(3aR,5S,7S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-7-hydroxy-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one

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  • Identifiers

    CAS number
    68776-45-4

    Molecular formula
    C15H20O3

    SMILES
    C[C@H]1C[C@@H](C[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 35.35%
    Woody 31.91%
    Spicy 31.16%
    Sweet 30.9%
    Mint 25.99%
    Tobacco 22.68%
    Nutty 22.61%
    Burnt 21.08%
    Phenolic 20.15%
    Coumarinic 18.97%

     

    Flavor
    Bitter 85.6%
    Cedarleaf 21.42%
    Minty 20.88%
    Lovage 20.26%
    Ripe apricot 19.7%
    Basil 19.57%
    Fenugreek 19.56%
    Leaves 19.4%
    Red fruit 19.38%
    Sweet-like 19.12%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    8.41 (weak base)

    Molecular weight
    248.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    623°C

    Flash point

    • 188.65 ˚C est.

  • Synonyms

    • 2-Hydroxyalantolactone
    • 68776-45-4
    • RefChem:905961
    • (3aR,5S,7S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-7-hydroxy-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one
    • 2alpha-Hydroxyalantolactone
    • (3aR,5S,7S,8aR,9aR)-7-hydroxy-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
    • (3ar,5s,7s,8ar,9ar)-7-hydroxy-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3h)-one
    • CHEMBL486020
    • MEGxp0_001639
    • orb1992237
    • SCHEMBL30689553
    • ACon1_001960
    • DTXSID50988485
    • CHEBI:190859
    • AKOS040734515
    • NCGC00179964-01
    • NCGC00179964-02
    • (3aR,5S,7S,8aR,9aR)-7-hydroxy-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[][1]benzouran-2-one
    • (3aR-(3aalpha,5beta,7alpha,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a-Octahydro-7-hydroxy-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one
    • 7-Hydroxy-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one
    • Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-7-hydroxy-5,8a-dimethyl-3-methylene-, (3aR-(3aalpha,5beta,7alpha,8abeta,9aalpha))-
    • 68776-45-4

