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

Overview IFRA Request a quote

  • Identifiers

    CAS number
    3162-56-9

    Molecular formula
    C15H20O4

    SMILES
    C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)[C@](C=CC3=O)(C)O)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 37.78%
    Woody 36.64%
    Spicy 34.06%
    Odorless 33.66%
    Burnt 26.74%
    Caramellic 26.49%
    Nutty 25.22%
    Mint 23.67%
    Tobacco 23.21%
    Coconut 21.64%

     

    Flavor
    Bitter 83.94%
    Minty 22.63%
    Cedarleaf 21.34%
    Fenugreek 20.4%
    Sweet-like 20.21%
    Lovage 19.97%
    Leaves 19.83%
    Ripe apricot 19.78%
    Cotton candy 19.62%
    Seedy 19.57%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    6.79 (neutral)

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    717°C

    Flash point

    • 195.3 ˚C est.

  • Synonyms

    • Vulgarin
    • 3162-56-9
    • DTXSID30928884
    • (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo(g)benzofuran-2,6-dione
    • (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g]benzofuran-2,6-dione
    • RefChem:401503
    • DTXCID601357646
    • (3S,3aS,5aR,9R,9aS,9bS)-3a,5,5a,9,9a,9b-Hexahydro-9-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione
    • Tauremisin
    • Barrelin
    • Tauremizin
    • Judaicin (eudesmane naphthofuran)
    • Judaicin
    • TAUREMIZINE
    • (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
    • Judaicin (sesquiterpene)
    • (3s,3as,5ar,9r,9as,9bs)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3h,4h)-dione
    • SMR000445685
    • (3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione
    • MLS000728573
    • MLS001185447
    • orb1991665
    • CHEMBL1422618
    • SCHEMBL29350406
    • CHEBI:10024
    • HMS2225C10
    • BB_NC-00703
    • BBL034028
    • MFCD01726765
    • STK013739
    • AKOS001483019
    • Vulgarin, >=90% (LC/MS-ELSD)
    • 3a,5,5a,9,9a,9b-Hexahydro-9-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione
    • Eudesm-2-en-12-oic acid, 4,6-alpha-dihydroxy-1-oxo-, gamma-lactone, (11S)-
    • NCGC00247310-01
    • NCGC00247310-02
    • NCGC00247310-03
    • (3S,3AS,5AR,9R,9AS,9BS)-9-HYDROXY-3,5A,9-TRIMETHYL-2H,3H,3AH,4H,5H,5AH,6H,9H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2,6-DIONE
    • (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,4,5,5a,9,9a-hexahydronaphtho[1,2-b]furan-2,6(3H,9bH)-dione
    • Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S,3aS,5aR,9R,9aS,9bS)-
    • Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9alpha,9aalpha,9bbeta))-
    • VS-12384
    • NS00094007
    • C09600
    • Q27108555
    • 9-HYDROXY-3,5A,9-TRIMETHYL-2H,3H,3AH,4H,5H,5AH,6H,9H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2,6-DIONE
    • 3162-56-9

