beta-THUJONE

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  • Identifiers

    CAS number
    471-15-8

    Molecular formula
    C10H16O

    SMILES
    C[C@H]1[C@H]2C[C@]2(CC1=O)C(C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1100.0

  • Odor profile

    Fragrance
    Woody 80.56%
    Herbal 63.83%
    Spicy 62.34%
    Mint 51.23%
    Camphoreous 49.32%
    Fresh 40.55%
    Cooling 39.98%
    Cedar 38.98%
    Pine 36.25%
    Earthy 33.71%

     

    Flavor
    Bitter 65.2%
    Herbal 31.24%
    Minty 29.11%
    Cedarleaf 25.62%
    Spice 22.53%
    Herb 21.8%
    Green 21.2%
    Woody 20.57%
    Lovage 20.24%
    Green tea 20.19%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    8.36 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    225°C

    Flash point

    • 65.19 ˚C est.

  • Synonyms

    • beta-Thujone
    • (+)-Isothujone
    • (+)-Thujone
    • (+)-3-Thujone
    • 471-15-8
    • Isothujone
    • d-Isothujone
    • (+)-beta-Thujone
    • D-beta-Thujone
    • THUJONE
    • .beta.-Thujone
    • (1S,4S,5R)-(+)-3-thujanone
    • trans-thujone
    • cis-Thujone
    • 8ZI5R3T54Q
    • NSC 67392
    • 3-Thujanone, (1S,4S,5R)-(+)-
    • .BETA.-THUJONE [MI]
    • (1S,4S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
    • CHEBI:50045
    • (1s,4s,5r)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
    • NSC-67392
    • [1S-(1alpha,4beta,5alpha)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one
    • 3-isothujone
    • (1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one (1S,4S,5R)-thujan-3-one
    • BICYCLO(3.1.0)HEXAN-3-ONE, 4-METHYL-1-(1-METHYLETHYL)-, (1S,4S,5R)
    • (+)-thujan-3-one
    • DTXSID20859476
    • UNII-8ZI5R3T54Q
    • NSC67392
    • beta Thujone
    • AI3-11501
    • EINECS 214-405-7
    • rel-(1R,4R,5S)-1-isopropyl-4-methylbicyclo(3.1.0)hexan-3-one
    • rel-(1R,4R,5S)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
    • rel-(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one
    • rel-(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
    • D-beta
    • NSC 407281
    • thujone (trans-)
    • (+)-cis-Thujone
    • (+)-b-Thujone
    • 3-Thujanone (8CI)
    • beta-thujone, 1S-(1alpha,4beta,5alpha)-isomer
    • SCHEMBL337540
    • beta-thujone, (1S-(1alpha,4alpha,5alpha))-isomer
    • (1S,4S,5R)-thujan-3-one
    • CHEMBL3277898
    • DTXSID7057575
    • CHEBI:50044
    • DTXCID90209404
    • USMNOWBWPHYOEA-XKSSXDPKSA-N
    • rel-(1R,4R,5S)-thujan-3-one
    • (1S,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
    • (+)-Isothujone ((+)-beta-Thujone)
    • AKOS006240449
    • LMPR0102120039
    • Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S-(1-alpha,4-beta,5-alpha))-
    • NS00076400
    • C20260
    • Q27121861

