[(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-acetyloxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate

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  • Identifiers

    CAS number
    53142-46-4

    Molecular formula
    C27H32O10

    SMILES
    C/C=C(\CO)/C(=O)OC/C(=C\C)/C(=O)O[C@@H]1C[C@]2(CO2)[C@@H]3[C@@H](C=C([C@@H]3[C@@H]4[C@@H]1C(=C)C(=O)O4)C)OC(=O)C

  • Odor profile

    Fragrance
    Odorless 51.11%
    Herbal 26.27%
    Mint 25.65%
    Sweet 23.84%
    Green 21.16%
    Woody 20.84%
    Cooling 18.81%
    Nutty 18.42%
    Spicy 18.05%
    Fresh 18.02%

     

    Flavor
    Bitter 84.85%
    Odorless 28.94%
    Bland 24.48%
    Very mild 22.05%
    Sweet-like 20.44%
    Cedarleaf 19.36%
    Parsley 18.96%
    Lovage 18.87%
    Heather 18.74%
    Broom 18.67%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    4.69 (weak acid)

    Molecular weight
    516.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    457°C

    Flash point

    • 178.39 ˚C est.

  • Synonyms

    • 53142-46-4
    • [(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-acetyloxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate
    • AC1NQYJF
    • C09551
    • CHEBI:9227
    • DTXSID30415128
    • Q27108320

