(5S,8R,8aR)-1,2,5,6,7,8-Hexahydro-3,8,9,9-tetramethyl-4H-5,8a-methanoazulen-4-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    5986-54-9

    Molecular formula
    C15H22O

    SMILES
    C[C@@H]1CC[C@@H]2C(=O)C3=C(CC[C@]13C2(C)C)C

  • Odor profile

    Woody 86.59%
    Cedar 52.99%
    Amber 50.05%
    Dry 48.2%
    Spicy 38.46%
    Musk 37.41%
    Tobacco 37.32%
    Vetiver 35.34%
    Camphoreous 33.86%
    Earthy 32.81%

    Scent© AI

  • Properties

    XLogP3-AA
    3.5

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    311°C

    Flash point est.
    127.26 ˚C

  • Synonyms

    • 5986-54-9
    • (5S,8R,8aR)-1,2,5,6,7,8-Hexahydro-3,8,9,9-tetramethyl-4H-5,8a-methanoazulen-4-one
    • JAWSHISYWRRQQQ-HFAKWTLXSA-N
    • DTXSID001132236

  • Applications

    This chiral bicyclic sesquiterpenoid ketone is used and studied widely for its warm woody–amber, dry cedar, slightly citrus-grapefruit nuance and good substantivity: employed as a middle/base-note odorant, fixative, and malodor masker in woody-amber perfumery, personal care, soaps, detergents, candles, and air care; evaluated in microencapsulation and polymer slow-release systems to enhance fabric and surface substantivity; used as a GC/GC-MS reference to build retention-index libraries and to develop enantioselective GC methods for terpenoids; serves as a chiral pool scaffold for aroma-chemical synthesis (hydrogenation, epoxidation, Baeyer–Villiger to amber lactones, Michael and Diels–Alder chemistry) and for asymmetric catalysis studies; investigated as a mosquito and tick repellent and as a repellent/antifeedant against stored-product insects in sustainable, controlled-release and impregnated-material formats; and applied in teaching and research on stereochemistry, chiroptical properties, and NMR/IR of robust bicyclic enone systems.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 240.55
    methanol 380.72
    isopropanol 216.07
    water 8.27
    ethyl acetate 489.22
    n-propanol 257.88
    acetone 677.26
    n-butanol 221.87
    acetonitrile 590.23
    DMF 975.37
    toluene 683.62
    isobutanol 175.2
    1,4-dioxane 1130.97
    methyl acetate 489.09
    THF 1806.05
    2-butanone 477.16
    n-pentanol 116.27
    sec-butanol 148.84
    n-hexane 25.93
    ethylene glycol 91.0
    NMP 647.51
    cyclohexane 74.5
    DMSO 426.11
    n-butyl acetate 256.04
    n-octanol 88.55
    chloroform 1616.05
    n-propyl acetate 215.53
    acetic acid 280.4
    dichloromethane 1366.05
    cyclohexanone 860.78
    propylene glycol 77.57
    isopropyl acetate 327.48
    DMAc 370.37
    2-ethoxyethanol 225.0
    isopentanol 179.72
    n-heptane 21.65
    ethyl formate 332.47
    1,2-dichloroethane 861.8
    n-hexanol 183.27
    2-methoxyethanol 521.83
    isobutyl acetate 158.29
    tetrachloromethane 314.42
    n-pentyl acetate 221.8
    transcutol 339.68
    n-heptanol 115.58
    ethylbenzene 183.32
    MIBK 305.31
    2-propoxyethanol 407.81
    tert-butanol 200.71
    MTBE 227.6
    2-butoxyethanol 225.09
    propionic acid 247.34
    o-xylene 269.1
    formic acid 160.2
    diethyl ether 399.96
    m-xylene 410.96
    p-xylene 234.36
    chlorobenzene 648.79
    dimethyl carbonate 310.52
    n-octane 12.16
    formamide 271.79
    cyclopentanone 1284.51
    2-pentanone 468.7
    anisole 335.95
    cyclopentyl methyl ether 705.26
    gamma-butyrolactone 1332.73
    1-methoxy-2-propanol 411.83
    pyridine 1040.06
    3-pentanone 364.63
    furfural 918.98
    n-dodecane 9.94
    diethylene glycol 295.97
    diisopropyl ether 130.21
    tert-amyl alcohol 133.65
    acetylacetone 561.63
    n-hexadecane 12.23
    acetophenone 279.75
    methyl propionate 435.05
    isopentyl acetate 239.04
