(3S,3aS,5aR,6S,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione

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  • Identifiers

    CAS number
    71327-31-6

    Molecular formula
    C15H20O4

    SMILES
    C[C@H]1[C@@H]2CC[C@]3([C@H](CC(=O)C(=C3[C@H]2OC1=O)C)O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 53.25%
    Caramellic 38.86%
    Woody 38.67%
    Burnt 34.0%
    Spicy 33.33%
    Nutty 27.93%
    Tobacco 26.9%
    Odorless 26.78%
    Coconut 25.44%
    Phenolic 25.42%

     

    Flavor
    Bitter 87.75%
    Cedarleaf 21.02%
    Sweet-like 20.49%
    Fenugreek 20.25%
    Lovage 20.23%
    Ripe apricot 19.77%
    Leaves 19.67%
    Seedy 19.55%
    Red fruit 19.35%
    Cotton candy 19.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    6.66 (neutral)

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    735°C

    Flash point

    • 198.06 ˚C est.

  • Synonyms

    • 71327-31-6
    • (3S,3aS,5aR,6S,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
    • (3S,3aS,5aR,6S,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,8(3H,4H)-dione
    • RefChem:208324
    • DTXSID301109852
    • 71327-31-6

  • Applications

    Chemical name: (3S,3aS,5aR,6S,9bS)-3a,5,5a,6,7,9b-Hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione; CAS number: 71327-31-6 is typically used as an intermediate in pharmaceutical and agrochemical synthesis, serving as a chiral building block for the preparation of more complex active compounds. It may be employed as a reactive diketone building block in organic synthesis, including routes to natural product analogs. In industry, it has potential applications as a precursor for specialty polymers and coatings, where the diketone/hydroxy functionality enables crosslinking or further functionalization. It is sometimes evaluated in fragrance or perfumery chemistry as a fragrance intermediate, and in research settings as a reference compound for method development and process optimization. Its actual use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 18.32
    methanol 55.91
    isopropanol 29.21
    water 1.36
    ethyl acetate 37.37
    n-propanol 21.54
    acetone 65.1
    n-butanol 23.65
    acetonitrile 26.4
    DMF 169.41
    toluene 34.08
    isobutanol 17.73
    1,4-dioxane 125.63
    methyl acetate 47.81
    THF 138.93
    2-butanone 55.15
    n-pentanol 11.64
    sec-butanol 11.41
    n-hexane 0.17
    ethylene glycol 15.22
    NMP 91.88
    cyclohexane 1.08
    DMSO 135.54
    n-butyl acetate 35.57
    n-octanol 8.97
    chloroform 161.6
    n-propyl acetate 29.48
    acetic acid 54.7
    dichloromethane 107.95
    cyclohexanone 97.44
    propylene glycol 8.03
    isopropyl acetate 34.36
    DMAc 119.74
    2-ethoxyethanol 45.67
    isopentanol 26.56
    n-heptane 0.2
    ethyl formate 36.44
    1,2-dichloroethane 59.66
    n-hexanol 19.69
    2-methoxyethanol 93.8
    isobutyl acetate 24.3
    tetrachloromethane 17.41
    n-pentyl acetate 27.5
    transcutol 100.59
    n-heptanol 14.03
    ethylbenzene 13.7
    MIBK 35.72
    2-propoxyethanol 79.78
    tert-butanol 35.89
    MTBE 9.17
    2-butoxyethanol 46.81
    propionic acid 29.74
    o-xylene 21.61
    formic acid 53.09
    diethyl ether 11.22
    m-xylene 23.35
    p-xylene 23.8
    chlorobenzene 47.33
    dimethyl carbonate 42.38
    n-octane 0.21
    formamide 87.83
    cyclopentanone 125.18
    2-pentanone 41.63
    anisole 36.23
    cyclopentyl methyl ether 30.06
    gamma-butyrolactone 136.2
    1-methoxy-2-propanol 66.52
    pyridine 105.18
