Nootkatone

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  • Identifiers

    CAS number
    4674-50-4

    Molecular formula
    C15H22O

    SMILES
    C[C@@H]1CC(=O)C=C2[C@]1(C[C@@H](CC2)C(=C)C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1799.0
    • Carbowax: 2344.0

  • Odor profile

    Woody 71.53%
    Sweet 47.49%
    Citrus 46.19%
    Fruity 43.36%
    Spicy 40.29%
    Dry 39.13%
    Tobacco 37.91%
    Fresh 37.62%
    Cedar 33.15%
    Orris 30.91%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 36-37 °C
    • Melting point: 45-46 °C ((+)(-)-Form)

    Boiling point

    • BP: 125 °C at 0.5 mm Hg

    Flash point est.
    113.32 ˚C

    Flash point expt.

    • 100 °C (212 °F) - closed cup

    Solubility expt.

    • Practically insoluble in water
    • Soluble in alcohol, oil
    • Soluble in oils; Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • NOOTKATONE
    • (+)-Nootkatone
    • 4674-50-4
    • Nootkanone
    • (+/-)-Nootkatone
    • Nootkatone, (+/-)-
    • Nootkatone (natural)
    • (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
    • Nootkatone (+/-)-form [MI]
    • (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
    • UNII-3K3OKV2A5A
    • 3K3OKV2A5A
    • UNII-IZ2Y119N4J
    • FEMA No. 3166
    • IZ2Y119N4J
    • DTXSID8047050
    • CHEBI:81377
    • 4.beta.H,5.alpha.-Eremophila-1(10),11-dien-2-one
    • NOOTKATONE [MI]
    • 1(10),11-Eremophiladien-2-one
    • EINECS 225-124-4
    • NOOTKATONE [FHFI]
    • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
    • DTXCID6027050
    • FEMA NO. 4941
    • 7betaH-Eremophila-1(10),11-dien-2-one -
    • HSDB 8272
    • 4Betah,5alpha-eremophila-1(10),11-dien-2-one
    • 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one
    • 4,4a,5,6,7,8-Hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone
    • (4RS,4Asr,6RS)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone
    • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-rel
    • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
    • 5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one
    • 4a,5-Dimethyl-1,2,3,4,4a,5,6,7-octahydro-7-keto-3-isopropenylnaphthalene
    • 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R-(4alpha,4aalpha,6beta))-
    • 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, (4R-(4alpha,4aalpha,6beta))-
    • 5,6-DIMETHYL-8-ISOPROPENYL-BICYCLO(4,4,0)-DEC-1-EN-3-ONE
    • MFCD04974578
    • 28834-25-5
    • 91416-23-8
    • 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLENE-ETHYL)-2(3H)-NAPHTHALENONE
    • 4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE
    • 2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R-(4.ALPHA.,4A.ALPHA.,6.BETA.))-
    • Nootkatone, (+)-
    • nootkaton
    • (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone; Nootkanone
    • (+)-Nootkatone, crystalline
    • Nootkatone, >=98%, FG
    • (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
    • SCHEMBL110855
    • CHEMBL446299
    • HY-N2195
    • 5,6-Dimethyl-8-isopropenyl-bicyclo
    • Tox21_302385
    • (+)-Nootkatone, analytical standard
    • s9071
    • STL562310
    • AKOS015955823
    • CCG-266714
    • (+)-Nootkatone, >=99.0% (GC)
    • NCGC00256230-01
    • AC-34548
    • AS-56160
    • XN168139
    • CAS-4674-50-4
    • (+)-Nootkatone, technical, >=85% (GC)
    • CS-0019503
    • N0920
    • C17914
    • Q417896
    • 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one
    • 7.BETA.H-EREMOPHILA-1(10),11-DIEN-2-ONE -
    • (4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one
    • 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
    • 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
    • 942-649-0

