3,8-Dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one, (3S,5R,8S)-

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  • Identifiers

    CAS number
    18374-76-0

    Molecular formula
    C15H22O

    SMILES
    C[C@H]1CC[C@H](CC2=C1C(=O)C[C@@H]2C)C(=C)C

  • Odor profile

    Woody 69.25%
    Mint 46.02%
    Spicy 45.51%
    Herbal 45.02%
    Sweet 42.21%
    Fresh 39.42%
    Tobacco 38.21%
    Citrus 37.5%
    Camphoreous 36.66%
    Dry 31.58%

    Scent© AI

  • Properties

    XLogP3-AA
    3.7

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    309°C

    Flash point est.
    99.41 ˚C

  • Synonyms

    • Rotundone
    • 18374-76-0
    • Fema No. 4867
    • U33H52BQ0P
    • UNII-U33H52BQ0P
    • Guaia-1(5),11-dien-2-one, (-)-
    • (-)-Rotundone
    • 3,8-Dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one, (3S,5R,8S)-
    • (3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
    • 3,4,5,6,7,8-Hexahydro-3alpha,8alpha-dimethyl-5alpha-(1-methylethenyl)azulene-1(2H)-one
    • Rotundone - 30%
    • Rotundone - 90%
    • SCHEMBL180456
    • CHEBI:191710
    • NUWMTBMCSQWPDG-SDDRHHMPSA-N
    • DTXSID301030485
    • FR165899
    • XR175543
    • Q15424773
    • (3s,5r,8s)-5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1(2h)-azulenone

