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74437

Sigma-Aldrich

(+)-Nootkatone

≥99.0% (GC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C15H22O
Número CAS:
4674-50-4
Peso molecular:
218.33
Beilstein:
4676969
Número CE:
225-124-4
Número MDL:
MFCD04974578
Código UNSPSC:
12352205
ID de substância PubChem:
57652450
NACRES:
NA.22

Nível de qualidade

100

Ensaio

≥99.0% (GC)

Formulário

crystals

atividade óptica

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

condição de armazenamento

under inert gas (Argon)

pf

35-39 °C

grupo funcional

ketone

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

WTOYNNBCKUYIKC-JMSVASOKSA-N

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Descrição geral

(+)-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.

Aplicação

(+)-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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H317

Classificações de perigo

Skin Sens. 1

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
BCCG2450
BCCG1262
BCBS9888
BCBP3002V
BCBP2224V

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Sigma-Aldrich

B8686

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Bergamottin analytical standard

Supelco

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Bergamottin

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Sigma-Aldrich

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Naringin

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Sigma-Aldrich

218251

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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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