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
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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
Quality Level
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
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.
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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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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)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 74437-2.5G | 04061832720142 |
| 74437-1G | 04061825936116 |