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PHL22642

Rotenone

phyproof® Reference Substance

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About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
83-79-4
Molecular Weight:
394.42
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
6773081
MDL number:
MFCD09025614
NACRES:
NA.24
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grade

primary reference standard

product line

phyproof® Reference Substance

assay

≥95.0% (HPLC)

manufacturer/tradename

PhytoLab

technique(s)

HPLC: suitable

bp

210-220 °C/0.5 mmHg (lit.)

mp

159-164 °C (lit.)

application(s)

food and beverages
pharmaceutical

format

neat ()

storage temp.

−20°C

SMILES string

COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C

InChI

1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChI key

JUVIOZPCNVVQFO-HBGVWJBISA-N

General description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Inhibitor of mitochondrial electron transport.
Rotenone is an inhibitor of mitochondrial electron transport at nicotinamide adenine dinucleotide (NADH):ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone acts as a neurotoxic agent which can produce Parkinson-like condition to serve as an animal model for the study of etiology and interventions. The primary mechanism of action of rotenone is complex I inhibition, followed by the generation of oxidative stress and oxidative damage. Because rotenone is lipophilic, it readily penetrates the brain, where it attaches to and inhibits mitochondrial complex I of electron chain transport (ETC).

Legal Information

phyproof is a registered trademark of PhytoLab GmbH & Co. KG

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pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
234482
228675

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Global Trade Item Number

SKUGTIN
PHL22642-10MG04065272279352