(1aR,4E,6R,6aR,9aS,10aR)-6-(Acetyloxy)-1a,3,6,6a,7,9a,10,10a-octahydro-4,10a-dimethyl-7-methyleneoxireno(8,9)cyclodeca(1,2-b)furan-8(2H)-one

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  • Identifiers

    CAS number
    28272-18-6

    Molecular formula
    C17H22O5

    SMILES
    C/C/1=C\[C@H]([C@H]2[C@H](C[C@@]3([C@H](O3)CC1)C)OC(=O)C2=C)OC(=O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 41.71%
    Mint 32.77%
    Odorless 30.5%
    Nutty 28.75%
    Spicy 27.72%
    Woody 26.7%
    Caramellic 25.86%
    Herbal 25.23%
    Coumarinic 24.57%
    Tobacco 23.63%

     

    Flavor
    Bitter 73.92%
    Minty 24.4%
    Cedarleaf 20.18%
    Cotton candy 20.05%
    Seedy 20.0%
    Extremely sweet 19.87%
    Fenugreek 19.85%
    Ripe apricot 19.8%
    Leaves 19.76%
    Lovage 19.67%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    6.73 (neutral)

    Molecular weight
    306.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    478°C

    Flash point

    • 160.39 ˚C est.

  • Synonyms

    • Pyrethrosin
    • Z13OX0769A
    • 28272-18-6
    • DTXSID701018639
    • NSC-22070
    • ((3aR,4R,6E,9S,10Z,11aR)-9-acetoxy-6,10-dimethyl-3-methylene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-4-yl) (E)-4-hydroxy-2-(((E)-2-(hydroxymethyl)but-2-enoyl)oxymethyl)but-2-enoate
    • RefChem:905673
    • DTXCID501476710
    • (1aR,4E,6R,6aR,9aS,10aR)-6-(Acetyloxy)-1a,3,6,6a,7,9a,10,10a-octahydro-4,10a-dimethyl-7-methyleneoxireno(8,9)cyclodeca(1,2-b)furan-8(2H)-one
    • [(1S,3R,5R,8E,10R,11R)-3,8-dimethyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-en-10-yl] acetate
    • CHEMBL517337
    • UNII-Z13OX0769A
    • OXIRENO(8,9)CYCLODECA(1,2-B)FURAN-8(2H)-ONE, 6-(ACETYLOXY)-1A,3,6,6A,7,9A,10,10A-OCTAHYDRO-4,10A-DIMETHYL-7-METHYLENE-, (1AR,4E,6R,6AR,9AS,10AR)-
    • Oxireno[8,9]cyclodeca[1,2-b]furan-8(2H)-one, 6-(acetyloxy)-1a,3,6,6a,7,9a,10,10a-octahydro-4,10a-dimethyl-7-methylene-, (1aR,4E,6R,6aR,9aS,10aR)-
    • NSC 22070
    • C09536
    • AI3-31868
    • PYRETHROSIN [MI]
    • CHEBI:8661
    • SCHEMBL5188143
    • Q27108132
    • (1aR,4E,6R,6aR,9aS,10aR)-4,10a-Dimethyl-7-methylidene-8-oxo-1a,2,3,6,6a,7,8,9a,10,10a-decahydrooxireno[8,9]cyclodeca[1,2-b]furan-6-yl acetate
    • Germacra-4,11(13)-dien-12-oic acid, 1-beta,10-epoxy-6-alpha,8-alpha-dihydroxy-, 12,8-lactone, acetate, (E)-
    • Germacra-4,11(13)-dien-12-oic acid, 1.beta.,10-epoxy-6.alpha.,8.alpha.-dihydroxy-, 12,8-lactone, acetate, (E)-
    • Germacra-4,11(13)-dien-12-oic acid, 1alpha,10alpha-epoxy-6,8beta-dihydroxy-, 12,8-lactone, acetate
    • Oxireno(8,9)cyclodeca(1,2-b)furan-8(2H)-one, 6-(acetyloxy)-1a,3,6,6a,7,9a,10,10a-octahydro-4,10a-dimethyl-7-methylene-, (1aR-(1aR*,4E,6R*,6aR*,9aS*,10aR*))-
    • 28272-18-6

