64947
Prochloraz
certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
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About This Item
Empirical Formula (Hill Notation):
C15H16Cl3N3O2
CAS Number:
Molecular Weight:
376.67
Beilstein/REAXYS Number:
8155344
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
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grade
certified reference material
TraceCERT®
Quality Level
product line
TraceCERT®
shelf life
limited shelf life, expiry date on the label
manufacturer/tradename
Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
application(s)
agriculture
environmental
format
neat
storage temp.
2-8°C
SMILES string
CCCN(CCOc1c(Cl)cc(Cl)cc1Cl)C(=O)n2ccnc2
InChI
1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3
InChI key
TVLSRXXIMLFWEO-UHFFFAOYSA-N
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General description
Prochloraz is a fungicide possessing imidazole moiety, which can show anti-androgenic activity in blocking androgens like testosterone from mediating their biological effects in the body. It is involved in the inhibition of cytochrome P450-dependent, 14α-demethylase activity required in the conversion of lanosterol to ergosterol, a key constituent of fungal cell membranes.
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.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com.
Application
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
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Legal Information
TraceCERT is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Antiandrogenic effects in vitro and in vivo of the fungicide prochloraz
Vinggaard MA, et al.
Toxicological Sciences, 69(2), 344-353 (2002)
Sarah Y Skolness et al.
Aquatic toxicology (Amsterdam, Netherlands), 103(3-4), 170-178 (2011-04-08)
Prochloraz is a fungicide known to cause endocrine disruption through effects on the hypothalamic-pituitary-gonadal (HPG) axis. To determine the short-term impacts of prochloraz on gene expression and steroid production, adult female fathead minnows (Pimephales promelas) were exposed to the chemical
Sofie Christiansen et al.
Environmental health perspectives, 117(12), 1839-1846 (2010-01-06)
By disrupting the action of androgens during gestation, certain chemicals present in food, consumer products, and the environment can induce irreversible demasculinization and malformations of sex organs among male offspring. However, the consequences of simultaneous exposure to such chemicals are
Anne Marie Vinggaard et al.
International journal of andrology, 29(1), 186-192 (2006-02-10)
Prochloraz is an imidazole fungicide that is widely used in Europe, Australia, Asia and South America within gardening and agriculture. Screening studies have shown that prochloraz elicits multiple mechanisms of action in vitro, as it antagonizes the androgen and the
Sandra Halwachs et al.
Toxicological sciences : an official journal of the Society of Toxicology, 131(2), 491-501 (2012-10-20)
The molecular mechanisms by which environmental pollutants including 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) or widely used imidazole fungicide prochloraz display their toxic effects in vertebrates are still not well understood. Using computer analysis, we recently identified nuclear aryl hydrocarbon receptor (AhR) binding sites
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