2306-22-1

Usage

Uses

Used in Food Industry:
(+/-)-CITRAMALIC ACID DIPOTASSIUM SALT is used as a flavor enhancer and acidity regulator for improving the taste and quality of processed foods and beverages.
Used in Pharmaceutical Industry:
(+/-)-CITRAMALIC ACID DIPOTASSIUM SALT has potential applications in the pharmaceutical industry, although specific uses are not detailed in the provided materials.
Used in Cosmetic Industry:
(+/-)-CITRAMALIC ACID DIPOTASSIUM SALT also has potential applications in the cosmetic industry, but the specific uses are not mentioned in the provided materials.

InChI:InChI=1/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)

Upstream product

• 503-74-2 3-methylbutyric acid 
• 151-50-8 potassium cyanide 
• 141-97-9 ethyl acetoacetate 
• 32814-36-1 2-chloromethyl-2-hydroxy-succinic acid dimethyl ester 
• 763-32-6 2-methyl-1-buten-4-ol 
• 31659-59-3 3-methylhexa-2,4 dienedioic acid 
• 93-51-6 2-Methoxy-4-methylphenol 
• 42860-79-7 4-hydroxy-2-methoxy-4-methyl-2,5-cyclohexadien-1-one 
• 110-83-8 cyclohexene 
• 19014-10-9 3-hydroxy-5-oxo-tetrahydro-furan-3-carboxylic acid 
• 32814-35-0 (+/-)-Methyl-γ-(p-toluolsulfonyloxy)-β-carbomethoxy-β-hydroxybutyrat 
• 773837-37-9 sodium cyanide 
• 3483-11-2 lithium acetoacetate 
• 123-76-2 levulinic acid 

Downstream Products

• 681236-64-6 (2S,3R)-3-hydroxy-3-methylpyrrolidine-2-carboxylic acid 
• 681236-64-6 (2R,3R)-3-hydroxy-3-methylproline 
• 93489-89-5 2-{(3S,9S,10R,13R,14R)-17-[(R)-3-Benzenesulfonyl-1-methyl-4-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy}-tetrahydro-pyran 
• 93489-92-0 C₄₅H₇₆O₅SSi₂ 
• 300-85-6 3-Hydroxybutyric acid 
• 80320-89-4 (R)-4-(2-Benzenesulfonyl-ethyl)-2,2,4-trimethyl-[1,3]dioxolane 

Relevant academic research and scientific papers

Stereochemistry of Enzymic Cyclisation of 3-Methyl-cis,cis-muconic Acid to form 3- and 4-Methylmuconolactone

Enzyme-catalysed cyclisation of 3-methyl-cis,cis-muconic acids proceeds by syn addition of carboxyl groups to double bonds to form (4S)-3-methylmuconolactone in Aspergillus niger and (4S)-4-methylmuconolactone in Pseudomonas putida.

Asymmetric synthesis of (R)(-)-dimethyl citramalate

An asymmetric synthesis of (R)(-)-dimethyl citramalate (1), involving halolactonization by using (S)(-)-proline as a chiral auxiliary, is reported.

Structure revision and assignment of absolute stereochemistry of a marine C21 bisfuranoterpene

The C21 bisfuranoterpene (-)-isotetradehydrofurospongin-1 (6), previously isolated from a Western Australian Spongia sp., has been reisolated from a specimen of Spirastrella papilosa collected during scientific trawling operations in the Great Australian Bight. A 2D NMR analysis of 6 has prompted reassignment of the published structure 5, while degradation and chiral HPLC analysis have allowed determination of the absolute stereochemistry.

Regio- and stereocontrolled hydrocyanation of chiral 2-alkylglycidamides with Et2AlCN: Synthesis of enantiomerically pure mono- and disubstituted malic acid derivatives

The opening of the oxirane ring of glycidamides with Et2AlCN takes place under mild conditions in a completely regio- and stereoselective manner to afford β-cyano carboxamide derivatives, which are immediate precursors of mono- and disubstituted malic acid derivatives. The complete control of the regioselectivity can be rationalized as a consequence of the association of the reagent with the carboxamide group prior to intramolecular cyanide transfer.

