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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
Molecular Formula C12H22O12
Molecular Weight 358.2959
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

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
172
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Galectin inhibitory disaccharides promote tumour immunity in a breast cancer model.
2010-12-28
Galactosyl conjugated N-succinyl-chitosan-graft-polyethylenimine for targeting gene transfer.
2010-12
Applications of hydroxy acids: classification, mechanisms, and photoactivity.
2010-11-24
Fluorine-18 labeled galactosylated chitosan for asialoglycoprotein-receptor-mediated hepatocyte imaging.
2010-08-15
Dissecting the in vivo metabolic potential of two human gut acetogens.
2010-07-16
Changes in the proteomic and metabolic profiles of Beta vulgaris root tips in response to iron deficiency and resupply.
2010-06-21
Development and in vitro characterization of galactosylated low molecular weight chitosan nanoparticles bearing doxorubicin.
2010-06
Galactosylated poly(2-(2-aminoethyoxy)ethoxy)phosphazene/DNA complex nanoparticles: in vitro and in vivo evaluation for gene delivery.
2010-04-12
Galactosylated solid lipid nanoparticles with cucurbitacin B improves the liver targetability.
2010-04
Lactobionic acid in a natural alkylpolyglucoside-based vehicle: assessing safety and efficacy aspects in comparison to glycolic acid.
2010-03
Acute acidification of stratum corneum membrane domains using polyhydroxyl acids improves lipid processing and inhibits degradation of corneodesmosomes.
2010-02
Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy.
2010-01
Self-assembly and characterization of Pluronic P105 micelles for liver-targeted delivery of silybin.
2009-12
Superparamagnetic iron oxide nanoparticles as a dual imaging probe for targeting hepatocytes in vivo.
2009-12
Effect of culture medium composition on Trichoderma reesei's morphology and cellulase production.
2009-12
Amphiphilic perfluoroalkyl carbohydrates as new tools for liver imaging.
2009-09-11
Immobilization of lactobionic acid on the surface of cadmium sulfide nanoparticles and their interaction with hepatocytes.
2009-09
Galactosylated LDL nanoparticles: a novel targeting delivery system to deliver antigen to macrophages and enhance antigen specific T cell responses.
2009-07-30
Maintenance of an acidic stratum corneum prevents emergence of murine atopic dermatitis.
2009-07
Kinetic modeling of a bi-enzymatic system for efficient conversion of lactose to lactobionic acid.
2009-04-01
Galactosylated fluorescent labeled micelles as a liver targeting drug carrier.
2009-03
Bubble-free oxygenation of a bi-enzymatic system: effect on biocatalyst stability.
2009-01-01
Involvement of Acetobacter orientalis in the production of lactobionic acid in Caucasian yogurt ("Caspian Sea yogurt") in Japan.
2009-01
Pxmp2 is a channel-forming protein in Mammalian peroxisomal membrane.
2009
Whole-cell bioreduction of aromatic alpha-keto esters using Candida tenuis xylose reductase and Candida boidinii formate dehydrogenase co-expressed in Escherichia coli.
2008-12-10
Production of lactose-free galacto-oligosaccharide mixtures: comparison of two cellobiose dehydrogenases for the selective oxidation of lactose to lactobionic acid.
2008-08-11
Lactose enhances cellulase production by the filamentous fungus Acremonium cellulolyticus.
2008-08
Rickets: an overview and future directions, with special reference to Bangladesh. A summary of the Rickets Convergence Group meeting, Dhaka, 26-27 January 2006.
2008-03
Purification and characterization of a carbohydrate: acceptor oxidoreductase from Paraconiothyrium sp. that produces lactobionic acid efficiently.
2008-03
Inherent toxicity of organ preservation solutions to cultured hepatocytes.
2008-02
Green oxidation of renewable carbohydrates: lactobionic acid production as an example.
2008
Nano-vectors for efficient liver specific gene transfer.
2008
Organic-inorganic mesoporous nanocarriers integrated with biogenic ligands.
2007-10
Oxidation of lactose to lactobionic acid by a Microdochium nivale carbohydrate oxidase: kinetics and operational stability.
2007-07-01
Scale-up of enzymatic production of lactobionic acid using the rotary jet head system.
2007-07-01
Characterization of the bga1-encoded glycoside hydrolase family 35 beta-galactosidase of Hypocrea jecorina with galacto-beta-D-galactanase activity.
2007-04
Quantification of lactobionic acid and sorbitol from enzymatic reaction of fructose and lactose by high-performance liquid chromatography.
2007-03-23
[Galactosylated derivatives of low-molecular-weight chitosan: production and properties].
2007-03-10
Synthesis of a novel glycoconjugated chitosan and preparation of its derived nanoparticles for targeting HepG2 cells.
2007-03
Identification of live liver cancer cells in a mixed cell system using galactose-conjugated fluorescent nanoparticles.
2007-02-15
Surface modification of magnetite nanoparticles using lactobionic acid and their interaction with hepatocytes.
2007-02
Superparamagnetic iron oxide nanoparticles coated with galactose-carrying polymer for hepatocyte targeting.
2007
Enzymatically oxidized lactose and derivatives thereof as potential protein cross-linkers.
2006-12-29
Tetranuclear copper(II) complexes bridged by alpha-D-glucose-1-phosphate and incorporation of sugar acids through the Cu4 core structural changes.
2006-08-21
Dynamic seeding and perfusion culture of hepatocytes with galactosylated vegetable sponge in packed-bed bioreactor.
2006-07
Asialoglycoprotein-receptor-targeted hepatocyte imaging using 99mTc galactosylated chitosan.
2006-05
Uronic acids functionalized polyethyleneimine (PEI)-polyethyleneglycol (PEG)-graft-copolymers as novel synthetic gene carriers.
2006-04
Chitosan nanoparticles for oral drug and gene delivery.
2006
Oxidation of lactose with bromine.
2005-12-12
Sugar-based gemini surfactants with peptide bonds-synthesis, adsorption, micellization, and biodegradability.
2005-11-08
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:43 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:43 GMT 2025
Record UNII
65R938S4DV
Record Status Validated (UNII)
Record Version
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Name Type Language
D-GLUCONIC ACID, 4-O-.BETA.-D-GALACTOPYRANOSYL-
Preferred Name English
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 [II]
Common Name English
LACTOBIONIC ACID [USP-RS]
Common Name English
LACTOBIONIC ACID [MI]
Common Name English
LACTOBIONIC ACID [MART.]
Common Name English
LACTOBIONIC ACID [EP MONOGRAPH]
Common Name English
Code System Code Type Description
EVMPD
SUB23538
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-538-3
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
PUBCHEM
7314
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
CAS
96-82-2
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
MERCK INDEX
m6661
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY Merck Index
SMS_ID
100000088995
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
RXCUI
1426414
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
ALTERNATIVE
CHEBI
143069
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048861
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
CONCEPT Industrial Aid
RS_ITEM_NUM
1356825
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
RXCUI
1426413
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
FDA UNII
65R938S4DV
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
WIKIPEDIA
LACTOBIONIC ACID
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
DAILYMED
65R938S4DV
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
NCI_THESAURUS
C83860
Created by admin on Mon Mar 31 17:34:43 GMT 2025 , Edited by admin on Mon Mar 31 17:34:43 GMT 2025
PRIMARY
Related Record Type Details
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 GLUBIONATE ANHYDROUS
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
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of LACTOBIONIC ACID
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