(3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione

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  • Identifiers

    CAS number
    89026-40-4

    Molecular formula
    C15H20O4

    SMILES
    CC(=O)CCC[C@@]1(C[C@@H]2[C@H](CC1=O)C(=C)C(=O)O2)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 42.29%
    Caramellic 38.52%
    Sweet 34.52%
    Burnt 29.57%
    Floral 26.9%
    Nutty 26.41%
    Mint 26.23%
    Tobacco 25.16%
    Odorless 22.29%
    Spicy 21.66%

     

    Flavor
    Bitter 49.66%
    Minty 33.43%
    Sweet 22.2%
    Fenugreek 21.37%
    Leaves 20.76%
    Celery 20.72%
    Maple 20.57%
    Lovage 20.54%
    Cotton candy 20.45%
    Extremely sweet 20.43%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    7.59 (neutral)

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    560°C

    Flash point

    • 188.25 ˚C est.

  • Synonyms

    • (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione
    • (3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzofuran-2,5-dione
    • 89026-40-4
    • RefChem:69147
    • (+)-Umbellifolide
    • Umbellifolide, (+)-
    • 9GAP3C3DDW
    • SCHEMBL21807699
    • CHEBI:181193
    • DTXSID801125340
    • (3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzouran-2,5-dione
    • (3aR,6R,7aR)-6-Methyl-3-methylidene-6-(4-oxopentyl)tetrahydro-1-benzofuran-2,5(3H,4H)-dione
    • (3AS,6S,7AS)-6-METHYL-3-METHYLIDENE-6-(4-OXIDANYLIDENEPENTYL)-3A,4,7,7A-TETRAHYDRO-1-BENZOFURAN-2,5-DIONE
    • 2,5(3H,4H)-Benzofurandione, tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-, (3aR,6R,7aR)-
    • 2,5(3H,4H)-Benzofurandione, tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-, [3aR-(3aalpha,6alpha,7aalpha)]-
    • NCGC00384721-01!(3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzofuran-2,5-dione
    • 89026-40-4

