Lactobionic acid

D-乳糖酸

Lactobionic acid is produced by oxidation of lactose. It is widely used in the food and in pharmaceutical field, due to its excellent biocompatibility, biodegradability, nontoxicity, chelating, amphiphilic and antioxidant properties.  Lactobionic acid is produced as a white solid powder, freely soluble in water and slightly soluble in anhydrous ethanol and methanol.

Lactobionic acid (LBA) is a bioactive compound that is obtained by the oxidation of lactose, a disaccharide sugar found in milk. It is classified as a bionic acid, which is a type of carbohydrate that contains both a carboxyl and a hydroxyl group. LBA was first discovered in the 1960s by a team of researchers at the DuPont Company, who were exploring the oxidation of lactose for industrial applications. Since then, LBA has gained widespread attention for its unique properties, which make it an attractive ingredient for various biotechnological, biomedical, and cosmetic applications.

Physical and Chemical Properties

LBA has a molecular weight of 358.3 g/mol and a chemical formula of C12H22O12. It is soluble in water but insoluble in most organic solvents, such as ethanol and chloroform. LBA is a white crystalline powder that is stable at room temperature and under neutral pH conditions. It is a weak acid with a pKa value of approximately 3.8, which means that it can easily dissociate in aqueous solutions to form a lactobionate anion and a hydrogen ion.

Synthesis and Characterization

LBA is synthesized by the oxidative reaction of lactose with an oxidizing agent, such as sodium hypochlorite or hydrogen peroxide, under alkaline conditions. The reaction generates LBA, lactose-6-phosphate, and other minor by-products. The synthesis of LBA is a complex process that involves several steps of reaction, separation, purification, and characterization. The purity and quality of LBA can be determined by various analytical techniques, such as high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy.

Analytical Methods

The analysis of LBA requires accurate and reliable analytical methods that can detect and quantify its concentration and purity. HPLC is the most commonly used technique for LBA analysis, which allows the separation and detection of LBA from other compounds in a sample. The HPLC method involves the use of a column packed with a stationary phase and a mobile phase that elutes the sample components based on their chemical properties. MS and NMR are also useful techniques for LBA analysis, which provide additional information on the chemical structure and composition of LBA.

Biological Properties

LBA exhibits several biological properties that make it a promising candidate for various medical and biotechnological applications. LBA has been shown to have antioxidant, anti-inflammatory, and anti-cancer properties, which may help to prevent and treat various diseases, such as diabetes, cardiovascular diseases, and cancer. LBA also has immunomodulatory effects, which may help to enhance the immune system and protect against infectious diseases. LBA has been shown to stimulate the growth and differentiation of skin cells, which may have applications in wound healing and tissue engineering.

Toxicity and Safety in Scientific Experiments

The safety and toxicity of LBA have been extensively studied in various animal and human experiments. LBA has been shown to have low toxicity and is generally considered safe for human consumption and use. LBA has been approved as a food additive by various regulatory agencies, such as the US Food and Drug Administration (FDA), the European Food Safety Authority (EFSA), and the Ministry of Health, Labour and Welfare (MHLW) in Japan.

Applications in Scientific Experiments

LBA has various applications in scientific experiments, including food, cosmetic, pharmaceutical, and biomedical applications. In the food industry, LBA is used as a food additive to improve the texture, flavor, and shelf life of food products. In the cosmetic industry, LBA is used as a moisturizing and anti-aging ingredient in skin care products. In the pharmaceutical industry, LBA is used as a drug delivery system and a therapeutic agent for various diseases. In the biomedical industry, LBA is used as a biomaterial for tissue engineering, regenerative medicine, and drug discovery.

Current State of Research

The current state of research on LBA is focused on exploring its potential applications in various fields and developing new methods for its synthesis, characterization, and analysis. There is growing interest in using LBA as a natural and safe alternative to synthetic compounds that have potential health risks and environmental impacts. The research is also investigating the molecular mechanisms of LBA action and its interactions with cells, tissues, and biological systems.

Potential Implications in Various Fields of Research and Industry

The potential implications of LBA in various fields of research and industry are numerous. In the food industry, LBA can be used to develop functional foods that have health benefits, such as reduced risk of diabetes, obesity, and cardiovascular diseases. In the cosmetic industry, LBA can be used to create innovative and effective skin care products that can enhance skin hydration, texture, and elasticity. In the pharmaceutical industry, LBA can be used to develop new drugs that target various diseases, such as cancer, inflammatory diseases, and neurological disorders. In the biomedical industry, LBA can be used to create tissue-engineered constructs that can promote the regeneration of damaged tissues and organs.

Limitations and Future Directions

There are several limitations and future directions of LBA research that need to be addressed. One of the main limitations is the high cost of LBA production, which hinders its widespread use in various applications. Future research efforts should focus on developing efficient and cost-effective methods for LBA synthesis and purification. Another limitation is the limited knowledge of LBA's molecular mechanisms of action and its interactions with biological systems. Future research efforts should focus on elucidating the molecular pathways that are involved in LBA's biological effects and identifying potential drug targets and biomarkers. Other future directions include exploring the potential applications of LBA in agriculture, environmental science, and biotechnology.

Title: Lactobionic Acid

CAS Registry Number: 96-82-2

CAS Name: 4-O-b-D-Galactopyranosyl-D-gluconic acid

Additional Names: 4-(b-D-galactosido)-D-gluconic acid

Molecular Formula: C12H22O12

Molecular Weight: 358.30

Percent Composition: C 40.23%, H 6.19%, O 53.58%

Literature References: Obtained by oxidation of lactose: Fischer, Meyer, Ber. 22, 362 (1889); Ruff, Ollendorff, ibid. 33, 1806 (1900); Isbell, J. Res. Natl. Bur. Stand. 11, 713 (1933); Margariello, US 2746916 (1956 to Nat. Dairy Res. Labs.); Eddy, Nature 181, 904 (1958); Nishizuka et al., J. Biol. Chem. 235, PC13 (1960). Manuf from lactose: Y. Sato et al., DE 2038230 (1971 to Hayashibara Co.), C.A. 74, 142296c (1971). Crystal structure of calcium salt: W. J. Cook, C. E. Bugg, Acta Crystallogr. B29, 215 (1973). NMR studies: T. Taga et al., Bull. Chem. Soc. Jpn. 51, 2278 (1978). For therapeutic use see Erythromycin Lactobionate.

Properties: Syrup. Freely sol in water, slightly sol in methanol, ethanol, glacial acetic acid. Dehydration by distillation with dioxane yields lactobionic d-lactone, C12H20O11, non-deliquescent crystals, dec 195-196°. Shows mutarotation. [a]D20 +53.0° initial (c = 8.8) ® [a]D20 +22.6° final (240 minutes).

Optical Rotation: [a]D20 +53.0° initial (c = 8.8) ® [a]D20 +22.6° final (240 minutes)

Derivative Type: Calcium salt

Additional Names: Calcium lactobionate

Molecular Formula: C24H42CaO24

Molecular Weight: 754.65

Percent Composition: C 38.20%, H 5.61%, Ca 5.31%, O 50.88%

Properties: Pentahydrate, hairlike needles in brushlike groups. When anhydr, slender needles from small amts of anhydr ethanol. [a]D20 +23.7° (c = 6.28). nD20 1.4583 (concd syrup just before crystallization). Freely sol in water.

Optical Rotation: [a]D20 +23.7° (c = 6.28)

Index of refraction: nD20 1.4583 (concd syrup just before crystallization)