(3aS,5aR,6R,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2,8(3H,4H)-dione

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  • Identifiers

    CAS number
    64929-15-3

    Molecular formula
    C15H18O4

    SMILES
    CC1=C2[C@@H]3[C@@H](CC[C@]2([C@@H](CC1=O)O)C)C(=C)C(=O)O3

    Safety labels

  • Odor profile

    Fragrance
    Sweet 54.02%
    Caramellic 41.6%
    Burnt 37.8%
    Woody 30.35%
    Spicy 29.69%
    Nutty 29.11%
    Odorless 27.88%
    Tobacco 26.53%
    Mint 25.22%
    Phenolic 23.19%

     

    Flavor
    Bitter 90.26%
    Lovage 19.96%
    Cedarleaf 19.89%
    Fenugreek 19.53%
    Sweet-like 19.23%
    Basil 18.96%
    Ripe apricot 18.91%
    Seedy 18.88%
    Leaves 18.84%
    Red fruit 18.6%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    6.98 (neutral)

    Molecular weight
    262.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    963°C

    Flash point

    • 201.03 ˚C est.

  • Synonyms

    • DTXSID701107389
    • 64929-15-3
    • (3aS,5aR,6R,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2,8(3H,4H)-dione
    • (3aS,5aR,6R,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2,8(3H,4H)-dione
    • RefChem:1050156
    • DTXCID001539040
    • Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,6,7,9b-hexahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9bS)-
    • CHEMBL5207260
    • Armexifolin (1-epi-Ludovicin C)
    • 87550-01-4
    • NS00094036
    • 64929-15-3

