D-Tartaric acid
[CAS# 147-71-7]

Identification

• Classification: Food additive >> Acidity regulator
• Name: D-Tartaric acid
• Synonyms: (2S,3S)-(-)-Tartaric acid; D(-)-Threaric acid; D(-)-Dihydroxysuccinic acid
• Molecular Formula: C₄H₆O₆
• Molecular Weight: 150.09
• CAS Registry Number: 147-71-7
• EC Number: 205-695-6
• SMILES: [C@H]([C@@H](C(=O)O)O)(C(=O)O)O

Properties

• Density: 1.76 g/mL
• Melting point: 166-170 °C
• Refractive index: 12.5
• Flash point: 210 °C
• alpha: -12.1 ° (c=20, H2O)
• Water solubility: 1394 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

D-tartaric acid is a naturally occurring organic acid first discovered by Swedish chemist Carl Wilhelm Scheele in the 18th century. Later, French chemist Louis Pasteur isolated D-tartaric acid from the compound tartaric acid found in grapes and wine. D-tartaric acid is one of the two enantiomers of tartaric acid, the other being L-tartaric acid. Its discovery has played a key role in understanding the stereochemistry and optical activity of organic compounds.

D-tartaric acid is widely used in the food and beverage industry as a food additive and flavoring agent. It is added to sourdough bread, soft drinks, candies, and juices to impart a sour taste and enhance flavor. D-tartaric acid is also used as a stabilizer and emulsifier in foods to improve texture and shelf life.

D-tartaric acid plays a vital role in winemaking as a natural component of grape juice and wine. It contributes to the acidity and flavor profile of wine, balancing sweetness and enhancing sourness. D-tartaric acid is also responsible for the formation of tartaric acid crystals, known as wine diamonds, during wine aging and storage. These crystals are removed by processes such as cold stabilization to prevent precipitation in bottled wine.

D-Tartaric acid is used as a chiral resolving agent and pH adjuster in pharmaceutical formulations. It resolves enantiomeric mixtures and purifies chiral drugs by crystallization or chromatographic techniques. D-Tartaric acid is also used as a buffer in oral medications and intravenous solutions to maintain pH stability and enhance drug solubility.

D-Tartaric acid is used in cosmetics and personal care products for its exfoliating and skin conditioning properties. It is used in skin care formulations such as facial scrubs, masks, and exfoliants to remove dead skin cells, improve skin texture, and promote cell turnover. D-Tartaric acid helps reveal smoother, more radiant skin and enhances the efficacy of other skin care ingredients.

D-Tartaric acid is a versatile building block used in organic synthesis to prepare a variety of fine chemicals, pharmaceutical intermediates, and specialty compounds. Its chirality and functional group reactivity make it possible to synthesize complex molecules with specific stereochemical properties. D-Tartaric acid derivatives are used in the production of agrochemicals, flavors, fragrances, and optical resolution agents.

D-Tartaric acid can be used in a variety of industrial processes, including metal surface treatment, textile dyeing, and water treatment. It is used as a complexing agent and pH adjuster in metal plating solutions to improve coating quality and adhesion. D-Tartaric acid is also used in textile dyeing processes as a mordant and dye auxiliary to improve color fastness and dye absorption.

References

2000. Aluminum speciation studies in biological fluids. Part 6. Quantitative investigation of aluminum(III)-tartrate complex equilibria and their potential implications for aluminum metabolism and toxicity. Journal of Inorganic Biochemistry, 81, 3.
DOI: 10.1016/s0162-0134(00)00072-6

2003. Effect of Tartaric Acid-Induced Cough on Pulmonary Function in Normal and Asthmatic Humans. American Journal of Physical Medicine & Rehabilitation, 82, 5.
DOI: 10.1097/00002060-200305000-00011

1964. Reversible dissociation of l-tartaric acid dehydrase into subunits. Biochimica et Biophysica Acta (BBA) - Specialized Section on Enzymological Subjects, 89, 1.
DOI: 10.1016/0926-6569(64)90298-6