  • Applications

    Nootkatone (CAS 4674-50-4) is a grapefruit-scented sesquiterpenoid that is bio-sourced or synthetically produced for premium flavoring in beverages, confectionery, ice cream, craft beers and light tobacco; as a fragrance note in perfumes, shampoos, body washes, scented candles and air fresheners; as an intermediate for oxo-carboxyaldehyde creation in fine-fragrance chemistry; and, importantly, as a new EPA-approved biopesticide active that repels mosquitoes, ticks, bedbugs, fleas and sand flies by disrupting insect neurotransmission while rapidly biodegrading and remaining safe for humans, pets, pollinators and the environment; moreover, nootkatone is investigated as an aroma marker for citrus juice traceability, a bitter-cool flavor enhancer for sports nutrition products, and a scaffold for synthesizing sesquiterpene derivatives with antioxidant, antibacterial and antifungal properties for cosmeceuticals and bio-based food packaging.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 763.74
    methanol 564.82
    isopropanol 1058.48
    water 0.74
    ethyl acetate 867.71
    n-propanol 809.29
    acetone 930.87
    n-butanol 714.19
    acetonitrile 794.03
    DMF 1212.43
    toluene 1039.18
    isobutanol 597.91
    1,4-dioxane 2296.97
    methyl acetate 808.85
    THF 2529.73
    2-butanone 980.58
    n-pentanol 293.08
    sec-butanol 555.14
    n-hexane 24.55
    ethylene glycol 70.19
    NMP 369.08
    cyclohexane 114.91
    DMSO 414.81
    n-butyl acetate 629.59
    n-octanol 193.88
    chloroform 2015.6
    n-propyl acetate 365.22
    acetic acid 223.02
    dichloromethane 1409.01
    cyclohexanone 1021.26
    propylene glycol 157.16
    isopropyl acetate 562.79
    DMAc 624.73
    2-ethoxyethanol 402.0
    isopentanol 561.25
    n-heptane 34.42
    ethyl formate 460.84
    1,2-dichloroethane 831.63
    n-hexanol 586.01
    2-methoxyethanol 910.89
    isobutyl acetate 271.4
    tetrachloromethane 238.83
    n-pentyl acetate 340.29
    transcutol 1516.3
    n-heptanol 221.35
    ethylbenzene 333.16
    MIBK 437.75
    2-propoxyethanol 831.92
    tert-butanol 1054.0
    MTBE 804.49
    2-butoxyethanol 394.45
    propionic acid 303.01
    o-xylene 433.32
    formic acid 65.68
    diethyl ether 791.06
    m-xylene 577.76
    p-xylene 414.44
    chlorobenzene 697.99
    dimethyl carbonate 258.35
    n-octane 18.28
    formamide 166.98
    cyclopentanone 1089.85
    2-pentanone 725.82
    anisole 592.79
    cyclopentyl methyl ether 669.76
    gamma-butyrolactone 937.71
    1-methoxy-2-propanol 864.03
    pyridine 1420.35
    3-pentanone 482.03
    furfural 804.75
    n-dodecane 15.46
    diethylene glycol 444.94
    diisopropyl ether 206.66
    tert-amyl alcohol 484.41
    acetylacetone 654.91
    n-hexadecane 18.82
    acetophenone 408.72
    methyl propionate 559.21
    isopentyl acetate 595.11
    trichloroethylene 1417.02
    n-nonanol 174.47
    cyclohexanol 540.78
    benzyl alcohol 416.21
    2-ethylhexanol 276.52
    isooctanol 175.99
    dipropyl ether 323.15
    1,2-dichlorobenzene 478.75
    ethyl lactate 165.96
    propylene carbonate 487.27
    n-methylformamide 513.96
    2-pentanol 435.39
    n-pentane 44.15
    1-propoxy-2-propanol 691.39
    1-methoxy-2-propyl acetate 668.25
    2-(2-methoxypropoxy) propanol 355.2
    mesitylene 304.16
    ε-caprolactone 753.45
    p-cymene 186.47
    epichlorohydrin 1333.38
    1,1,1-trichloroethane 914.26
    2-aminoethanol 233.44
    morpholine-4-carbaldehyde 832.35
    sulfolane 496.89
    2,2,4-trimethylpentane 24.18
    2-methyltetrahydrofuran 1280.02
    n-hexyl acetate 412.41
    isooctane 30.97
    2-(2-butoxyethoxy)ethanol 548.15
    sec-butyl acetate 290.35
    tert-butyl acetate 535.91
    decalin 45.72
    glycerin 172.98
    diglyme 945.91
    acrylic acid 206.26
    isopropyl myristate 176.26
    n-butyric acid 545.16
    acetyl acetate 412.79
    di(2-ethylhexyl) phthalate 155.75
    ethyl propionate 334.84
    nitromethane 578.37
    1,2-diethoxyethane 714.89
    benzonitrile 652.26
    trioctyl phosphate 109.67
    1-bromopropane 584.61
    gamma-valerolactone 1369.48
    n-decanol 133.87
    triethyl phosphate 147.19
    4-methyl-2-pentanol 271.83
    propionitrile 886.62
    vinylene carbonate 549.42
    1,1,2-trichlorotrifluoroethane 450.04
    DMS 364.26
    cumene 198.55
    2-octanol 157.81
    2-hexanone 361.4
    octyl acetate 209.9
    limonene 227.28
    1,2-dimethoxyethane 881.8
    ethyl orthosilicate 145.13
    tributyl phosphate 134.61
    diacetone alcohol 510.17
    N,N-dimethylaniline 322.49
    acrylonitrile 882.35
    aniline 794.26
    1,3-propanediol 483.33
    bromobenzene 731.29
    dibromomethane 900.6
    1,1,2,2-tetrachloroethane 1065.85
    2-methyl-cyclohexyl acetate 265.42
    tetrabutyl urea 162.92
    diisobutyl methanol 179.4
    2-phenylethanol 516.99
    styrene 385.88
    dioctyl adipate 204.31
    dimethyl sulfate 237.42
    ethyl butyrate 355.14
    methyl lactate 238.54
    butyl lactate 247.51
    diethyl carbonate 232.18
    propanediol butyl ether 345.95
    triethyl orthoformate 236.31
    p-tert-butyltoluene 200.45
    methyl 4-tert-butylbenzoate 328.56
    morpholine 2295.01
    tert-butylamine 610.34
    n-dodecanol 102.63
    dimethoxymethane 895.77
    ethylene carbonate 485.52
    cyrene 263.0
    2-ethoxyethyl acetate 482.33
    2-ethylhexyl acetate 415.26
    1,2,4-trichlorobenzene 529.08
    4-methylpyridine 1396.38
    dibutyl ether 270.73
    2,6-dimethyl-4-heptanol 179.4
    DEF 523.08
    dimethyl isosorbide 588.41
    tetrachloroethylene 552.78
    eugenol 327.91
    triacetin 338.88
    span 80 291.54
    1,4-butanediol 119.74
    1,1-dichloroethane 1103.11
    2-methyl-1-pentanol 253.32
    methyl formate 383.54
    2-methyl-1-butanol 418.76
    n-decane 27.53
    butyronitrile 867.79
    3,7-dimethyl-1-octanol 226.83
    1-chlorooctane 129.9
    1-chlorotetradecane 54.72
    n-nonane 25.08
    undecane 20.09
    tert-butylcyclohexane 43.91
    cyclooctane 33.91
    cyclopentanol 539.74
    tetrahydropyran 1946.77
    tert-amyl methyl ether 370.57
    2,5,8-trioxanonane 559.15
    1-hexene 149.21
    2-isopropoxyethanol 328.29
    2,2,2-trifluoroethanol 99.22
    methyl butyrate 398.82

