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Merck
CN

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:
4674-50-4
Molecular Weight:
218.33
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
57652450
EC Number:
225-124-4
Beilstein/REAXYS Number:
4676969
MDL number:
MFCD04974578
Assay:
≥99.0% (GC)
Form:
crystals

Key Documents

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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

100

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

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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Certificates of Analysis (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)
Robert A Jordan et al.
Journal of medical entomology, 49(1), 101-106 (2012-02-09)
We conducted field trials to compare the relative repellent activity of two natural product compounds (nootkatone and carvacrol) with commercially available plant-derived (EcoSMART organic insect repellent) and permethrin-based (Repel Permanone) repellents against adult Ixodes scapularis Say and Amblyomma americanum (L.)
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
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)
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