Lactobionic acid

Base Information

• Chemical Name: Lactobionic acid
• CAS No.: 96-82-2
• Molecular Formula: C₁₂H₂₂O₁₂
• Molecular Weight: 358.299
• Hs Code.: 29400000
• European Community (EC) Number: 202-538-3,600-978-4
• UNII: 65R938S4DV
• DSSTox Substance ID: DTXSID3048861
• Nikkaji Number: J4.724D
• Wikipedia: Lactobionic_acid
• Wikidata: Q6138969
• NCI Thesaurus Code: C83860
• Metabolomics Workbench ID: 58861
• ChEMBL ID: CHEMBL3039602
• Mol file: 96-82-2.mol

Synonyms:calcium lactobionate anhydrous;copper lactobionate;ferric lactobionate;lactobionate;lactobionic acid;lactobionic acid, calcium salt (2:1);lactobionic acid, monosodium salt

Chemical Property of Lactobionic acid

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 7.15E-35mmHg at 25°C
• Melting Point: 113-118 °C(lit.)
• Refractive Index: 26 ° (C=8.8, H2O)
• Boiling Point: 864.7 °C at 760 mmHg
• PKA: 3.28±0.35(Predicted)
• Flash Point: 319.1 °C
• PSA: 217.60000
• Density: 1.79 g/cm³
• LogP: -5.66890
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: 10 g/100 mL
• Water Solubility.: 10 g/100 mL
• XLogP3: -5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 358.11112613
• Heavy Atom Count: 24
• Complexity: 406

Purity/Quality:

99%, ^*data from raw suppliers

Lactobionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)O
• 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
• Recent NIPH Clinical Trials: Relationship between equol producer status and intestinal microflora and effects of supplementation with equol and lactobionic acid on metabolic and bone parameters in healthy postmenopausal women
• 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.
• Uses: Lactobionic acid is mainly used in preservation solutions for organ transplantation. It is used to produce erythromycine lactobionate. Arginine metabolite in bovine brain; clonidine-displacing substance activity An inhibitor of matrix metalloproteinases
• Clinical Use: Erythromycin lactobionate is a salt with enhanced water solubility that is used for injections.

Technology Process of Lactobionic acid

There total 5 articles about Lactobionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

D-(+)-lactose (63-42-3) → lactobionic acid (96-82-2,534-41-8,534-42-9,51267-45-9,58459-39-5,69728-97-8,21675-39-8)

Guidance literature:

With oxygen; for 2h; Reagent/catalyst;

DOI:10.1016/j.apcata.2015.01.009

Reference yield: 96.1%

LACTOSE (5965-66-2) → lactobionic acid (96-82-2,534-41-8,534-42-9,51267-45-9,58459-39-5,69728-97-8,21675-39-8)

Guidance literature:

With oxygen; In water; at 39.84 ℃; for 3h; under 760.051 Torr; Schlenk technique;

DOI:10.1246/cl.160364

Reference yield:

lactobionolactone (5965-65-1,42776-28-3,52762-22-8) → lactobionic acid (96-82-2,534-41-8,534-42-9,51267-45-9,58459-39-5,69728-97-8,21675-39-8)

Guidance literature:

With trifluoroacetic acid; In 2-methoxy-ethanol; toluene;

DOI:10.1039/b513944a

upstream raw materials:

3-O-β-D-galactopyranosyl-D-arabinose

D-(+)-lactose

lactobionolactone

LACTOSE

Downstream raw materials:

lactobionolactone

N-[1-(dodecylcarbamoyl-2-(trityl)imidazolyl)ethyl]-22-lactobionamido-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluorodocosanamide

C₂₂H₃₄N₂O₁₃

erythromycin lactobionate

Refernces

• 1、 Meyer, Nathalie,Renders, Coralie,Lanckman, Rapha?l,Devillers, Michel,Hermans, Sophie. "Gold as active phase of BN-supported catalysts for lactose oxidation". . p. 549 - 558. Retrieved 2015/01/30.
• 2、 Gutierrez, Luis-Felipe,Hamoudi, Safia,Belkacemi, Khaled. "Selective production of lactobionic acid by aerobic oxidation of lactose over gold crystallites supported on mesoporous silica". body text. p. 94 - 103. Retrieved 2012/04/10.