Lactobionic acid

• CAS: 96-82-2
• Catalog Number: ACM96822-3
• Category: Main Products
• Molecular Weight: 358.3
• Molecular Formula: C12H22O12
• Synonyms: 4-O-β-D-Galactopyranosyl-D-gluconic acid
• IUPAC Name: (2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
• SMILES: C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5+,6+,7-,8-,9-,10-,12+/m1/s1
• InChI Key: JYTUSYBCFIZPBE-AMTLMPIISA-N
• Boiling Point: 410.75 °C
• Melting Point: 113-118 °C(lit.)
• Flash Point: 319.1 °C
• Density: 1.4662 g/cm³
• Appearance: White to off-white powder
• Storage: Inert atmosphere, room temperature
• Active Content: 90%
• Complexity: 406
• Exact Mass: 358.11112613
• Isomeric 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
• Monoisotopic Mass: 358.11112613
• Physical State: Solid
• pKa: 3.28±0.35(Predicted)
• Refractive Index: 26 ° (C=8.8, H₂O)
• Topological Polar Surface Area: 218 Ų

Case Study

Antimicrobial Activity of Lactobionic Acid: An Alternative Natural Food Preservative

Sáez-Orviz, Sara, et al. Journal of the Science of Food and Agriculture 102.9 (2022): 3495-3502.

Known as a polyhydroxy acid, lactobionic acid (LBA) is created by the joining of galactose and gluconic acid. It has found multiple uses in the food industry thanks to its chelating, moisturizing, and antioxidant properties, which have also been discovered to be antimicrobial in nature. Lactobionic acid has emerged as a natural food preservative alternative to synthetic substances. It disrupts cell integrity, downregulates virulence, and causes metabolic dysfunction in a variety of pathogenic bacteria, with a broad spectrum of activity that would make it a versatile choice for application in the food industry.
Mechanisms of Action
1. For gram-positive bacteria (S. aureus):
LBA causes a loss of cell membrane integrity and a subsequent leakage of internal cellular components such as alkaline phosphatase and nucleotides. ABC transporters as well as stress-response proteins are downregulated by LBA, which is detrimental to the cell's metabolism. LBA downregulates the virulence of the bacteria, as well as the biofilm forming potential and its capacity to adhere to hosts, greatly decreasing the possibility of infection.
2. For gram-negative bacteria (P. fluorescens, V. parahaemolyticus):
The permeability of the outer membrane is increased, which results in hypoosmotic shock and subsequent cell dysfunction. Folate biosynthesis is inhibited by LBA, which is detrimental for the processes of DNA and protein synthesis. DNA intercalation of LBA takes place. Reductions in intracellular ATP levels and protein leakage increases post-treatment.

Exploiting the Antioxidant and Prebiotic Properties of Lactobionic Acid for Functional Ingredient Development

Goderska, Kamila. Applied Microbiology and Biotechnology 103.9 (2019): 3737-3751.

The study described the antioxidant and prebiotic activity of lactobionic acid (LBA) as a means of proving its potential as a functional ingredient. The experiments demonstrated that LBA not only promotes the growth of probiotics but also inhibits oxidation processes.
Prebiotic Properties
· LBA showed a significant impact on the growth of the tested strains of probiotics. In particular, it had the most pronounced effect on Lactobacillus fermentum at a concentration of 16 mg/cm3.
· The growth kinetics analysis of the probiotic cultures also revealed an extended log-phase for Lactobacillus fermentum and Lactobacillus acidophilus CH-5, which suggested an increase in their proliferation rate.
· Promoting effects of LBA on the growth of Lactococcus lactis, Bifidobacterium bifidum, and multiple Lactobacillus species were also confirmed.
Antioxidant Efficacy
· In accelerated oxidation tests using cold-pressed rapeseed oil stored at 60°C, LBA effectively reduced peroxide formation.
· The highest inhibition of oxidation-19.6% reduction in peroxide value-was observed on day 10 with an LBA concentration of 10 mg/cm³.
· At a dosage of 22.03 mg/cm³, LBA achieved a 7.3% reduction in oxidation over the same period.

Custom Q&A

What is the molecular formula of lactobionic acid?

The molecular formula of lactobionic acid is C12H22O12.

What is the molecular weight of lactobionic acid?

The molecular weight of lactobionic acid is 358.30 g/mol.

What is the IUPAC name of lactobionic acid?

The IUPAC name of lactobionic acid is (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid.

What are the synonyms of lactobionic acid?

The synonyms of lactobionic acid include LACTOBIONIC ACID, 96-82-2, 4-O-beta-D-Galactopyranosyl-D-gluconic acid, 4-(beta-D-Galactosido)-D-gluconic acid, and DTXSID3048861.

What is the InChIKey of lactobionic acid?

The InChIKey of lactobionic acid is JYTUSYBCFIZPBE-AMTLMPIISA-N.

What is the CAS number of lactobionic acid?

The CAS number of lactobionic acid is 96-82-2.

Is lactobionic acid a disaccharide?

Yes, lactobionic acid is a disaccharide formed between beta-D-galactose and D-gluconic acid.

What is the role of lactobionic acid?

Lactobionic acid has a role as an antioxidant.

What are some related compounds of lactobionic acid?

Some related compounds of lactobionic acid include calcium salt, calcium glubionate salt, potassium salt, erythromycin salt, and clarithromycin salt.

How is the molecular weight of lactobionic acid computed?

The molecular weight of lactobionic acid is computed by PubChem 2.2.