74437

(+)-Nootkaton

≥99.0% (GC)

• Synonym(e): (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone
• Empirische Formel (Hill-System): C₁₅H₂₂O
• CAS-Nummer: 4674-50-4
• Molekulargewicht: 218.33
• Beilstein: 4676969
• EG-Nummer: 225-124-4
• MDL-Nummer: MFCD04974578
• UNSPSC-Code: 12352205
• PubChem Substanz-ID: 57652450
• NACRES: NA.22

Eigenschaften

• Assay: ≥99.0% (GC)
• Form: crystals
• Optische Aktivität: [α]20/D +182.0±5.0°, c = 1% in ethanol
• Lagerbedingungen: under inert gas (Argon)
• mp (Schmelzpunkt): 35-39 °C
• Funktionelle Gruppe: ketone
• Lagertemp.: 2-8°C
• SMILES String: C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C
• InChI: 1S/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
• InChIKey: WTOYNNBCKUYIKC-JMSVASOKSA-N

Beschreibung

Allgemeine Beschreibung

(+)-nootkatone, a bicyclic conjugated sesquiterpene ketone[1] with a grapefruit-like flavor, is commonly used in fragrance, food, cosmetics and pharmaceutical industry. It can be synthesized from (+)-valencene via biotransformation.[2] (+)-nootkatone is the active ingredient responsible for the antiplatelet effect of Cyperus rotundus, a well-known oriental traditional medicine.[3] It also shows promising efficacy against Staphylococcus aureus biofilms.[4]

Anwendung

(+)-Nootkatone can be used:

• In the iron(III) porphyrin catalyzed alkene aziridination reaction with organic azides under photo-irradiation condition.[5]
• As a substrate to synthesize its corresponding triene derivative through reduction-elimination reaction using iridium catalyst.[6]

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H317
• P-Sätze: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Gefahreneinstufungen: Skin Sens. 1
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 2
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)