  • Applications

    beta-THUJONE (CAS 471-15-8) is a natural aroma-chemical component derived from essential oils of Artemisia and related plants; in industry it is primarily used as an odorant note in perfumery/fragrance and as a flavor/aroma component in food applications at restricted levels; it is also found in cosmetics and personal care products where a distinctive herbal note may be desired; in industrial manufacturing it can serve as an intermediate in the synthesis of other terpenoids or as a fragrance ingredient in scent systems for cleaning or household products; use is subject to local regulations and formulation limits.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1150.49
    methanol 1202.47
    isopropanol 1126.47
    water 16.76
    ethyl acetate 1003.91
    n-propanol 944.48
    acetone 1335.81
    n-butanol 751.61
    acetonitrile 1158.04
    DMF 1258.69
    toluene 455.29
    isobutanol 697.06
    1,4-dioxane 1753.46
    methyl acetate 1131.33
    THF 1778.15
    2-butanone 1054.67
    n-pentanol 382.11
    sec-butanol 656.03
    n-hexane 47.85
    ethylene glycol 429.58
    NMP 435.54
    cyclohexane 80.68
    DMSO 750.11
    n-butyl acetate 489.2
    n-octanol 236.37
    chloroform 1969.18
    n-propyl acetate 465.76
    acetic acid 592.48
    dichloromethane 1484.97
    cyclohexanone 765.6
    propylene glycol 473.63
    isopropyl acetate 722.43
    DMAc 780.44
    2-ethoxyethanol 799.64
    isopentanol 613.85
    n-heptane 36.95
    ethyl formate 602.74
    1,2-dichloroethane 953.48
    n-hexanol 495.12
    2-methoxyethanol 1557.6
    isobutyl acetate 357.09
    tetrachloromethane 371.26
    n-pentyl acetate 326.99
    transcutol 1419.62
    n-heptanol 267.84
    ethylbenzene 271.03
    MIBK 537.19
    2-propoxyethanol 1080.73
    tert-butanol 979.53
    MTBE 858.61
    2-butoxyethanol 570.36
    propionic acid 592.56
    o-xylene 273.25
    formic acid 326.53
    diethyl ether 793.72
    m-xylene 331.82
    p-xylene 398.75
    chlorobenzene 583.83
    dimethyl carbonate 394.14
    n-octane 23.67
    formamide 540.89
    cyclopentanone 1085.34
    2-pentanone 807.39
    anisole 653.16
    cyclopentyl methyl ether 576.28
    gamma-butyrolactone 1100.29
    1-methoxy-2-propanol 1206.26
    pyridine 1095.16
    3-pentanone 556.05
    furfural 994.29
    n-dodecane 21.51
    diethylene glycol 933.69
    diisopropyl ether 275.42
    tert-amyl alcohol 567.5
    acetylacetone 990.56
    n-hexadecane 24.86
    acetophenone 455.18
    methyl propionate 724.18
    isopentyl acetate 494.99
    trichloroethylene 1597.12
    n-nonanol 215.28
    cyclohexanol 402.93
    benzyl alcohol 443.7
    2-ethylhexanol 226.61
    isooctanol 214.2
    dipropyl ether 283.58
    1,2-dichlorobenzene 471.91
    ethyl lactate 262.08
    propylene carbonate 580.05
    n-methylformamide 850.5
    2-pentanol 496.83
    n-pentane 64.18
    1-propoxy-2-propanol 662.7
    1-methoxy-2-propyl acetate 653.76
    2-(2-methoxypropoxy) propanol 401.15
    mesitylene 209.2
    ε-caprolactone 653.24
    p-cymene 145.75
    epichlorohydrin 1473.85
    1,1,1-trichloroethane 1024.25
    2-aminoethanol 671.08
    morpholine-4-carbaldehyde 908.94
    sulfolane 711.94
    2,2,4-trimethylpentane 36.05
    2-methyltetrahydrofuran 913.97
    n-hexyl acetate 441.9
    isooctane 40.11
    2-(2-butoxyethoxy)ethanol 556.88
    sec-butyl acetate 375.35
    tert-butyl acetate 653.54
    decalin 46.68
    glycerin 556.76
    diglyme 1091.27
    acrylic acid 506.19
    isopropyl myristate 180.66
    n-butyric acid 709.31
    acetyl acetate 634.59
    di(2-ethylhexyl) phthalate 157.34
    ethyl propionate 458.61
    nitromethane 1297.92
    1,2-diethoxyethane 578.74
    benzonitrile 599.42
    trioctyl phosphate 112.45
    1-bromopropane 545.12
    gamma-valerolactone 1387.13
    n-decanol 155.93
    triethyl phosphate 160.09
    4-methyl-2-pentanol 339.94
    propionitrile 885.57
    vinylene carbonate 609.79
    1,1,2-trichlorotrifluoroethane 767.4
    DMS 475.11
    cumene 194.95
    2-octanol 187.2
    2-hexanone 465.77
    octyl acetate 215.22
    limonene 153.65
    1,2-dimethoxyethane 1194.48
    ethyl orthosilicate 156.44
    tributyl phosphate 135.65
    diacetone alcohol 652.08
    N,N-dimethylaniline 332.93
    acrylonitrile 1067.75
    aniline 570.79
    1,3-propanediol 925.99
    bromobenzene 558.03
    dibromomethane 920.85
    1,1,2,2-tetrachloroethane 1189.54
    2-methyl-cyclohexyl acetate 240.87
    tetrabutyl urea 153.74
    diisobutyl methanol 178.7
    2-phenylethanol 489.96
    styrene 318.53
    dioctyl adipate 192.17
    dimethyl sulfate 420.08
    ethyl butyrate 339.18
    methyl lactate 409.87
    butyl lactate 257.06
    diethyl carbonate 254.36
    propanediol butyl ether 430.57
    triethyl orthoformate 233.6
    p-tert-butyltoluene 150.92
    methyl 4-tert-butylbenzoate 364.63
    morpholine 1558.53
    tert-butylamine 583.12
    n-dodecanol 117.19
    dimethoxymethane 1054.57
    ethylene carbonate 536.22
    cyrene 295.31
    2-ethoxyethyl acetate 531.07
    2-ethylhexyl acetate 336.22
    1,2,4-trichlorobenzene 514.35
    4-methylpyridine 956.16
    dibutyl ether 241.55
    2,6-dimethyl-4-heptanol 178.7
    DEF 551.1
    dimethyl isosorbide 551.35
    tetrachloroethylene 827.35
    eugenol 367.13
    triacetin 361.41
    span 80 301.08
    1,4-butanediol 334.98
    1,1-dichloroethane 1234.35
    2-methyl-1-pentanol 315.5
    methyl formate 682.5
    2-methyl-1-butanol 498.34
    n-decane 34.55
    butyronitrile 766.83
    3,7-dimethyl-1-octanol 245.79
    1-chlorooctane 149.64
    1-chlorotetradecane 62.4
    n-nonane 31.83
    undecane 26.45
    tert-butylcyclohexane 51.04
    cyclooctane 30.02
    cyclopentanol 491.08
    tetrahydropyran 1022.77
    tert-amyl methyl ether 439.02
    2,5,8-trioxanonane 613.18
    1-hexene 177.86
    2-isopropoxyethanol 573.71
    2,2,2-trifluoroethanol 381.53
    methyl butyrate 515.17