  • Applications

    In terpene chemistry R&D, 3,8-Dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one, (3S,5R,8S)- (CAS 18374-76-0) is used as a reference standard and reactive scaffold to probe mechanisms, kinetics, and stereoselectivity on a sesquiterpenone framework; its activated ketone and isopropenyl handle make it a convenient intermediate for reductions, oxidations, Michael additions, and stereocontrolled derivatizations, enabling libraries of novel derivatives for screening odor, materials, and biological properties; it is also valuable for developing/calibrating analytical methods (GC-MS, chiral HPLC), tracing botanical origin and chemical fingerprints of sesquiterpene-rich essential oils, studying stability during storage, and teaching absolute-configuration determination and spectroscopy in advanced organic chemistry.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1527.1
    methanol 1702.04
    isopropanol 2014.23
    water 0.97
    ethyl acetate 1714.56
    n-propanol 1679.13
    acetone 2514.79
    n-butanol 1547.91
    acetonitrile 2668.18
    DMF 2608.73
    toluene 2577.19
    isobutanol 1361.82
    1,4-dioxane 4113.42
    methyl acetate 1781.94
    THF 4866.84
    2-butanone 2410.62
    n-pentanol 808.83
    sec-butanol 1348.06
    n-hexane 117.97
    ethylene glycol 126.41
    NMP 1634.08
    cyclohexane 421.93
    DMSO 1295.23
    n-butyl acetate 1397.54
    n-octanol 386.05
    chloroform 8145.2
    n-propyl acetate 1036.02
    acetic acid 791.17
    dichloromethane 6117.47
    cyclohexanone 3552.08
    propylene glycol 242.08
    isopropyl acetate 1075.56
    DMAc 1213.67
    2-ethoxyethanol 755.02
    isopentanol 1297.53
    n-heptane 79.04
    ethyl formate 1411.41
    1,2-dichloroethane 3079.82
    n-hexanol 1058.39
    2-methoxyethanol 1487.44
    isobutyl acetate 669.34
    tetrachloromethane 1096.65
    n-pentyl acetate 835.82
    transcutol 2546.72
    n-heptanol 442.54
    ethylbenzene 847.84
    MIBK 986.51
    2-propoxyethanol 1281.8
    tert-butanol 1495.2
    MTBE 1589.76
    2-butoxyethanol 704.24
    propionic acid 979.97
    o-xylene 983.63
    formic acid 213.19
    diethyl ether 1816.79
    m-xylene 1262.97
    p-xylene 1072.31
    chlorobenzene 2505.13
    dimethyl carbonate 526.93
    n-octane 35.43
    formamide 431.23
    cyclopentanone 3489.0
    2-pentanone 1708.57
    anisole 1320.52
    cyclopentyl methyl ether 1693.05
    gamma-butyrolactone 3086.7
    1-methoxy-2-propanol 1220.38
    pyridine 4510.82
    3-pentanone 1190.63
    furfural 2421.92
    n-dodecane 25.28
    diethylene glycol 658.31
    diisopropyl ether 450.36
    tert-amyl alcohol 993.16
    acetylacetone 1491.64
    n-hexadecane 32.04
    acetophenone 1055.69
    methyl propionate 1157.05
    isopentyl acetate 1242.51
    trichloroethylene 5837.73
    n-nonanol 321.09
    cyclohexanol 1632.96
    benzyl alcohol 1097.65
    2-ethylhexanol 564.89
    isooctanol 367.53
    dipropyl ether 610.25
    1,2-dichlorobenzene 1645.56
    ethyl lactate 345.58
    propylene carbonate 1600.71
    n-methylformamide 1384.2
    2-pentanol 987.13
    n-pentane 143.8
    1-propoxy-2-propanol 929.21
    1-methoxy-2-propyl acetate 1018.77
    2-(2-methoxypropoxy) propanol 532.13
    mesitylene 651.29
    ε-caprolactone 2392.15
    p-cymene 399.36
    epichlorohydrin 3686.37
    1,1,1-trichloroethane 3207.37
    2-aminoethanol 386.29
    morpholine-4-carbaldehyde 1955.06
    sulfolane 1955.24
    2,2,4-trimethylpentane 76.8
    2-methyltetrahydrofuran 3358.96
    n-hexyl acetate 1026.6
    isooctane 73.92
    2-(2-butoxyethoxy)ethanol 804.19
    sec-butyl acetate 666.02
    tert-butyl acetate 968.72
    decalin 138.39
    glycerin 284.46
    diglyme 1657.51
    acrylic acid 730.04
    isopropyl myristate 306.59
    n-butyric acid 1611.35
    acetyl acetate 883.11
    di(2-ethylhexyl) phthalate 311.17
    ethyl propionate 779.2
    nitromethane 1810.89
    1,2-diethoxyethane 1151.55
    benzonitrile 2195.47
    trioctyl phosphate 210.38
    1-bromopropane 1974.02
    gamma-valerolactone 3412.29
    n-decanol 213.32
    triethyl phosphate 288.4
    4-methyl-2-pentanol 511.86
    propionitrile 2305.44
    vinylene carbonate 1660.89
    1,1,2-trichlorotrifluoroethane 1476.45
    DMS 780.43
    cumene 472.65
    2-octanol 330.29
    2-hexanone 1072.69
    octyl acetate 392.81
    limonene 504.53
    1,2-dimethoxyethane 1824.68
    ethyl orthosilicate 286.79
    tributyl phosphate 268.3
    diacetone alcohol 824.96
    N,N-dimethylaniline 677.28
    acrylonitrile 2377.67
    aniline 2120.35
    1,3-propanediol 803.61
    bromobenzene 2706.09
    dibromomethane 4015.84
    1,1,2,2-tetrachloroethane 3949.43
    2-methyl-cyclohexyl acetate 532.66
    tetrabutyl urea 326.35
    diisobutyl methanol 320.52
    2-phenylethanol 1076.97
    styrene 1118.91
    dioctyl adipate 405.03
    dimethyl sulfate 599.74
    ethyl butyrate 803.76
    methyl lactate 426.08
    butyl lactate 512.85
    diethyl carbonate 494.97
    propanediol butyl ether 597.92
    triethyl orthoformate 495.33
    p-tert-butyltoluene 373.27
    methyl 4-tert-butylbenzoate 633.51
    morpholine 4214.59
    tert-butylamine 952.54
    n-dodecanol 151.43
    dimethoxymethane 1541.11
    ethylene carbonate 1504.61
    cyrene 553.55
    2-ethoxyethyl acetate 1033.22
    2-ethylhexyl acetate 904.87
    1,2,4-trichlorobenzene 1830.37
    4-methylpyridine 4291.98
    dibutyl ether 554.73
    2,6-dimethyl-4-heptanol 320.52
    DEF 1388.64
    dimethyl isosorbide 1005.45
    tetrachloroethylene 2439.03
    eugenol 621.69
    triacetin 706.91
    span 80 497.2
    1,4-butanediol 283.53
    1,1-dichloroethane 3942.1
    2-methyl-1-pentanol 747.18
    methyl formate 1108.58
    2-methyl-1-butanol 1151.3
    n-decane 50.25
    butyronitrile 2340.27
    3,7-dimethyl-1-octanol 397.06
    1-chlorooctane 306.89
    1-chlorotetradecane 100.02
    n-nonane 48.94
    undecane 33.68
    tert-butylcyclohexane 113.35
    cyclooctane 101.79
    cyclopentanol 1558.56
    tetrahydropyran 4562.2
    tert-amyl methyl ether 779.45
    2,5,8-trioxanonane 896.42
    1-hexene 588.32
    2-isopropoxyethanol 569.26
    2,2,2-trifluoroethanol 338.74
    methyl butyrate 1180.51

    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 5.1%
Agarwood 2 Aquilaria agallocha Roxb., fam. Thymelaeaceae 0.1%