(1R,3aS,4R,7S,8aR)-1,4-Dimethyl-7-(propan-2-yl)octahydro-4,7-epoxyazulen-3(2H)-one

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  • Identifiers

    CAS number
    3466-16-8

    Molecular formula
    C15H24O2

    SMILES
    C[C@@H]1CC(=O)[C@H]2[C@@H]1C[C@@]3(CC[C@]2(O3)C)C(C)C

    Safety labels

  • Odor profile

    Fragrance
    Herbal 61.36%
    Woody 60.73%
    Mint 53.64%
    Fresh 51.33%
    Spicy 50.21%
    Camphoreous 43.99%
    Cooling 43.84%
    Green 42.91%
    Earthy 38.71%
    Pine 32.35%

     

    Flavor
    Green 51.18%
    Minty 48.46%
    Bitter 38.55%
    Herbal 33.96%
    Fresh 27.59%
    Earthy 27.11%
    Fruity 27.09%
    Cedarleaf 23.94%
    Tropical 23.69%
    Herb 23.5%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.63 (weak base)

    Molecular weight
    236.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    317°C

    Flash point

    • 132.35 ˚C est.

  • Synonyms

    • beta-Kessyl ketone
    • CHEBI:173714
    • DTXSID201122548
    • (1R,2S,5R,6R,8S)-1,5-dimethyl-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-3-one
    • (1R,3aS,4R,7S,8aR)-1,4-Dimethyl-7-(propan-2-yl)octahydro-4,7-epoxyazulen-3(2H)-one
    • 3466-16-8
    • 4,7-Epoxyazulen-3(2H)-one, octahydro-1,4-dimethyl-7-(1-methylethyl)-, (1R,3aS,4R,7S,8aR)-
    • 3466-16-8

