Lactobionic acid
[CAS# 96-82-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Fluoropyrimidine
• Name: Lactobionic acid
• Synonyms: 4-O-beta-D-Galactopyranosyl-D-gluconic acid
• Molecular Formula: C₁₂H₂₂O₁₂
• Molecular Weight: 358.30
• CAS Registry Number: 96-82-2
• EC Number: 202-538-3
• SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C(=O)O)O)O)O)O)O)O

Properties

• Melting point: 113-118 °C
• alpha: 22.8 ° (c=10, H2O)
• Water solubility: 10 g/100 mL

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

Lactobionic acid is a compound derived from the combination of gluconic acid and galactose, first synthesized in the 1960s by oxidative modification of gluconic acid with galactose. The resulting compound, lactobionic acid, has a biomimetic acid structure (a carboxylic acid group attached to a carbohydrate portion), which enhances its solubility and biocompatibility.

Lactobionic acid consists of a gluconic acid core and a galactose molecule linked by a lactone ring and is highly soluble in water and alcohol. It is stable under normal storage conditions and resistant to heat and pH changes.

Lactobionic acid can be used as a stabilizer in drug formulations, especially for proteins and enzymes. Its ability to form complexes with metal ions helps prevent drug degradation, extend shelf life and improve efficacy.

It can be used in organ preservation solutions due to its ability to mitigate oxidative stress during low-temperature storage. Lactobionic acid protects tissues from damage and prolongs the survival time of organ transplants.

Lactobionic acid is used in cosmetics and skin care products for its moisturizing properties, attracting water molecules to hydrate the skin without causing irritation, suitable for sensitive skin.

Lactobionic acid acts as an antioxidant by scavenging free radicals that cause skin aging. Its mild exfoliating properties promote cell renewal, improve skin texture, and reduce fine lines and wrinkles.

Lactobionic acid is used as a food additive, primarily in dietary supplements and functional foods. Lactobionic acid enhances the stability of vitamins and nutrients, extending their shelf life and maintaining their nutritional value.

Lactobionic acid is used in cryopreservation of cells and tissues in biotechnology. Lactobionic acid maintains the integrity of cells by minimizing the formation of ice crystals during freezing, which is essential for maintaining cell viability after thawing.

Lactobionic acid is used in biosensors to detect pathogens and environmental pollutants. Lactobionic acid-modified surfaces enhance the specificity and sensitivity of biosensor devices, allowing for rapid and accurate detection.

Lactobionic acid acts as a chelator, binding to metal ions such as calcium and magnesium. This property is essential in research to study metal-protein interactions and develop metal detoxification therapies.

Studies have shown that as carrier molecules in gene delivery systems, lactobionic acid conjugates help deliver therapeutic genes to liver cells in a targeted manner, with the potential to treat liver diseases and genetic disorders.

References

2022. The antimicrobial and bioactive properties of lactobionic acid. Journal of the Science of Food and Agriculture, 102(10).
DOI: 10.1002/jsfa.11823

2022. Conjugates of lactobionic acid and IR820: New photosensitizers for efficient photodynamic therapy of hepatoma cells. Drug Development Research, 83(7).
DOI: 10.1002/ddr.22007

2024. Quantitative Analysis of Lactobionic Acid in Bioreactor Cultures and Selected Biological Activities. Molecules (Basel, Switzerland), 29(22).
DOI: 10.3390/molecules29225400