CRM03054
Tetramethrin
mixture of stereoisomers, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
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About This Item
Empirical Formula (Hill Notation):
C19H25NO4
CAS Number:
Molecular Weight:
331.41
Beilstein/REAXYS Number:
8807938
MDL number:
UNSPSC Code:
41116107
Recommended Products
grade
certified reference material
TraceCERT®
Quality Level
product line
TraceCERT®
shelf life
limited shelf life, expiry date on the label
composition
cis-Tetramethrin, <25.0% (minor component)
manufacturer/tradename
Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
storage temp.
−20°C
SMILES string
C\C(C)=C\C1C(C(=O)OCN2C(=O)C3=C(CCCC3)C2=O)C1(C)C
InChI
1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3
InChI key
CXBMCYHAMVGWJQ-UHFFFAOYSA-N
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General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. This CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ. Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate. Download your certificate at: http://www.sigma-aldrich.com.
Tetramethrin, a type I pyrethroid, is used worldwide to protect crops and mammals from a variety of pests such as flies, fleas, mosquitoes, headlice, and mites. Tetramethrin is a synthetic pyrethroid insecticide, that binds to voltage-gated sodium channels of insect nerves and prevents its transition from an activated (ion-conducting) to an inactivated (non-conducting) state. This leads to a permanent depolarization of axonal membranes, causing paralysis and death of an insect.
Tetramethrin is not approved for use in the EU.
The maximum residue limits (MRLs) of pyrethroids compounds in fruits and fruit juices have been set at 0.02 to 0.5 mg/kg in China (GB2763-2019), and 0.02 to 0.3 mg/kg in European Union (EU) (Part A of Annex to Reg. 396/2005), respectively.
Tetramethrin, a type I pyrethroid, is used worldwide to protect crops and mammals from a variety of pests such as flies, fleas, mosquitoes, headlice, and mites. Tetramethrin is a synthetic pyrethroid insecticide, that binds to voltage-gated sodium channels of insect nerves and prevents its transition from an activated (ion-conducting) to an inactivated (non-conducting) state. This leads to a permanent depolarization of axonal membranes, causing paralysis and death of an insect.
Tetramethrin is not approved for use in the EU.
The maximum residue limits (MRLs) of pyrethroids compounds in fruits and fruit juices have been set at 0.02 to 0.5 mg/kg in China (GB2763-2019), and 0.02 to 0.3 mg/kg in European Union (EU) (Part A of Annex to Reg. 396/2005), respectively.
Application
It is intended to be used as a certified reference material (CRM) for calibration in chromatography and other analytical techniques. Tetramethrin in CRM may also find its use as described below:
- Study of Estrogenic activity of tetramethrin in uterine CaBP-9k gene expression and a uterotrophic assay, and androgenic activity in Hershberger assay
- To synthesize bis-dihydroxyboron fluorescein complexes for developing a ratiometric fluorescence probe used in the direct detection of pyrethroid residues in fruit juices
- Separation of the four isomers of tetramethrin with ecotoxicity test and quantitative analysis in agrochemical formulations using chiral electrokinetic chromatography methodology
- Residual detection of acetanilide, pentylenetetrazole, phenacetin, and tetramethrin in porcine muscle, pasteurized milk, and eggs by liquid chromatography-electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) method
- To test glucocorticoid-like activity of propylparaben, butylparaben, diethylhexyl phthalate, and tetramethrin mixtures in different combinations at real human exposure levels
Legal Information
TraceCERT is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - STOT SE 2 Inhalation
target_organs
Nervous system
Storage Class
6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 2
Certificates of Analysis (COA)
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Linda M Field et al.
European biophysics journal : EBJ, 46(7), 675-679 (2017-01-11)
The pyrethroid insecticides are a very successful group of compounds that have been used extensively for the control of arthropod pests of agricultural crops and vectors of animal and human disease. Unfortunately, this has led to the development of resistance
An efficiently ratiometric fluorescent probe based on bis-dihydroxyboron fluorescein complexes for detection of pyrethroid residues in fruit juices
Fang F, et al.
Microchemical Journal, Devoted to the Application of Microtechniques in All Branches of Science, 106954 null
M Greño et al.
The Science of the total environment, 800, 149496-149496 (2021-08-14)
The separation of the four isomers of tetramethrin was performed for the first time using a cyclodextrin-micellar electrokinetic chromatography methodology. Using sodium deoxycholate and 2-hydroxypropyl-β-CD as chiral selectors, tetramethrin isomers were separated with resolution values of 1.7 and 1.1 for
Soon Sun Kim et al.
Journal of toxicology and environmental health. Part A, 68(23-24), 2277-2289 (2005-12-06)
Tetramethrin, a synthetic pyrethroid insecticide, is used globally for agriculture, and thus potential environmental exposure to tetramethrin is a concern. Environmental chemicals that are hormonally active (particularly estrogen or androgen) may adversely affect the reproductive and endocrine systems. However, little
Ivana Klopčič et al.
Toxicology letters, 232(2), 376-383 (2014-12-03)
Endocrine-disrupting compounds can interfere with the endocrine organs or hormone system and cause tumors, birth defects and developmental disorders in humans. The estrogen-like activity of compounds has been widely studied but little is known concerning their possible modulation of the
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