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Sakuranetin

analytical standard

Synonym(s):

4′-5-Dihydroxy-7-methoxyflavanone, 7-O-Methylnaringenin, Naringenin 7-O-methyl ether

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About This Item

Empirical Formula (Hill Notation):
C16H14O5
CAS Number:
Molecular Weight:
286.28
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

Assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤5.0% water

application(s)

food and beverages

format

neat

SMILES string

COc1cc(O)c2C(=O)C[C@H](Oc2c1)c3ccc(O)cc3

InChI

1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

InChI key

DJOJDHGQRNZXQQ-AWEZNQCLSA-N

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General description

Sakuranetin is classified under the flavonoids family of phytoalexins.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Sakuranetin may be used as an analytical reference standard for the determination of sakuranetin in:
  • Aerial parts of Rhus retinorrhoea and Rhus tripartita by chloroform and methanol extractions followed by high performance thin-layer chromatography (HPTLC).
  • Rhamnus davurica by high performance liquid chromatography (HPLC) coupled to tandem mass spectrometry with electrospray ionization (ESI-MS/MS) as well as affinity ultrafiltration followed by analysis using ESI-HPLC-MS/MS.
  • Royal jelly nutraceutical products by turbulent flow chromatography (TFC) combined with LC-Extractive-Orbitrap analyzer equipped with ESI.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

For this product we use the non-stereospecific CAS number. It is expected that the natural enantiomer is predominant, however the substance is prone to racemization in solution. The product is therefore not specified stereospecifically and is only recommended to be used for non-stereospecific analysis.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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S Tamogami et al.
FEBS letters, 401(2-3), 239-242 (1997-01-20)
Amino acid conjugates of jasmonic acid are found to elicit production of the flavonoid phytoalexin, sakuranetin in rice leaves. The elicitation is shown to arise from induction of naringenin 7-O-methyltransferase, a key enzyme of sakuranetin biosynthesis. The (-)-phenylalanine conjugate, one
Inter-species comparative antioxidant assay and HPTLC analysis of sakuranetin in the chloroform and ethanol extracts of aerial parts of Rhus retinorrhoea and Rhus tripartita.
Alam P, et al.
Pharmaceutical biology, 55(1), 1450-1457 (2017)
Takafumi Shimizu et al.
The Journal of biological chemistry, 287(23), 19315-19325 (2012-04-12)
Sakuranetin, the major flavonoid phytoalexin in rice, is induced by ultraviolet (UV) irradiation, CuCl(2) treatment, jasmonic acid treatment, and infection by phytopathogens. It was recently demonstrated that sakuranetin has anti-inflammatory activity, anti-mutagenic activity, anti-pathogenic activities against Helicobacter pylori, Leishmania, and
Analysis of flavonoids in Rhamnus davurica and its antiproliferative activities.
Chen G, et al.
Molecules (Basel), 21(10), 1275-1275 (2016)
Young-Ho Jung et al.
Journal of proteome research, 5(10), 2586-2598 (2006-10-07)
We analyzed a unique rice (Oryza sativa L.) blast lesion mimic (blm) mutant for differentially expressed proteins in leaves of one- and two-week-old seedlings manifesting the lesion mimic phenotype. Gel-based one- and two-dimensional electrophoresis (1- and 2-DGE) was performed using

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