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About This Item
Empirical Formula (Hill Notation):
C15H22O
CAS Number:
Molecular Weight:
218.33
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
EC Number:
225-124-4
Beilstein/REAXYS Number:
4676969
MDL number:
Assay:
≥99.0% (GC)
Form:
crystals
InChI key
WTOYNNBCKUYIKC-JMSVASOKSA-N
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
SMILES string
C[C@@H]1CC(=O)C=C2CC[C@H](C[C@@]12C)C(C)=C
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
Quality Level
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Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Iridium-catalysed highly selective reduction--elimination of steroidal 4-en-3-ones to 3, 5-dienes in water
Li J, et al.
Green Chemistry, 21(8), 2088-2094 (2019)
Iron porphyrin catalysed light driven C-H bond amination and alkene aziridination with organic azides
Du Y, et al.
Chemical Science, 11(18), 4680-4686 (2020)
Inhibition of multidrug-resistant foodborne Staphylococcus aureus biofilms by a natural terpenoid (+)-nootkatone and related molecular mechanism
Farha AK, et al.
Food Control, 112(18), 107154-107154 (2020)
Marc C Dolan et al.
Journal of economic entomology, 102(6), 2316-2324 (2010-01-15)
We evaluated the ability of the natural, plant-derived acaricides nootkatone and carvacrol to suppress Ixodes scapularis Say and Amblyomma americanum (L.) (Acari: Ixodidae). Aqueous formulations of 1 and 5% nootkatone applied by backpack sprayer to the forest litter layer completely
Rick G Kelsey et al.
Journal of chemical ecology, 31(11), 2653-2670 (2005-11-08)
We measured the concentrations of extractable bioactive compounds in heartwood of live yellow-cedar (Chamaecyparis nootkatensis) trees and five classes of standing snags (1-5, averaging 4, 14, 26, 51, and 81 years-since-death, respectively) to determine how the concentrations changed in the
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