  • Applications

    CAS 28272-18-6, the compound (1aR,4E,6R,6aR,9aS,10aR)-6-(Acetyloxy)-1a,3,6,6a,7,9a,10,10a-octahydro-4,10a-dimethyl-7-methyleneoxireno(8,9)cyclodeca(1,2-b)furan-8(2H)-one, is primarily used as a synthetic intermediate and chiral building block in organic synthesis, enabling stereoselective routes to pharmaceuticals and other specialty chemicals. It may function as a reactive monomer or crosslinking component in polymer and coating formulations, influencing network structure and cure behavior. In fragrance and cosmetics development, rigid bicyclic lactone motifs can be evaluated as structural elements or odor-related fragments within regulated formulations. In industrial manufacturing, process chemistry and scale-up studies may treat it as a reactive intermediate for the preparation of more complex products, subject to safety and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 56.89
    methanol 146.7
    isopropanol 44.35
    water 0.67
    ethyl acetate 98.35
    n-propanol 50.69
    acetone 187.73
    n-butanol 45.11
    acetonitrile 121.89
    DMF 337.83
    toluene 35.38
    isobutanol 37.94
    1,4-dioxane 284.91
    methyl acetate 128.09
    THF 315.38
    2-butanone 132.31
    n-pentanol 44.1
    sec-butanol 36.21
    n-hexane 0.57
    ethylene glycol 39.2
    NMP 354.37
    cyclohexane 2.12
    DMSO 282.45
    n-butyl acetate 59.28
    n-octanol 20.66
    chloroform 362.15
    n-propyl acetate 81.05
    acetic acid 222.3
    dichloromethane 309.79
    cyclohexanone 181.53
    propylene glycol 49.13
    isopropyl acetate 63.69
    DMAc 394.7
    2-ethoxyethanol 148.54
    isopentanol 47.07
    n-heptane 0.56
    ethyl formate 90.35
    1,2-dichloroethane 121.45
    n-hexanol 31.31
    2-methoxyethanol 229.27
    isobutyl acetate 63.18
    tetrachloromethane 16.04
    n-pentyl acetate 44.88
    transcutol 391.92
    n-heptanol 20.13
    ethylbenzene 19.9
    MIBK 60.36
    2-propoxyethanol 150.39
    tert-butanol 48.5
    MTBE 26.91
    2-butoxyethanol 86.12
    propionic acid 101.13
    o-xylene 22.3
    formic acid 143.93
    diethyl ether 30.05
    m-xylene 24.08
    p-xylene 34.11
    chlorobenzene 68.09
    dimethyl carbonate 89.81
    n-octane 0.35
    formamide 207.64
    cyclopentanone 246.22
    2-pentanone 83.74
    anisole 83.93
    cyclopentyl methyl ether 66.54
    gamma-butyrolactone 314.67
    1-methoxy-2-propanol 161.46
    pyridine 202.21
    3-pentanone 64.94
    furfural 294.07
    n-dodecane 0.64
    diethylene glycol 164.02
    diisopropyl ether 8.72
    tert-amyl alcohol 34.63
    acetylacetone 147.97
    n-hexadecane 0.77
    acetophenone 108.59
    methyl propionate 96.96
    isopentyl acetate 59.64
    trichloroethylene 357.7
    n-nonanol 21.17
    cyclohexanol 46.81
    benzyl alcohol 98.51
    2-ethylhexanol 19.98
    isooctanol 17.99
    dipropyl ether 17.21
    1,2-dichlorobenzene 66.8
    ethyl lactate 68.9
    propylene carbonate 168.55
    n-methylformamide 178.69
    2-pentanol 22.15
    n-pentane 0.57