  • Applications

    Chemical name (3aS,5aR,6R,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2,8(3H,4H)-dione, CAS 64929-15-3, is primarily used as a synthetic intermediate and chiral building block in pharmaceutical and fine chemicals, thanks to its defined stereochemistry within the hexahydro-6-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2,8(3H,4H)-dione core. It is also evaluated as a fragrance intermediate or odor-active component for cosmetics and perfumery, where it may contribute to aroma formulations. In organic synthesis R&D, it serves as a versatile precursor for transformations on the polycyclic scaffold. Additionally, it can be employed in polymer and coating applications as a specialty precursor for resins or crosslinking systems.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.95
    methanol 35.29
    isopropanol 21.37
    water 0.34
    ethyl acetate 30.61
    n-propanol 15.51
    acetone 51.64
    n-butanol 18.91
    acetonitrile 17.16
    DMF 138.7
    toluene 25.53
    isobutanol 12.24
    1,4-dioxane 96.72
    methyl acetate 34.43
    THF 134.66
    2-butanone 44.25
    n-pentanol 8.4
    sec-butanol 9.25
    n-hexane 0.11
    ethylene glycol 8.47
    NMP 74.11
    cyclohexane 0.67
    DMSO 110.74
    n-butyl acetate 27.07
    n-octanol 5.82
    chloroform 95.22
    n-propyl acetate 20.73
    acetic acid 37.01
    dichloromethane 69.26
    cyclohexanone 79.69
    propylene glycol 4.89
    isopropyl acetate 28.39
    DMAc 100.75
    2-ethoxyethanol 36.48
    isopentanol 22.89
    n-heptane 0.14
    ethyl formate 24.74
    1,2-dichloroethane 42.78
    n-hexanol 15.16
    2-methoxyethanol 82.61
    isobutyl acetate 15.84
    tetrachloromethane 10.31
    n-pentyl acetate 21.12
    transcutol 97.88
    n-heptanol 10.22
    ethylbenzene 9.32
    MIBK 32.4
    2-propoxyethanol 67.56
    tert-butanol 29.77
    MTBE 8.39
    2-butoxyethanol 37.61
    propionic acid 18.49
    o-xylene 15.54
    formic acid 34.4
    diethyl ether 9.47
    m-xylene 16.99
    p-xylene 15.07
    chlorobenzene 30.85
    dimethyl carbonate 36.11
    n-octane 0.13
    formamide 63.17
    cyclopentanone 102.84
    2-pentanone 37.29
    anisole 29.68
    cyclopentyl methyl ether 26.64
    gamma-butyrolactone 103.33
    1-methoxy-2-propanol 62.95
    pyridine 78.76
    3-pentanone 25.53
    furfural 104.14
    n-dodecane 0.2
    diethylene glycol 66.54
    diisopropyl ether 3.89
    tert-amyl alcohol 12.54
    acetylacetone 63.98
    n-hexadecane 0.25
    acetophenone 40.63
    methyl propionate 29.2
    isopentyl acetate 30.8
    trichloroethylene 107.96
    n-nonanol 6.84
    cyclohexanol 18.39
    benzyl alcohol 34.77
    2-ethylhexanol 8.5
    isooctanol 9.61
    dipropyl ether 4.98
    1,2-dichlorobenzene 31.3
    ethyl lactate 19.04
    propylene carbonate 50.77
    n-methylformamide 59.18
    2-pentanol 8.93
    n-pentane 0.18
    1-propoxy-2-propanol 33.84
    1-methoxy-2-propyl acetate 47.47
    2-(2-methoxypropoxy) propanol 36.23
    mesitylene 9.52
    ε-caprolactone 52.61
    p-cymene 6.96
    epichlorohydrin 111.14
    1,1,1-trichloroethane 33.55
    2-aminoethanol 12.64
    morpholine-4-carbaldehyde 117.76
    sulfolane 109.04
    2,2,4-trimethylpentane 0.23
    2-methyltetrahydrofuran 34.94
    n-hexyl acetate 21.22
    isooctane 0.28
    2-(2-butoxyethoxy)ethanol 43.32
    sec-butyl acetate 15.89
    tert-butyl acetate 33.3
    decalin 0.57
    glycerin 21.97
    diglyme 92.23
    acrylic acid 23.03
    isopropyl myristate 9.66
    n-butyric acid 36.07
    acetyl acetate 34.73
    di(2-ethylhexyl) phthalate 17.67
    ethyl propionate 20.78
    nitromethane 80.4
    1,2-diethoxyethane 22.32
    benzonitrile 41.53
    trioctyl phosphate 11.37
    1-bromopropane 9.62
    gamma-valerolactone 136.31
    n-decanol 4.92
    triethyl phosphate 15.54
    4-methyl-2-pentanol 10.22
    propionitrile 20.0
    vinylene carbonate 58.39
    1,1,2-trichlorotrifluoroethane 75.92
    DMS 35.96
    cumene 6.54
    2-octanol 5.51
    2-hexanone 19.68
    octyl acetate 12.13
    limonene 6.65
    1,2-dimethoxyethane 77.45
    ethyl orthosilicate 14.03
    tributyl phosphate 12.24
    diacetone alcohol 48.55
    N,N-dimethylaniline 19.67
    acrylonitrile 40.35
    aniline 39.44
    1,3-propanediol 36.47
    bromobenzene 28.01
    dibromomethane 32.09
    1,1,2,2-tetrachloroethane 75.77
    2-methyl-cyclohexyl acetate 22.77
    tetrabutyl urea 18.56
    diisobutyl methanol 6.81
    2-phenylethanol 39.81
    styrene 10.99
    dioctyl adipate 17.16
    dimethyl sulfate 62.39
    ethyl butyrate 18.75
    methyl lactate 30.25
    butyl lactate 21.98
    diethyl carbonate 16.52
    propanediol butyl ether 22.58
    triethyl orthoformate 17.14
    p-tert-butyltoluene 6.77
    methyl 4-tert-butylbenzoate 36.14
    morpholine 80.95
    tert-butylamine 8.58
    n-dodecanol 3.47
    dimethoxymethane 94.31
    ethylene carbonate 49.9
    cyrene 47.3
    2-ethoxyethyl acetate 37.6
    2-ethylhexyl acetate 21.37
    1,2,4-trichlorobenzene 38.4
    4-methylpyridine 76.08
    dibutyl ether 4.96
    2,6-dimethyl-4-heptanol 6.81
    DEF 36.95
    dimethyl isosorbide 69.7
    tetrachloroethylene 55.88
    eugenol 40.4
    triacetin 30.97
    span 80 25.46
    1,4-butanediol 9.6
    1,1-dichloroethane 30.84
    2-methyl-1-pentanol 10.97
    methyl formate 52.16
    2-methyl-1-butanol 13.27
    n-decane 0.32
    butyronitrile 18.46
    3,7-dimethyl-1-octanol 7.84
    1-chlorooctane 2.42
    1-chlorotetradecane 1.11
    n-nonane 0.21
    undecane 0.24
    tert-butylcyclohexane 0.46
    cyclooctane 0.25
    cyclopentanol 20.57
    tetrahydropyran 37.44
    tert-amyl methyl ether 6.76
    2,5,8-trioxanonane 61.74
    1-hexene 0.85
    2-isopropoxyethanol 26.53
    2,2,2-trifluoroethanol 27.79
    methyl butyrate 26.94

    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