(3aS,5aR,9bR)-3a,4,5,5a,6,7,8,9b-Octahydro-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2(3H)-one

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  • Identifiers

    CAS number
    27579-97-1

    Molecular formula
    C15H20O2

    SMILES
    CC1=C2[C@H]3[C@@H](CC[C@]2(CCC1)C)C(=C)C(=O)O3

    Safety labels

  • Odor profile

    Fragrance
    Woody 52.19%
    Sweet 44.04%
    Tobacco 40.05%
    Spicy 34.86%
    Mint 33.01%
    Coconut 28.54%
    Powdery 27.85%
    Coumarinic 27.02%
    Hay 25.91%
    Lactonic 25.67%

     

    Flavor
    Bitter 68.03%
    Lovage 21.86%
    Minty 21.6%
    Ripe apricot 20.8%
    Cedarleaf 20.76%
    Red fruit 20.47%
    Basil 20.32%
    Outdoor 19.6%
    Parsley 19.5%
    Coumarin 19.38%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    8.65 (weak base)

    Molecular weight
    232.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    427°C

    Flash point

    • 166.56 ˚C est.

  • Synonyms

    • Frullanolide
    • 27579-97-1
    • ZPN5AE55ES
    • (3aS,5aR,9bR)-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
    • (3AS,5AR,9BR)-3A,4,5,5A,6,7,8,9B-OCTAHYDRO-5A,9-DIMETHYL-3-METHYLENENAPHTHO(1,2-B)FURAN-2(3H)-ONE
    • Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,8,9b-octahydro-5a,9-dimethyl-3-methylene-, (3aS-(3aalpha,5abeta,9balpha))-
    • (3aS,5aR,9bR)-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo(g)(1)benzofuran-2-one
    • RefChem:141564
    • (3aS,5aR,9bR)-5a,9-dimethyl-3-methylene-4,5,6,7,8,9b-hexahydro-3aH-benzo(g)benzofuran-2-one
    • 62860-37-1
    • Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,8,9b-octahydro-5a,9-dimethyl-3-methylene-, (3aalpha,5abeta,9balpha)-(+-)-
    • AC1L4POH
    • AC1Q69UB
    • TOURNEFORTIOLIDE
    • UNII-ZPN5AE55ES
    • CHEBI:5177
    • SCHEMBL14987851
    • DTXSID70212032
    • C09454
    • Q27106677
    • (3aS,5aR,9bR)-5a,9-Dimethyl-3-methylidene-3a,4,5,5a,6,7,8,9b-octahydronaphtho[1,2-b]furan-2(3H)-one
    • NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,8,9B-OCTAHYDRO-5A,9-DIMETHYL-3-METHYLENE-, (3AS,5AR,9BR)-
    • NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,8,9B-OCTAHYDRO-5A,9-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,5A.BETA.,9B.ALPHA.))-
    • 27579-97-1

