Shihulimonin A

Overview IFRA Request a quote

  • Identifiers

    CAS number
    99026-99-0

    Molecular formula
    C26H30O10

    SMILES
    C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=CC(=O)OC5O)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 38.4%
    Odorless 36.14%
    Spicy 35.49%
    Woody 35.0%
    Nutty 28.15%
    Mint 26.17%
    Coumarinic 25.96%
    Lactonic 25.92%
    Coconut 25.3%
    Tobacco 23.85%

     

    Flavor
    Bitter 93.84%
    Cedarleaf 21.47%
    Sweet-like 20.46%
    Ripe apricot 19.82%
    Red fruit 19.51%
    Bland 19.47%
    Parsley 19.21%
    Lovage 19.11%
    Fenugreek 18.66%
    Cotton candy 18.49%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    4.53 (weak acid)

    Molecular weight
    502.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    955°C

    Flash point

    • 192.85 ˚C est.

  • Synonyms

    • Shihulimonin A
    • 99026-99-0
    • DTXSID901317453
    • RefChem:931683
    • DTXCID601747265
    • limonexic acid
    • (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(2-Hydroxy-5-oxo-2H-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
    • Limonexin; Shihulimonin A
    • CHEMBL4763648
    • SCHEMBL31570937
    • CHEBI:186090
    • HY-N3382
    • AKOS040761986
    • FS-9222
    • CS-0024056
    • (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(2-hydroxy-5-oxo-2H-uran-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
    • (2aR,4aR,4bR,5aS,8R,8aS,10aR,10bR,14aS)-8-(2,5-Dihydro-2-hydroxy-5-oxo-3-furanyl)decahydro-2,2,4a,8a-tetramethyl-11H,13H-oxireno[d]pyrano[4 inverted exclamation marka,3 inverted exclamation marka:3,3a]isobenzofuro[5,4-f][2]benzopyran-4,6,13(2H,5aH)-trione
    • (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(2-Hydroxy-5-oxo-2,5-dihydrofuran-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
    • 99026-99-0

