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Tenuazonic acid

analytical standard

Synonym(s):

(5S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-2H-pyrrol-2-one, (S)-3-Acetyl-5-(S)-sec-butyltetramic acid, (S)-3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H15NO3
CAS Number:
Molecular Weight:
197.23
Beilstein:
3589518
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@@H]1NC(=O)C(C(C)=O)=C1O

InChI

1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1

InChI key

CEIZFXOZIQNICU-XNCJUZBTSA-N

General description

Tenuazonic acid is a biologically active compound and its mode of action involves the inhibition of protein biosynthesis.
Tenuazonic acid is a mycotoxin, which belongs to the class of tetramic acids, the largest family of natural products. It is generally isolated from phytopathogenic fungal species like Alternaria alternata, A. longipes and A. tenuissima.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Tenuazonic acid may be used as an analytical reference standard for the quantification of the analyte in the following:
  • Cornflakes using high-performance liquid chromatography (HPLC) technique.
  • Human urine samples using isotope dilution assay method and liquid chromatography coupled to a hybrid triple quadrupole/linear ion trap mass spectrometer.
  • Cereals using high-performance liquid chromatography–electrospray ionization ion-trap multistage mass spectrometry (HPLC- ESI ion-trap (IT) MS2). ESI Fourier transform-ion cyclotron resonance tandem mass spectrometry (FTICR-MS2) technique is used for product characterization, post derivatization with 2,4-dinitrophenylhydrazine.

Reconstitution

Dried down, ~100 μg/mL after reconstitution with 1 mL of water

Analysis Note

purity : ≥96.0% (HPLC)

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Recent advances in tenuazonic acid as a potential herbicide
Chen S and Qiang S
Pesticide Biochemistry and Physiology (2017)
Simultaneous determination of ochratoxin A and cyclopiazonic, mycophenolic, and tenuazonic acids in cornflakes by solid-phase microextraction coupled to high-performance liquid chromatography
Aresta A, et al.
Journal of Agricultural and Food Chemistry, 51(18), 5232-5237 (2003)
Determination of tenuazonic acid in human urine by means of a stable isotope dilution assay
Asam S, et al.
Analytical and Bioanalytical Chemistry, 405(12), 4149-4158 (2013)
David Siegel et al.
Journal of chromatography. A, 1216(21), 4582-4588 (2009-04-14)
Tenuazonic acid (TA) is a major Alternaria mycotoxin. In the present work a novel approach for the detection of TA in cereals by liquid chromatography-ion-trap multistage mass spectrometry after derivatization with 2,4-dinitrophenylhydrazine is described. The product of the derivatization reaction
Stefan Asam et al.
Journal of agricultural and food chemistry, 59(7), 2980-2987 (2011-03-05)
A stable isotope dilution assay (SIDA) for the Alternaria mycotoxin tenuazonic acid was developed. Therefore, [(13)C(6),(15)N]-tenuazonic acid was synthesized from [(13)C(6),(15)N]-isoleucine by Dieckmann intramolecular cyclization after acetoacetylation with diketene. The synthesized [(13)C(6),(15)N]-tenuazonic acid was used as the internal standard for

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