  • Applications

    This compound, (3aR,5S,7S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-7-hydroxy-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one, CAS 68776-45-4, is mainly used as an intermediate and chiral building block in organic synthesis. It can serve as a scaffold for the development of pharmaceutical or agrochemical candidates, and may be evaluated as a fragrance intermediate or odorant in perfumery and cosmetics. The rigid bicyclic lactone framework can be employed as a precursor for specialty polymers or resin formulations, potentially influencing material properties. Additional potential applications include use as a synthesis intermediate for coatings, inks, and cleaning formulations, under appropriate regulatory limits and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 76.87
    methanol 193.05
    isopropanol 96.59
    water 0.47
    ethyl acetate 145.38
    n-propanol 92.08
    acetone 219.61
    n-butanol 100.58
    acetonitrile 98.0
    DMF 525.82
    toluene 115.17
    isobutanol 66.2
    1,4-dioxane 437.91
    methyl acetate 139.75
    THF 729.74
    2-butanone 159.73
    n-pentanol 41.69
    sec-butanol 44.91
    n-hexane 0.66
    ethylene glycol 25.52
    NMP 302.21
    cyclohexane 3.44
    DMSO 256.38
    n-butyl acetate 105.26
    n-octanol 29.87
    chloroform 365.49
    n-propyl acetate 81.39
    acetic acid 138.12
    dichloromethane 298.13
    cyclohexanone 271.76
    propylene glycol 38.21
    isopropyl acetate 112.91
    DMAc 253.77
    2-ethoxyethanol 110.4
    isopentanol 91.26
    n-heptane 1.41
    ethyl formate 104.4
    1,2-dichloroethane 159.5
    n-hexanol 71.66
    2-methoxyethanol 293.98
    isobutyl acetate 68.06
    tetrachloromethane 22.29
    n-pentyl acetate 75.03
    transcutol 722.47
    n-heptanol 36.95
    ethylbenzene 28.79
    MIBK 108.81
    2-propoxyethanol 221.48
    tert-butanol 111.37
    MTBE 55.75
    2-butoxyethanol 104.76
    propionic acid 92.08
    o-xylene 48.55
    formic acid 83.64
    diethyl ether 64.82
    m-xylene 86.27
    p-xylene 40.04
    chlorobenzene 129.68
    dimethyl carbonate 120.09
    n-octane 0.85
    formamide 141.83
    cyclopentanone 395.42
    2-pentanone 144.39
    anisole 97.6
    cyclopentyl methyl ether 177.24
    gamma-butyrolactone 454.52
    1-methoxy-2-propanol 247.64
    pyridine 269.19
    3-pentanone 95.78
    furfural 344.43
    n-dodecane 1.3
    diethylene glycol 203.36
    diisopropyl ether 23.06
    tert-amyl alcohol 46.14
    acetylacetone 219.74
    n-hexadecane 1.58
    acetophenone 104.67
    methyl propionate 134.11
    isopentyl acetate 107.87
    trichloroethylene 406.32
    n-nonanol 30.38
    cyclohexanol 86.6
    benzyl alcohol 92.93
    2-ethylhexanol 37.4
    isooctanol 33.39
    dipropyl ether 34.47
    1,2-dichlorobenzene 108.8
    ethyl lactate 63.57
    propylene carbonate 222.61
    n-methylformamide 228.87
    2-pentanol 51.89
    n-pentane 1.21
    1-propoxy-2-propanol 137.64
    1-methoxy-2-propyl acetate 177.52
    2-(2-methoxypropoxy) propanol 124.37
    mesitylene 42.29
    ε-caprolactone 229.39
    p-cymene 24.71
    epichlorohydrin 455.55
    1,1,1-trichloroethane 110.97
    2-aminoethanol 58.55
    morpholine-4-carbaldehyde 415.01
    sulfolane 351.2
    2,2,4-trimethylpentane 1.51
    2-methyltetrahydrofuran 244.29
    n-hexyl acetate 95.36
    isooctane 2.06
    2-(2-butoxyethoxy)ethanol 179.45
    sec-butyl acetate 63.42
    tert-butyl acetate 122.64
    decalin 2.69
    glycerin 90.02
    diglyme 322.79
    acrylic acid 100.54
    isopropyl myristate 38.91
    n-butyric acid 153.66
    acetyl acetate 127.39
    di(2-ethylhexyl) phthalate 53.37
    ethyl propionate 73.4
    nitromethane 280.73
    1,2-diethoxyethane 144.4
    benzonitrile 137.08
    trioctyl phosphate 37.69
    1-bromopropane 52.33
    gamma-valerolactone 522.72
    n-decanol 22.97
    triethyl phosphate 46.01
    4-methyl-2-pentanol 45.68
    propionitrile 88.77
    vinylene carbonate 225.54
    1,1,2-trichlorotrifluoroethane 212.9
    DMS 118.48
    cumene 21.25
    2-octanol 23.65
    2-hexanone 69.1
    octyl acetate 49.41
    limonene 28.1
    1,2-dimethoxyethane 218.91
    ethyl orthosilicate 42.68
    tributyl phosphate 45.66
    diacetone alcohol 147.31
    N,N-dimethylaniline 58.68
    acrylonitrile 146.5
    aniline 147.69
    1,3-propanediol 129.71
    bromobenzene 124.27
    dibromomethane 134.36
    1,1,2,2-tetrachloroethane 272.76
    2-methyl-cyclohexyl acetate 72.76
    tetrabutyl urea 58.04
    diisobutyl methanol 28.25
    2-phenylethanol 104.6
    styrene 35.87
    dioctyl adipate 62.41
    dimethyl sulfate 162.17
    ethyl butyrate 72.11
    methyl lactate 105.57
    butyl lactate 78.04
    diethyl carbonate 57.01
    propanediol butyl ether 111.43
    triethyl orthoformate 61.56
    p-tert-butyltoluene 24.44
    methyl 4-tert-butylbenzoate 99.42
    morpholine 433.43
    tert-butylamine 38.7
    n-dodecanol 17.02
    dimethoxymethane 375.1
    ethylene carbonate 187.64
    cyrene 133.06
    2-ethoxyethyl acetate 142.89
    2-ethylhexyl acetate 78.21
    1,2,4-trichlorobenzene 137.92
    4-methylpyridine 262.29
    dibutyl ether 31.52
    2,6-dimethyl-4-heptanol 28.25
    DEF 142.68
    dimethyl isosorbide 232.65
    tetrachloroethylene 142.7
    eugenol 107.19
    triacetin 120.95
    span 80 94.59
    1,4-butanediol 32.86
    1,1-dichloroethane 145.79
    2-methyl-1-pentanol 44.44
    methyl formate 202.01
    2-methyl-1-butanol 59.06
    n-decane 2.02
    butyronitrile 97.57
    3,7-dimethyl-1-octanol 38.8
    1-chlorooctane 14.92
    1-chlorotetradecane 6.17
    n-nonane 1.46
    undecane 1.59
    tert-butylcyclohexane 2.41
    cyclooctane 1.42
    cyclopentanol 108.61
    tetrahydropyran 249.11
    tert-amyl methyl ether 37.8
    2,5,8-trioxanonane 213.07
    1-hexene 5.02
    2-isopropoxyethanol 83.28
    2,2,2-trifluoroethanol 64.32
    methyl butyrate 91.78

    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