Shyobunone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    21698-44-2

    Molecular formula
    C15H24O

    SMILES
    CC(C)[C@@H]1CC[C@@]([C@@H](C1=O)C(=C)C)(C)C=C

  • Odor profile

    Herbal 78.8%
    Mint 67.79%
    Woody 63.41%
    Camphoreous 54.15%
    Spicy 52.7%
    Green 52.54%
    Fresh 47.77%
    Fruity 47.55%
    Citrus 46.87%
    Cooling 43.88%

    Scent© AI

  • Properties

    XLogP3-AA
    4.9

    Molecular weight
    220.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    264°C

    Flash point est.
    114.93 ˚C

  • Synonyms

    • SHYOBUNONE
    • 21698-44-2
    • Shyobunon
    • (+)-Shyobunone
    • 92NQU4WN5A
    • (2S,3S,6S)-3-ethenyl-3-methyl-6-propan-2-yl-2-prop-1-en-2-ylcyclohexan-1-one
    • CHEBI:68148
    • p-Menthan-3-one, 2-isopropenyl-1-vinyl-, (1S,2R,4S)-
    • (2S,3S,6S)-3-Ethenyl-3-methyl-2-(1-methylethenyl)-6-(1-methylethyl)cyclohexanone
    • Cyclohexanone, 3-ethenyl-3-methyl-2-(1-methylethenyl)-6-(1-methylethyl)-, (2S,3S,6S)-
    • Cyclohexanone, 3-ethenyl-3-methyl-2-(1-methylethenyl)-6-(1-methylethyl)-, (2S-(2alpha,3beta,6alpha))-
    • UNII-92NQU4WN5A
    • CHEMBL1814552
    • DTXSID401019945
    • HY-N1304
    • (2S)-3alpha-Vinyl-3-methyl-2beta-(1-methylvinyl)-6beta-isopropylcyclohexanone
    • AKOS032962114
    • FS-9572
    • DA-77831
    • CS-0016708
    • Q27136638
    • CYCLOHEXANONE, 3-ETHENYL-3-METHYL-2-(1-METHYLETHENYL)-6-(1-METHYLETHYL)-, (2S-(2.ALPHA.,3.BETA.,6.ALPHA.))-

