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74437

Sigma-Aldrich

(+)-Nootkatone

≥99.0% (GC)

Sinonimo/i:

(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

Formula empirica (notazione di Hill):
C15H22O
Numero CAS:
4674-50-4
Peso molecolare:
218.33
Beilstein:
4676969
Numero CE:
225-124-4
Numero MDL:
MFCD04974578
Codice UNSPSC:
12352205
ID PubChem:
57652450
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥99.0% (GC)

Forma fisica

crystals

Attività ottica

[α]20/D +182.0±5.0°, c = 1% in ethanol

Condizioni di stoccaggio

under inert gas (Argon)

Punto di fusione

35-39 °C

Gruppo funzionale

ketone

Temperatura di conservazione

2-8°C

Stringa SMILE

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
WTOYNNBCKUYIKC-JMSVASOKSA-N

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Descrizione generale

(+)-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.

Applicazioni

(+)-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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H317

Classi di pericolo

Skin Sens. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG2450
BCCG1262
BCBS9888
BCBP3002V
BCBP2224V

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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)
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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