    Scent© AI

1 4

IFRA standard 51

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

Specification
Nootkatone used as a fragrance ingredient should be at least 98% pure, with a melting point of at least 32°C. Lower purity grades may not be used as a fragrance ingredient.

Botanical

Name CAS Botanical Proportion
Amomum muricarpum Amomum muricarpum Elm, fam. Zingiberaceae 10.8%
Lemon (Spain) 7 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.02%
Grapefruit (Israel) 2 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.14%
Grapefruit (Israel) 1 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.3%
Grapefruit (USA) 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.1%
Lemon (Italy-Sicily) 7 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Lemon (Israel) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Satsuma mandarin peel 1 Citrus unshiu Marcovitch, fam. Rutaceae 0.03%
Orange, bitter (Spain) 1 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.13%
Orange, bitter (Spain) 2 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.13%
Orange, sweet (USA-Florida) 1 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Midseason, fam. Rutaceae 0.01%
Orange, sweet (USA-Florida) 4 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange, sweet (Israel) 1 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.02%
Orange, sweet (Israel) 2 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Shamouti, fam. Rutaceae 0.03%
Orange, sweet (Italy) 2 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange, sweet (Spain) 1 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange, sweet (USA-California) 2 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Navel, fam. Rutaceae 0.01%
Orange, sweet (USA-Florida) 2 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange, sweet (USA-Florida) 3 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Brazil, fam. Rutaceae 0.01%
Grapefruit (Italy) 1 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.1%
Orange, sweet (USA-Florida) 5 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.02%
Orange, sweet (USA-Florida) 6 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange, sweet, deterpenized 8008-57-9 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.5%
Annual wormwood (China) 1 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.3%
Grapefruit (Brazil) 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.06%
Grapefruit (Japan) 1 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.84%
Mandarin (Brazil) 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Orange, sweet (China) 2 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Orange, sweet (Italy) 5 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Clementine (Italy) 2 Citrus clementina Hort. ex Tan., (C. deliciosa Ten. var. Clementina) 0.01%
Clementine x Lemon (Italy) 1 Citrus clementina Hort. ex Tan. x Citrus limon (L.) Burm., fam. Rutaceae 0.01%
Orange, bitter (Italy) 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.01%
Annual wormwood (France) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.01%
Orange, sweet (USA) (hydrocarbon-free) 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.73%
Grapefruit (Italy) 2 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.74%
Bitter orange leaf (Petitgrain) (Spain) 2 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.03%
Lemon 2 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.06%
Mandarin 3 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Acacia confusa flower (China) Acacia confusa Merr., fam. Mimosaceae (Leguminosae) 0.37%
Bergamot (Italy) 4 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.04%
Rosa rugosa (China) 1 Rosa rugosa Thunb. (hybrids), fam. Rosaceae 0.3%
Lemon (Italy-Sicily) 11 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Clementine (Italy) 3a Citrus clementina Hort. ex Tan., cultivar Oroval, fam. Rutaceae 0.01%
Clementine (Italy) 3b Citrus clementina Hort. ex Tan., cultivar Monreal, fam. Rutaceae 0.01%
Clementine (Italy) 3c Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.01%
Lemon (Uruguay) 8a 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Lemon (Uruguay) 8b 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Grapefruit (Italy) 4a 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.24%
Grapefruit (Italy) 4b 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 1.28%
Grapefruit (Italy) 4c 8016-20-4 Citrus paradisi MacFayden, fam. Rutaceae 4.95%