Welcome to LookChem.com Sign In|Join Free

CAS

  • or

96-82-2

Post Buying Request

96-82-2 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

96-82-2 Usage

Description

Lactobionic acid (C12H22O12) is a disaccharide obtained from the oxidation of lactose. Chemically, Lactobionic acid is made up of a galactose moiety that is bonded to a gluconic acid molecule through an ether-like bond. The compound can be dehydrated to a lactone. Lactobionic acid is widely used in the chemical, food and pharmaceutical industries due to its chelating, emulsifying, humectant and chelating properties. Lactobionic acid and its constituent salts are essential as food additives due to excellent solubility, good taste, and health-promoting aspects. The compound may also be essential in the synthesis of targetable and biocompatible drug delivery systems.

Properties

Lactobionic acid has a molecular weight of 358.296 g/mol and a monoisotopic mass of 358.111 g/mol, which is also its exact mass. The compound has a heavy atom count of 24. Lactobionic acid has a melting point of 113-118°C and a boiling point of about 410.75°C. It is a white to off-white powder with a solubility of 10 g/100 mL in water and a density of about 1.4662. It is also slightly soluble in anhydrous methanol and ethanol. Lactobionic acid is hygroscopic, and it has a good water retention potential hence its applicability to cosmetic products. The compound and its constituent mineral salts (Ca, Na, and K lactobionate) are produced commercially for medical and industrial applications and in some cases for research purposes.

Preparation

The selective transformation of lactose into Lactobionic acid entails the oxidation of the radical aldehyde category of glucose on the lactose molecule to the carboxylic classification. The production of Lactobionic acid entails various processes which may include enzymatic synthesis, microbial production, biocatalytic oxidation, electrochemical oxidation and heterogeneous catalytic oxidation.

Extraction and Purification

To enhance the productive capacity of Lactobionic acid, the enzymatic reaction can be cut off after several hours of activity and the unchanged substrates can be re-injected into the cycle after the elimination of useful products. The effective process of separation is through liquid chromatography particularly because the recovered species are pure. Exposing the solution made of lactobionate ions through a sequence of ion-transfer resins produces a pure solution of Lactobionic acid with minimal amounts of calcium ions. Different techniques such as crystallization, evaporation, electrodialysis and ethanol precipitation can be employed to obtain Lactobionic acid.

Physiological & Commercial Applications

Lactobionic acid is an essential compound based on its chelating properties and its ability to form complex bonds with Ca, Fe, Cu, and Mn. Its incorporation into food additives can stimulate mineral absorption and Ca2+ in the intestines hence enhancing one’s health. Lactobionic acid is unaffected by digestive enzymes hence it is a valuable ingredient in the preparation of functional foods. It is poorly absorbed into the linings of the intestines hence it can also be a Bifidus booster molecule for functional beverages and foods. It enhances the healing process of wounds hence it is valuable in oral, skin, nail, hair and vaginal mucosa care. As an antioxidant, Lactobionic acid acts by suppressing the synthesis of hydroxyl radicals due to its iron chelating ability. As a food additive, Lactobionic acid functions as an acidifier in products containing fermented milk, an aging suppressor for bread, an antioxidant, and as a gelling or stabilizing medium in desserts. In cosmetics, Lactobionic acid is applied as an active ingredient in regenerative and antiaging skin-care products based on its therapeutic properties. Its metal chelation potential suppresses the degeneration potential of metalloproteinase enzymes, which decreases the appearance of aging wrinkles. In the chemical industry, Lactobionic acid is an active ingredient (sugar-based surfactant) in biodegradable detergents. It may also be used in drug delivery systems, nanoparticle diagnosis and tissue engineering.

