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44889

Supelco

(+)-Nootkatone

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C15H22O
CAS Number:
Molecular Weight:
218.33
Beilstein:
4676969
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

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

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

InChI key

WTOYNNBCKUYIKC-JMSVASOKSA-N

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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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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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