26400-45-3

Basic information

• Product Name: dehydroretronecine
• Synonyms: dehydroretronecine;6,7-DIHYDRO-7-HYDROXY-1-HYDROXYMETHYL-5H-PYRROLIZINE;2,3-Dihydro-1-hydroxy-1H-pyrrolizine-7-methanol;Dehdroheliotridine
• CAS NO: 26400-45-3
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.18
• Mol File: 26400-45-3.mol

Chemical Properties

• Boiling Point: 293.1°C at 760 mmHg
• Flash Point: 131.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000801mmHg at 25°C
• Refractive Index: 1.599
• PKA: 14.70±0.10(Predicted)
• CAS DataBase Reference: dehydroretronecine(CAS DataBase Reference)
• NIST Chemistry Reference: dehydroretronecine(26400-45-3)
• EPA Substance Registry System: dehydroretronecine(26400-45-3)

Safety Data

• Hazardous Substances Data: 26400-45-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production Industry:
Dehydroretronecine is used as a precursor chemical for the synthesis of other compounds in the chemical production industry. Its unique molecular structure allows for the creation of various chemical derivatives that can be utilized in different applications.
Used in Pharmaceutical Industry:
Dehydroretronecine is used as an active pharmaceutical ingredient for the development of drugs targeting specific medical conditions. Its unique chemical properties enable it to interact with biological systems, offering potential therapeutic benefits.
Used in Agrochemical Industry:
Dehydroretronecine is used as a component in the development of agrochemicals, such as pesticides and herbicides, due to its ability to target and control specific pests and weeds in agricultural settings.
Used in Research and Development:
Dehydroretronecine is used as a research compound in scientific studies and experiments, contributing to the understanding of its chemical properties, potential applications, and mechanisms of action.

InChI:InChI=1/C8H11NO2/c1-11-7-3-5-9-4-2-6(10)8(7)9/h3,5-6,10H,2,4H2,1H3

Upstream product

• 23291-96-5 monocrotaline pyrrole 
• 23246-96-0 riddelliine 

Relevant articles and documents

Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin

Pyrrolizidine alkaloid-containing plants are probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids exert toxicity through metabolism to dehydropyrrolizidine alkaloids that bind to cellular protein and

Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine

Riddelliine, a widespread naturally occurring genotoxic pyrrolizidine alkaloid, induced liver tumors in rats and mice in an NTP 2-year carcinogenicity bioassay. We have determined that riddelliine induces liver tumors in rats through a genotoxic mechanism involving the formation of (±)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP), which reacts with DNA to form a set of eight DNA adducts. To determine the relevance to humans of the results obtained in experimental animals, the metabolism of riddelliine was conducted using human liver microsomes. As with rat liver microsomes, DHP and riddelliine N-oxide were major metabolites in incubations conducted with human liver microsomes. The levels of DHP and riddelliine N-oxide were 0.20-0.62 and 0.03-0.15 nmol/min/mg protein, respectively, which are comparable to those obtained from rat liver microsomal metabolism. When metabolism was conducted in the presence of calf thymus DNA, the same set of eight DHP-derived DNA adducts was formed. Both the metabolism pattern and DNA adduct profile were very similar to those obtained from rat liver microsomes. When metabolism was conducted in the presence of the P450 3A4 enzyme inhibitor triacetyleandomycin, the formation of DHP and riddelliine N-oxide was reduced 84 and 92%, respectively. For DHP formation, the Km values were determined to be 0.37 ± 0.05 and 0.66 ± 0.08 mM from female rats and female humans; the Vmax values from female rat and human liver microsomal metabolism were 0.48 ± 0.03 and 1.70 ± 0.09 nmol/min/mg protein, respectively. These results strongly indicate the mechanistic data on liver tumor induction obtained for riddelliine in laboratory rodents is highly relevant to humans.