28463-14-1

Basic information

• Product Name: (2S,3R,E)-5-Ethylidene-2-hydroxy-2-hydroxymethyl-3-methylhexanedioic acid
• Synonyms: (2S,3R,E)-5-Ethylidene-2-hydroxy-2-hydroxymethyl-3-methylhexanedioic acid;Retronecic acid
• CAS NO: 28463-14-1
• Molecular Formula: C10H16 O6
• Molecular Weight: 232.2304
• Mol File: 28463-14-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 542.8°Cat760mmHg
• Flash Point: 296.1°C
• Appearance: /
• Density: 1.352g/cm³
• Vapor Pressure: 4.79E-14mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: (2S,3R,E)-5-Ethylidene-2-hydroxy-2-hydroxymethyl-3-methylhexanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,E)-5-Ethylidene-2-hydroxy-2-hydroxymethyl-3-methylhexanedioic acid(28463-14-1)
• EPA Substance Registry System: (2S,3R,E)-5-Ethylidene-2-hydroxy-2-hydroxymethyl-3-methylhexanedioic acid(28463-14-1)

Safety Data

• Hazardous Substances Data: 28463-14-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O6/c1-3-7(8(12)13)4-6(2)10(16,5-11)9(14)15/h3,6,11,16H,4-5H2,1-2H3,(H,12,13)(H,14,15)/b7-3+

Upstream product

• 480-54-6 retrorsine 
• 480-85-3 retronecine 
• 15503-87-4 usaramine 
• 480-54-6 retrorsine 
• 106060-37-1 dimethyl (E)-1,2-diacetoxy-3-methylhept-5-ene-2,5-dicarboxylate 
• 33935-64-7 methyl 2-(bromomethyl)-2-butenoate 
• 22787-68-4 methyl 2-(1-acetoxyethyl)acrylate 
• 98837-36-6 methyl 3-hydroxy-2-methylenebutyrate 
• 106060-30-4 dimethyl 5-ethylidene-3-methyl-2-methylenehexane-2,5-dicarboxylate 
• 106060-29-1 4-(1-chloroethyl)-4-methoxycarbonyl-2,2-dimethyl-1,3-dioxolane 
• 106060-28-0 4-(1-hydroxymethyl)-4-methoxycarbonyl-2,2-dimethyl-1,3-dioxolane 
• 106060-26-8 methyl 3-acetoxy-2-hydroxy-2-hydroxymethylbutanoate 
• 106060-35-9 dimethyl 3-methyl-5,6-epoxyhept-1-ene-2,5-dicarboxylate 
• 106060-27-9 4-(1-acetoxyethyl)-4-methoxycarbonyl-2,2-dimethyl-1,3-dioxolane 

Relevant articles and documents

Synthesis of New Macrocycles. Part 6. Pyridine-retronecate, a New Synthetic Alkaloid

Reaction of 2,6-bis(bromomethyl)pyridine with the naturally-occuring C10 necic acid, retronecic acid, results in the formation of a new semi-synthetic cyclic diester alkaloid, pyridine-retronecate.This product is an analogue of a pyrrolizidine alkaloid and retains those characteristics normally held responsible for the toxity of this class of alkaloids.Biological tests carried out on mice injected with retrorsine and with the synthetic analogue suggest that the cytotoxic effects are similar.

Necic Acid Synthons. Part 5. Total Synthesis of (+/-)-Retronecic Acid and Related Compounds via Zinc-Mediated Coupling of Halogeno-esters

Zinc-mediated coupling of suitably substituted halogeno esters affords access to (+/-)-retronecic acid (2) and related intermediates.These approaches lead to racemic retronecic acid on the one hand and to a diastereoisomeric mixture of the acid on the other.