What is the NOOTKATONE?

NOOTKATONE is colourless crystal, while it's Molecular Formula is C15H22O. colourless crystal 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.

What is the CAS number for NOOTKATONE?

The CAS number of NOOTKATONE is 4674-50-4.

What is NOOTKATONE (4674-50-4) used for?

(+)-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.InChI:InChI=1/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

What is the NOOTKATONE?

NOOTKATONE is colourless crystal, while it's Molecular Formula is C15H22O. colourless crystal 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.

What is the CAS number for NOOTKATONE?

The CAS number of NOOTKATONE is 4674-50-4.

What is NOOTKATONE (4674-50-4) used for?

(+)-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.InChI:InChI=1/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

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4674-50-4

Product Name：Nootkatone
Molecular Formula：C₁₅H₂₂O
Specifications：99%
Molecular Weight：218.339

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Product Details;

CasNo： 4674-50-4

Molecular Formula： C₁₅H₂₂O

Appearance： colourless crystal

Factory Sells Best Quality Nootkatone 4674-50-4 with stock

Molecular Formula:C15H22O
Molecular Weight:218.339
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

NOOTKATONE(Cas 4674-50-4) Usage

Preparation	By oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.
Definition	ChEBI: A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).
Aroma threshold values	Detection: 170 to 800 ppb
Taste threshold values	Taste characteristics at 20 ppm: grapefruit, citrus, orange and butter.
General Description	(+)-nootkatone, a bicyclic conjugated sesquiterpene ketone with a grapefruit-like flavor, is commonly used in fragrance, food, cosmetics and pharmaceutical industry. It can be synthesized from (+)-valencene via biotransformation. (+)-nootkatone is the active ingredient responsible for the antiplatelet effect of Cyperus rotundus, a well-known oriental traditional medicine. It also shows promising efficacy against Staphylococcus aureus biofilms.

InChI:InChI=1/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

4674-50-4 Relevant articles

Preparation of (-)-aristolochene from (+)-valencene: Absolute configuration of (+)-aristolochene from Aspergillus terreus

Cane,Salaski,Prabhakaran

, p. 1943 - 1944 (1990)

The absolute configuration of (+)-aristo...

Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation

Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori

, p. 1513 - 1514 (2005)

Nootkatone (2), the most important and e...

Selective enzymatic synthesis of the grapefruit flavor (+)-nootkatone

Schulz, Sebastian,Girhard, Marco,Gassmeyer, Sarah K.,J?ger, Vera D.,Schwarze, Daniel,Vogel, Andreas,Urlacher, Vlada B.

, p. 601 - 604 (2015)

(+)-Nootkatone is a high-value sesquiter...

Manganese complex catalyst for valencene oxidation: The first use of metalloporphyrins for the selective production of nootkatone

DeFreitas-Silva, Gilson,Moreira Meireles, Alexandre,Robles-Azocar, Patrícia,da Silva, Vinicius Santos,de Melo, Carla Nunes

, (2021)

This work describes the oxidation of val...

Sesquiterpenoids from the fruits of Alpinia oxyphylla and their anti-acetylcholinesterase activity

Chen, Ping,Wang, Pei-Pei,Jiao, Ze-Zhao,Xiang, Lan

, p. 388 - 397 (2014)

Fourteen sesquiterpenoids were isolated ...

METHOD FOR THE MANUFACTURE OF α,β-UNSATURATED KETONES

-

Page/Page column 13, (2021/10/30)

A method for the manufacture of an α,β-u...

PROCESS FOR THE PREPARATION OF NOOTKATONE BY USING A IRON (III) PORPHYRIN COMPLEX CATALYST

-

Page/Page column 5-7, (2020/12/29)

An allylic oxidation process comprising:...

Pd-Catalyzed aerobic oxidation of the sesquiterpene isolongifolene: A green and heterogeneous process

Nunes de Melo, Carla,Robles-Azocar, Patrícia Alejandra,Rodrigues, Yuri Blanc

, (2020/12/25)

The oxidation of the sesquiterpene isolo...

4674-50-4 Process route

: 17334-55-3
β-gurjunene

: 10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3
valencene

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With culture medium of Mucor species; Czapek-pepton medium; at 30 ℃; for 168h;	0.7% 0.6%

: 72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With sodium acetate; In water; acetic acid; at 100 ℃; for 2h;	93%
With sodium acetate; acetic acid; at 100 ℃; for 2h; Inert atmosphere;	93%
With sodium acetate; acetic acid; at 100 ℃; for 2h;	93%
With aluminum oxide; In hexane; at 60 ℃; for 24h; Yield given;

4674-50-4 Upstream products

10219-75-7
valencene
20489-50-3
(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one
72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone
67779-29-7
2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

4674-50-4 Downstream products

114394-01-3
urodiolenone
114394-01-3
11S-urodiolenone
114394-01-3
11R-urodiolenone
438536-22-2
nootkatone-11,12-epoxide

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