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Merck
CN

44889

(+)-Nootkatone

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C15H22O
CAS Number:
4674-50-4
Molecular Weight:
218.33
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329756559
EC Number:
225-124-4
Beilstein/REAXYS Number:
4676969
MDL number:
MFCD04974578

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

grade

analytical standard

assay

≥99.0% (GC)

shelf life

limited shelf life, expiry date on the label

storage condition

under inert gas (Argon)

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

impurities

≤1.0% water

mp

35-39 °C

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

(+)-Nootkatone is a bicyclic conjugated sesquiterpene ketone, which is found as an important flavoring constituent in grapes. It can be synthesized from the sesquiterpene hydrocarbon valencene. It finds applications as an antiulcer drug and has insecticidal activity against Drosophila melanogaster.

Application

(+)-Nootkatone may be used as a reference standard in the determination of (+)-nootkatone in Alpinia oxyphylla oil using gas chromatography coupled with flame ionization detector (GC-FID).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

pcodes

P280

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH9892
BCCF3883
BCCD1182
BCCC0023
BCBX6477

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Conversion of valencene to nootkatone.
Hunter KLG and Brogden BW
Journal of Food Science, 30(5), 876-878 (1965)
Sesquiterpenes. I. Nootkatone, a new grapefruit flavor constituent.
MacLeod WD and Buigues NM.
Journal of Food Science, 29(5), 565-568 (1964)
Marco A Fraatz et al.
Applied microbiology and biotechnology, 83(1), 35-41 (2009-04-01)
Due to its pleasant grapefruit-like aroma and various further interesting molecular characteristics, (+)-nootkatone represents a highly sought-after specialty chemical. (+)-Nootkatone is accumulated in its producer plants in trace amounts only, and the demand of the food, cosmetics and pharmaceutical industry
Qing Miao et al.
Journal of pharmaceutical and biomedical analysis, 102, 436-442 (2014-12-03)
Analytical methods for quantitative analysis and chemical fingerprinting of volatile oils from Alpinia oxyphylla were established. The volatile oils were prepared by hydrodistillation, and the yields were between 0.82% and 1.33%. The developed gas chromatography-flame ionization detection (GC-FID) method showed
Boyuan Wang et al.
Molecular cell, 80(1), 29-42 (2020-08-29)
(p)ppGpp is a nucleotide messenger universally produced in bacteria following nutrient starvation. In E. coli, ppGpp inhibits purine nucleotide synthesis by targeting several different enzymes, but the physiological significance of their inhibition is unknown. Here, we report the structural basis of

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