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74437

Sigma-Aldrich

(+)-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

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About This Item

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

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

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

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Allgemeine Beschreibung

(+)-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.

Anwendung

(+)-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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H317

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)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

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)
Katarina Cankar et al.
FEBS letters, 585(1), 178-182 (2010-12-01)
Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the
Robert W Behle et al.
Journal of medical entomology, 48(6), 1120-1127 (2012-01-14)
Nootkatone is a component of grapefruit oil that is toxic to the disease-vectoring tick, Ixodes scapularis Say, but unfortunately causes phytotoxicity to treated plants and has a short residual activity due to volatility. We prepared a lignin-encapsulated nootkatone formulation to
Betty C R Zhu et al.
Pest management science, 66(8), 875-878 (2010-07-06)
Research has shown that the family of grapefruit flavors called nootkatones have significant repellant and toxic effects to Formosan subterranean termites (Coptotermes formosanus Shiraki). Nineteen synthetic nootkatone derivatives, along with three commercially available nootkatone derivatives, were tested for repellent activity
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