Cyanide as a primordial reductant enables a protometabolic reductive glyoxylate pathway

Investigation of prebiotic metabolic pathways is predominantly based on abiotically replicating the reductive citric acid cycle. While attractive from a parsimony point of view, attempts using metal/mineral-mediated reductions have produced complex mixtures with inefficient and uncontrolled reactions. Here we show that cyanide acts as a mild and efficient reducing agent mediating abiotic transformations of tricarboxylic acid intermediates and derivatives. The hydrolysis of the cyanide adducts followed by their decarboxylation enables the reduction of oxaloacetate to malate and of fumarate to succinate, whereas pyruvate and α-ketoglutarate themselves are not reduced. In the presence of glyoxylate, malonate and malononitrile, alternative pathways emerge that bypass the challenging reductive carboxylation steps to produce metabolic intermediates and compounds found in meteorites. These results suggest a simpler prebiotic forerunner of today’s metabolism, involving a reductive glyoxylate pathway without oxaloacetate and α-ketoglutarate—implying that the extant metabolic reductive carboxylation chemistries are an evolutionary invention mediated by complex metalloproteins. [Figure not available: see fulltext.].

Catalytic Aerobic Oxidation of Lignocellulose-Derived Levulinic Acid in Aqueous Solution: A Novel Route to Synthesize Dicarboxylic Acids for Bio-Based Polymers

The world is facing grand and ever-increasing pressures on energy and environmental issues. Using carbon-neutral biomass to prepare monomers such as dicarboxylic acids for degradable polymers is of great significance and an urgent but challenging task. Herein, we report a catalytic route for the synthesis of 2-hydroxy-2-methylsuccinic acid, an excellent monomer: e.g., it is able to remarkably enhance the comprehensive properties of polybutylene succinate as shown herein. By catalytic aerobic oxidation of levulinic acid, a bulk platform chemical derived from lignocellulose, the target product was obtained with a very high selectivity of up to ca. 95%. The mild reaction conditions below 100 °C in water and the low-cost reusable heterogeneous catalyst further make the process highly attractive for applications. This process was also found to be effective for the conversion of homologues of levulinic acid to dicarboxylic acids. We studied the C-C bond rearrangement and the roles of catalysts in the reaction that are highly likely involved in a superoxide anion radical mechanism. This study may provide inspiration for the synthesis of bio-based dicarboxylic acids via alternative routes.

Method for preparing hydroxy dibasic acid by catalyzing oxidation of acetyl acid raw material

The invention provides a method for preparing hydroxy dibasic acid by catalyzing oxidation of an acetyl acid raw material. A two-component catalytic system is adopted. One or more than two of metal or metal oxides in transition metal ruthenium, palladium, platinum, gold, silver, nickel, cobalt, copper, molybdenum, iron, rhodium and iridium form a first catalytic component. One or more than two of an alkaline compound of calcium and an alkaline compound of strontium form a second catalytic component. According to the method, an acetyl acid compound is used as a reaction raw material and is subjected to a one-step catalytic oxidation process under the hydrothermal conditions that the temperature is 50-170 DEG C and the oxygen pressure is greater than 0.1 MPa, so that the hydroxyl dibasic acid is prepared from the acetyl acid compound with high efficiency, high selectivity and high yield. Compared with the existing hydroxyl dibasic acid synthesis route, the method provided by the invention has the remarkable advantages of mild reaction conditions, environmental friendliness, high oxidation efficiency, easiness in recovery of the heterogeneous catalyst, good practicability, good application prospect and the like.

Anchimeric-Assisted Spontaneous Hydrolysis of Cyanohydrins Under Ambient Conditions: Implications for Cyanide-Initiated Selective Transformations

Nitrile/cyanide hydrolysis is of importance from the perspective of organic chemistry, especially, prebiotic chemistry. Herein we report that cyanohydrins, generated by the reaction of cyanide with β-keto acids and γ-keto-alcohols, spontaneously hydrolyze

Chemical compositions of secondary organic aerosol from the ozonolysis of cyclohexene in the absence of seed particles

The composition of the aerosol from the ozonolysis of cyclohexene in the absence of seed particles has been investigated by laboratory chamber experiments. The aerosol collected on filters was analyzed by a liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry. Low-molecular weight products, i.e., dicarboxylic acids, oxocarboxylic acids, and hydroxydicarboxylic acids, as well as oligomers with molecular weights more than 200 were found in the aerosol. Copyright

Glycosides of polyenoic branched fatty acids from myxomycetes

The determination of chemical structures of five novel compounds, i.e. one multibranched polyunsaturated fatty acid ((2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2, 4,8,10,12,16-octadecahexaenoic acid) and its four glycosides from seven different myxomycetes is described. The absolute configuration of both hydroxyl groups was determined. The glycosides containing glucose, mannose and rhamnose. These compounds were identified by means of 1H and 13C NMR, MS, UV and IR spectra. Three of them were identified in Arcyria cinerea (Bull.) Pers., two in A. denudata (L.) Wetts., and A. nutans (Bull.) Grev., Fuligo septica (L.) Wigg., Lycogala epidendrum (L.) Fries, Physarum polycephalum Schwein., and Trichia varia Pers. contained one of the identified glycosides each.