13588-16-4

Basic information

• Product Name: necic acid
• Synonyms: necic acid;(2R,3R,Z)-5-Ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid
• CAS NO: 13588-16-4
• Molecular Formula: C10H16O5
• Molecular Weight: 216.23
• Mol File: 13588-16-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 145-146°
• Boiling Point: 466.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.241±0.06 g/cm3(Predicted)
• Refractive Index: 1.518
• PKA: 3.95±0.27(Predicted)
• CAS DataBase Reference: necic acid(CAS DataBase Reference)
• NIST Chemistry Reference: necic acid(13588-16-4)
• EPA Substance Registry System: necic acid(13588-16-4)

Safety Data

• Hazardous Substances Data: 13588-16-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O5/c1-4-7(8(11)12)5-6(2)10(3,15)9(13)14/h4,6,15H,5H2,1-3H3,(H,11,12)(H,13,14)/b7-4-/t6?,10-/m1/s1

Upstream product

• 77147-54-7 trans-6-Cyan-6-hydroxy-5-methyl-2-hepten-3-carbonsaeure 
• 130-01-8 senecionine 
• 64-17-5 ethanol 
• 18003-17-3 (R)-5-((Z)-ethylidene)-2-hydroxy-2-methyl-3-methylen-adipic acid 
• 6582-61-2 2(E)-ethylidene-5-(methoxycarbonyl)-4,5-dimethyl-5-pentanolide 
• 81165-19-7 5-methoxycarbonyl-4,5-cis-dimethyl-5-peantanolide 
• 81165-20-0 (2R,3R)-5-(1-Hydroxy-ethyl)-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 3055-21-8 (+/-)-integerrinecic acid lactone 
• 520-65-0 rosmarinine 
• 157240-90-9 senecic acid lactone methyl ester 
• 28822-16-4 2R,3S-Senecinsaeurelacton 
• 159999-65-2 ethyl (2Z)-2-ethylidene-4-methyl-5-oxohexanoate 
• 77147-53-6 (2E)-2-ethylidene-4-methyl-5-oxohexanoic acid 
• 84184-60-1 ethyl 2-(1-acetoxyethyl)acrylate 

Downstream Products

• 2064-81-5 Dihydrosyneilesinolid B 
• 130-01-8 senecionine 
• 75-07-0 acetaldehyde 

Relevant articles and documents

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USPALLATINE, A PYRROLIZIDINE ALKALOID FROM SENECIO USPALLATENSIS

A new pyrrolizidine alkaloid uspallatine was isolated from roots of Senecio uspallatensis together with the previously known retrorsine.The structure of the new alkaloid was established by spectroscopical data and chemical transformation.Key Word Index - Senecio uspallatensis; Compositae; pyrrolizidine alkaloids; uspallatine.

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).

Necic Acid Synthons. Part 1. Total Synthesis of Integerrinecic Acid

The synthesis of racemic integerrinecic acid from ethyl acrylate is described.Overall, five steps are involved.A key synthon in the synthesis, ethyl (2Z)-2-bromomethylbut-2-enoate, can undergo either allylic substitution or substitution with rearrangement, and opens the way for a 'general' synthesis toa range of necic acids.