Chemical Properties

White to off-white crystalline powder

Uses

Different sources of media describe the Uses of 96-82-2 differently. You can refer to the following data:
1. Lactobionic acid is mainly used in preservation solutions for organ transplantation. It is used to produce erythromycine lactobionate.
2. Arginine metabolite in bovine brain; clonidine-displacing substance activity
3. 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 96-82-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 96-82:
(4*9)+(3*6)+(2*8)+(1*2)=72
72 % 10 = 2
So 96-82-2 is a valid CAS Registry Number.
InChI:InChI=1/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

96-82-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (Y0000257)  Lactobionicacid  European Pharmacopoeia (EP) Reference Standard

  • 96-82-2

  • Y0000257

  • 1,880.19CNY

  • Detail
  • Aldrich

  • (153516)  Lactobionicacid  97%

  • 96-82-2

  • 153516-25G

  • 877.50CNY

  • Detail
  • Aldrich

  • (153516)  Lactobionicacid  97%

  • 96-82-2

  • 153516-100G

  • 2,664.09CNY

  • Detail

96-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name lactobionic acid

1.2 Other means of identification

Product number -
Other names D-Gluconic acid, 4-O-β-D-galactopyranosyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:96-82-2 SDS

96-82-2Relevant articles and documents

Aqueous oxidation of sugars into sugar acids using hydrotalcite-supported gold nanoparticle catalyst under atmospheric molecular oxygen

Tomar, Ravi,Sharma, Jatin,Nishimura, Shun,Ebitani, Kohki

supporting information, p. 843 - 845 (2016/07/16)

Hydrotalcite-supported gold nanoparticles show good activity as a heterogeneous catalyst for the oxidation of monosaccharides (xylose, ribose, galactose and mannose) and disaccharides (lactose and cellobiose) into the corresponding sugar acids under external base-free conditions in water solvent using atmospheric pressure of molecular oxygen. The produced sugar acids were thoroughly identified by 1H-, 13C-, and HMQC-NMR and ESI-FT-ICR MS spectroscopic techniques.

Boron nitride as an alternative support of Pd catalysts for the selective oxidation of lactose

Meyer, Nathalie,Bekaert, Kevin,Pirson, Damien,Devillers, Michel,Hermans, Sophie

, p. 170 - 174 (2013/01/15)

The potential of boron nitride as innovative support for the selective oxidation of carbohydrates has been evaluated. Pd/h-BN catalysts as well as Pd/α-Al2O3 have been synthesized by two different methods for comparison: dry impregnation and deposition-precipitation. It is shown that BN is a suitable alternative to alumina and carbon for sugar oxidation in liquid phase. Very active and selective Pd/h-BN catalysts were obtained by the two synthetic methods under consideration.

Production of lactose-free galacto-oligosaccharide mixtures: comparison of two cellobiose dehydrogenases for the selective oxidation of lactose to lactobionic acid

Maischberger, Thomas,Nguyen, Thu-Ha,Sukyai, Prakit,Kittl, Roman,Riva, Sergio,Ludwig, Roland,Haltrich, Dietmar

, p. 2140 - 2147 (2008/12/21)

Galacto-oligosaccharides, complex mixtures of various sugars, are produced by transgalactosylation from lactose using β-galactosidase and are of great interest for food and feed applications because of their prebiotic properties. Most galacto-oligosaccharide preparations currently available in the market contain a significant amount of monosaccharides and lactose. The mixture of galacto-oligosaccharides (GalOS) in this study produced from lactose using recombinant β-galactosidase from Lactobacillus reuteri contains 48% monosaccharides, 26.5% lactose and 25.5% GalOS. To remove efficiently both monosaccharides and lactose from this GalOS mixture containing significant amounts of prebiotic non-lactose disaccharides, a biocatalytic approach coupled with subsequent chromatographic steps was used. Lactose was first oxidised to lactobionic acid using fungal cellobiose dehydrogenases, and then lactobionic acid and monosaccharides were removed by ion-exchange and size-exclusion chromatography. Two different cellobiose dehydrogenases (CDH), originating from Sclerotium rolfsii and Myriococcum thermophilum, were compared with respect to their applicability for this process. CDH from S. rolfsii showed higher specificity for the substrate lactose, and only few other components of the GalOS mixture were oxidised during prolonged incubation. Since these sugars were only converted once lactose oxidation was almost complete, careful control of the CDH-catalysed reaction will significantly reduce the undesired oxidation, and hence subsequent removal, of any GalOS components. Removal of ions and monosaccharides by the chromatographic steps gave an essentially pure GalOS product, containing less than 0.3% lactose and monosaccharides, in a yield of 60.3%.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 96-82-2