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L2398

Sigma-Aldrich

Lactobionic acid

≥97% (TLC), cell impermeant agent

Synonym(s):

4-O-β-D-Galactopyranosyl-D-gluconic acid

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About This Item

Empirical Formula (Hill Notation):
C12H22O12
CAS Number:
Molecular Weight:
358.30
Beilstein:
95054
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic (organic

Organic)

Assay

≥97% (TLC)

form

powder

color

white

mp

113-118 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

room temp

SMILES string

OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)C(O)=O

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

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General description

Lactobionic acid, a derivative of lactose, is an aldonic acid obtained from gluconic acid and galactose. It is a potential chelating agent, preservative and a prebiotic.

Application

Cell impermeant agent used for organ preservation
Lactobionic acid has been used as a control for the chemical characterization of the lactobionic acid produced by Zymomonas mobilis.

Biochem/physiol Actions

Lactobionic acid has a role as an antioxidant and stabilizer-gelling agent. It is used as an ingredient in foods and pharmaceutical products.
Reported to inhibit production of hydroxyl radicals. Cryptic inhibitor of matrix metalloproteinases (MMP). Resistant to dietary metabolism but stimulates intestinal calcium absorption in rat.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J A Wahlberg et al.
Transplantation, 43(1), 5-8 (1987-01-01)
A new flushout solution for preservation of the pancreas was tested in the dog model of segmental pancreas autotransplantation. The solution osmolality was 320 mOsm/L, K+ = 120 mM, Na+ = 30 mM, and it contained the anion, lactobionate, and
Lactobionic acid produced by Zymomonas mobilis: alternative to prepare targeted nanoparticles
Valle TA, et al.
Pharmaceutica Analytica Acta, 4, 1-5 (2013)
Lactobionic acid: a high value-added lactose derivative for food and pharmaceutical applications
International dairy journal, 26(2), 103-111 (2012)
J H Southard et al.
Annual review of medicine, 46, 235-247 (1995-01-01)
Organ preservation is the supply line for organ transplantation. Currently, the liver, pancreas, and kidney can be successfully preserved for up to two days by flushing the organs with the University of Wisconsin (UW) organ preservation solution and storing them
C Charloux et al.
Free radical biology & medicine, 19(5), 699-704 (1995-11-01)
Superoxide and hydroxyl free radicals are strongly implicated in the deleterious effects of reperfusion of grafted organs. Iron ions are critical in the Fenton-like reaction that generates oxygen-free radicals from H2O2. Using the ADP/Fe2+/H2O2 .OH-generating system, we demonstrated that components

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