    trichloroethylene 1589.94
    n-nonanol 83.5
    cyclohexanol 258.61
    benzyl alcohol 239.89
    2-ethylhexanol 104.28
    isooctanol 95.65
    dipropyl ether 134.72
    1,2-dichlorobenzene 506.34
    ethyl lactate 119.09
    propylene carbonate 546.03
    n-methylformamide 600.91
    2-pentanol 147.15
    n-pentane 34.89
    1-propoxy-2-propanol 240.42
    1-methoxy-2-propyl acetate 322.38
    2-(2-methoxypropoxy) propanol 158.63
    mesitylene 230.76
    ε-caprolactone 616.67
    p-cymene 102.03
    epichlorohydrin 1313.64
    1,1,1-trichloroethane 822.62
    2-aminoethanol 145.54
    morpholine-4-carbaldehyde 759.79
    sulfolane 926.39
    2,2,4-trimethylpentane 17.42
    2-methyltetrahydrofuran 792.2
    n-hexyl acetate 261.78
    isooctane 22.32
    2-(2-butoxyethoxy)ethanol 201.01
    sec-butyl acetate 157.66
    tert-butyl acetate 324.17
    decalin 34.76
    glycerin 144.92
    diglyme 447.52
    acrylic acid 247.66
    isopropyl myristate 96.65
    n-butyric acid 355.18
    acetyl acetate 337.4
    di(2-ethylhexyl) phthalate 103.32
    ethyl propionate 235.6
    nitromethane 828.74
    1,2-diethoxyethane 198.49
    benzonitrile 501.01
    trioctyl phosphate 77.46
    1-bromopropane 419.23
    gamma-valerolactone 1277.77
    n-decanol 58.77
    triethyl phosphate 99.9
    4-methyl-2-pentanol 111.38
    propionitrile 546.79
    vinylene carbonate 602.57
    1,1,2-trichlorotrifluoroethane 481.91
    DMS 307.63
    cumene 116.63
    2-octanol 83.57
    2-hexanone 197.48
    octyl acetate 117.65
    limonene 123.12
    1,2-dimethoxyethane 409.91
    ethyl orthosilicate 95.05
    tributyl phosphate 84.92
    diacetone alcohol 277.28
    N,N-dimethylaniline 195.06
    acrylonitrile 770.2
    aniline 460.29
    1,3-propanediol 234.71
    bromobenzene 706.3
    dibromomethane 825.95
    1,1,2,2-tetrachloroethane 909.17
    2-methyl-cyclohexyl acetate 160.33
    tetrabutyl urea 111.23
    diisobutyl methanol 73.9
    2-phenylethanol 274.69
    styrene 227.61
    dioctyl adipate 121.34
    dimethyl sulfate 394.08
    ethyl butyrate 169.07
    methyl lactate 184.83
    butyl lactate 143.51
    diethyl carbonate 125.93
    propanediol butyl ether 137.06
    triethyl orthoformate 127.48
    p-tert-butyltoluene 107.24
    methyl 4-tert-butylbenzoate 264.53
    morpholine 982.48
    tert-butylamine 132.85
    n-dodecanol 43.24
    dimethoxymethane 830.7
    ethylene carbonate 507.84
    cyrene 199.9
    2-ethoxyethyl acetate 293.56
    2-ethylhexyl acetate 188.16
    1,2,4-trichlorobenzene 528.38
    4-methylpyridine 898.89
    dibutyl ether 97.32
    2,6-dimethyl-4-heptanol 73.9
    DEF 379.69
    dimethyl isosorbide 330.66
    tetrachloroethylene 714.26
    eugenol 235.43
    triacetin 218.64
    span 80 135.65
    1,4-butanediol 83.41
    1,1-dichloroethane 779.69
    2-methyl-1-pentanol 103.27
    methyl formate 537.76
    2-methyl-1-butanol 161.04
    n-decane 17.14
    butyronitrile 459.36
    3,7-dimethyl-1-octanol 83.69
    1-chlorooctane 77.94
    1-chlorotetradecane 31.44
    n-nonane 15.41
    undecane 12.87
    tert-butylcyclohexane 30.77
    cyclooctane 30.57
    cyclopentanol 332.83
    tetrahydropyran 846.1
    tert-amyl methyl ether 154.95
    2,5,8-trioxanonane 260.42
    1-hexene 87.82
    2-isopropoxyethanol 156.91
    2,2,2-trifluoroethanol 198.72
    methyl butyrate 271.13

    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

Botanical

Name CAS Botanical Proportion
Cyperus scariosus Cyperus scariosus R.Br., fam. Cupressaceae 7.6%
Patchouli (India) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 2.28%
Patchouli (Indonesia) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.05%
Cyperus maculatus rhizome Cyperus maculatus Boeck, fam. Cyperaceae 1.0%