| Identification | Back Directory | [Name]
NOOTKATONE | [CAS]
4674-50-4 | [Synonyms]
NONANOL
FEMA 3166
NOOTKATONE
Nootkatane
Zinc05225089
NOOTKATONE-55/60%
NOOTKATONE 65-70%
NOOTKATONE WITH GC
NOOTKATONE, NATURAL
2(3h)-naphthalenone,
NOOTKATONE 98% CRYSTALS
NOOTKATONE DISTILLED 50%
(+)-nootkatone, crystalline
(+)-Nootkatone >=99.0% (GC)
4aalpha,6beta)]-[4theta-(4alph
NOOTKATONE EX-CITRUS 70% NATURAL
(+)-NOOTKATONE, CRYSTALLINE, 98+%
4betaH,5alpha-Eremophila-1(10),11-dien-2-one
4betaH,5alpha-Eremorphila-1(10)11-dien-2-one
4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one
(+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE
4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3h)-naphthalenon
(4R)-4,4a,5,6,7,8-Hexahydro-6α-isopropenyl-4β,4aβ-dimethylnaphthalene-2(3H)-one
(4R)-4β,4aβ-Dimethyl-6α-isopropenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-one
(4R)-4,4a,5,6,7,8-Hexahydro-4,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one
(4R)-4,4a,5,6,7,8-Hexahydro-4β,4aβ-dimethyl-6α-(1-methylethenyl)naphthalen-2(3H)-one
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone,[4R-(4.alpha.,4a.alpha.4
(4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalin-2(3H)-on
[4R-(4alpha,4aalpha,6beta)]-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one
4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4alpha,4aalpha,6beta)]-
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4alpha,4aalpha,6beta)]-
4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-,[4R-(4.alpha.,4a.alpha.,6.beta.)]-2(3H)-Naphthalenone
2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-,[4R-(4.alpha.,4a.alpha.,6.beta.)]- | [EINECS(EC#)]
225-124-4 | [Molecular Formula]
C15H22O | [MDL Number]
MFCD00036591 | [MOL File]
4674-50-4.mol | [Molecular Weight]
218.33 |
| Chemical Properties | Back Directory | [Appearance]
viscous yellow liquid or crystals with a citrus odour; | [Melting point ]
35-39 °C
| [Boiling point ]
125°C 0,5mm | [density ]
0,997 g/cm3 | [FEMA ]
3166 | [refractive index ]
n20/D 1.52
| [Fp ]
99°C | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
White to Pale Yellow | [Odor]
at 100.00 %. grapefruit peel citrus gardenia woody | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [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 | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
viscous yellow liquid or crystals with a citrus odour; | [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). | [Description]
Nootkatone has a pleasant taste. It may be prepared by oxidation of valencene (a sesquiterpene) with tertiary butyl chromate. | [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. | [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. |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
tert-Butyl chromate-->Valencene | [Preparation Products]
(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-methylethylidene)naphthalen-2(3H)-one |
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