  • Applications

    The compound (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione is primarily handled as a synthetic intermediate in fine chemical manufacturing; it is commonly evaluated for use as a building block in pharmaceutical and agrochemical research to construct more complex molecules. In perfumery and cosmetics, it may serve as a fragrance precursor or aroma-active intermediate, contributing to scent profiles when incorporated in formulations under appropriate controls. In polymer and materials contexts, it can be used as a functional monomer or modifier to introduce rigid benzofurandione motifs into specialty polymers; in coatings and inks, it may be explored as a reactive intermediate for resin formulations. The compound may also be considered for other niche applications in research settings, and its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 328.93
    methanol 799.71
    isopropanol 297.83
    water 2.5
    ethyl acetate 457.57
    n-propanol 229.04
    acetone 667.73
    n-butanol 196.79
    acetonitrile 410.41
    DMF 1243.0
    toluene 130.06
    isobutanol 159.97
    1,4-dioxane 913.58
    methyl acetate 404.61
    THF 960.82
    2-butanone 370.95
    n-pentanol 127.34
    sec-butanol 157.6
    n-hexane 0.72
    ethylene glycol 86.37
    NMP 452.49
    cyclohexane 3.16
    DMSO 613.7
    n-butyl acetate 151.32
    n-octanol 45.32
    chloroform 759.93
    n-propyl acetate 207.6
    acetic acid 649.18
    dichloromethane 598.41
    cyclohexanone 451.18
    propylene glycol 117.15
    isopropyl acetate 278.31
    DMAc 744.26
    2-ethoxyethanol 450.16
    isopentanol 200.09
    n-heptane 0.64
    ethyl formate 288.92
    1,2-dichloroethane 282.6
    n-hexanol 96.27
    2-methoxyethanol 925.21
    isobutyl acetate 131.23
    tetrachloromethane 32.35
    n-pentyl acetate 92.24
    transcutol 1598.44
    n-heptanol 47.65
    ethylbenzene 56.03
    MIBK 199.04
    2-propoxyethanol 407.0
    tert-butanol 311.79
    MTBE 116.71
    2-butoxyethanol 184.47
    propionic acid 253.7
    o-xylene 69.23
    formic acid 423.51
    diethyl ether 130.91
    m-xylene 84.61
    p-xylene 84.61
    chlorobenzene 174.65
    dimethyl carbonate 241.86
    n-octane 0.65
    formamide 828.23
    cyclopentanone 516.01
    2-pentanone 299.57
    anisole 245.89
    cyclopentyl methyl ether 191.21
    gamma-butyrolactone 679.74
    1-methoxy-2-propanol 626.2
    pyridine 519.55
    3-pentanone 169.18
    furfural 669.07
    n-dodecane 1.2
    diethylene glycol 420.88
    diisopropyl ether 30.08
    tert-amyl alcohol 170.51
    acetylacetone 578.44
    n-hexadecane 1.44
    acetophenone 255.96
    methyl propionate 303.67
    isopentyl acetate 155.23
    trichloroethylene 792.96
    n-nonanol 45.95
    cyclohexanol 152.18
    benzyl alcohol 262.23
    2-ethylhexanol 41.45
    isooctanol 42.43
    dipropyl ether 33.16
    1,2-dichlorobenzene 158.26
    ethyl lactate 124.61
    propylene carbonate 389.96
    n-methylformamide 655.42
    2-pentanol 107.6
    n-pentane 0.94
    1-propoxy-2-propanol 195.39
    1-methoxy-2-propyl acetate 277.2
    2-(2-methoxypropoxy) propanol 225.31
    mesitylene 37.48
    ε-caprolactone 429.09
    p-cymene 21.5
    epichlorohydrin 752.55
    1,1,1-trichloroethane 207.49
    2-aminoethanol 187.09
    morpholine-4-carbaldehyde 867.14
    sulfolane 480.79
    2,2,4-trimethylpentane 1.48
    2-methyltetrahydrofuran 344.34
    n-hexyl acetate 138.63
    isooctane 1.42
    2-(2-butoxyethoxy)ethanol 352.31
    sec-butyl acetate 154.57
    tert-butyl acetate 240.01
    decalin 2.99
    glycerin 231.51
    diglyme 663.96
    acrylic acid 245.92
    isopropyl myristate 50.6
    n-butyric acid 414.83
    acetyl acetate 345.76
    di(2-ethylhexyl) phthalate 71.23
    ethyl propionate 171.16
    nitromethane 1153.89
    1,2-diethoxyethane 264.25
    benzonitrile 284.35
    trioctyl phosphate 40.34
    1-bromopropane 69.2
    gamma-valerolactone 968.14
    n-decanol 32.35
    triethyl phosphate 56.54
    4-methyl-2-pentanol 82.48
    propionitrile 221.89
    vinylene carbonate 399.63
    1,1,2-trichlorotrifluoroethane 454.98
    DMS 199.98
    cumene 31.72
    2-octanol 30.22
    2-hexanone 163.57
    octyl acetate 65.23
    limonene 23.07
    1,2-dimethoxyethane 705.11
    ethyl orthosilicate 49.02
    tributyl phosphate 56.11
    diacetone alcohol 329.05
    N,N-dimethylaniline 118.11
    acrylonitrile 368.99
    aniline 278.32
    1,3-propanediol 372.6
    bromobenzene 153.97
    dibromomethane 237.5
    1,1,2,2-tetrachloroethane 547.13
    2-methyl-cyclohexyl acetate 93.65
    tetrabutyl urea 74.0
    diisobutyl methanol 28.44
    2-phenylethanol 180.06
    styrene 77.33
    dioctyl adipate 85.91
    dimethyl sulfate 305.38
    ethyl butyrate 108.78
    methyl lactate 206.92
    butyl lactate 100.0
    diethyl carbonate 87.98
    propanediol butyl ether 196.33
    triethyl orthoformate 75.13
    p-tert-butyltoluene 20.66
    methyl 4-tert-butylbenzoate 137.12
    morpholine 866.99
    tert-butylamine 87.89
    n-dodecanol 22.77
    dimethoxymethane 713.12
    ethylene carbonate 331.28
    cyrene 214.03
    2-ethoxyethyl acetate 224.5
    2-ethylhexyl acetate 101.59
    1,2,4-trichlorobenzene 201.41
    4-methylpyridine 548.35
    dibutyl ether 46.33
    2,6-dimethyl-4-heptanol 28.44
    DEF 313.75
    dimethyl isosorbide 350.23
    tetrachloroethylene 284.31
    eugenol 169.07
    triacetin 208.77
    span 80 147.76
    1,4-butanediol 126.39
    1,1-dichloroethane 295.79
    2-methyl-1-pentanol 125.63
    methyl formate 532.37
    2-methyl-1-butanol 140.2
    n-decane 1.83
    butyronitrile 231.8
    3,7-dimethyl-1-octanol 59.61
    1-chlorooctane 15.41
    1-chlorotetradecane 6.57
    n-nonane 1.29
    undecane 1.44
    tert-butylcyclohexane 2.41
    cyclooctane 1.0
    cyclopentanol 164.13
    tetrahydropyran 341.13
    tert-amyl methyl ether 73.14
    2,5,8-trioxanonane 442.55
    1-hexene 7.89
    2-isopropoxyethanol 272.05
    2,2,2-trifluoroethanol 247.94
    methyl butyrate 235.11

    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