Annonacin A

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  • Identifiers

    CAS number
    130853-76-8

    Molecular formula
    C35H64O7

    SMILES
    CCCCCCCCCCCCC(C1CCC(O1)C(CCCCC(CCCCCC(CC2=CC(OC2=O)C)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Oily 39.91%
    Odorless 33.48%
    Lactonic 32.88%
    Fruity 32.52%
    Sweet 31.45%
    Fresh 31.04%
    Peach 29.96%
    Fatty 27.71%
    Milky 26.82%
    Waxy 26.59%

     

    Flavor
    Mild 29.95%
    Fatty 29.62%
    Odorless 29.52%
    Bland 27.75%
    Herbal 24.89%
    Waxy 24.76%
    Oily 24.04%
    Floral 21.84%
    Sweet-like 21.28%
    Bitter 21.27%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    8.4

    pKa est.
    8.72 (weak base)

    Molecular weight
    596.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1809°C

    Melting point expt.

    • 65.3 - 68.4 °C

    Flash point

    • 250.71 ˚C est.

  • Synonyms

    • Annonacin A
    • 130853-76-8
    • 2-methyl-4-[2,8,13-trihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl]-2H-furan-5-one
    • 2-methyl-4-(2,8,13-trihydroxy-13-(5-(1-hydroxytridecyl)oxolan-2-yl)tridecyl)-2H-furan-5-one
    • RefChem:112868
    • Asitrilobin B
    • 5-Methyl-3-(2,8,13-trihydroxy-13-(5-(1-hydroxytridecyl)tetrahydrofuran-2-yl)tridecyl)furan-2(5H)-one
    • Neuro_000230
    • SCHEMBL2037224
    • DTXSID50926943
    • B0005-305397
    • 5-Methyl-3-{2,8,13-trihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}furan-2(5H)-one
    • 130853-76-8

