 9.76
    trioctyl phosphate 2.08
    1-bromopropane 2.49
    gamma-valerolactone 42.67
    n-decanol 0.63
    triethyl phosphate 3.07
    4-methyl-2-pentanol 0.56
    propionitrile 8.53
    vinylene carbonate 18.23
    1,1,2-trichlorotrifluoroethane 24.27
    DMS 6.6
    cumene 0.94
    2-octanol 0.51
    2-hexanone 6.0
    octyl acetate 2.25
    limonene 1.14
    1,2-dimethoxyethane 9.97
    ethyl orthosilicate 2.49
    tributyl phosphate 2.01
    diacetone alcohol 5.86
    N,N-dimethylaniline 3.09
    acrylonitrile 16.7
    aniline 5.07
    1,3-propanediol 2.7
    bromobenzene 7.01
    dibromomethane 11.05
    1,1,2,2-tetrachloroethane 16.54
    2-methyl-cyclohexyl acetate 5.08
    tetrabutyl urea 3.51
    diisobutyl methanol 0.56
    2-phenylethanol 7.07
    styrene 2.02
    dioctyl adipate 3.62
    dimethyl sulfate 18.2
    ethyl butyrate 3.6
    methyl lactate 7.19
    butyl lactate 3.57
    diethyl carbonate 3.47
    propanediol butyl ether 3.3
    triethyl orthoformate 2.93
    p-tert-butyltoluene 0.86
    methyl 4-tert-butylbenzoate 7.12
    morpholine 11.56
    tert-butylamine 0.36
    n-dodecanol 0.41
    dimethoxymethane 12.71
    ethylene carbonate 12.73
    cyrene 15.37
    2-ethoxyethyl acetate 7.11
    2-ethylhexyl acetate 3.35
    1,2,4-trichlorobenzene 10.72
    4-methylpyridine 13.38
    dibutyl ether 0.56
    2,6-dimethyl-4-heptanol 0.56
    DEF 7.98
    dimethyl isosorbide 13.68
    tetrachloroethylene 11.68
    eugenol 8.34
    triacetin 7.01
    span 80 4.87
    1,4-butanediol 1.92
    1,1-dichloroethane 7.02
    2-methyl-1-pentanol 1.41
    methyl formate 12.1
    2-methyl-1-butanol 0.97
    n-decane 0.05
    butyronitrile 4.73
    3,7-dimethyl-1-octanol 0.8
    1-chlorooctane 0.4
    1-chlorotetradecane 0.17
    n-nonane 0.03
    undecane 0.04
    tert-butylcyclohexane 0.08
    cyclooctane 0.05
    cyclopentanol 2.56
    tetrahydropyran 5.16
    tert-amyl methyl ether 1.07
    2,5,8-trioxanonane 9.95
    1-hexene 0.32
    2-isopropoxyethanol 4.67
    2,2,2-trifluoroethanol 9.43
    methyl butyrate 5.9

    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