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74437 Aldrich

(+)-Nootkatone

≥99.0% (GC)

  • CAS Number 4674-50-4

  • Empirical Formula (Hill Notation) C15H22O

  • Molecular Weight 218.33

  •  Beilstein Registry Number 4676969

  •  EC Number 225-124-4

  •  MDL number MFCD04974578

  •  PubChem Substance ID 24886481

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Properties

Related Categories Asymmetric Synthesis, Cell Biology, Chemical Synthesis, Chiral Building Blocks, Citrus aurantium (Seville orange),
assay   ≥99.0% (GC)
optical activity   [α]20/D +181±3°, c = 1% in ethanol
mp   35-39 °C

Description

Packaging

2.5 g in glass bottle

Price and Availability

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(+)-Nootkatone

analytical standard

(+)-Nootkatone

technical, ≥85% (GC)

(+)-Valencene

technical, ≥70%

(−)-Isolongifolen-9-one

≥99.5% (sum of enantiomers, GC)

(<I>S</I>)<WBR>-<WBR>(+)<WBR>-<WBR>4,4a,5,6,7,8-<WBR>Hexahydro-<WBR>4a-<WBR>methyl-<WBR>2(3H)<WBR>-<WBR>naphthalenone

purum, ≥97.0% (sum of enantiomers, GC)

Safety & Documentation

Safety Information

WGK Germany 
2
Flash Point(F) 
212 °F
Flash Point(C) 
100 °C

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene. Cankar K, van Houwelingen A, Bosch D, et al. FEBS Lett. 585(1), 178-82, (2011)

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(+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction. Tsoyi K, Jang HJ, Lee YS, et al. J. Ethnopharmacol. 137(3), 1311-7, (2011)

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Use of novel compounds for pest control: insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar. Panella NA, Dolan MC, Karchesy JJ, et al. J. Med. Entomol. 42(3), 352-8, (2005)

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Functional expression of a valencene dioxygenase from Pleurotus sapidus in E. coli. Zelena K, Krings U, and Berger RG Bioresour. Technol. 108, 231-9, (2012)

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Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone. Seo EJ, Lee DU, Kwak JH, et al. J. Ethnopharmacol. 135(1), 48-54, (2011)

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Efficacy of plant-derived and synthetic compounds on clothing as repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae). Jordan RA, Schulze TL, and Dolan MC J. Med. Entomol. 49(1), 101-6, (2012)

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Susceptibility of four tick species, Amblyomma americanum, Dermacentor variabilis, Ixodes scapularis, and Rhipicephalus sanguineus (Acari: Ixodidae), to nootkatone from essential oil of grapefruit. Flor-Weiler LB, Behle RW, and Stafford KC J. Med. Entomol. 48(2), 322-6, (2011)

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Nootkatone--a biotechnological challenge. Fraatz MA, Berger RG, and Zorn H Appl. Microbiol. Biotechnol. 83(1), 35-41, (2009)

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CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase. Ly TT, Khatri Y, Zapp J, et al. Appl. Microbiol. Biotechnol. 95(1), 123-33, (2012)

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Ability of two natural products, nootkatone and carvacrol, to suppress Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in a Lyme disease endemic area of New Jersey. Dolan MC, Jordan RA, Schulze TL, et al. J. Econ. Entomol. 102(6), 2316-24, (2009)

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Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK. Murase T, Misawa K, Haramizu S, et al. Am. J. Physiol. Endocrinol. Metab. 299(2), E266-75, (2010)

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Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum. Kaspera R, Krings U, Nanzad T, et al. Appl. Microbiol. Biotechnol. 67(4), 477-83, (2005)

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Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites. Anna Gliszczyńska et al Bioorg. Med. Chem. 19, 2464-9, (2011)

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Anti-diarrheal constituents of Alpinia oxyphylla. Zhang J, Wang S, Li Y, et al. Fitoterapia 89, 149-56, (2013)

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Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation. Furusawa M, Hashimoto T, Noma Y, et al. Chem. Pharm. Bull. 53(11), 1513-4, (2005)

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Suppression of host-seeking Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) nymphs after dual applications of plant-derived acaricides in New Jersey. Jordan RA, Dolan MC, Piesman J, et al. J. Econ. Entomol. 104(2), 659-64, (2011)

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Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae). Zhu BC, Henderson G, Sauer AM, et al. Pest Manag. Sci. 66(8), 875-8, (2010)

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Biotransformation of citrus aromatics nootkatone and valencene by microorganisms. Furusawa M, Hashimoto T, Noma Y, et al. Chem. Pharm. Bull. 53(11), 1423-9, (2005)

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A-Z of nutritional supplements: dietary supplements, sports nutrition foods and ergogenic aids for health and performance--Part 27. Jones AM, Haramizu S, Ranchordas M, et al. Br. J. Sports Med. 45(15), 1246-8, (2011)

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Experimental use of two standard tick collection methods to evaluate the relative effectiveness of several plant-derived and synthetic repellents against Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae). Schulze TL, Jordan RA, and Dolan MC J. Econ. Entomol. 104(6), 2062-7, (2011)

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Efficacy and environmental persistence of nootkatone for the control of the blacklegged tick (Acari: Ixodidae) in residential landscapes. Bharadwaj A, Stafford KC, and Behle RW J. Med. Entomol. 49(5), 1035-44, (2012)

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An efficient and economic asymmetric synthesis of (+)-nootkatone, tetrahydronootkatone, and derivatives. Sauer AM, Crowe WE, Henderson G, et al. Org. Lett. 11(16), 3530-3, (2009)

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A formulation to encapsulate nootkatone for tick control. Behle RW, Flor-Weiler LB, Bharadwaj A, et al. J. Med. Entomol. 48(6), 1120-7, (2011)

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Catalytic oxidation of concentrated orange oil phase by synthetic metallic complexes biomimetic to MMO enzyme. Fernandes IA, Esmelindro MC, Corazza ML, et al. J. Sci. Food Agric. 90(9), 1460-6, (2010)

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Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in southeast Alaska. Kelsey RG, Hennon PE, Huso M, et al. J. Chem. Ecol. 31(11), 2653-70, (2005)

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Biologically important eremophilane sesquiterpenes from alaska cedar heartwood essential oil and their semi-synthetic derivatives. Khasawneh MA, Xiong Y, Peralta-Cruz J, et al. Molecules 16(6), 4775-85, (2011)

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Merck 14,10291

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