U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O12
Molecular Weight 358.2959
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LACTOBIONIC ACID

SMILES

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

InChIKey=JYTUSYBCFIZPBE-AMTLMPIISA-N
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

HIDE SMILES / InChI

Description

LBA (4-O-beta-D-galactopyranosyl-D-gluconic acid) is an aldonic acid obtained from the oxidation of lactose, with high potential applications as an ingredient in foods and pharmaceutical products, because of its antioxidant, chelating and humectant properties.

Originator

Fischer, E.|Meyer, J.
1
Sources: Fischer, E., & Meyer, J. (1889). Oxydation des milchzuckers. Berichte Der Deutschen Chemischen Gesellschaft, 22, 361-364.
Curator's Comment: reference retrieved from http://www.jbc.org/content/171/1/213.full.pdf

Approval Year

2000
171
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anionic polysaccharides. A class of substances with hepatoprotective and antiadhesive properties in rat liver preservation.
2002 Jan
Preparation of alginate/galactosylated chitosan scaffold for hepatocyte attachment.
2002 Jul
Toxicological studies on Lactose Oxidase from Microdochium nivale expressed in Fusarium venenatum.
2004 Jun
Hepatocyte-targeted nuclear imaging using 99mTc-galactosylated chitosan: conjugation, targeting, and biodistribution.
2005 Jan
Uronic acids functionalized polyethyleneimine (PEI)-polyethyleneglycol (PEG)-graft-copolymers as novel synthetic gene carriers.
2006 Apr
Dynamic seeding and perfusion culture of hepatocytes with galactosylated vegetable sponge in packed-bed bioreactor.
2006 Jul
Characterization of the bga1-encoded glycoside hydrolase family 35 beta-galactosidase of Hypocrea jecorina with galacto-beta-D-galactanase activity.
2007 Apr
Identification of live liver cancer cells in a mixed cell system using galactose-conjugated fluorescent nanoparticles.
2007 Feb 15
Oxidation of lactose to lactobionic acid by a Microdochium nivale carbohydrate oxidase: kinetics and operational stability.
2007 Jul 1
Synthesis of a novel glycoconjugated chitosan and preparation of its derived nanoparticles for targeting HepG2 cells.
2007 Mar
Green oxidation of renewable carbohydrates: lactobionic acid production as an example.
2008
Lactose enhances cellulase production by the filamentous fungus Acremonium cellulolyticus.
2008 Aug
Whole-cell bioreduction of aromatic alpha-keto esters using Candida tenuis xylose reductase and Candida boidinii formate dehydrogenase co-expressed in Escherichia coli.
2008 Dec 10
Purification and characterization of a carbohydrate: acceptor oxidoreductase from Paraconiothyrium sp. that produces lactobionic acid efficiently.
2008 Mar
Pxmp2 is a channel-forming protein in Mammalian peroxisomal membrane.
2009
Kinetic modeling of a bi-enzymatic system for efficient conversion of lactose to lactobionic acid.
2009 Apr 1
Superparamagnetic iron oxide nanoparticles as a dual imaging probe for targeting hepatocytes in vivo.
2009 Dec
Effect of culture medium composition on Trichoderma reesei's morphology and cellulase production.
2009 Dec
Involvement of Acetobacter orientalis in the production of lactobionic acid in Caucasian yogurt ("Caspian Sea yogurt") in Japan.
2009 Jan
Bubble-free oxygenation of a bi-enzymatic system: effect on biocatalyst stability.
2009 Jan 1
Maintenance of an acidic stratum corneum prevents emergence of murine atopic dermatitis.
2009 Jul
Galactosylated fluorescent labeled micelles as a liver targeting drug carrier.
2009 Mar
Immobilization of lactobionic acid on the surface of cadmium sulfide nanoparticles and their interaction with hepatocytes.
2009 Sep
Amphiphilic perfluoroalkyl carbohydrates as new tools for liver imaging.
2009 Sep 11
Galactosylated LDL nanoparticles: a novel targeting delivery system to deliver antigen to macrophages and enhance antigen specific T cell responses.
2009 Sep-Oct
Galactosylated solid lipid nanoparticles with cucurbitacin B improves the liver targetability.
2010 Apr
Galactosylated poly(2-(2-aminoethyoxy)ethoxy)phosphazene/DNA complex nanoparticles: in vitro and in vivo evaluation for gene delivery.
2010 Apr 12
Acute acidification of stratum corneum membrane domains using polyhydroxyl acids improves lipid processing and inhibits degradation of corneodesmosomes.
2010 Feb
Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy.
2010 Jan
Development and in vitro characterization of galactosylated low molecular weight chitosan nanoparticles bearing doxorubicin.
2010 Jun
Lactobionic acid in a natural alkylpolyglucoside-based vehicle: assessing safety and efficacy aspects in comparison to glycolic acid.
2010 Mar
Patents

Patents

JP2011527675A
1

Sample Use Guides

In Vivo Use Guide
Dermo-cosmetic products with high concentration of lactobionic acid (5%, 10%, 15%, 22% ). Combines the benefits of safe exfoliation with hydration, regeneration, and soothing of the skin. Dedicated for sensitive skin and skin prone to distended and broken capillaries, skin irritated after aesthetic treatments and dermatologic therapies.
Route of Administration: Topical
In Vitro Use Guide
Lactobionic acid (250 or 500 uM) treatment induced significant reduction of triglycerides and oil droplet formation in adipocytes as well as decreased expression of major lipogenic and adipogenic markers (e.g. CEBPa/Cebpa, SREBP-1c/Srebpf1, PPARg/Pparg) in a dose-dependent manner.
Name Type Language
LACTOBIONIC ACID
EP   II   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
LACTOBIONATE
Common Name English
Lactobionic acid [WHO-DD]
Common Name English
LACTOBIONIC ACID [EP IMPURITY]
Common Name English
LACTOBIONIC ACID [INCI]
Common Name English
LACTOBIONIC ACID [II]
Common Name English
LACTOBIONIC ACID [USP-RS]
Common Name English
LACTOBIONIC ACID [MI]
Common Name English
LACTOBIONIC ACID [MART.]
Common Name English
D-GLUCONIC ACID, 4-O-.BETA.-D-GALACTOPYRANOSYL-
Common Name English
LACTOBIONIC ACID [EP MONOGRAPH]
Common Name English
Code System Code Type Description
EVMPD
SUB23538
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-538-3
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
PUBCHEM
7314
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
CAS
96-82-2
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
MERCK INDEX
m6661
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY Merck Index
RXCUI
1426414
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
ALTERNATIVE
CHEBI
143069
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048861
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
CONCEPT Industrial Aid
RS_ITEM_NUM
1356825
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
RXCUI
1426413
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
FDA UNII
65R938S4DV
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
WIKIPEDIA
LACTOBIONIC ACID
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
DAILYMED
65R938S4DV
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
NCI_THESAURUS
C83860
Created by admin on Fri Dec 15 15:00:09 GMT 2023 , Edited by admin on Fri Dec 15 15:00:09 GMT 2023
PRIMARY
SALT/SOLVATE (PARENT)
Structure of CLARITHROMYCIN LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of CALCIUM LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of ERYTHROMYCIN LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of LEVDOBUTAMINE LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of CALCIUM BROMOLACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of POTASSIUM LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of AZITHROMYCIN LACTOBIONATE
SALT/SOLVATE (PARENT)
Structure of CALCIUM GLUBIONATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966