480-85-3

Basic information

• Product Name: retronecine
• Synonyms: (1R)-2,3,5,7aβ-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol;(1R)-2,3,5,7aβ-Tetrahydro-1α-hydroxy-1H-pyrrolizine-7-methanol;(1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol;Retronecin
• CAS NO: 480-85-3
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.196
• Mol File: 480-85-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 119-120°
• Boiling Point: 291.3°Cat760mmHg
• Flash Point: 161.4°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000211mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: 2-8°C
• Solubility: Ethanol (Slightly), Methanol (Slightly)
• PKA: 14.48±0.40(Predicted)
• CAS DataBase Reference: retronecine(CAS DataBase Reference)
• NIST Chemistry Reference: retronecine(480-85-3)
• EPA Substance Registry System: retronecine(480-85-3)

Safety Data

• RIDADR: 1544
• WGK Germany: 3
• RTECS: VH7175000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 480-85-3(Hazardous Substances Data)

Usage

Uses

(+)-Retronecine, is a Pyrrolizidine alkaloid (PA) , which is a hepatotoxic, that is, damaging to the liver. It is also tumorigenic. It can also be used as an intermediate for the synthesis of (+)-Lycopsamine (L487525), and (E325580).

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 
• 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 
• 70866-60-3 4-(tert-Butyl-dimethyl-silanyloxy)-5-[(E)-3-hydroxy-1-(tetrahydro-pyran-2-yloxymethyl)-propenyl]-pyrrolidin-2-one 
• 74400-34-3 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dienoic acid methyl ester 
• 74400-35-4 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dien-1-ol 
• 74400-36-5 (Z)-3-(Tetrahydro-pyran-2-yloxymethyl)-penta-2,4-dienal 
• 74400-30-9 (1R,7aS)-1-Hydroxy-7-hydroxymethyl-1,2,5,7a-tetrahydro-pyrrolizin-3-one 
• 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 
• 548-90-3 trichodesmine 

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 articles and documents

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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 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.