480-85-3

Usage

Uses

Used in Pharmaceutical Synthesis:
Retronecine is used as an intermediate in the synthesis of various compounds, such as (+)-Lycopsamine (L487525) and (E325580). Its role in the pharmaceutical industry is crucial for the development of new drugs and therapeutic agents.
Used in Research and Development:
Due to its hepatotoxic and tumorigenic properties, retronecine is utilized in research and development for studying the effects of these characteristics on the liver and the development of tumors. This helps in understanding the underlying mechanisms and potentially developing treatments or preventive measures against liver damage and tumor formation.

InChI:InChI=1/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1

Upstream product

• 480-81-9 seneciphylline 
• 480-54-6 retrorsine 
• 548-90-3 trichodesmine 
• 76465-88-8 (4S,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate 
• 480-54-6 retrorsine 
• 74400-30-9 (1R,7aS)-1-Hydroxy-7-hydroxymethyl-1,2,5,7a-tetrahydro-pyrrolizin-3-one 
• 74400-36-5 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dienal 
• 74400-35-4 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dien-1-ol 
• 74400-34-3 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dienoic acid methyl ester 
• 74400-32-1 (1R,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(tetrahydro-pyran-2-yloxymethyl)-1,2,5,7a-tetrahydro-pyrrolizin-3-one 
• 74400-38-7 C₃₅H₄₇NO₅Si 
• 74400-37-6 C₂₉H₃₃NO₅ 
• 74400-41-2 Methanesulfonic acid (E)-3-[3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl ester 
• 70866-61-4 5-(tert-Butyl-dimethyl-silanyloxy)-4-(tetrahydro-pyran-2-yloxymethyl)-2,4a,5,6-tetrahydro-pyrrolo[1,2-b][1,2]oxazin-7-one 

Downstream Products

• 95363-37-4 9-O-Benzoylretronecine 
• 76040-28-3 (7aR)-1t-hydroxy-7-hydroxymethyl-4-methyl-(4ξ,7ar)-2,3,5,7a-tetrahydro-1H-pyrrolizinium; iodide 
• 34081-90-8 isatinecic acid 
• 28463-14-1 retronecic acid 
• 74612-20-7 13,13-dimethyl-1,2-didehydrocrotalanine 
• 82296-60-4 4-Dimethylcarbamoyl-3,3-dimethyl-butyric acid (1R,7aR)-7-hydroxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester 
• 82296-59-1 4-Dimethylcarbamoyl-3,3-dimethyl-butyric acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 82296-72-8 7-O-(hydrogen 3,3-diphenylglutaryl)retronecine 
• 82296-73-9 9-O-(hydrogen 3,3-diphenylglutaryl)retronecine 
• 63503-32-2 Phenyl-acetic acid (1R,7aR)-7-hydroxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester 
• 95363-38-5 Phenyl-acetic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 480-82-0 (+)-indicine 
• 10285-06-0 intermedine 
• 76405-16-8 (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 

Relevant academic research and scientific papers

ISO-LYCOPSAMINE, A PYRROLIZIDINE ALKALOID FROM HELIOTROPIUM KERALENSE

The pyrrolizidine alkaloids of Heliotropium keralense have been isolatedand characterized.They are iso-lycopsamine, a new pyrrolizidine alkaloid, intermedine and retronecine. iso-Lycopsamine was formulated as 1,2-dehydro-1-hydroxymethyl-7β-(+)-viridifloroxy-8α-pyrrolizidine on the basis of spectroscopic measurements and hydrolysis.

Pyrrolizidine Alkaloid Biosynthesis. Synthesis of 3H-Labelled Trachelanthamidine and Isoretronecanol and their Incorporation into Three Pyrrolizidine Bases (Necines)

(+/-)-Isoretronecanol (22) and (+/-)-trachelanthamidine (24) were prepared by 1,3-dipolar cycloaddition of N-formylproline with ethyl propiolate followed by reduction steps.These 3H-labelled 1-hydroxymethylpyrrolizidines together with putrescine were fed to Senecio isatideus which produces retrorsine (1); S. pleistocephalus which yields rosmarinine (8); and Cynoglossum officinale which affords echinatine (5).The double labelling experiments demonstrated that isoretronecanol is incorporated much more efficiently into rosmarinine than into retrorsine or echinatine, whereas trachelanthamidine is a much more efficient precursor for retrorsine and echinatine.Base hydrolysis of retrorsine and echinatine labelled with trachelanthamidine and of rosmarinine labelled with isoretronecanol established that most of the 3H-label was in the base portions, retronecine (2), heliotridine (6), and rosmarinecine (9), respectively.Further degradation of retronecine and rosmarinecine showed that most of the radioactivity was confined to the β-alanine (4) portion.The biosynthetic pathways to isoretronecanol and trachelanthamidine apparently diverge prior to the formation of these 1-hydroxymethylpyrrolizidines, probably during the cyclisation of an immonium ion (14) to form the 1-formylpyrrolizidines (15) and (17).

Pyrrolizidine Alkaloid Biosynthesis. Synthesis of 13C-Labelled Putrescines and their Incorporation into Retronecine

The biosynthesis of the retronecine (3) portion of the pyrrolizidine alkaloid retrorsine (1) has been studied in Senecio isatideus plants using 13C-labelled putrescines.Samples of -(10), -(8), and -putrescine (9) were prepared a

Pyrrolizidine Alkaloids. Biosynthesis of Trichodesmic Acid

14C-Labelled threonine (3), isoleucine (4), valine (5), and leucine (6) were incorporated specifically into trichodesmic acid (12), the necic acid component of the pyrrolizidine alkaloid trichodesmine (2) produced by Crotalaria globifera.Degradation of the 14C-labelled trichodesmic acid showed that threonine and isoleucine mainly lable one half of the C10 acid, while valine and leucine predominantly lable the other half of the acid.