74437

(+)-Nootkatone

≥99.0% (GC)

• Synonym(s): (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone
• Empirical Formula (Hill Notation): C₁₅H₂₂O
• CAS Number: 4674-50-4
• Molecular Weight: 218.33
• Beilstein/REAXYS Number: 4676969
• EC Number: 225-124-4
• MDL number: MFCD04974578
• UNSPSC Code: 12352205
• PubChem Substance ID: 57652450
• NACRES: NA.22

Properties

• assay: ≥99.0% (GC)
• form: crystals
• optical activity: [α]20/D +182.0±5.0°, c = 1% in ethanol
• storage condition: under inert gas (Argon)
• mp: 35-39 °C
• functional group: ketone
• storage temp.: 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
• InChI key: WTOYNNBCKUYIKC-JMSVASOKSA-N

Description

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.

Application

(+)-Nootkatone can be used:

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)