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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:
610-88-8
Poids moléculaire :
197.23
Numéro Beilstein :
3589518
Numéro MDL:
MFCD00242648
Code UNSPSC :
85151701
ID de substance PubChem :
329755583
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

100

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
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Conseils de prudence

P301 + P310

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
BCCK5090
BCCK0991
BCCJ1114
BCCG4348
BCCF6858

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Andrea Patriarca et al.
International journal of food microbiology, 291, 135-143 (2018-12-01)
The group of the small-spored Alternaria species is particularly relevant in foods due to its high frequency and wide distribution in different crops. These species are responsible for the accumulation of mycotoxins and bioactive secondary metabolites in food. The taxonomy
Yong-Chul Jeong et al.
The Journal of organic chemistry, 76(5), 1342-1354 (2011-01-22)
The synthesis of 3-acyltetramic acids, the substructure of bioactive natural products, via O-acylation of tetramic acids with carboxylic acids followed by acyl migration, has been investigated. This acylation sequence is mediated by N,N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) and is very
Shiguo Chen et al.
Plant physiology and biochemistry : PPB, 52, 38-51 (2012-02-07)
3-Acetyl-5-isopropyltetramic acid (3-AIPTA), a derivate of tetramic acid, is responsible for brown leaf-spot disease in many plants and often kills seedlings of both mono- and dicotyledonous plants. To further elucidate the mode of action of 3-AIPTA, during 3-AIPTA-induced cell necrosis
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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