  • Applications

    Shyobunone (CAS 21698-44-2) is a natural sesquiterpene ketone found predominantly in calamus (Acorus spp.) essential oils and some other aromatic plants; in practice it is used and studied in several ways: (1) as a fragrance material with warm woody, slightly camphoraceous and herbal facets that add dryness, depth and persistence to woody, fougère, spicy-aromatic and classic accords, typically at trace levels or as an olfactory reference; (2) as an analytical/QA reference standard in GC–MS/GC–FID for identification, quantitation, provenance tracing and authentication of calamus oils and herbal preparations, and as a chemotaxonomic marker; (3) as a structural scaffold/precursor for semisynthesis and odor optimization of sesquiterpene derivatives in natural products chemistry; (4) as a preclinical research target for sesquiterpene-typical bioactivities such as antibacterial, antioxidant, insect-repellent/inhibitory effects and enzyme modulation, while pharmaceutical utility remains unproven; (5) as a component in lab-scale food-preservation studies via essential-oil blends with antimicrobial action; direct use in flavorings is uncommon due to regulatory constraints associated with calamus, so shyobunone’s role is mainly in R&D, with strict compliance to safety frameworks (e.g., IFRA, REACH) and attention to stereoisomers (isoshyobunone/epimers), impurities and purity when used in cosmetics, perfumery or research.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1198.93
    methanol 1274.26
    isopropanol 1445.76
    water 0.95
    ethyl acetate 660.45
    n-propanol 1130.81
    acetone 891.17
    n-butanol 1143.84
    acetonitrile 918.87
    DMF 1019.51
    toluene 1003.67
    isobutanol 1011.75
    1,4-dioxane 1835.53
    methyl acetate 625.43
    THF 3187.96
    2-butanone 825.79
    n-pentanol 727.41
    sec-butanol 1065.92
    n-hexane 242.23
    ethylene glycol 88.02
    NMP 965.5
    cyclohexane 572.92
    DMSO 452.27
    n-butyl acetate 727.89
    n-octanol 446.32
    chloroform 3062.3
    n-propyl acetate 405.73
    acetic acid 546.53
    dichloromethane 1976.78
    cyclohexanone 1642.74
    propylene glycol 195.43
    isopropyl acetate 479.05
    DMAc 568.04
    2-ethoxyethanol 402.56
    isopentanol 932.52
    n-heptane 178.76
    ethyl formate 542.71
    1,2-dichloroethane 1079.61
    n-hexanol 1187.0
    2-methoxyethanol 755.7
    isobutyl acetate 314.47
    tetrachloromethane 537.18
    n-pentyl acetate 462.16
    transcutol 977.05
    n-heptanol 456.34
    ethylbenzene 412.86
    MIBK 514.51
    2-propoxyethanol 891.12
    tert-butanol 1251.33
    MTBE 929.6
    2-butoxyethanol 442.75
    propionic acid 470.62
    o-xylene 466.51
    formic acid 138.77
    diethyl ether 1070.75
    m-xylene 657.32
    p-xylene 517.98
    chlorobenzene 998.18
    dimethyl carbonate 190.28
    n-octane 65.63
    formamide 186.79
    cyclopentanone 1591.84
    2-pentanone 766.64
    anisole 479.38
    cyclopentyl methyl ether 1168.42
    gamma-butyrolactone 1402.9
    1-methoxy-2-propanol 723.72
    pyridine 1506.65
    3-pentanone 505.59
    furfural 884.81
    n-dodecane 43.46
    diethylene glycol 406.8
    diisopropyl ether 317.86
    tert-amyl alcohol 819.07
    acetylacetone 551.05
    n-hexadecane 51.65
    acetophenone 395.97
    methyl propionate 457.81
    isopentyl acetate 669.39
    trichloroethylene 2003.24
    n-nonanol 349.18
    cyclohexanol 1310.22
    benzyl alcohol 464.89
    2-ethylhexanol 550.87
    isooctanol 361.14
    dipropyl ether 483.79
    1,2-dichlorobenzene 652.79
    ethyl lactate 174.6
    propylene carbonate 785.2
    n-methylformamide 508.33
    2-pentanol 796.39
    n-pentane 297.66
    1-propoxy-2-propanol 680.17
    1-methoxy-2-propyl acetate 519.91
    2-(2-methoxypropoxy) propanol 331.79
    mesitylene 376.33
    ε-caprolactone 1135.45
    p-cymene 280.57
    epichlorohydrin 1474.36
    1,1,1-trichloroethane 1285.08
    2-aminoethanol 288.76
    morpholine-4-carbaldehyde 835.11
    sulfolane 940.67
    2,2,4-trimethylpentane 102.26
    2-methyltetrahydrofuran 2032.29
    n-hexyl acetate 664.78
    isooctane 92.94
    2-(2-butoxyethoxy)ethanol 460.97
    sec-butyl acetate 294.14
    tert-butyl acetate 481.19
    decalin 150.41
    glycerin 195.71
    diglyme 697.52
    acrylic acid 340.07
    isopropyl myristate 224.94
    n-butyric acid 872.48
    acetyl acetate 350.14
    di(2-ethylhexyl) phthalate 218.99
    ethyl propionate 319.52
    nitromethane 626.9
    1,2-diethoxyethane 530.72
    benzonitrile 750.24
    trioctyl phosphate 168.94
    1-bromopropane 1068.29
    gamma-valerolactone 1509.42
    n-decanol 247.16
    triethyl phosphate 168.17
    4-methyl-2-pentanol 432.42
    propionitrile 945.67
    vinylene carbonate 693.84
    1,1,2-trichlorotrifluoroethane 623.76
    DMS 320.0
    cumene 268.57
    2-octanol 352.66
    2-hexanone 525.2
    octyl acetate 287.87
    limonene 401.02
    1,2-dimethoxyethane 789.99
    ethyl orthosilicate 177.15
    tributyl phosphate 186.67
    diacetone alcohol 485.34
    N,N-dimethylaniline 316.18
    acrylonitrile 805.1
    aniline 815.99
    1,3-propanediol 493.93
    bromobenzene 1042.59
    dibromomethane 1599.78
    1,1,2,2-tetrachloroethane 1512.26
    2-methyl-cyclohexyl acetate 365.34
    tetrabutyl urea 236.21
    diisobutyl methanol 266.32
    2-phenylethanol 604.37
    styrene 468.47
    dioctyl adipate 269.46
    dimethyl sulfate 234.15
    ethyl butyrate 388.81
    methyl lactate 207.44
    butyl lactate 313.75
    diethyl carbonate 246.05
    propanediol butyl ether 435.59
    triethyl orthoformate 278.16
    p-tert-butyltoluene 273.55
    methyl 4-tert-butylbenzoate 374.56
    morpholine 2075.58
    tert-butylamine 939.57
    n-dodecanol 175.7
    dimethoxymethane 687.11
    ethylene carbonate 626.86
    cyrene 329.31
    2-ethoxyethyl acetate 438.05
    2-ethylhexyl acetate 522.23
    1,2,4-trichlorobenzene 710.42
    4-methylpyridine 1562.67
    dibutyl ether 409.7
    2,6-dimethyl-4-heptanol 266.32
    DEF 600.18
    dimethyl isosorbide 600.38
    tetrachloroethylene 993.0
    eugenol 338.24
    triacetin 332.55
    span 80 371.91
    1,4-butanediol 198.14
    1,1-dichloroethane 1498.91
    2-methyl-1-pentanol 584.07
    methyl formate 420.38
    2-methyl-1-butanol 889.17
    n-decane 85.1
    butyronitrile 1207.11
    3,7-dimethyl-1-octanol 368.26
    1-chlorooctane 318.19
    1-chlorotetradecane 108.75
    n-nonane 90.16
    undecane 59.69
    tert-butylcyclohexane 125.88
    cyclooctane 162.21
    cyclopentanol 1219.74
    tetrahydropyran 2681.09
    tert-amyl methyl ether 554.78
    2,5,8-trioxanonane 455.97
    1-hexene 609.03
    2-isopropoxyethanol 324.09
    2,2,2-trifluoroethanol 160.47
    methyl butyrate 448.46

    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
Calamus (Italy) root 8015-79-0 Acorus calamus L., fam. Araceae 1.24%
Calamus (Mongolia) root 8015-79-0 Acorus calamus L., fam. Araceae 3.7%
Calamus (Canada) root 8015-79-0 Acorus calamus L., fam. Araceae 2.09%
Calamus (Japan) 2 root 8015-79-0 Acorus calamus L., fam. Araceae 1.8%