Nootkatone

Base Information

• Chemical Name: Nootkatone
• CAS No.: 4674-50-4
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• Hs Code.: 29142990
• European Community (EC) Number: 225-124-4,942-649-0
• UNII: IZ2Y119N4J,3K3OKV2A5A
• DSSTox Substance ID: DTXSID8047050
• Nikkaji Number: J14.286G
• Wikipedia: Nootkatone
• Wikidata: Q417896
• Metabolomics Workbench ID: 134374
• ChEMBL ID: CHEMBL446299
• Mol file: 4674-50-4.mol

Synonyms:nootkatone;nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer

Chemical Property of Nootkatone

Chemical Property:

• Appearance/Colour: colourless crystal
• Vapor Pressure: 0.000358mmHg at 25°C
• Melting Point: 36-37 °C
• Refractive Index: n20/D 1.52
• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 142.1 °C
• PSA: 17.07000
• Density: 0.96 g/cm³
• LogP: 3.90420
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in ethanol and chloroform. Partly soluble in water.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 364

Purity/Quality:

98%min ^*data from raw suppliers

Nootkatone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC(=O)C=C2C1(CC(CC2)C(=C)C)C
• Isomeric SMILES: C[C@@H]1CC(=O)C=C2[C@]1(C[C@@H](CC2)C(=C)C)C
• Description: Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate. (+)-Nootkatone is sesquiterpene ketone originally isolated from grapefruit juice and peel oil with diverse biological activity. It is lethal against ticks, fleas, and mosquitoes with LC50 values of 0.0029, 0.0061, and 0.0046% w/v, respectively. Pretreatment of wood with (+)-nootkatone reduces tunnel lengths, feeding, and survival rates in C. formosanus termites. (+)-Nootkatone (10-100 μM) dose-dependently activates AMPKα1 and AMPKα2 in C2C12 mouse myoblast lysate containing a substrate peptide. It dose-dependently inhibits platelet aggregation induced by collagen, thrombin , and arachidonic acid when used at concentrations ranging from 10 to 100 μM with almost complete inhibition at the highest concentration. 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.
• Uses: Nootkatone is an effective repellent/insecticide against mosquitos, and may repel bed bugs, head lice and other insects. Nootkatone in spray form has been shown as an effective repellent/insecticide against deer ticks and lone star ticks.

Technology Process of Nootkatone

There total 41 articles about Nootkatone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone (72453-44-2) → (+)-nootkatone (4674-50-4)

Guidance literature:

With sodium acetate; In water; acetic acid; at 100 ℃; for 2h;

Reference yield: 83.0%

valencene (10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3) + semicarbazide hydrochloride (563-41-7) → (+)-nootkatone (4674-50-4)

Guidance literature:

valencene; With manganese(IV) oxide; In dichloromethane; at -25 ℃; for 0.5h;

With tert.-butylhydroperoxide; In dichloromethane; water; at -10 ℃; for 9h; Reflux;

semicarbazide hydrochloride; Further stages;

Reference yield: 82.0%

valencene (10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3) → (+)-nootkatone (4674-50-4)

Guidance literature:

With Czapek-pepton medium; Pallavicinia subcilita; at 30 ℃; for 168h; pH=7.0;

DOI:10.1248/cpb.53.1513

upstream raw materials:

valencene

(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

Refernces

• 1、 Marshall,Ruden. "". . p. 1239. Retrieved 1970.
• 2、 Ishida et al.. "". . p. 934. Retrieved 1970.
• 3、 Schulz, Sebastian,Girhard, Marco,Gassmeyer, Sarah K.,J?ger, Vera D.,Schwarze, Daniel,Vogel, Andreas,Urlacher, Vlada B.. "Selective enzymatic synthesis of the grapefruit flavor (+)-nootkatone". . p. 601 - 604. Retrieved 2015.
• 4、 Chen, Ping,Wang, Pei-Pei,Jiao, Ze-Zhao,Xiang, Lan. "Sesquiterpenoids from the fruits of Alpinia oxyphylla and their anti-acetylcholinesterase activity". . p. 388 - 397. Retrieved 2014.
• 5、 -. "PROCESS FOR THE PREPARATION OF NOOTKATONE BY USING A IRON (III) PORPHYRIN COMPLEX CATALYST". Page/Page column 5-7. . Retrieved 2020/12/29.