A natural sesquiterpene with diverse biological activity
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Isomer(s)
36157Aristolone 34294α-Cyperone
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(+)-Nootkatone

Item No. 24910

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,4aS,6R)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone
CAS Number
4674-50-4
Molecular Formula
C15H22O
Formula Weight
218.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 20 mg/mlEthanol: 33 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
238 nm
SMILES
CC([C@@H]1CCC2=CC(C[C@@H](C)[C@]2(C)C1)=O)=C
InChi Code
InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
InChi Key
WTOYNNBCKUYIKC-JMSVASOKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $39

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    1 g

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    5 g

    $251

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    Product Description

    (+)-Nootkatone is sesquiterpene ketone originally isolated from grapefruit juice and peel oil with diverse biological activity.1,2 It is lethal against ticks, fleas, and mosquitoes with LC50 values of 0.0029, 0.0061, and 0.0046% w/v, respectively.2 Pretreatment of wood with (+)-nootkatone reduces tunnel lengths, feeding, and survival rates in C. formosanus termites.3 (+)-Nootkatone (10-100 µM) dose-dependently activates AMPKα1 and AMPKα2 in C2C12 mouse myoblast lysate containing a substrate peptide.4 It dose-dependently inhibits platelet aggregation induced by collagen, thrombin (Item No. 13188), and arachidonic acid (Item No. 90010) when used at concentrations ranging from 10 to 100 μM with almost complete inhibition at the highest concentration.5 In vivo, (+)-nootkatone (3-30 mg/kg, p.o.) dose-dependently increases the length of tail bleeding time in mice. (+)-Nootkatone (0.1-0.3%, p.o.) dose-dependently reduces body weight and plasma glucose levels in mice fed a high-fat and high-sucrose diet.4 Formulations containing (+)-nootkatone have been used in the control of insects and ticks.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. MacLeod, W.D., Jr., and Buigues, N.M. Sesquiterpenes. I. Nootkatone, A new grapefruit flavor constituent. J. Food Sci. 29(5), 565 - 568 (2006).

    2. Panella, N.A., Dolan, M.C., Karchesy, J.J., et al. Use of novel compounds for pest control: Insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar. J. Med. Entomol. 42(3), 352-358 (2005).

    3. Maistrello, L., Henderson, G., and Laine, R.A. Comparative effects of vetiver oil, nootkatone and disodium octaborate tetrahydrate on Coptotermes formosanus and its symbiotic fauna. Pest. Manag. Sci. 59(1), 58-68 (2003).

    4. Murase, T., Misawa, K., Haramizu, S., et al. Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK. Am. J. Physiol. Endocrinol. Metab. 299(2), E266-E275 (2010).

    5. Seo, E.J., Lee, D.-U., Kwak, J.H., et al. Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone. J. Ethnopharmacol. 135(1), 48-54 (2011).