  • Applications

    Shihulimonin A (CAS 99026-99-0) is a natural product that is mainly studied as a chemical scaffold for pharmaceutical synthesis and biologically active derivatives, and is often used as an intermediate in organic synthesis and in medicinal chemistry research. It is also investigated for potential applications in fragrance/odorant fields and may serve as an ingredient or additive in cosmetics and personal care products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.3
    methanol 1.6
    isopropanol 0.09
    water 0.03
    ethyl acetate 3.45
    n-propanol 0.2
    acetone 12.94
    n-butanol 0.11
    acetonitrile 23.9
    DMF 25.09
    toluene 0.49
    isobutanol 0.1
    1,4-dioxane 8.41
    methyl acetate 7.68
    THF 11.77
    2-butanone 3.7
    n-pentanol 0.13
    sec-butanol 0.06
    n-hexane 0.01
    ethylene glycol 0.8
    NMP 45.89
    cyclohexane 0.01
    DMSO 38.61
    n-butyl acetate 1.18
    n-octanol 0.12
    chloroform 16.09
    n-propyl acetate 2.42
    acetic acid 22.16
    dichloromethane 16.9
    cyclohexanone 5.63
    propylene glycol 0.3
    isopropyl acetate 1.4
    DMAc 25.81
    2-ethoxyethanol 2.84
    isopentanol 0.1
    n-heptane 0.01
    ethyl formate 4.93
    1,2-dichloroethane 5.54
    n-hexanol 0.12
    2-methoxyethanol 4.45
    isobutyl acetate 1.09
    tetrachloromethane 0.66
    n-pentyl acetate 0.91
    transcutol 2.96
    n-heptanol 0.14
    ethylbenzene 0.2
    MIBK 0.96
    2-propoxyethanol 3.51
    tert-butanol 0.11
    MTBE 0.14
    2-butoxyethanol 1.88
    propionic acid 2.75
    o-xylene 0.25
    formic acid 17.69
    diethyl ether 0.33
    m-xylene 0.26
    p-xylene 0.38
    chlorobenzene 2.1
    dimethyl carbonate 9.23
    n-octane 0.0
    formamide 28.6
    cyclopentanone 17.49
    2-pentanone 1.61
    anisole 1.52
    cyclopentyl methyl ether 0.98
    gamma-butyrolactone 35.66
    1-methoxy-2-propanol 1.89
    pyridine 12.91
    3-pentanone 1.74
    furfural 39.67
    n-dodecane 0.0
    diethylene glycol 5.6
    diisopropyl ether 0.07
    tert-amyl alcohol 0.08
    acetylacetone 10.79
    n-hexadecane 0.01
    acetophenone 3.82
    methyl propionate 4.2
    isopentyl acetate 0.93
    trichloroethylene 28.03
    n-nonanol 0.15
    cyclohexanol 0.14
    benzyl alcohol 1.39
    2-ethylhexanol 0.09
    isooctanol 0.12
    dipropyl ether 0.25
    1,2-dichlorobenzene 2.4
    ethyl lactate 2.1
    propylene carbonate 10.75
    n-methylformamide 17.74
    2-pentanol 0.04
    n-pentane 0.0
    1-propoxy-2-propanol 1.3
    1-methoxy-2-propyl acetate 3.17
    2-(2-methoxypropoxy) propanol 2.24
    mesitylene 0.13
    ε-caprolactone 5.68
    p-cymene 0.12
    epichlorohydrin 28.87
    1,1,1-trichloroethane 3.9
    2-aminoethanol 0.76
    morpholine-4-carbaldehyde 30.46
    sulfolane 40.1
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.8
    n-hexyl acetate 0.9
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 2.3
    sec-butyl acetate 0.84
    tert-butyl acetate 1.17
    decalin 0.01
    glycerin 2.03
    diglyme 6.28
    acrylic acid 8.32
    isopropyl myristate 0.28
    n-butyric acid 1.84
    acetyl acetate 8.55
    di(2-ethylhexyl) phthalate 1.02
    ethyl propionate 2.11
    nitromethane 156.47
    1,2-diethoxyethane 0.84
    benzonitrile 4.75
    trioctyl phosphate 0.45
    1-bromopropane 0.41
    gamma-valerolactone 39.72
    n-decanol 0.1
    triethyl phosphate 1.1
    4-methyl-2-pentanol 0.05
    propionitrile 3.69
    vinylene carbonate 17.55
    1,1,2-trichlorotrifluoroethane 26.42
    DMS 3.54
    cumene 0.12
    2-octanol 0.06
    2-hexanone 1.56
    octyl acetate 0.49
    limonene 0.11
    1,2-dimethoxyethane 6.26
    ethyl orthosilicate 0.7
    tributyl phosphate 0.52
    diacetone alcohol 1.98
    N,N-dimethylaniline 0.72
    acrylonitrile 15.29
    aniline 1.07
    1,3-propanediol 0.76
    bromobenzene 2.1
    dibromomethane 4.17
    1,1,2,2-tetrachloroethane 10.64
    2-methyl-cyclohexyl acetate 1.25
    tetrabutyl urea 0.92
    diisobutyl methanol 0.06
    2-phenylethanol 1.45
    styrene 0.33
    dioctyl adipate 0.99
    dimethyl sulfate 19.72
    ethyl butyrate 1.18
    methyl lactate 4.58
    butyl lactate 1.14
    diethyl carbonate 1.45
    propanediol butyl ether 1.08
    triethyl orthoformate 0.91
    p-tert-butyltoluene 0.09
    methyl 4-tert-butylbenzoate 2.31
    morpholine 5.65
    tert-butylamine 0.03
    n-dodecanol 0.07
    dimethoxymethane 8.66
    ethylene carbonate 9.64
    cyrene 8.39
    2-ethoxyethyl acetate 3.02
    2-ethylhexyl acetate 0.72
    1,2,4-trichlorobenzene 4.21
    4-methylpyridine 5.39
    dibutyl ether 0.13
    2,6-dimethyl-4-heptanol 0.06
    DEF 3.05
    dimethyl isosorbide 6.89
    tetrachloroethylene 6.33
    eugenol 2.96
    triacetin 3.56
    span 80 1.5
    1,4-butanediol 0.44
    1,1-dichloroethane 2.72
    2-methyl-1-pentanol 0.11
    methyl formate 22.18
    2-methyl-1-butanol 0.08
    n-decane 0.01
    butyronitrile 1.41
    3,7-dimethyl-1-octanol 0.11
    1-chlorooctane 0.06
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.36
    tetrahydropyran 1.13
    tert-amyl methyl ether 0.12
    2,5,8-trioxanonane 4.89
    1-hexene 0.04
    2-isopropoxyethanol 1.4
    2,2,2-trifluoroethanol 13.51
    methyl butyrate 2.51

    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