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Merck
CN

35977

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:
28540-82-1
Molecular Weight:
414.50
NACRES:
NA.24
PubChem Substance ID:
329755240
UNSPSC Code:
85151701
MDL number:
MFCD00133844

Key Documents

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InChI key

SIIRBDOFKDACOK-LFXZBHHUSA-N

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

grade

analytical standard

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

Quality Level

100

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

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
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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9155
BCCG2240
BCCF7977
BCCD1985
BCBZ8279

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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)
Inhibition of chloroplast development by tentoxin.
Bennett J.
Phytochemistry, 15(2), 263-265 (1976)
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)
The sequence and optical configuration of the amino acids in tentoxin.
Koncewicz M, et al.
Biochemical and Biophysical Research Communications, 53(2), 653-658 (1973)
Georg Groth et al.
The Journal of biological chemistry, 277(23), 20117-20119 (2002-04-12)
In contrast to the homologous bacterial and mitochondrial enzymes the chloroplast F(1)-ATPase (CF(1)) is strongly affected by the phytopathogenic inhibitor tentoxin. Based on structural information obtained from crystals of a CF(1)-tentoxin co-complex (Groth, G. (2002) Proc. Natl. Acad. Sci. U.
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