  • Applications

    (1R,3aS,4R,7S,8aR)-1,4-Dimethyl-7-(propan-2-yl)octahydro-4,7-epoxyazulen-3(2H)-one (CAS 3466-16-8) is principally used as a structural scaffold and organic synthesis intermediate with relevance to several real-world applications: as a fragrance component in perfumery and cosmetic formulations; as an intermediate in the synthesis of additional aroma compounds for fragrance development; as a fragrance additive in household cleaning products and other consumer formulations; as a chiral building block and lactone-derived segment for polymers and plastics; as a specialty epoxy-lactone scaffold for coatings and inks; and as a potential synthetic intermediate in pharmaceutical or agrochemical research, all subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 169.88
    methanol 274.4
    isopropanol 207.67
    water 5.64
    ethyl acetate 478.17
    n-propanol 215.69
    acetone 561.95
    n-butanol 205.19
    acetonitrile 468.6
    DMF 698.56
    toluene 675.13
    isobutanol 211.05
    1,4-dioxane 802.96
    methyl acetate 562.17
    THF 1199.23
    2-butanone 595.49
    n-pentanol 128.67
    sec-butanol 195.95
    n-hexane 19.29
    ethylene glycol 90.51
    NMP 821.66
    cyclohexane 86.14
    DMSO 466.8
    n-butyl acetate 309.92
    n-octanol 134.78
    chloroform 2435.72
    n-propyl acetate 283.88
    acetic acid 310.99
    dichloromethane 1731.67
    cyclohexanone 1023.48
    propylene glycol 115.46
    isopropyl acetate 341.03
    DMAc 628.49
    2-ethoxyethanol 204.09
    isopentanol 199.72
    n-heptane 17.94
    ethyl formate 344.5
    1,2-dichloroethane 825.71
    n-hexanol 198.62
    2-methoxyethanol 376.28
    isobutyl acetate 229.87
    tetrachloromethane 333.4
    n-pentyl acetate 275.45
    transcutol 560.75
    n-heptanol 128.59
    ethylbenzene 274.26
    MIBK 291.61
    2-propoxyethanol 365.19
    tert-butanol 203.06
    MTBE 222.88
    2-butoxyethanol 239.6
    propionic acid 351.73
    o-xylene 361.06
    formic acid 136.71
    diethyl ether 249.6
    m-xylene 404.54
    p-xylene 363.03
    chlorobenzene 834.44
    dimethyl carbonate 286.27
    n-octane 10.89
    formamide 205.82
    cyclopentanone 1204.66
    2-pentanone 424.22
    anisole 432.36
    cyclopentyl methyl ether 518.68
    gamma-butyrolactone 1289.41
    1-methoxy-2-propanol 313.53
    pyridine 1073.46
    3-pentanone 400.34
    furfural 1113.22
    n-dodecane 12.27
    diethylene glycol 289.83
    diisopropyl ether 112.65
    tert-amyl alcohol 172.91
    acetylacetone 582.97
    n-hexadecane 15.2
    acetophenone 445.14
    methyl propionate 431.74
    isopentyl acetate 308.45
    trichloroethylene 1845.4
    n-nonanol 118.94
    cyclohexanol 355.66
    benzyl alcohol 372.45
    2-ethylhexanol 131.89
    isooctanol 117.08
    dipropyl ether 126.95
    1,2-dichlorobenzene 716.16
    ethyl lactate 189.36
    propylene carbonate 749.22
    n-methylformamide 409.35
    2-pentanol 151.67
    n-pentane 26.69
    1-propoxy-2-propanol 243.6
    1-methoxy-2-propyl acetate 377.66
    2-(2-methoxypropoxy) propanol 243.69
    mesitylene 234.86
    ε-caprolactone 848.22
    p-cymene 150.06
    epichlorohydrin 1147.98
    1,1,1-trichloroethane 865.64
    2-aminoethanol 142.28
    morpholine-4-carbaldehyde 848.48
    sulfolane 1064.54
    2,2,4-trimethylpentane 22.2
    2-methyltetrahydrofuran 766.65
    n-hexyl acetate 382.23
    isooctane 18.34
    2-(2-butoxyethoxy)ethanol 278.21
    sec-butyl acetate 228.41
    tert-butyl acetate 299.77
    decalin 48.82
    glycerin 186.93
    diglyme 533.99
    acrylic acid 367.6
    isopropyl myristate 137.54
    n-butyric acid 370.84
    acetyl acetate 440.6
    di(2-ethylhexyl) phthalate 172.98
    ethyl propionate 275.28
    nitromethane 701.12
    1,2-diethoxyethane 219.24
    benzonitrile 654.05
    trioctyl phosphate 117.28
    1-bromopropane 428.44
    gamma-valerolactone 1277.93
    n-decanol 87.41
    triethyl phosphate 143.19
    4-methyl-2-pentanol 114.73
    propionitrile 433.44
    vinylene carbonate 820.85
    1,1,2-trichlorotrifluoroethane 671.53
    DMS 450.24
    cumene 180.14
    2-octanol 105.97
    2-hexanone 281.99
    octyl acetate 182.59
    limonene 168.45
    1,2-dimethoxyethane 391.36
    ethyl orthosilicate 123.59
    tributyl phosphate 142.83
    diacetone alcohol 280.58
    N,N-dimethylaniline 267.47
    acrylonitrile 606.29
    aniline 551.73
    1,3-propanediol 202.82
    bromobenzene 936.36
    dibromomethane 1054.06
    1,1,2,2-tetrachloroethane 1311.09
    2-methyl-cyclohexyl acetate 231.37
    tetrabutyl urea 168.04
    diisobutyl methanol 88.02
    2-phenylethanol 356.11
    styrene 330.55
    dioctyl adipate 201.31
    dimethyl sulfate 416.28
    ethyl butyrate 225.22
    methyl lactate 253.87
    butyl lactate 221.8
    diethyl carbonate 187.34
    propanediol butyl ether 233.08
    triethyl orthoformate 161.95
    p-tert-butyltoluene 137.75
    methyl 4-tert-butylbenzoate 319.06
    morpholine 723.14
    tert-butylamine 129.73
    n-dodecanol 65.84
    dimethoxymethane 447.86
    ethylene carbonate 652.99
    cyrene 290.03
    2-ethoxyethyl acetate 377.43
    2-ethylhexyl acetate 255.22
    1,2,4-trichlorobenzene 833.51
    4-methylpyridine 1039.49
    dibutyl ether 129.29
    2,6-dimethyl-4-heptanol 88.02
    DEF 391.97
    dimethyl isosorbide 435.78
    tetrachloroethylene 855.95
    eugenol 301.49
    triacetin 402.76
    span 80 215.1
    1,4-butanediol 96.39
    1,1-dichloroethane 872.38
    2-methyl-1-pentanol 144.98
    methyl formate 418.47
    2-methyl-1-butanol 197.88
    n-decane 21.31
    butyronitrile 362.44
    3,7-dimethyl-1-octanol 138.11
    1-chlorooctane 116.22
    1-chlorotetradecane 44.32
    n-nonane 18.65
    undecane 15.54
    tert-butylcyclohexane 36.92
    cyclooctane 31.33
    cyclopentanol 402.25
    tetrahydropyran 710.72
    tert-amyl methyl ether 185.8
    2,5,8-trioxanonane 351.91
    1-hexene 82.22
    2-isopropoxyethanol 167.69
    2,2,2-trifluoroethanol 222.15
    methyl butyrate 344.34

    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