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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

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
Protective effects of lactobionate in modified phosphate-buffered sucrose.
2001 Feb-Mar
Polynorbornene polycationic polymers as gene transfer agents. Influence of the counterion for in vitro transfection.
2004 Nov 5
Wide nanoscopic pore of maxi-anion channel suits its function as an ATP-conductive pathway.
2004 Sep
Hepatocyte-targeted nuclear imaging using 99mTc-galactosylated chitosan: conjugation, targeting, and biodistribution.
2005 Jan
Synergistic effect of poly(ethylenimine) on the transfection efficiency of galactosylated chitosan/DNA complexes.
2005 Jul 20
Sugar-based gemini surfactants with peptide bonds-synthesis, adsorption, micellization, and biodegradability.
2005 Nov 8
Chitosan nanoparticles for oral drug and gene delivery.
2006
Uronic acids functionalized polyethyleneimine (PEI)-polyethyleneglycol (PEG)-graft-copolymers as novel synthetic gene carriers.
2006 Apr
Tetranuclear copper(II) complexes bridged by alpha-D-glucose-1-phosphate and incorporation of sugar acids through the Cu4 core structural changes.
2006 Aug 21
Dynamic seeding and perfusion culture of hepatocytes with galactosylated vegetable sponge in packed-bed bioreactor.
2006 Jul
Asialoglycoprotein-receptor-targeted hepatocyte imaging using 99mTc galactosylated chitosan.
2006 May
Surface modification of magnetite nanoparticles using lactobionic acid and their interaction with hepatocytes.
2007 Feb
Pxmp2 is a channel-forming protein in Mammalian peroxisomal membrane.
2009
Self-assembly and characterization of Pluronic P105 micelles for liver-targeted delivery of silybin.
2009 Dec
Involvement of Acetobacter orientalis in the production of lactobionic acid in Caucasian yogurt ("Caspian Sea yogurt") in Japan.
2009 Jan
Galactosylated fluorescent labeled micelles as a liver targeting drug carrier.
2009 Mar
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
Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy.
2010 Jan
Changes in the proteomic and metabolic profiles of Beta vulgaris root tips in response to iron deficiency and resupply.
2010 Jun 21
Applications of hydroxy acids: classification, mechanisms, and photoactivity.
2010 Nov 24
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
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