    3-pentanone 31.99
    furfural 142.72
    n-dodecane 0.33
    diethylene glycol 87.83
    diisopropyl ether 4.64
    tert-amyl alcohol 13.9
    acetylacetone 76.92
    n-hexadecane 0.42
    acetophenone 50.06
    methyl propionate 35.93
    isopentyl acetate 38.52
    trichloroethylene 151.27
    n-nonanol 9.99
    cyclohexanol 23.51
    benzyl alcohol 47.05
    2-ethylhexanol 11.04
    isooctanol 12.81
    dipropyl ether 5.81
    1,2-dichlorobenzene 46.33
    ethyl lactate 25.58
    propylene carbonate 70.8
    n-methylformamide 79.97
    2-pentanol 10.81
    n-pentane 0.25
    1-propoxy-2-propanol 40.19
    1-methoxy-2-propyl acetate 55.31
    2-(2-methoxypropoxy) propanol 41.93
    mesitylene 13.02
    ε-caprolactone 71.06
    p-cymene 9.77
    epichlorohydrin 130.33
    1,1,1-trichloroethane 50.87
    2-aminoethanol 20.13
    morpholine-4-carbaldehyde 144.6
    sulfolane 133.79
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 39.85
    n-hexyl acetate 28.56
    isooctane 0.4
    2-(2-butoxyethoxy)ethanol 49.66
    sec-butyl acetate 21.67
    tert-butyl acetate 36.61
    decalin 0.94
    glycerin 31.62
    diglyme 102.73
    acrylic acid 37.13
    isopropyl myristate 12.55
    n-butyric acid 46.78
    acetyl acetate 47.98
    di(2-ethylhexyl) phthalate 23.13
    ethyl propionate 26.35
    nitromethane 113.16
    1,2-diethoxyethane 25.95
    benzonitrile 60.97
    trioctyl phosphate 15.25
    1-bromopropane 13.42
    gamma-valerolactone 167.68
    n-decanol 7.21
    triethyl phosphate 18.92
    4-methyl-2-pentanol 11.75
    propionitrile 28.5
    vinylene carbonate 87.18
    1,1,2-trichlorotrifluoroethane 95.69
    DMS 47.25
    cumene 9.88
    2-octanol 7.95
    2-hexanone 26.13
    octyl acetate 16.04
    limonene 8.88
    1,2-dimethoxyethane 86.81
    ethyl orthosilicate 17.09
    tributyl phosphate 16.47
    diacetone alcohol 50.34
    N,N-dimethylaniline 25.22
    acrylonitrile 56.27
    aniline 50.18
    1,3-propanediol 47.31
    bromobenzene 42.16
    dibromomethane 50.64
    1,1,2,2-tetrachloroethane 104.94
    2-methyl-cyclohexyl acetate 28.67
    tetrabutyl urea 23.19
    diisobutyl methanol 8.37
    2-phenylethanol 50.0
    styrene 15.63
    dioctyl adipate 21.61
    dimethyl sulfate 72.56
    ethyl butyrate 23.78
    methyl lactate 37.72
    butyl lactate 28.58
    diethyl carbonate 21.29
    propanediol butyl ether 29.43
    triethyl orthoformate 20.16
    p-tert-butyltoluene 9.21
    methyl 4-tert-butylbenzoate 42.93
    morpholine 93.24
    tert-butylamine 11.32
    n-dodecanol 5.14
    dimethoxymethane 96.93
    ethylene carbonate 71.4
    cyrene 58.39
    2-ethoxyethyl acetate 48.59
    2-ethylhexyl acetate 27.89
    1,2,4-trichlorobenzene 54.36
    4-methylpyridine 94.71
    dibutyl ether 6.7
    2,6-dimethyl-4-heptanol 8.37
    DEF 41.98
    dimethyl isosorbide 76.47
    tetrachloroethylene 77.0
    eugenol 49.91
    triacetin 41.13
    span 80 31.55
    1,4-butanediol 14.98
    1,1-dichloroethane 48.16
    2-methyl-1-pentanol 13.88
    methyl formate 73.28
    2-methyl-1-butanol 16.15
    n-decane 0.54
    butyronitrile 25.12
    3,7-dimethyl-1-octanol 10.22
    1-chlorooctane 3.8
    1-chlorotetradecane 1.71
    n-nonane 0.36
    undecane 0.42
    tert-butylcyclohexane 0.71
    cyclooctane 0.4
    cyclopentanol 27.48
    tetrahydropyran 46.91
    tert-amyl methyl ether 7.14
    2,5,8-trioxanonane 68.95
    1-hexene 1.2
    2-isopropoxyethanol 33.95
    2,2,2-trifluoroethanol 44.4
    methyl butyrate 34.94

    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