    1-propoxy-2-propanol 83.21
    1-methoxy-2-propyl acetate 98.5
    2-(2-methoxypropoxy) propanol 114.97
    mesitylene 12.75
    ε-caprolactone 168.21
    p-cymene 11.72
    epichlorohydrin 316.12
    1,1,1-trichloroethane 76.94
    2-aminoethanol 65.98
    morpholine-4-carbaldehyde 377.78
    sulfolane 291.39
    2,2,4-trimethylpentane 0.75
    2-methyltetrahydrofuran 129.3
    n-hexyl acetate 62.81
    isooctane 0.6
    2-(2-butoxyethoxy)ethanol 142.85
    sec-butyl acetate 52.35
    tert-butyl acetate 58.63
    decalin 1.94
    glycerin 98.14
    diglyme 247.54
    acrylic acid 117.33
    isopropyl myristate 25.31
    n-butyric acid 104.24
    acetyl acetate 96.96
    di(2-ethylhexyl) phthalate 46.2
    ethyl propionate 60.79
    nitromethane 399.31
    1,2-diethoxyethane 79.55
    benzonitrile 107.39
    trioctyl phosphate 25.93
    1-bromopropane 30.33
    gamma-valerolactone 410.54
    n-decanol 15.49
    triethyl phosphate 37.59
    4-methyl-2-pentanol 20.2
    propionitrile 75.85
    vinylene carbonate 183.11
    1,1,2-trichlorotrifluoroethane 237.6
    DMS 87.96
    cumene 14.22
    2-octanol 11.93
    2-hexanone 77.55
    octyl acetate 35.31
    limonene 12.96
    1,2-dimethoxyethane 245.92
    ethyl orthosilicate 31.83
    tributyl phosphate 33.36
    diacetone alcohol 95.66
    N,N-dimethylaniline 52.97
    acrylonitrile 123.52
    aniline 70.43
    1,3-propanediol 90.86
    bromobenzene 67.69
    dibromomethane 124.45
    1,1,2,2-tetrachloroethane 213.04
    2-methyl-cyclohexyl acetate 61.43
    tetrabutyl urea 46.99
    diisobutyl methanol 12.13
    2-phenylethanol 76.75
    styrene 25.88
    dioctyl adipate 50.95
    dimethyl sulfate 138.94
    ethyl butyrate 50.45
    methyl lactate 97.44
    butyl lactate 57.9
    diethyl carbonate 47.42
    propanediol butyl ether 99.48
    triethyl orthoformate 42.75
    p-tert-butyltoluene 10.15
    methyl 4-tert-butylbenzoate 71.15
    morpholine 265.98
    tert-butylamine 15.73
    n-dodecanol 11.18
    dimethoxymethane 194.81
    ethylene carbonate 143.47
    cyrene 164.47
    2-ethoxyethyl acetate 92.29
    2-ethylhexyl acetate 45.82
    1,2,4-trichlorobenzene 94.56
    4-methylpyridine 159.65
    dibutyl ether 18.63
    2,6-dimethyl-4-heptanol 12.13
    DEF 108.27
    dimethyl isosorbide 178.93
    tetrachloroethylene 115.72
    eugenol 90.17
    triacetin 102.71
    span 80 79.04
    1,4-butanediol 53.9
    1,1-dichloroethane 96.48
    2-methyl-1-pentanol 45.41
    methyl formate 158.41
    2-methyl-1-butanol 38.67
    n-decane 0.95
    butyronitrile 68.19
    3,7-dimethyl-1-octanol 23.55
    1-chlorooctane 7.35
    1-chlorotetradecane 3.48
    n-nonane 0.67
    undecane 0.76
    tert-butylcyclohexane 1.36
    cyclooctane 0.73
    cyclopentanol 63.54
    tetrahydropyran 112.84
    tert-amyl methyl ether 22.53
    2,5,8-trioxanonane 184.67
    1-hexene 4.5
    2-isopropoxyethanol 106.43
    2,2,2-trifluoroethanol 87.15
    methyl butyrate 86.73

    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