Description
D-Tartaric acid, also known as (S, S)-tartrate or D-threaric acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. D-Tartaric acid has been detected but not quantified in loquats (Eriobotrya japonica). This could make D-tartaric acid a potential biomarker for consuming these foods. D-Tartaric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve as defense or signalling molecules. In some cases, they are molecules that arise from the incomplete metabolism of other secondary metabolites.
Uses
D-(-)-Tartaric acid is commonly used as a resolving agent in organic synthesis. It is the synthetic enantiomer of L-(+)-Tartaric acid and is utilized in the production of synthetic analgesics. Tartaric acid is the second largest alpha hydroxy acid (AHA) in terms of size, with glycolic acid being the smallest and citric acid being the largest. It serves as a precursor for the synthesis of ester derivatives such as D-tartaric acid diethyl ester, D-tartaric acid dimethyl ester, and D-tartaric acid diiso-propyl ester. Moreover, it is employed in the creation of chiral aziridine derivative, which is a common intermediate for manufacturing hydroxyethylamine class HIV protease inhibitors like saquinavir, amprenavir, and nelfinavir. In the food industry, it is extensively used as a beer foaming agent, for regulating food acidity, and as a flavoring agent. However, due to its challenging workability and potential skin irritation, it is not frequently utilized in cosmetic or anti-aging preparations.
Definition
ChEBI: D-tartaric acid(147-71-7) is the D-enantiomer of tartaric acid. It has a role as an Escherichia coli metabolite. It is a conjugate acid of a D-tartrate(1-). It is an enantiomer of a L-tartaric acid.
Biotechnological Production
Tartaric acid is generally produced from crude tartar and lees, which are
byproducts of wine production. However, there are a few reports of fermentative
production of tartaric acid by Gluconobacter suboxydans growing on
Glucose or sorbitol. Vanadate plays a central role in this process.
The microorganism forms 5-keto-D-gluconic acid, which is oxidized to tartaric
acid. The vanadium catalyzes this reaction. Product concentrations up
to 2.96 g.L-1 have been observed after 3 days of fermentation.
General Description
D-(-)-Tartaric acid is a polycrystalline solid, widely used as food additive. It has been reported to exhibit piezoelectric effect.
Purification Methods
Crystallise the acid from distilled H2O or *benzene/diethyl ether containing 5% of pet ether (b 60-80o) (1:1). Soxhlet extraction with diethyl ether has been used to remove an impurity absorbing at 265nm. It has also been crystallised from absolute EtOH/hexane and dried in a vacuum for 18hours [Kornblum & Wade J Org Chem 52 5301 1987]. [Beilstein 3 IV 1229.]
