Lactobionic acid (4-''O''-β-galactopyranosyl-D-gluconic acid) is a

sugar acid A Sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its chain. Main classes of sugar acids include: * Aldonic acids, in which the aldehyde group (−CHO) located at the initial end ( position 1) of an ...

. It is a

disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...

formed from

gluconic acid Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4COOH. It is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid. In aqueous solution at neutral pH, gluconic acid f ...

and

galactose Galactose (, '' galacto-'' + ''-ose'', "milk sugar"), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecu ...

. It can be formed by oxidation of lactose. The

carboxylate In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylat ...

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...

of lactobionic acid is known as lactobionate. As an acid, lactobionic acid can form

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...

with mineral cations such as

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar t ...

potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosph ...

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...

and

zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodi ...

. Calcium lactobionate is a food additive used as a stabilizer. Potassium lactobionate is added to organ preservation solutions such as

Viaspan Viaspan was the trademark under which the University of Wisconsin cold storage solution (also known as University of Wisconsin solution or UW solution) was sold. Currently, UW solution is sold under the Belzer UW trademark and others like Bel-Gen o ...

or CoStorSol to provide

osmotic Osmosis (, ) is the spontaneous net movement or diffusion of solvent molecules through a selectively-permeable membrane from a region of high water potential (region of lower solute concentration) to a region of low water potential (region o ...

support and prevent cell swelling. Mineral salts of lactobionic acid are also used for mineral supplementation. Lactobionic acid is also used in the cosmetics industry as an antioxidant{{Cite journal , last1=Tasic-Kostov , first1=M. , last2=Pavlovic , first2=D. , last3=Lukic , first3=M. , last4=Jaksic , first4=I. , last5=Arsic , first5=I. , last6=Savic , first6=S. , date=2012-10-12 , title=Lactobionic acid as antioxidant and moisturizing active in alkyl polyglucoside-based topical emulsions: the colloidal structure, stability and efficacy evaluation , url=https://pubmed.ncbi.nlm.nih.gov/22691034 , journal=International Journal of Cosmetic Science , volume=34 , issue=5 , pages=424–434 , doi=10.1111/j.1468-2494.2012.00732.x , issn=1468-2494 , pmid=22691034, s2cid=2854711 and in the pharmaceutical industry as an

excipient An excipient is a substance formulated alongside the active ingredient of a medication, included for the purpose of long-term stabilization, bulking up solid formulations that contain potent active ingredients in small amounts (thus often referred ...

for formulation. For example, the antibiotic erythromycin is used as the salt

erythromycin lactobionate Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used during ...

when intravenously delivered.

References

Disaccharides Sugar acids Vicinal diols Alpha hydroxy acids