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Tenuazonic acid

analytical standard

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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
Empirical Formula (Hill Notation):
C10H15NO3
CAS Number:
610-88-8
Molecular Weight:
197.23
Beilstein:
3589518
MDL number:
MFCD00242648
PubChem Substance ID:
329755583
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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

Related Categories

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
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

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

Regulatory Information

高风险级别生物产品--毒素类产品

Certificates of Analysis (COA)

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

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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)
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)
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
Sergey Dobretsov et al.
Biofouling, 27(8), 893-905 (2011-09-03)
Seventy eight natural products from chemical libraries containing compounds from marine organisms (sponges, algae, fungi, tunicates and cyanobacteria) and terrestrial plants, were screened for the inhibition of bacterial quorum sensing (QS) using a reporter strain Chromobacterium violaceum CV017. About half
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