L(+)-Tartaric acid
[CAS# 87-69-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glycine derivatives
• Name: L(+)-Tartaric acid
• Synonyms: (+)-Tartaric acid; L(+)-Dihydroxysuccinic acid; Natural tartaric acid
• Molecular Formula: C₄H₆O₆
• Molecular Weight: 150.09
• CAS Registry Number: 87-69-4
• EC Number: 201-766-0
• FEMA: 3044
• SMILES: [C@@H]([C@H](C(=O)O)O)(C(=O)O)O

Properties

• Density: 1.76
• Melting point: 168-172 °C
• Boiling point: 275 °C
• Refractive index: -12.5
• Flash point: 150 °C
• alpha: 12 ° (c=20, H2O)
• Water solubility: 1390 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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1	H314
Skin corrosion	Skin Corr.	1A	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

The history of L(+)-tartaric acid dates back to antiquity, primarily in relation to winemaking. Early winemakers used the term "tartar" to describe the crystalline deposits found in wine barrels. However, it was not until the late 18th century that the compound was scientifically isolated and understood.

Swedish chemist Carl Wilhelm Scheele first isolated tartaric acid from potassium tartrate in 1769. His pioneering work laid the foundation for understanding the chemical properties and potential uses of the acid. Later, French chemist Jean-Baptiste Biot discovered its optical activity, and renowned scientist Louis Pasteur further elucidated its stereochemistry in 1848, distinguishing the L(+)-enantiomer as the naturally occurring biologically active form.

L(+)-tartaric acid (C4H6O6) is a white crystalline compound with a strong sour taste. It is soluble in water and alcohol, forming stable and effective solutions that can be used in a variety of applications. The L(+) form of tartaric acid is optically active and rotates plane-polarized light to the right, a property that contributes to its biological activity and compatibility. This dicarboxylic acid has two chiral centers that are able to form stable complexes with metal ions and other molecules. Its ability to act as a chelating agent and buffer makes it valuable in different industries.

L(+)-Tartaric acid is essential to the winemaking industry, as it occurs naturally in grapes and helps increase the acidity of wine. It plays an important role in the fermentation process, helping to stabilize pH and prevent spoilage. It also affects the taste and aging potential of wine, providing the characteristic sourness and freshness of many wines.

In baking, L(+)-Tartaric acid is used as a leavening agent along with baking soda to produce carbon dioxide gas, which helps the dough rise. This reaction is essential to achieve the desired texture in baked goods such as cakes, cookies, and pastries. It also acts as an acidulant in various foods, enhancing flavor and acting as a natural preservative.

L(+)-Tartaric acid is used in candies and jellies to create a rich flavor and improve the texture and stability of candies. It also helps control crystallization, ensuring a smooth and consistent product.

L(+)-Tartaric acid is used as an excipient in pharmaceutical formulations. Its buffering properties help stabilize active ingredients and increase the bioavailability of drugs. It is also used in the production of effervescent tablets, where it reacts with bicarbonate to produce effervescence, which helps in the rapid dissolution and absorption of drugs.

L(+)-Tartaric acid is used in cosmetics, especially in skin care products, where it acts as an exfoliant and pH regulator. Its ability to chelate metals also makes it useful in stabilizing formulations to prevent discoloration and degradation of active ingredients.

In the chemical industry, tartaric acid is used as a chelating agent to help control metal ions in various processes including dyeing and tanning. It is also used in the synthesis of certain organic compounds and as a catalyst in chemical reactions.

References

2024. Synthesis, growth, structural, optical, thermal and dielectric properties of novel bis(tetra-ethylammonium) bis(hydrogen l-tartarate) l-tartaric acid monohydrate single crystals. Journal of Materials Science: Materials in Electronics, 35(12).
DOI: 10.1007/s10854-024-12402-0

2013. Enantioseparation of tartaric acid by ligand‐exchange capillary electrophoresis using contactless conductivity detection. Journal of Separation Science, 36(18).
DOI: 10.1002/jssc.201300507

2012. Mechanism of change in enantiomer migration order of enantioseparation of tartaric acid by ligand exchange capillary electrophoresis with Cu(II) and Ni(II)-D‐quinic acid systems. ELECTROPHORESIS, 33(4).
DOI: 10.1002/elps.201100512