  • Applications

    Annonacin A (CAS 130853-76-8) is primarily used in academic and industrial research on acetogenins, serving as a reference compound for natural products chemistry and pharmacology and is evaluated for bioactivity, including inhibition of mitochondrial complex I, to inform mechanism studies and lead-structure exploration. In analytical workflows, it supports method development and plant metabolite profiling of Annona species. The compound is also investigated as a scaffold for structure–activity relationship (SAR) studies within the acetogenin class and is of interest for agricultural research into eco-friendly bioactive metabolites. Applications in consumer products are limited and subject to local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.28
    methanol 9.41
    isopropanol 2.17
    water 0.09
    ethyl acetate 8.11
    n-propanol 5.2
    acetone 12.22
    n-butanol 4.55
    acetonitrile 2.76
    DMF 23.58
    toluene 4.19
    isobutanol 3.15
    1,4-dioxane 20.67
    methyl acetate 6.71
    THF 77.17
    2-butanone 13.48
    n-pentanol 5.22
    sec-butanol 3.47
    n-hexane 0.39
    ethylene glycol 0.88
    NMP 87.62
    cyclohexane 0.74
    DMSO 45.29
    n-butyl acetate 7.88
    n-octanol 8.88
    chloroform 33.93
    n-propyl acetate 8.41
    acetic acid 18.15
    dichloromethane 30.85
    cyclohexanone 42.12
    propylene glycol 2.14
    isopropyl acetate 8.14
    DMAc 73.94
    2-ethoxyethanol 19.1
    isopentanol 4.12
    n-heptane 0.48
    ethyl formate 7.22
    1,2-dichloroethane 14.39
    n-hexanol 3.99
    2-methoxyethanol 19.54
    isobutyl acetate 6.39
    tetrachloromethane 4.64
    n-pentyl acetate 23.22
    transcutol 90.26
    n-heptanol 7.88
    ethylbenzene 3.7
    MIBK 9.31
    2-propoxyethanol 19.22
    tert-butanol 2.87
    MTBE 5.22
    2-butoxyethanol 29.53
    propionic acid 8.13
    o-xylene 4.2
    formic acid 8.36
    diethyl ether 4.27
    m-xylene 3.51
    p-xylene 4.23
    chlorobenzene 7.1
    dimethyl carbonate 7.03
    n-octane 0.41
    formamide 10.71
    cyclopentanone 51.07
    2-pentanone 12.33
    anisole 9.09
    cyclopentyl methyl ether 20.57
    gamma-butyrolactone 53.15
    1-methoxy-2-propanol 16.14
    pyridine 18.44
    3-pentanone 10.84
    furfural 40.12
    n-dodecane 0.32
    diethylene glycol 8.51
    diisopropyl ether 1.69
    tert-amyl alcohol 4.86
    acetylacetone 19.8
    n-hexadecane 0.37
    acetophenone 15.14
    methyl propionate 9.55
    isopentyl acetate 9.45
    trichloroethylene 35.33
    n-nonanol 9.71
    cyclohexanol 7.12
    benzyl alcohol 8.66
    2-ethylhexanol 3.68
    isooctanol 6.78
    dipropyl ether 5.48
    1,2-dichlorobenzene 9.61
    ethyl lactate 8.55
    propylene carbonate 23.5
    n-methylformamide 10.98
    2-pentanol 2.69
    n-pentane 0.28
    1-propoxy-2-propanol 15.31
    1-methoxy-2-propyl acetate 15.85
    2-(2-methoxypropoxy) propanol 25.45
    mesitylene 2.08
    ε-caprolactone 47.25
    p-cymene 2.69
    epichlorohydrin 51.86
    1,1,1-trichloroethane 11.97
    2-aminoethanol 3.33
    morpholine-4-carbaldehyde 58.48
    sulfolane 103.17
    2,2,4-trimethylpentane 0.41
    2-methyltetrahydrofuran 28.37
    n-hexyl acetate 25.29
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 36.87
    sec-butyl acetate 7.33
    tert-butyl acetate 12.22
    decalin 0.84
    glycerin 5.39
    diglyme 68.01
    acrylic acid 8.3
    isopropyl myristate 6.77
    n-butyric acid 15.66
    acetyl acetate 8.3
    di(2-ethylhexyl) phthalate 9.56
    ethyl propionate 8.19
    nitromethane 26.16
    1,2-diethoxyethane 18.81
    benzonitrile 7.21
    trioctyl phosphate 6.89
    1-bromopropane 5.8
    gamma-valerolactone 94.12
    n-decanol 5.42
    triethyl phosphate 7.44
    4-methyl-2-pentanol 2.28
    propionitrile 2.98
    vinylene carbonate 21.48
    1,1,2-trichlorotrifluoroethane 49.67
    DMS 10.88
    cumene 2.86
    2-octanol 5.43
    2-hexanone 11.82
    octyl acetate 10.69
    limonene 4.04
    1,2-dimethoxyethane 27.59
    ethyl orthosilicate 8.09
    tributyl phosphate 7.79
    diacetone alcohol 17.63
    N,N-dimethylaniline 8.74
    acrylonitrile 4.45
    aniline 5.87
    1,3-propanediol 5.7
    bromobenzene 7.24
    dibromomethane 14.8
    1,1,2,2-tetrachloroethane 34.83
    2-methyl-cyclohexyl acetate 12.36
    tetrabutyl urea 12.56
    diisobutyl methanol 2.31
    2-phenylethanol 8.01
    styrene 3.45
    dioctyl adipate 13.62
    dimethyl sulfate 20.85
    ethyl butyrate 8.42
    methyl lactate 10.55
    butyl lactate 21.89
    diethyl carbonate 5.02
    propanediol butyl ether 23.7
    triethyl orthoformate 10.8
    p-tert-butyltoluene 2.56
    methyl 4-tert-butylbenzoate 27.49
    morpholine 30.8
    tert-butylamine 1.51
    n-dodecanol 3.09
    dimethoxymethane 19.39
    ethylene carbonate 17.6
    cyrene 32.21
    2-ethoxyethyl acetate 33.98
    2-ethylhexyl acetate 8.08
    1,2,4-trichlorobenzene 13.52
    4-methylpyridine 14.03
    dibutyl ether 8.58
    2,6-dimethyl-4-heptanol 2.31
    DEF 19.11
    dimethyl isosorbide 46.05
    tetrachloroethylene 22.7
    eugenol 24.56
    triacetin 30.64
    span 80 23.93
    1,4-butanediol 3.06
    1,1-dichloroethane 8.69
    2-methyl-1-pentanol 5.73
    methyl formate 8.6
    2-methyl-1-butanol 4.91
    n-decane 0.81
    butyronitrile 3.48
    3,7-dimethyl-1-octanol 6.34
    1-chlorooctane 4.96
    1-chlorotetradecane 1.29
    n-nonane 0.65
    undecane 0.47
    tert-butylcyclohexane 0.58
    cyclooctane 0.41
    cyclopentanol 9.52
    tetrahydropyran 19.56
    tert-amyl methyl ether 6.86
    2,5,8-trioxanonane 40.21
    1-hexene 1.67
    2-isopropoxyethanol 13.46
    2,2,2-trifluoroethanol 10.37
    methyl butyrate 12.2

    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