NOOTKATONE Chemical Properties

Melting point:

35-39 °C

Boiling point:

125°C 0,5mm

Density 

0,997 g/cm³

refractive index 

n20/D 1.52

FEMA 

3166 | NOOTKATONE

Flash point:

99°C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Pale Yellow

Odor

at 100.00 %. grapefruit peel citrus gardenia woody

Odor Type

citrus

optical activity

[α]20/D +182.0±5.0°, c = 1% in ethanol

Water Solubility 

Slightly soluble in ethanol and chloroform. Partly soluble in water.

JECFA Number

1398

BRN 

4676969

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

WTOYNNBCKUYIKC-UHFFFAOYSA-N

LogP

3.84

EPA Substance Registry System

2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- (4674-50-4)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

2

TSCA 

Yes

HS Code 

29142990

Hazardous Substances Data

4674-50-4(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

NOOTKATONE Usage And Synthesis

Description

Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.

Description

(+)-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.

Chemical Properties

Nootkatone has a powerful fruity sweet, citrusy, grapefruit peel oil-like aroma.

Chemical Properties

viscous yellow liquid or crystals with a citrus odour;

Chemical Properties

NOOTKATONE has been isolated from grapefruit peel and juice and identified in other citrus oils as well. The commercially available product is a colorless to yellowish liquid with a typical grapefruit odor.
Nootkatone can be prepared by oxidation of valencene, a sesquiterpene hydrocarbon isolated from orange oils. The oxidation can be accomplished either by chemical or by biotechnological methods.
Nootkatone is used for flavoring beverages.

Occurrence

Reported found in grapefruit oil and juice; traces are also reported found in the oils of bergamot, lemon, lime, orange and tangerine; also reported formed in canned orange juice on storage.

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.

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.

NOOTKATONE(4674-50-4)Related Product Information

• DIHYDRO CUMINYL ALCOHOL
• (+)-NOOTKATONE
• Triethylaluminum
• Ethanol
• HEPTANOPHENONE
• Edible essence
• VINYLCYCLOHEXANE
• NOOTKATONE
• 3,5-Dimethyl-2-cyclohexen-1-one
• VALENCENE
• NOOTKATONE(SG)
• 1,6-Octadiene
• 2,6-DIMETHYL-1,6-HEPTADIENE
• NOOTKATONE50%
• (-)-nootkatone,5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
• NOOTKATONE(SECONDARY STANDARD)
• NOOTKATONE81%
• NOOTKATONE97%