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

    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%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    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 est.
    65.19 ˚C

  • 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 applied primarily as a flavor and fragrance ingredient imparting the characteristic herbal, camphoraceous warmth of wormwood, sage, and thuja leaf oils, used at very low levels in alcoholic beverages, foods, and personal care products containing natural essential oils, and as an analytical reference standard (GC-MS/HPLC) for qualitative and quantitative determination of thujone in essential oils, botanicals, and beverages to support quality control, traceability, and regulatory compliance; in research, β-thujone serves as a model compound to study neurotoxicology (GABA-A antagonism) and safety thresholds, as a biochemical probe for monoterpenoid biosynthetic pathways and chemotype variation in Artemisia/Salvia/Thuja, for preliminary assessment of bioactivities such as insect repellency/inhibition, and as a building block in organic synthesis of monoterpenone derivatives; because of its neurotoxicity and irritancy, the use of β-thujone in foods and beverages is strictly limited and must comply with applicable regulations.

  • 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%