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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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Lactobionic acid: a high value-added lactose derivative for food and pharmaceutical applications
International dairy journal, 26(2), 103-111 (2012)
Lactobionic acid produced by Zymomonas mobilis: alternative to prepare targeted nanoparticles
Valle TA, et al.
Pharmaceutica Analytica Acta, 4, 1-5 (2013)
R Brommage et al.
The Journal of nutrition, 123(12), 2186-2194 (1993-12-01)
Lactulose is a disaccharide analogue of lactose that is resistant to metabolism in the small intestine but not in the large intestine. The effects of lactulose and other sugars on intestinal Ca absorption were determined from the decrease in the
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
G A Upadhya et al.
Hepatology (Baltimore, Md.), 31(5), 1115-1122 (2000-05-05)
UW solution and HTK solution are both used for cold preservation of liver allografts. Although they are about equally effective, their compositions are very different, and they were formulated using different rationales. The authors recently showed an important role for

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