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74437 Sigma-Aldrich

(+)-Nootkatone

≥99.0% (GC)

  • CAS Number 4674-50-4

  • Empirical Formula (Hill Notation) C15H22O

  • Molecular Weight 218.33

  •  Beilstein/REAXYS Number 4676969

  •  EC Number 225-124-4

  •  MDL number MFCD04974578

  •  PubChem Substance ID 57652450

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Cell Biology, Chemical Synthesis, Chiral Building Blocks, Citrus aurantium (Seville orange),
assay   ≥99.0% (GC)
optical activity   [α]20/D +182.0±5.0°, c = 1% in ethanol
storage condition   under inert gas
mp   35-39 °C
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.

Packaging

2.5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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