[4R-(4α,4aα,6β)]-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalin-2(3H)-on Chemische Eigenschaften,Einsatz,Produktion Methoden
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate.
Chemische Eigenschaften
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.
Verwenden
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.
synthetische
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).
Allgemeine Beschreibung
(+)-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.
[4R-(4α,4aα,6β)]-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalin-2(3H)-on Upstream-Materialien And Downstream Produkte
Upstream-Materialien
[1R-(1α,7β,8α)]-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalin
tert-Butyl chromate
Downstream Produkte
(1R)-1,2,6,7,8,8a-Hexahydro-1,8aα-dimethyl-7β-(1-methylethenyl)naphthalene
(4R-cis)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethyliden)naphthalin-2(3H)-on
