Complaint
| Product Name: | Lactobionic acid |
| Synonyms: | 4-O-BETA-D-GALACTOPYRANOSYL-D-GLUCONIC ACID;LACTOBIONIC ACID;4-O-β-D-Galactopyranosyl-D-gluconic acid;LACTOBIONIC ACID FREE ACID;LACTOBIONIC ACID 97%;4-[β-D-Galactosido]-D-gluconic acid;Lactobionic Acid (mixture of Acid form and Lactone form);D-Gluconic acid, 4-O-.beta.-D-galactopyranosyl- |
| CAS: | 96-82-2 |
| MF: | C12H22O12 |
| MW: | 358.3 |
| EINECS: | 202-538-3 |
| Product Categories: | Biochemistry;Disaccharides;Sugar Acids;Sugars |
| Mol File: | 96-82-2.mol |
| Lactobionic acid Chemical Properties |
| Melting point | 113-118 °C(lit.) |
| alpha | 22.8 º (c=10, H2O) |
| Boiling point | 410.75°C (rough estimate) |
| density | 1.4662 (rough estimate) |
| refractive index | 26 ° (C=8.8, H2O) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | 10 g/100 mL |
| pka | 3.28±0.35(Predicted) |
| form | Powder |
| color | White to Off-white |
| optical activity | [α]20/D +25°, c = 10 in H2O |
| Water Solubility | 10 g/100 mL |
| Merck | 5342 |
| BRN | 95054 |
| CAS DataBase Reference | 96-82-2(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 24/25-36-26 |
| WGK Germany | 1 |
| HS Code | 29400000 |
| Chemical Properties | White to off-white crystalline powder |
| Uses | Lactobionic acid is mainly used in preservation solutions for organ transplantation. It is used to produce erythromycine lactobionate. |
| Uses | food additive |
| Uses | Arginine metabolite in bovine brain; clonidine-displacing substance activity |
| Uses | An inhibitor of matrix metalloproteinases |
| Definition | ChEBI: A disaccharide formed between beta-D-galactose and D-gluconic acid. |
| Biotechnological Production | Currently, lactobionic acid is produced by chemical synthesis using refined lactose as feedstock. This process is expensive due to the energy demand. Alternatively, Acidic Organic Compounds in Beverage, Food, and Feed Production 111 enzymatic processes have been suggested. For example, lactose could be reacted to lactobionic acid using an enzymatic system with co-factor regeneration. First, lactose is converted to lactobionolactone by a cellobiose dehydrogenase. This reaction requires an electron acceptor, which is regenerated by a laccase reducing oxygen to water. Finally, lactobionolactone spontaneously hydrolyzes to lactobionic acid. Moreover, microbial production of lactobionic acid has been described. In a fed-batch cultivation of Burkolderia cepacia growing in a complex medium (lactose, salts, peptone, and yeast extract), a final titer of 400 g.L-1, a yield of approximately 1.0 g of lactobionic acid per gram of lactose, and a productivity of 1.67 g.L-1.h-1 have been achieved. Another promising strategy for an inexpensive biotechnological process is the utilization of cheap raw materials. For example, lactobionic acid could be obtained from concentrated cheese whey by fermentation with Pseudomonas taetrolens. In a fed-batch process, a product concentration of 164 g.L-1 with a productivity of 2.05 g.L-1.h-1 and a yield of 0.82 g of lactobionic acid per gram of lactose have been observed. Furthermore, whole-cell biocatalysis using permeabilized Zymonmonas mobilis cells and an equimolar mixture of lactose and fructose has been tested. In a batch process, a maximum lactobionic acid concentration of 268 g.L-1 and a conversion rate of 72 % within 24 h have been measured. The productivity of lactobionic acid was 11.2 g.L-1.h-1 . |
| Clinical Use | Erythromycin lactobionate is a salt with enhanced water solubility that is used for injections. |
| Purification Methods | Crystallise lactobionic acid from water by addition of EtOH. [NMR: Taga et al. Bull Chem Soc Jpn 51 2278 1978, Beilstein 17 III/IV 3392, 17/7 V 436.] |
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