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

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  • Identifiers

    CAS number
    35481-83-5

    Molecular formula
    C15H20O4

    SMILES
    C[C@@H]1CCC(=O)[C@H]2[C@]1(CC3=C(C(=O)O[C@]3(C2)O)C)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 49.21%
    Spicy 41.05%
    Sweet 38.12%
    Mint 31.77%
    Tobacco 31.65%
    Lactonic 31.43%
    Coconut 29.16%
    Odorless 26.47%
    Coumarinic 25.74%
    Herbal 24.6%

     

    Flavor
    Bitter 66.2%
    Minty 29.71%
    Ripe apricot 22.56%
    Cedarleaf 22.49%
    Red fruit 22.32%
    Lovage 21.93%
    Leaves 21.16%
    Coumarin 21.14%
    Fenugreek 21.0%
    Seedy 20.9%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    7.11 (neutral)

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    544°C

    Flash point

    • 195.08 ˚C est.

  • Synonyms

    • Istanbulin A
    • 35481-83-5
    • (4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-2,8-dione
    • (4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo(f)(1)benzofuran-2,8-dione
    • RefChem:906132
    • (4aS,5R,8aR,9aS)-4a,6,7,8a,9,9a-Hexahydro-9a-hydroxy-3,4a,5-trimethylnaphtho(2,3-b)furan-2,8(4H,5H)-dione
    • Istanbulin-A
    • Naphtho(2,3-b)furan-2,8(4H,5H)-dione, 4a,6,7,8a,9,9a-hexahydro-9a-hydroxy-3,4a,5-trimethyl-, (4aS-(4aalpha,5alpha,8abeta,9abeta))-
    • (-)-Istanbulin A
    • SCHEMBL30218834
    • DTXSID90956885
    • CHEBI:174481
    • (4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[][1]benzouran-2,8-dione
    • (4aS,5R,8aR,9aS)-9a-Hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydronaphtho[2,3-b]furan-2,8(4H,5H)-dione
    • 9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4H,5H- naphtho[2,3-b]furan-2,8-dione
    • 9a-Hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydronaphtho[2,3-b]furan-2,8(4H,5H)-dione
    • 35481-83-5

