Tartaric Acid and Its O‐Acyl Derivatives. Part 1. Synthesis of Tartaric Acid and O‐Acyl Tartaric Acids and Anhydrides

Synoradzki, Ludwik; Ruśkowski, Paweł; Bernaś, Urszula

doi:10.1002/chin.200526235

Cited by 3 publications

(4 citation statements)

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Section: Identification Synthesis and Biosynthesis Chicoric Acidmentioning

confidence: 99%

“…Chicoric acid can be obtained from isolated and purified plant materials (Table 1 ) or synthesized (Scarpati and Oriente, 1958 ; Synoradzki et al, 2005 ). Pure chicoric acid is a white powder (Synoradzki et al, 2005 ; personal observation), and now available as a purified standard via numerous chemical companies (e.g., Cerilliant Chemical Company, Indofine Chemical Company, Inc., Sigma-Aldrich Co, LLC, etc.). The most abundant natural form is L-chicoric acid [i.e., (-)-chicoric acid, 2,3-dicaffeoyl-L-tartaric acid, 2,3- O -dicaffeoyltartaric acid, 2R,3R- O -dicaffeoyltartaric acid, or di- E -caffeoyl-(2R-3R)-(-)-tartaric acid] and has been reported in the majority of the plants listed in Table 1 , but the stereoisomer meso -chicoric acid (i.e., dicaffeoyl- meso -tartaric acid or di- E -caffeoyl-(2R-3S)-(-)-tartaric acid) has also been reported at a lesser levels in horsetail sprouts ( Equisetum arvense L.) (Veit et al, 1991 , 1992 ; Hohlfeld et al, 1996 ), iceberg lettuce ( Lactuca sativa L.) (Baur et al, 2004 ; Luna et al, 2012 ), and purple coneflower ( Echinacea purpurea L. Monech) (Perry et al, 2001 ).…”

Section: Identification Synthesis and Biosynthesis Chicoric Acidmentioning

confidence: 99%

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Chicoric acid: chemistry, distribution, and production

2013

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Though chicoric acid was first identified in 1958, it was largely ignored until recent popular media coverage cited potential health beneficial properties from consuming food and dietary supplements containing this compound. To date, plants from at least 63 genera and species have been found to contain chicoric acid, and while the compound is used as a processing quality indicator, it may also have useful health benefits. This review of chicoric acid summarizes research findings and highlights gaps in research knowledge for investigators, industry stakeholders, and consumers alike. Additionally, chicoric acid identification, and quantification methods, biosynthesis, processing improvements to increase chicoric acid retention, and potential areas for future research are discussed.

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Section: Identification Synthesis and Biosynthesis Chicoric Acidmentioning

confidence: 99%

Section: Identification Synthesis and Biosynthesis Chicoric Acidmentioning

confidence: 99%

Chicoric acid: chemistry, distribution, and production

2013

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“…Traditionally, L-tartaric acid is produced from crude potassium tartrate which is obtained during wine making. Currently, L-tartaric acid is produced biotechnologically from cis-epoxysuccinic acid [109].…”

Section: Malic Acid and L-tartaric Acidmentioning

confidence: 99%

Organic Chemicals from Bioprocesses in China

Huang

Lin

et al. 2010

Biotechnology in China II

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Over the last 20 years, China has successfully established a modern biotechnology industry from almost nothing. Presently, China is a major producer of a vast array of products involving bioprocesses, for some China is even the world's top producer. The ever-increasing list of products includes organic acids, amino acids, antibiotics, solvents, chiral chemicals, biopesticides, and biopolymers. Herein, the research and development of bioprocesses in China will be reviewed briefly. We will concentrate on three categories of products: small molecules produced via fermentation, biopolymers produced via fermentation and small chemicals produced by enzyme-catalyzed reactions. In comparison with the traditional chemical process, in which, nonrenewable mineral resources are generally used, products in the first and second categories noted above can use renewable bioresources as raw materials. The bioprocesses are generally energy saving and environmentally benign. For products developed via the third category, although the raw materials still need to be obtained from mineral resources, the biocatalysts are more effective with higher selectivity and productivity, and the bioprocesses occur under ambient temperature and pressure, therefore, these are "green processes." Most of the products such as citric acid, xanthan and acrylamide etc., discussed in this paper have been in large-scale commercial production in China. Also introduced herein are three scientists, Prof.

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“…Tartaric acid derivatives have been the subject of numerous studies and display selective ion complexation or ion transport [ 9 ], chiral recognition [ 10 ] and molecular catalysis [ 11 ]. Since tartaric acid esters are hydrolytically too labile [ 12 ], the aim was to synthesize long chain tartaric acid amides (tartramides). A 10 member series of ceramide analogues was designed, where the polar portion of ceramide has been replaced by an inverse bioisosteric amide and the lipophilic portion of the C 18 alkyl moiety of ceramide has been replaced with various long chain (8–18) alkylamines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Long-Chain Tartaric Acid Diamides as Novel Ceramide-Like Compounds

et al. 2010

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Ceramides play a crucial role in the barrier function of the skin as well as in transmembrane signaling. In this study long aliphatic chain tartaric acid diamides able to replace ceramides in an in vitro model of the stratum corneum lipid matrix due to their similar physico-chemical properties were synthesized from diacetoxysuccinic anhydride in four steps. Their pro-apoptotic effect on fibroblast cells was also investigated.

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Tartaric Acid and Its O‐Acyl Derivatives. Part 1. Synthesis of Tartaric Acid and O‐Acyl Tartaric Acids and Anhydrides

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 3 publications

References 1 publication

Chicoric acid: chemistry, distribution, and production

Chicoric acid: chemistry, distribution, and production

Organic Chemicals from Bioprocesses in China

Synthesis and Characterization of Long-Chain Tartaric Acid Diamides as Novel Ceramide-Like Compounds

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