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Supelco

Tentoxin

analytical standard

Synonym(s):

Cyclo[N-methyl-L-alanyl-L-leucyl-(αZ)-α,β-didehydro-N-methylphenylalanylglycyl]

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About This Item

Empirical Formula (Hill Notation):
C22H30N4O4
CAS Number:
Molecular Weight:
414.50
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)C[C@@H]1NC(=O)[C@H](C)N(C)C(=O)CNC(=O)C(=C\c2ccccc2)\N(C)C1=O

InChI

1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1

InChI key

SIIRBDOFKDACOK-LFXZBHHUSA-N

General description

Tentoxin is a phytotoxic tetrapeptide, produced in some Alternaria species. It is known to inhibit cyclic photophosphorylation.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Tentoxin may be used as an analytical reference standard for the determination of the analyte in tomato and food matrices by chromatography techniques.

Analysis Note

purity : ≥97.0% (HPLC)

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Application of an LC--MS/MS based multi-mycotoxin method for the semi-quantitative determination of mycotoxins occurring in different types of food infected by moulds.
Sulyok M, et al.
Food Chemistry, 119(1), 408-416 (2010)
Inhibition of chloroplast development by tentoxin.
Bennett J.
Phytochemistry, 15(2), 263-265 (1976)
Development and validation of a LC-ESI-MS/MS method for the determination of Alternaria toxins alternariol, alternariol methyl-ether and tentoxin in tomato and tomato-based products.
Rodriguez-Carrasco Y, et al.
Toxins, 8(11), 328-328 (2016)
Feng He et al.
Biochemistry, 47(2), 836-844 (2007-12-21)
Two highly conserved amino acid residues, an arginine and a glutamine, located near the C-terminal end of the gamma subunit, form a "catch" by hydrogen bonding with residues in an anionic loop on one of the three catalytic beta subunits
Stephen O Duke et al.
Toxins, 3(8), 1038-1064 (2011-11-10)
Some of the most potent phytotoxins are synthesized by microbes. A few of these share molecular target sites with some synthetic herbicides, but many microbial toxins have unique target sites with potential for exploitation by the herbicide industry. Compounds from

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