(3aR,4R,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-one

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  • Identifiers

    CAS number
    24164-13-4

    Molecular formula
    C17H22O4

    SMILES
    C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/CC1)/C)OC(=O)C)C(=C)C(=O)O2

    Safety labels

  • Odor profile

    Fragrance
    Sweet 53.0%
    Mint 45.81%
    Herbal 42.25%
    Spicy 41.21%
    Green 33.71%
    Woody 33.15%
    Coumarinic 31.66%
    Tobacco 31.54%
    Hay 29.9%
    Floral 29.08%

     

    Flavor
    Bitter 49.75%
    Minty 32.12%
    Spice 24.39%
    Mint 20.41%
    Extremely sweet 20.14%
    Cotton candy 20.12%
    Seedy 20.1%
    Fenugreek 20.09%
    Leaves 20.0%
    Lovage 19.83%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    7.28 (neutral)

    Molecular weight
    290.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    420°C

    Flash point

    • 176.95 ˚C est.

  • Synonyms

    • epi-Tulipinolide
    • 24164-13-4
    • CHEBI:10552
    • DTXSID801107594
    • (3aR,4R,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-one
    • (3aR,4R,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one
    • RefChem:1050143
    • DTXCID401539242
    • ((3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-4-yl) acetate
    • EPITULIPINOLIDE
    • Eupatolide acetate
    • C09566
    • CHEMBL4865017
    • SCHEMBL16318602
    • FS-9641
    • [(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
    • HY-120320
    • CS-0077569
    • (3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl acetate
    • 24164-13-4

