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Tenuazonic acid

analytical standard

Synonyme(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

Formule empirique (notation de Hill):
C10H15NO3
Numéro CAS:
Poids moléculaire :
197.23
Numéro Beilstein :
3589518
Numéro MDL:
Code UNSPSC :
85151701
ID de substance PubChem :
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

Durée de conservation

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

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

CEIZFXOZIQNICU-XNCJUZBTSA-N

Description générale

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

Remarque sur l'analyse

purity : ≥96.0% (HPLC)

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

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)
Recent advances in tenuazonic acid as a potential herbicide
Chen S and Qiang S
Pesticide Biochemistry and Physiology (2017)
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)
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
A Rico-Yuste et al.
Food chemistry, 243, 357-364 (2017-11-18)
Molecularly imprinted porous polymer microspheres selective to Alternaria mycotoxins, alternariol (AOH) and alternariol monomethyl ether (AME), were synthesized and applied to the extraction of both mycotoxins in food samples. The polymer was prepared using 4-vinylpiridine (VIPY) and methacrylamide (MAM) as

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