  • Applications

    Applications for this chiral naphtho(2,3-b)furan-2,8(4H,5H)-dione derivative are primarily as a building block in pharmaceutical and fine-chemical synthesis, where it is commonly evaluated as a chiral intermediate for the preparation of biologically active molecules. It may also be explored in fragrance and cosmetics contexts as a niche aroma compound or odorant, depending on formulation constraints. In materials science, it can serve as a specialty intermediate for polymers, coatings, and inks, contributing to crosslinkable or rigid-structure components. Additionally, it is used in research and development settings as a versatile synthetic precursor for route development and structure–activity studies, with use subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.63
    methanol 48.82
    isopropanol 26.98
    water 0.26
    ethyl acetate 49.22
    n-propanol 22.43
    acetone 88.52
    n-butanol 21.33
    acetonitrile 34.14
    DMF 251.66
    toluene 35.03
    isobutanol 16.22
    1,4-dioxane 151.12
    methyl acetate 66.76
    THF 223.02
    2-butanone 81.86
    n-pentanol 9.74
    sec-butanol 13.18
    n-hexane 0.12
    ethylene glycol 11.8
    NMP 151.25
    cyclohexane 0.72
    DMSO 179.49
    n-butyl acetate 39.75
    n-octanol 6.24
    chloroform 217.18
    n-propyl acetate 32.14
    acetic acid 49.51
    dichloromethane 141.53
    cyclohexanone 108.38
    propylene glycol 10.31
    isopropyl acetate 39.22
    DMAc 183.72
    2-ethoxyethanol 43.43
    isopentanol 21.92
    n-heptane 0.12
    ethyl formate 38.26
    1,2-dichloroethane 73.98
    n-hexanol 16.37
    2-methoxyethanol 109.75
    isobutyl acetate 24.6
    tetrachloromethane 14.89
    n-pentyl acetate 25.69
    transcutol 97.5
    n-heptanol 10.25
    ethylbenzene 13.73
    MIBK 38.18
    2-propoxyethanol 89.77
    tert-butanol 30.25
    MTBE 9.93
    2-butoxyethanol 43.77
    propionic acid 33.76
    o-xylene 19.26
    formic acid 41.56
    diethyl ether 12.05
    m-xylene 21.34
    p-xylene 24.22
    chlorobenzene 52.56
    dimethyl carbonate 55.51
    n-octane 0.11
    formamide 86.64
    cyclopentanone 179.79
    2-pentanone 48.2
    anisole 49.14
    cyclopentyl methyl ether 35.25
    gamma-butyrolactone 192.19
    1-methoxy-2-propanol 82.45
    pyridine 143.68
    3-pentanone 36.04
    furfural 184.79
    n-dodecane 0.17
    diethylene glycol 82.82
    diisopropyl ether 3.99
    tert-amyl alcohol 13.31
    acetylacetone 94.22
    n-hexadecane 0.22
    acetophenone 62.13
    methyl propionate 51.13
    isopentyl acetate 42.45
    trichloroethylene 216.9
    n-nonanol 7.19
    cyclohexanol 21.2
    benzyl alcohol 50.62
    2-ethylhexanol 8.62
    isooctanol 9.05
    dipropyl ether 5.53
    1,2-dichlorobenzene 51.7
    ethyl lactate 27.32
    propylene carbonate 91.41
    n-methylformamide 105.08
    2-pentanol 9.23
    n-pentane 0.15
    1-propoxy-2-propanol 42.57
    1-methoxy-2-propyl acetate 66.24
    2-(2-methoxypropoxy) propanol 43.81
    mesitylene 10.51
    ε-caprolactone 89.27
    p-cymene 7.99
    epichlorohydrin 195.74
    1,1,1-trichloroethane 59.8
    2-aminoethanol 20.51
    morpholine-4-carbaldehyde 200.2
    sulfolane 183.45
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 59.22
    n-hexyl acetate 28.22
    isooctane 0.23
    2-(2-butoxyethoxy)ethanol 50.24
    sec-butyl acetate 24.33
    tert-butyl acetate 41.96
    decalin 0.68
    glycerin 33.11
    diglyme 111.84
    acrylic acid 41.28
    isopropyl myristate 11.48
    n-butyric acid 51.9
    acetyl acetate 54.05
    di(2-ethylhexyl) phthalate 22.94
    ethyl propionate 32.09
    nitromethane 141.12
    1,2-diethoxyethane 25.8
    benzonitrile 64.04
    trioctyl phosphate 14.08
    1-bromopropane 15.67
    gamma-valerolactone 233.21
    n-decanol 4.95
    triethyl phosphate 20.07
    4-methyl-2-pentanol 9.0
    propionitrile 35.71
    vinylene carbonate 107.15
    1,1,2-trichlorotrifluoroethane 123.37
    DMS 55.06
    cumene 8.7
    2-octanol 5.37
    2-hexanone 29.06
    octyl acetate 15.48
    limonene 7.21
    1,2-dimethoxyethane 101.25
    ethyl orthosilicate 16.75
    tributyl phosphate 16.01
    diacetone alcohol 59.15
    N,N-dimethylaniline 27.75
    acrylonitrile 74.35
    aniline 59.31
    1,3-propanediol 45.67
    bromobenzene 50.78
    dibromomethane 62.3
    1,1,2,2-tetrachloroethane 150.23
    2-methyl-cyclohexyl acetate 31.14
    tetrabutyl urea 22.83
    diisobutyl methanol 6.37
    2-phenylethanol 55.49
    styrene 17.45
    dioctyl adipate 22.14
    dimethyl sulfate 101.57
    ethyl butyrate 24.24
    methyl lactate 47.8
    butyl lactate 28.05
    diethyl carbonate 23.52
    propanediol butyl ether 29.16
    triethyl orthoformate 20.76
    p-tert-butyltoluene 7.55
    methyl 4-tert-butylbenzoate 45.46
    morpholine 129.17
    tert-butylamine 8.03
    n-dodecanol 3.36
    dimethoxymethane 128.15
    ethylene carbonate 81.86
    cyrene 65.25
    2-ethoxyethyl acetate 50.36
    2-ethylhexyl acetate 29.9
    1,2,4-trichlorobenzene 64.88
    4-methylpyridine 125.39
    dibutyl ether 4.97
    2,6-dimethyl-4-heptanol 6.37
    DEF 51.84
    dimethyl isosorbide 92.31
    tetrachloroethylene 89.03
    eugenol 52.99
    triacetin 44.49
    span 80 31.64
    1,4-butanediol 11.85
    1,1-dichloroethane 60.71
    2-methyl-1-pentanol 11.61
    methyl formate 89.88
    2-methyl-1-butanol 14.44
    n-decane 0.28
    butyronitrile 27.41
    3,7-dimethyl-1-octanol 8.1
    1-chlorooctane 2.5
    1-chlorotetradecane 1.09
    n-nonane 0.18
    undecane 0.21
    tert-butylcyclohexane 0.54
    cyclooctane 0.25
    cyclopentanol 29.79
    tetrahydropyran 55.77
    tert-amyl methyl ether 7.46
    2,5,8-trioxanonane 73.59
    1-hexene 1.11
    2-isopropoxyethanol 31.99
    2,2,2-trifluoroethanol 36.88
    methyl butyrate 42.62

    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