  • Applications

    CAS 24164-13-4 corresponds to the bicyclic lactone (3aR,4R,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-one. In practice, the compound is typically encountered as a fragrance-related ingredient and fragrance intermediate, employed to impart or modify fruity and floral notes and sometimes as a lightweight fixative in perfumery. It may also find application as a specialty aroma component in cosmetics and personal care formulations and in household products such as air fresheners and cleaners where controlled odor release is desired. Additionally, it is often evaluated as an organic-synthesis intermediate for pharmaceutical or agrochemical research, or as a building block in specialty polymer or coating formulations, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 110.84
    methanol 198.16
    isopropanol 99.88
    water 0.46
    ethyl acetate 142.37
    n-propanol 115.54
    acetone 226.94
    n-butanol 110.67
    acetonitrile 110.28
    DMF 560.34
    toluene 140.05
    isobutanol 100.97
    1,4-dioxane 388.34
    methyl acetate 163.21
    THF 631.18
    2-butanone 209.26
    n-pentanol 106.78
    sec-butanol 103.35
    n-hexane 2.79
    ethylene glycol 28.25
    NMP 682.15
    cyclohexane 9.27
    DMSO 353.04
    n-butyl acetate 117.24
    n-octanol 46.08
    chloroform 856.48
    n-propyl acetate 122.41
    acetic acid 262.32
    dichloromethane 650.28
    cyclohexanone 366.13
    propylene glycol 63.03
    isopropyl acetate 97.75
    DMAc 595.79
    2-ethoxyethanol 170.31
    isopentanol 117.19
    n-heptane 1.96
    ethyl formate 118.23
    1,2-dichloroethane 284.01
    n-hexanol 92.2
    2-methoxyethanol 242.2
    isobutyl acetate 105.59
    tetrachloromethane 45.95
    n-pentyl acetate 94.45
    transcutol 550.04
    n-heptanol 50.66
    ethylbenzene 71.81
    MIBK 105.14
    2-propoxyethanol 203.04
    tert-butanol 109.65
    MTBE 65.66
    2-butoxyethanol 128.84
    propionic acid 146.87
    o-xylene 82.05
    formic acid 116.8
    diethyl ether 66.81
    m-xylene 96.46
    p-xylene 105.97
    chlorobenzene 196.86
    dimethyl carbonate 122.92
    n-octane 1.31
    formamide 163.95
    cyclopentanone 454.61
    2-pentanone 142.27
    anisole 157.7
    cyclopentyl methyl ether 193.86
    gamma-butyrolactone 530.08
    1-methoxy-2-propanol 205.02
    pyridine 349.05
    3-pentanone 126.66
    furfural 431.18
    n-dodecane 1.9
    diethylene glycol 173.24
    diisopropyl ether 22.71
    tert-amyl alcohol 101.16
    acetylacetone 198.23
    n-hexadecane 2.3
    acetophenone 192.84
    methyl propionate 153.9
    isopentyl acetate 122.34
    trichloroethylene 739.78
    n-nonanol 45.2
    cyclohexanol 143.95
    benzyl alcohol 183.88
    2-ethylhexanol 56.35
    isooctanol 43.65
    dipropyl ether 40.38
    1,2-dichlorobenzene 174.51
    ethyl lactate 88.68
    propylene carbonate 297.75
    n-methylformamide 211.69
    2-pentanol 69.71
    n-pentane 2.66
    1-propoxy-2-propanol 128.47
    1-methoxy-2-propyl acetate 149.68
    2-(2-methoxypropoxy) propanol 158.39
    mesitylene 47.76
    ε-caprolactone 318.0
    p-cymene 36.43
    epichlorohydrin 527.69
    1,1,1-trichloroethane 206.2
    2-aminoethanol 73.59
    morpholine-4-carbaldehyde 562.82
    sulfolane 539.47
    2,2,4-trimethylpentane 3.46
    2-methyltetrahydrofuran 307.17
    n-hexyl acetate 126.69
    isooctane 2.54
    2-(2-butoxyethoxy)ethanol 192.59
    sec-butyl acetate 88.32
    tert-butyl acetate 98.79
    decalin 8.37
    glycerin 110.39
    diglyme 335.52
    acrylic acid 153.25
    isopropyl myristate 50.38
    n-butyric acid 180.98
    acetyl acetate 133.95
    di(2-ethylhexyl) phthalate 83.79
    ethyl propionate 97.45
    nitromethane 367.81
    1,2-diethoxyethane 130.79
    benzonitrile 187.56
    trioctyl phosphate 49.48
    1-bromopropane 110.08
    gamma-valerolactone 590.88
    n-decanol 33.11
    triethyl phosphate 65.1
    4-methyl-2-pentanol 54.0
    propionitrile 100.63
    vinylene carbonate 299.95
    1,1,2-trichlorotrifluoroethane 356.35
    DMS 146.16
    cumene 49.28
    2-octanol 33.61
    2-hexanone 129.38
    octyl acetate 68.0
    limonene 42.57
    1,2-dimethoxyethane 282.72
    ethyl orthosilicate 59.09
    tributyl phosphate 63.44
    diacetone alcohol 142.61
    N,N-dimethylaniline 118.14
    acrylonitrile 147.66
    aniline 187.81
    1,3-propanediol 118.38
    bromobenzene 191.87
    dibromomethane 347.73
    1,1,2,2-tetrachloroethane 516.04
    2-methyl-cyclohexyl acetate 109.73
    tetrabutyl urea 82.93
    diisobutyl methanol 30.59
    2-phenylethanol 144.11
    styrene 86.96
    dioctyl adipate 92.38
    dimethyl sulfate 203.23
    ethyl butyrate 87.14
    methyl lactate 122.83
    butyl lactate 98.7
    diethyl carbonate 76.06
    propanediol butyl ether 137.88
    triethyl orthoformate 72.22
    p-tert-butyltoluene 32.02
    methyl 4-tert-butylbenzoate 134.54
    morpholine 414.49
    tert-butylamine 46.37
    n-dodecanol 25.04
    dimethoxymethane 268.67
    ethylene carbonate 230.29
    cyrene 221.96
    2-ethoxyethyl acetate 152.15
    2-ethylhexyl acetate 99.51
    1,2,4-trichlorobenzene 249.54
    4-methylpyridine 367.78
    dibutyl ether 42.67
    2,6-dimethyl-4-heptanol 30.59
    DEF 201.54
    dimethyl isosorbide 276.94
    tetrachloroethylene 299.42
    eugenol 151.82
    triacetin 159.55
    span 80 130.22
    1,4-butanediol 68.16
    1,1-dichloroethane 262.09
    2-methyl-1-pentanol 119.62
    methyl formate 175.61
    2-methyl-1-butanol 117.26
    n-decane 2.99
    butyronitrile 103.21
    3,7-dimethyl-1-octanol 50.43
    1-chlorooctane 23.07
    1-chlorotetradecane 10.16
    n-nonane 2.24
    undecane 2.32
    tert-butylcyclohexane 6.17
    cyclooctane 2.9
    cyclopentanol 170.09
    tetrahydropyran 275.24
    tert-amyl methyl ether 62.02
    2,5,8-trioxanonane 243.38
    1-hexene 20.87
    2-isopropoxyethanol 131.42
    2,2,2-trifluoroethanol 101.22
    methyl butyrate 136.21

    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