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.11 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.24 %
Category 2
Products applied to the axillae
 0.21 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.24 %
Category 3
Products applied to the face/body using fingertips
 0.032 % Category 8
Products with significant anogenital exposure
 0.0053 %
Category 4
Products related to fine fragrance
 1.4 % Category 9
Products with body and hand exposure, primarily rinse off
 0.13 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.095 % Category 10A
Household care products with mostly hand contact
 0.13 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.032 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0.22 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.016 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0.0053 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.0053 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.0053 %
Category 6
Products with oral and lip exposure
 0.095 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 9.5 %

Botanical

Name CAS Botanical Proportion
Cistus (Spain) 1 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 0.1%
Mentha requienii 1 Mentha requienii Bentham, fam. Lamiaceae (Labiatae) 0.05%
Mentha requienii 2 Mentha requienii Bentham, fam. Lamiaceae (Labiatae) 0.05%
Pennyroyal 4 8013-99-8 Mentha pulegium L., fam. Lamiaceae (Labiatae) 0.05%
Rhanterium Rhanterium epapposum Oliv. 0.6%
Rosemary (Spain) 3 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Wormwood (Mugwort) (Spain) 1 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 63.3%
Sassafras 1 8006-80-2 Sassafras albidum (Nutt.) Nees, fam. Lauraceae 0.1%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.14%
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Fennel, pepper (Turkey) Foeniculum vulgare Miller, ssp. piperitum, fam. Apiaceae (Umbelliferae) 0.01%
Sage, dalmatian (Italy) 2 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 14.45%
Cinnamomum parthenoxylum (China) 1e Cinnamomum parthenoxylum (Jack) Nees, fam. Lauraceae 1.81%
Patchouli (China) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.01%
Santolina chamaecyparisus 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.15%
Tansy (Finland) 2a 8016-87-3 Tanacetum vulgare L. germacrene chemotype, fam. Asteraceae (Compositae) 7.3%
Tansy (Finland) 2b 8016-87-3 Tanacetum vulgare L. umbellulone chemotype, fam. Asteraceae (Compositae) 12.2%
Eucalyptus camaldulensis (Egypt) fruit Eucalyptus camaldulensis Dehn. var. brevirostris, fam. Myrtaceae 0.17%
Satureja parvifolia (Argentina) Satureja parvifolia (Phil.) Epl., fam. Lamiaceae (Labiatae) 0.1%