  • Applications

    For the chemical (3aS,5aR,9bR)-3a,4,5,5a,6,7,8,9b-Octahydro-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2(3H)-one (CAS 27579-97-1), potential applications include use as an organic-synthesis intermediate and as a chiral building block for pharmaceutical and agrochemical research. It may be evaluated for fragrance applications in perfumery, serving as a potential odor-active intermediate or aroma precursor. In cosmetics and personal care, it may be considered as a fragrance ingredient or compatible component. In industrial manufacturing, it can function as a specialty monomer or crosslinking component in polymer systems and coatings. Additionally, it is being explored as a scaffold for lactone-based materials in materials science and R&D.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 227.04
    methanol 298.47
    isopropanol 375.74
    water 0.24
    ethyl acetate 441.14
    n-propanol 313.67
    acetone 605.12
    n-butanol 367.57
    acetonitrile 261.01
    DMF 1071.15
    toluene 772.86
    isobutanol 274.43
    1,4-dioxane 1134.88
    methyl acetate 468.72
    THF 1667.57
    2-butanone 628.47
    n-pentanol 121.52
    sec-butanol 192.1
    n-hexane 3.02
    ethylene glycol 26.75
    NMP 663.97
    cyclohexane 28.94
    DMSO 267.3
    n-butyl acetate 401.55
    n-octanol 63.92
    chloroform 1877.53
    n-propyl acetate 244.97
    acetic acid 193.15
    dichloromethane 1390.93
    cyclohexanone 1145.26
    propylene glycol 47.07
    isopropyl acetate 383.5
    DMAc 562.48
    2-ethoxyethanol 179.62
    isopentanol 353.17
    n-heptane 4.59
    ethyl formate 330.45
    1,2-dichloroethane 812.08
    n-hexanol 213.7
    2-methoxyethanol 447.47
    isobutyl acetate 215.55
    tetrachloromethane 150.05
    n-pentyl acetate 248.06
    transcutol 901.78
    n-heptanol 88.05
    ethylbenzene 151.81
    MIBK 354.85
    2-propoxyethanol 458.88
    tert-butanol 368.09
    MTBE 281.71
    2-butoxyethanol 205.45
    propionic acid 209.32
    o-xylene 263.9
    formic acid 64.96
    diethyl ether 263.59
    m-xylene 402.45
    p-xylene 232.34
    chlorobenzene 730.97
    dimethyl carbonate 214.51
    n-octane 2.61
    formamide 144.72
    cyclopentanone 1281.06
    2-pentanone 544.55
    anisole 318.4
    cyclopentyl methyl ether 513.36
    gamma-butyrolactone 1126.94
    1-methoxy-2-propanol 401.58
    pyridine 1208.46
    3-pentanone 341.71
    furfural 854.52
    n-dodecane 3.67
    diethylene glycol 263.52
    diisopropyl ether 91.18
    tert-amyl alcohol 175.07
    acetylacetone 539.73
    n-hexadecane 4.68
    acetophenone 325.18
    methyl propionate 347.31
    isopentyl acetate 415.04
    trichloroethylene 1719.01
    n-nonanol 64.82
    cyclohexanol 366.68
    benzyl alcohol 292.21
    2-ethylhexanol 107.74
    isooctanol 82.21
    dipropyl ether 89.33
    1,2-dichlorobenzene 538.36
    ethyl lactate 104.93
    propylene carbonate 574.41
    n-methylformamide 407.07
    2-pentanol 196.5
    n-pentane 8.48
    1-propoxy-2-propanol 278.41
    1-methoxy-2-propyl acetate 444.44
    2-(2-methoxypropoxy) propanol 217.89
    mesitylene 193.05
    ε-caprolactone 767.67
    p-cymene 98.95
    epichlorohydrin 1299.77
    1,1,1-trichloroethane 650.74
    2-aminoethanol 83.47
    morpholine-4-carbaldehyde 809.91
    sulfolane 672.78
    2,2,4-trimethylpentane 7.93
    2-methyltetrahydrofuran 815.06
    n-hexyl acetate 284.91
    isooctane 9.71
    2-(2-butoxyethoxy)ethanol 297.44
    sec-butyl acetate 205.86
    tert-butyl acetate 350.34
    decalin 13.92
    glycerin 83.05
    diglyme 587.74
    acrylic acid 184.32
    isopropyl myristate 106.74
    n-butyric acid 437.62
    acetyl acetate 309.68
    di(2-ethylhexyl) phthalate 126.97
    ethyl propionate 198.71
    nitromethane 453.98
    1,2-diethoxyethane 316.98
    benzonitrile 600.32
    trioctyl phosphate 80.98
    1-bromopropane 321.83
    gamma-valerolactone 1417.38
    n-decanol 47.22
    triethyl phosphate 102.3
    4-methyl-2-pentanol 152.65
    propionitrile 392.78
    vinylene carbonate 592.89
    1,1,2-trichlorotrifluoroethane 413.88
    DMS 315.07
    cumene 97.04
    2-octanol 62.86
    2-hexanone 239.92
    octyl acetate 127.91
    limonene 109.55
    1,2-dimethoxyethane 438.7
    ethyl orthosilicate 99.64
    tributyl phosphate 106.1
    diacetone alcohol 304.14
    N,N-dimethylaniline 176.4
    acrylonitrile 484.53
    aniline 626.71
    1,3-propanediol 235.58
    bromobenzene 818.0
    dibromomethane 757.57
    1,1,2,2-tetrachloroethane 1172.34
    2-methyl-cyclohexyl acetate 197.59
    tetrabutyl urea 129.71
    diisobutyl methanol 78.98
    2-phenylethanol 341.18
    styrene 201.45
    dioctyl adipate 156.04
    dimethyl sulfate 234.59
    ethyl butyrate 207.05
    methyl lactate 153.28
    butyl lactate 178.01
    diethyl carbonate 152.52
    propanediol butyl ether 165.69
    triethyl orthoformate 152.7
    p-tert-butyltoluene 95.6
    methyl 4-tert-butylbenzoate 241.78
    morpholine 1087.16
    tert-butylamine 186.66
    n-dodecanol 36.53
    dimethoxymethane 676.4
    ethylene carbonate 528.22
    cyrene 217.63
    2-ethoxyethyl acetate 387.77
    2-ethylhexyl acetate 301.03
    1,2,4-trichlorobenzene 596.25
    4-methylpyridine 1302.15
    dibutyl ether 91.59
    2,6-dimethyl-4-heptanol 78.98
    DEF 434.57
    dimethyl isosorbide 452.24
    tetrachloroethylene 645.37
    eugenol 232.79
    triacetin 247.62
    span 80 180.75
    1,4-butanediol 56.24
    1,1-dichloroethane 839.95
    2-methyl-1-pentanol 139.34
    methyl formate 328.71
    2-methyl-1-butanol 234.24
    n-decane 5.69
    butyronitrile 426.28
    3,7-dimethyl-1-octanol 96.46
    1-chlorooctane 47.66
    1-chlorotetradecane 20.41
    n-nonane 4.12
    undecane 4.42
    tert-butylcyclohexane 11.84
    cyclooctane 7.67
    cyclopentanol 390.41
    tetrahydropyran 978.49
    tert-amyl methyl ether 144.54
    2,5,8-trioxanonane 353.42
    1-hexene 28.09
    2-isopropoxyethanol 151.09
    2,2,2-trifluoroethanol 96.26
    methyl butyrate 269.93

    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