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HomeProduct name listNOOTKATONE

NOOTKATONE

Synonym(s):(+)-Nootkatone

  • CAS NO.:4674-50-4
  • Empirical Formula: C15H22O
  • Molecular Weight: 218.33
  • MDL number: MFCD00036591
  • EINECS: 225-124-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-24 19:19:26
NOOTKATONE Structural

What is NOOTKATONE?

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

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.

Chemical properties

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

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.

The Uses of NOOTKATONE

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.

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).

Preparation

By oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.

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.

Properties of NOOTKATONE

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  neat
form  Solid
color  White to Pale Yellow Low-Melting
Odor at 100.00 %. grapefruit peel citrus gardenia woody
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.
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 for NOOTKATONE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H317:Sensitisation, Skin
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for NOOTKATONE

InChIKey WTOYNNBCKUYIKC-UHFFFAOYSA-N

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