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Merck
CN

36465

Avenanthramide C

analytical standard

Synonym(s):

2-{[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]amino}-5-hydroxybenzoic acid, N-[3′,4′-Dihydroxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid, Avenanthramide Bc

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About This Item

Empirical Formula (Hill Notation):
C16H13NO6
CAS Number:
116764-15-9
Molecular Weight:
315.28
Beilstein:
3624543
MDL number:
MFCD23380831
UNSPSC Code:
85151701
PubChem Substance ID:
329755350
NACRES:
NA.24

Key Documents

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grade

analytical standard

Quality Level

100

Assay

≥98.0% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

format

neat

storage temp.

2-8°C

SMILES string

OC1=CC=C(NC(/C=C/C2=CC(O)=C(O)C=C2)=O)C(C(O)=O)=C1

InChI

1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

InChI key

IDUUXROOZBOOPH-QHHAFSJGSA-N

Related Categories

General description

Avenanthramides are a class of substituted N-cinnamoylanthranilic acids present mainly in oats.

Application

Avenanthramide C may be used as a reference standard for the determination of avenanthramide C in:
  • Oat seeds and seedlings by reversed phase ultra-high performance liquid chromatography equipped with photodiode array deterctor (RP-UHPLC-PDA) and electrospray ionization ion trap mass spectrometry (ESI-IT-MS).
  • Oat-containing products by HPLC combined with triple quadrupole mass spectrometry (TQMS).

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

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
GHS07

Signal Word

Warning

Hazard Statements

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN2699
BCCM3354
BCCJ8901
BCCK7439
BCCH3933

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Selective and sensitive LC-MS determination of avenanthramides in oats.
Jastrebova J, et al.
Chromatographia, 63(9-10), 419-423 (2006)
Maria Guadalupe Quiroz Vazquez et al.
Biophysical chemistry, 263, 106391-106391 (2020-05-16)
The misfolding of protein and its assembly into amyloid fibrils with a characteristic β-sheet-rich secondary structure, cause a lot of illnesses. Polyphenols have been extensively studied as a class of amyloid inhibitors, whose effect depends on the position and number
Rapid quantitation of avenanthramides in oat-containing products by high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (HPLC-TQMS).
Xie Z, et al.
Food Chemistry, 224(9-10), 280-288 (2017)
Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa).
de Bruijn WJC, et al.
Food Chemistry, 63(9-10), 419-423 (2018)
Oswaldo Hernandez-Hernandez et al.
Food chemistry, 343, 128408-128408 (2020-11-08)
From a mutagenized oat population, produced by ethyl methanesulfonate mutagenesis, hulled grains from 17 lines with elevated avenanthramide (AVN) content were selected and their AVN structures, concentrations and antioxidant potentials were determined by HPLC-MS2 and HPLC equipped with an on-line

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