103404-94-0

Basic information

• Product Name: (plus,minus)-homocitric acid lactone
• Synonyms: (PLUS,MINUS)-HOMOCITRIC ACID LACTONE
• CAS NO: 103404-94-0
• Molecular Formula: C₇H₈O₆
• Molecular Weight: 188.13
• Mol File: 103404-94-0.mol

Chemical Properties

• CAS DataBase Reference: (plus,minus)-homocitric acid lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (plus,minus)-homocitric acid lactone(103404-94-0)
• EPA Substance Registry System: (plus,minus)-homocitric acid lactone(103404-94-0)

Safety Data

• Hazardous Substances Data: 103404-94-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(PLUS,MINUS)-HOMOCITRIC ACID LACTONE is used as an intermediate for the synthesis of various pharmaceutical compounds due to its role in the biosynthesis of lysine and threonine. Its presence in certain fungi also makes it a subject of interest for potential therapeutic applications.
Used in Biochemical Research:
(PLUS,MINUS)-HOMOCITRIC ACID LACTONE is utilized as a research compound for studying the metabolic pathways and enzyme mechanisms involved in the biosynthesis of amino acids, particularly lysine and threonine. This can contribute to the development of novel biocatalysts and bioprocesses in the field of biotechnology.
Used in Drug Development:
(PLUS,MINUS)-HOMOCITRIC ACID LACTONE is employed as a key building block in the development of new drugs targeting various medical conditions. Its unique structure and properties make it a valuable component in the design and synthesis of innovative pharmaceutical agents.
Used in Nutritional Supplements:
Given its involvement in the biosynthesis of essential amino acids, (PLUS,MINUS)-HOMOCITRIC ACID LACTONE may be used as an additive in the development of nutritional supplements aimed at supporting protein synthesis and overall health.

Upstream product

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• 790294-80-3 (R)-2-Hydroxy-2-(2-hydroxy-ethyl)-pentanedioic acid dimethyl ester 
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Relevant articles and documents

Enantioselective syntheses of (-)- and (+)-homocitric acid lactones

Highly enantioselective syntheses of enantiomers of homocitric acid lactones (R)-5a and (S)-5b are described. Thermal Diels-Alder cycloadditions of 2a and 2b to 1,3-butadiene produced adducts 3a and 3b, respectively. Oxidative ozonolysis of latter adducts gave products 4a and 4b which after acid treatment afforded a mixture with 5a and 5b as major component. Acid lactones 5a and 5b were converted into their dimethyl esters 6a and 6b which were purified by chromatography. After saponification, the products obtained were crystallized to yield (-)- and (+)-homocitric acid lactones ((R)-5a and (S)-5b). Diastereomeric excess (de) of Diels-Alder adducts 3a and 3b was determined by means of Mosher esters of glycols 8a, 8b, and racemic 8. Diels-Alder cycloaddition products of lactones 2a and 2b to 1,3-butadiene showed a diastereoselectivity of 96%.

Expeditious biomimetically-inspired approaches to racemic homocitric acid lactone and per-homocitrate

Two concise and flexible biomimetically-inspired approaches to homocitric acid lactone (3) and its higher homolog, triethyl per-homocitrate (12), are presented herein. The key steps include an efficient indium metal-mediated allylation-oxidative cleavage procedure and a one-step ethoxycarbonylmethylation of α-oxo-diesters.

Asymmetric Synthesis of Homocitric Acid Lactone

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.

A short enantioselective synthesis of homocitric acid-γ-lactone and 4-hydroxy-homocitric acid-γ-lactones

A simple method for the synthesis of enantiopure homocitric acid γ-lactone and its 4-hydroxy analogues starting from spiro-γ- dilactone, in up to 74% isolated yield is described.

Enantioselective synthesis of (R)-homocitric acid lactone

An expedient enantioselective approach to (R)-homocitric acid lactone from an ephedrine-derived morpholine-dione, a cationic glycolate equivalent, is described.

3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: An approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methyl

Enantioselective synthesis of isotopically labeled homocitric acid lactone

A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically 13C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.

Enantioselective synthesis of (S)-homocitric acid lactone and (R)-per-homocitric acid lactone involving organocatalysis

A concise enantioselective synthesis of (S)-homocitric acid lactone and its homolog, via an organocatalytic vinylogous Mukaiyama-Michael reaction of a silyloxy furan derivative and acrolein, is described.

An improved synthesis of trisodium (U)-homocitrate from citric acid

A method of synthesis of trisodium (R)-homocitrate starting from citric acid is reported. The procedure affords the final product of high optical purity with satisfactory yield.

A facile method for synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones and related α-hydroxy dicarboxylic acids from D- or L-malic acid

We report here a simple and convenient route for the stereoselective synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones, which play very important roles in biochemistry. The method involves only three steps, starting from the readily available met