  • Applications

    [(E)-2-[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-acetyloxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl]oxycarbonylbut-2-enyl] (E)-2-(hydroxymethyl)but-2-enoate (CAS 53142-46-4) is a complex chiral ester used primarily as an intermediate in organic synthesis. In industry it is commonly evaluated as a chiral building block for pharmaceutical and agrochemical syntheses. It can function as a reactive monomer or co-monomer in specialty polymers, coatings, and adhesives, enabling advanced polymer architectures via ester and epoxide functionalities. Additionally, its azulene-containing framework makes it a candidate fragrance intermediate in perfumery and cosmetics research, and in process chemistry as a high-value intermediate. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 35.84
    methanol 81.22
    isopropanol 17.96
    water 0.07
    ethyl acetate 70.34
    n-propanol 37.28
    acetone 157.31
    n-butanol 24.07
    acetonitrile 52.02
    DMF 249.71
    toluene 11.22
    isobutanol 19.35
    1,4-dioxane 114.89
    methyl acetate 91.66
    THF 216.95
    2-butanone 125.74
    n-pentanol 21.75
    sec-butanol 19.92
    n-hexane 0.29
    ethylene glycol 14.88
    NMP 416.52
    cyclohexane 0.52
    DMSO 281.41
    n-butyl acetate 22.14
    n-octanol 6.2
    chloroform 184.95
    n-propyl acetate 37.08
    acetic acid 272.19
    dichloromethane 171.57
    cyclohexanone 149.68
    propylene glycol 24.99
    isopropyl acetate 28.32
    DMAc 373.96
    2-ethoxyethanol 96.52
    isopentanol 16.05
    n-heptane 0.21
    ethyl formate 51.68
    1,2-dichloroethane 75.3
    n-hexanol 8.76
    2-methoxyethanol 135.8
    isobutyl acetate 19.04
    tetrachloromethane 9.29
    n-pentyl acetate 19.34
    transcutol 98.75
    n-heptanol 7.44
    ethylbenzene 4.43
    MIBK 25.35
    2-propoxyethanol 76.48
    tert-butanol 14.11
    MTBE 11.64
    2-butoxyethanol 40.14
    propionic acid 96.31
    o-xylene 5.54
    formic acid 118.19
    diethyl ether 19.76
    m-xylene 4.66
    p-xylene 6.4
    chlorobenzene 24.77
    dimethyl carbonate 70.98
    n-octane 0.12
    formamide 140.44
    cyclopentanone 241.57
    2-pentanone 67.31
    anisole 22.94
    cyclopentyl methyl ether 35.15
    gamma-butyrolactone 300.98
    1-methoxy-2-propanol 91.46
    pyridine 118.41
    3-pentanone 59.25
    furfural 184.92
    n-dodecane 0.15
    diethylene glycol 61.54
    diisopropyl ether 2.58
    tert-amyl alcohol 15.88
    acetylacetone 105.39
    n-hexadecane 0.17
    acetophenone 44.13
    methyl propionate 89.09
    isopentyl acetate 18.46
    trichloroethylene 256.72
    n-nonanol 6.82
    cyclohexanol 18.16
    benzyl alcohol 33.18
    2-ethylhexanol 5.18
    isooctanol 6.09
    dipropyl ether 7.51
    1,2-dichlorobenzene 23.67
    ethyl lactate 32.47
    propylene carbonate 98.51
    n-methylformamide 148.65
    2-pentanol 9.75
    n-pentane 0.29
    1-propoxy-2-propanol 37.36
    1-methoxy-2-propyl acetate 41.97
    2-(2-methoxypropoxy) propanol 39.93
    mesitylene 2.08
    ε-caprolactone 131.91
    p-cymene 2.22
    epichlorohydrin 276.15
    1,1,1-trichloroethane 46.88
    2-aminoethanol 34.04
    morpholine-4-carbaldehyde 244.51
    sulfolane 350.49
    2,2,4-trimethylpentane 0.26
    2-methyltetrahydrofuran 80.67
    n-hexyl acetate 22.74
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 48.05
    sec-butyl acetate 19.54
    tert-butyl acetate 22.36
    decalin 0.39
    glycerin 54.27
    diglyme 87.21
    acrylic acid 122.95
    isopropyl myristate 6.69
    n-butyric acid 82.04
    acetyl acetate 59.43
    di(2-ethylhexyl) phthalate 15.68
    ethyl propionate 35.0
    nitromethane 395.04
    1,2-diethoxyethane 24.02
    benzonitrile 31.4
    trioctyl phosphate 8.78
    1-bromopropane 21.86
    gamma-valerolactone 367.07
    n-decanol 4.36
    triethyl phosphate 14.02
    4-methyl-2-pentanol 5.57
    propionitrile 39.33
    vinylene carbonate 115.2
    1,1,2-trichlorotrifluoroethane 225.52
    DMS 32.72
    cumene 2.56
    2-octanol 3.87
    2-hexanone 43.09
    octyl acetate 11.74
    limonene 3.23
    1,2-dimethoxyethane 95.44
    ethyl orthosilicate 11.41
    tributyl phosphate 10.81
    diacetone alcohol 47.02
    N,N-dimethylaniline 13.42
    acrylonitrile 72.66
    aniline 26.63
    1,3-propanediol 47.4
    bromobenzene 23.0
    dibromomethane 72.27
    1,1,2,2-tetrachloroethane 136.88
    2-methyl-cyclohexyl acetate 20.87
    tetrabutyl urea 17.15
    diisobutyl methanol 2.73
    2-phenylethanol 22.36
    styrene 6.53
    dioctyl adipate 18.8
    dimethyl sulfate 135.32
    ethyl butyrate 20.83
    methyl lactate 65.61
    butyl lactate 23.52
    diethyl carbonate 15.23
    propanediol butyl ether 33.63
    triethyl orthoformate 15.39
    p-tert-butyltoluene 1.85
    methyl 4-tert-butylbenzoate 30.24
    morpholine 138.46
    tert-butylamine 3.9
    n-dodecanol 2.74
    dimethoxymethane 134.41
    ethylene carbonate 78.93
    cyrene 91.95
    2-ethoxyethyl acetate 40.87
    2-ethylhexyl acetate 14.14
    1,2,4-trichlorobenzene 42.22
    4-methylpyridine 75.66
    dibutyl ether 5.36
    2,6-dimethyl-4-heptanol 2.73
    DEF 84.65
    dimethyl isosorbide 68.94
    tetrachloroethylene 73.65
    eugenol 33.39
    triacetin 46.78
    span 80 33.31
    1,4-butanediol 25.19
    1,1-dichloroethane 54.6
    2-methyl-1-pentanol 16.66
    methyl formate 115.15
    2-methyl-1-butanol 19.07
    n-decane 0.26
    butyronitrile 27.36
    3,7-dimethyl-1-octanol 5.42
    1-chlorooctane 2.29
    1-chlorotetradecane 0.82
    n-nonane 0.19
    undecane 0.19
    tert-butylcyclohexane 0.27
    cyclooctane 0.16
    cyclopentanol 35.2
    tetrahydropyran 53.3
    tert-amyl methyl ether 11.56
    2,5,8-trioxanonane 62.31
    1-hexene 2.14
    2-isopropoxyethanol 49.98
    2,2,2-trifluoroethanol 87.22
    methyl butyrate 46.9

    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