  • Applications

    Chemical name: (3S,3aS,5aR,9R,9aS,9bS)-3a,5,5a,9,9a,9b-Hexahydro-9-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione; CAS 3162-56-9. This compound is primarily used as an intermediate and chiral building block in pharmaceutical and agrochemical synthesis; it can serve as a precursor for specialty polymers and resin systems in the plastics industry; it also functions as a precursor or functional scaffold in coatings and ink formulations; its hydroxy and diketone functionalities allow controlled chemical modification under appropriate conditions; use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.16
    methanol 113.25
    isopropanol 35.16
    water 2.31
    ethyl acetate 55.38
    n-propanol 31.81
    acetone 97.57
    n-butanol 29.5
    acetonitrile 56.96
    DMF 379.27
    toluene 65.33
    isobutanol 25.34
    1,4-dioxane 176.71
    methyl acetate 69.8
    THF 276.69
    2-butanone 79.87
    n-pentanol 20.54
    sec-butanol 17.0
    n-hexane 0.53
    ethylene glycol 22.63
    NMP 228.97
    cyclohexane 2.17
    DMSO 215.45
    n-butyl acetate 40.09
    n-octanol 14.62
    chloroform 271.5
    n-propyl acetate 40.73
    acetic acid 83.79
    dichloromethane 198.39
    cyclohexanone 146.6
    propylene glycol 17.5
    isopropyl acetate 42.74
    DMAc 192.89
    2-ethoxyethanol 55.9
    isopentanol 28.72
    n-heptane 0.61
    ethyl formate 54.56
    1,2-dichloroethane 88.99
    n-hexanol 30.43
    2-methoxyethanol 133.98
    isobutyl acetate 32.89
    tetrachloromethane 22.11
    n-pentyl acetate 33.54
    transcutol 96.79
    n-heptanol 19.58
    ethylbenzene 22.85
    MIBK 45.02
    2-propoxyethanol 98.43
    tert-butanol 35.63
    MTBE 11.55
    2-butoxyethanol 49.42
    propionic acid 52.9
    o-xylene 34.2
    formic acid 81.04
    diethyl ether 17.99
    m-xylene 45.61
    p-xylene 34.62
    chlorobenzene 78.23
    dimethyl carbonate 68.19
    n-octane 0.51
    formamide 128.15
    cyclopentanone 218.28
    2-pentanone 59.64
    anisole 49.55
    cyclopentyl methyl ether 63.03
    gamma-butyrolactone 253.67
    1-methoxy-2-propanol 94.89
    pyridine 159.41
    3-pentanone 50.01
    furfural 219.85
    n-dodecane 0.74
    diethylene glycol 112.94
    diisopropyl ether 7.44
    tert-amyl alcohol 16.02
    acetylacetone 101.97
    n-hexadecane 0.91
    acetophenone 68.35
    methyl propionate 65.22
    isopentyl acetate 39.9
    trichloroethylene 228.42
    n-nonanol 15.46
    cyclohexanol 37.63
    benzyl alcohol 63.89
    2-ethylhexanol 17.24
    isooctanol 16.88
    dipropyl ether 11.72
    1,2-dichlorobenzene 66.76
    ethyl lactate 38.23
    propylene carbonate 113.13
    n-methylformamide 164.24
    2-pentanol 15.57
    n-pentane 0.62
    1-propoxy-2-propanol 51.64
    1-methoxy-2-propyl acetate 64.53
    2-(2-methoxypropoxy) propanol 49.51
    mesitylene 22.64
    ε-caprolactone 113.99
    p-cymene 14.68
    epichlorohydrin 205.71
    1,1,1-trichloroethane 69.06
    2-aminoethanol 32.67
    morpholine-4-carbaldehyde 249.41
    sulfolane 233.53
    2,2,4-trimethylpentane 0.69
    2-methyltetrahydrofuran 83.4
    n-hexyl acetate 39.78
    isooctane 0.79
    2-(2-butoxyethoxy)ethanol 52.66
    sec-butyl acetate 29.46
    tert-butyl acetate 41.1
    decalin 2.1
    glycerin 52.25
    diglyme 105.28
    acrylic acid 66.41
    isopropyl myristate 18.14
    n-butyric acid 66.43
    acetyl acetate 64.85
    di(2-ethylhexyl) phthalate 29.8
    ethyl propionate 39.74
    nitromethane 193.5
    1,2-diethoxyethane 30.13
    benzonitrile 86.04
    trioctyl phosphate 21.21
    1-bromopropane 27.3
    gamma-valerolactone 262.52
    n-decanol 11.79
    triethyl phosphate 24.41
    4-methyl-2-pentanol 15.88
    propionitrile 51.59
    vinylene carbonate 138.57
    1,1,2-trichlorotrifluoroethane 131.92
    DMS 60.04
    cumene 15.68
    2-octanol 11.87
    2-hexanone 39.76
    octyl acetate 23.29
    limonene 15.58
    1,2-dimethoxyethane 110.91
    ethyl orthosilicate 21.73
    tributyl phosphate 23.13
    diacetone alcohol 58.74
    N,N-dimethylaniline 37.39
    acrylonitrile 95.05
    aniline 74.65
    1,3-propanediol 53.71
    bromobenzene 75.42
    dibromomethane 94.9
    1,1,2,2-tetrachloroethane 159.44
    2-methyl-cyclohexyl acetate 35.89
    tetrabutyl urea 33.65
    diisobutyl methanol 11.97
    2-phenylethanol 60.33
    styrene 25.94
    dioctyl adipate 29.96
    dimethyl sulfate 117.11
    ethyl butyrate 31.17
    methyl lactate 63.94
    butyl lactate 34.19
    diethyl carbonate 27.72
    propanediol butyl ether 37.93
    triethyl orthoformate 26.55
    p-tert-butyltoluene 13.05
    methyl 4-tert-butylbenzoate 52.41
    morpholine 147.29
    tert-butylamine 12.82
    n-dodecanol 8.93
    dimethoxymethane 173.63
    ethylene carbonate 108.93
    cyrene 81.5
    2-ethoxyethyl acetate 50.55
    2-ethylhexyl acetate 31.37
    1,2,4-trichlorobenzene 79.57
    4-methylpyridine 144.65
    dibutyl ether 10.31
    2,6-dimethyl-4-heptanol 11.97
    DEF 72.0
    dimethyl isosorbide 97.18
    tetrachloroethylene 99.9
    eugenol 57.83
    triacetin 54.23
    span 80 39.61
    1,4-butanediol 22.69
    1,1-dichloroethane 78.2
    2-methyl-1-pentanol 21.14
    methyl formate 146.66
    2-methyl-1-butanol 21.8
    n-decane 1.18
    butyronitrile 44.43
    3,7-dimethyl-1-octanol 15.8
    1-chlorooctane 7.47
    1-chlorotetradecane 3.49
    n-nonane 0.86
    undecane 0.91
    tert-butylcyclohexane 1.54
    cyclooctane 0.92
    cyclopentanol 50.41
    tetrahydropyran 77.13
    tert-amyl methyl ether 11.39
    2,5,8-trioxanonane 77.13
    1-hexene 3.26
    2-isopropoxyethanol 41.32
    2,2,2-trifluoroethanol 58.07
    methyl butyrate 51.82

    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