23107-12-2

Basic information

• Product Name: DEHYDRORETRONECINE
• Synonyms: (1R)-2,3-Dihydro-1-hydroxy-1H-pyrrolizine-7-methanol;(7R)-7-Hydroxy-6,7-dihydro-5H-pyrrolizine-1-methanol;Retronecine pyrrole
• CAS NO: 23107-12-2
• Molecular Formula: C8H11 N O2
• Molecular Weight: 153.20
• Mol File: 23107-12-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 276.1°C (rough estimate)
• Flash Point: 172.3°C
• Appearance: /
• Density: 1.1577 (rough estimate)
• Vapor Pressure: 7.54E-06mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• CAS DataBase Reference: DEHYDRORETRONECINE(CAS DataBase Reference)
• NIST Chemistry Reference: DEHYDRORETRONECINE(23107-12-2)
• EPA Substance Registry System: DEHYDRORETRONECINE(23107-12-2)

Safety Data

• Hazardous Substances Data: 23107-12-2(Hazardous Substances Data)

Usage

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H11NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,3,7,10-11H,2,4-5H2/t7-/m1/s1

Upstream product

• 480-85-3 retronecine 
• 315-22-0 monocrotaline 

Downstream Products

• 1207683-09-7 5-(deoxyguanosin-N2-yl)dehydrosupinidine 
• 1207683-08-6 7-hydroxy-9-(deoxyguanosin-N²-yl)dehydrosupinidine 
• 81498-75-1 7-(deoxyguanosin-N2-yl)dehydrosupinidine 
• 81498-76-2 7-(deoxyguanosin-N2-yl)dehydrosupinidine 
• 1207683-10-0 7-(deoxyguanosin-N²-yl)-dehydrosupinidine 
• 1207683-11-1 7-(deoxyguanosin-N²-yl)-dehydrosupinidine 

Relevant articles and documents

Development of a 32p-postlabeling/HPLC method for detection of dehydroretronecine-derived DNA adducts in vivo and in vitro

Pyrrolizidine alkaloids are naturally occurring genotoxic chemicals produced by a large number of plants. Metabolism of pyrrolizidine alkaloids in vivo and in vitro generates dehydroretronecine (DHR) as a common reactive metabolite. In this study, we report the development of a 32P-postlabeling/HPLC method for detection of (i) two DHR-3′-dGMP and four DHR-3′-dAMP adducts and (ii) a set of eight DHR-derived DNA adducts in vitro and in vivo. The approach involves (1) synthesis of DHR-3′-dGMP, DHR-3′-dAMP, and DHR-3′,5′dG-bisphosphate standards and characterization of their structures by mass and 1H NMR spectral analyses, (2) development of optimal conditions for enzymatic DNA digestion, adduct enrichment, and 32P-postlabeling, and (3) development of optimal HPLC conditions. Using this methodology, we have detected eight DHR-derived DNA adducts, including the two epimeric DHR-3′,5′-dG-bisphosphate adducts both in vitro and in vivo.

High-performance liquid chromatography electrospray ionization tandem mass spectrometry for the detection and quantitation of pyrrolizidine alkaloid-derived DNA adducts in vitro and in viwo

Pyrrolizidine alkaloid-containing plants are widespread in the world and are probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolism to exert their genotoxicity and tumorigenicity. We have determined that the metabolism of a series of tumorigenic pyrrolizidine alkaloids in Vitro or in ViVo generates a common set of (±)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived DNA adducts that are responsible for tumor induction. The identification and quantitation of the DHP-derived DNA adducts formed in ViVo and in Vitro were accomplished previously by 32P-postlabeling/HPLC methodology. In this article, we report the development of a sensitive and specific liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ES-MS/MS) method to detect DHP-derived DNA adducts formed in Vitro and in ViVo. The method is used to quantify the levels of DHP-2′-deoxyguanosine (dG) and DHP-2′-deoxyadenosine (dA) adducts by multiple reaction monitoring (MRM) analysis in the presence of known quantities of isotopically labeled DHP-dG and DHP-dA internal standards. This HPLC-ES-MS/MS method is accurate and precise. When applied to liver samples from rats treated with the pyrrolizidine alkaloids riddelliine and monocrotaline, the method provided significant new information regarding the mechanism of DNA adduct formation.