Gluconolactone

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H10O6
Molecular Weight	178.14
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PHOQVHQSTUBQQK-SQOUGZDYSA-N

InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C6H10O6
Molecular Weight	178.14
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019481s013lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.hindawi.com/journals/ecam/2014/169130/ https://www.food.gov.uk/science/additives/enumberlist#h_7

Gluconolactone, a lactone of D-glucuronic acid, is a food additive with the E number E575. Gluconolactone is commonly found in honey, fruit juices, wine. In medcine, gluconolactone is used as a component of irrigation solution Renacidin for dissolution of bladder calculi of the struvite or apatite variety, and to prevent or minimize encrustations of indwelling urinary tract catheters.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcium 10 Target ID: CHEMBL2364030 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21999455	Chelating Agent 139

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bladder calculi 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019481s013lbl.pdf	Primary		Approved 8583	RENACIDIN Approved Use Renacidin Irrigation is indicated for use by local irrigation in the dissolution of renal calculi composed of apatite (a calcium carbonate phosphate compound) or struvite (magnesium ammonium phosphates in patients who are not candidates for surgical removal of the calculi. It may also be used as adjunctive therapy to dissolve residual apatite or struvite calculi and fragments after surgery or to achieve partial dissolution of renal calculi to facilitate surgical removal. Renacidin Irrigation is also indicated for dissolution of bladder calculi of the struvite or apatite variety by local intermittent irrigation through a urethral catheter or cystostomy catheter as an alternative or adjunct to surgical procedures. Renacidin Irrigation is also indicated for use as an intermittent irritating solution to prevent or minimize encrustations of indwelling urinary tract catheters. Since many complications are experienced by patients receiving infusions of Renacidin Irrigation into the renal pelvis, considerable caution must be employed. Additionally, hospitalization is prolonged for days to weeks when chemolytic therapy is used in lieu of, or following surgery. For these reasons, use of this therapy should be reserved for selected patients. Renacidin Irrigation is not indicated for dissolution of calcium oxalate, uric acid or cysteine calculi. Launch Date 1990
Urinary catheterization 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019481s013lbl.pdf	Secondary		Approved 8583	RENACIDIN Approved Use Renacidin Irrigation is indicated for use by local irrigation in the dissolution of renal calculi composed of apatite (a calcium carbonate phosphate compound) or struvite (magnesium ammonium phosphates in patients who are not candidates for surgical removal of the calculi. It may also be used as adjunctive therapy to dissolve residual apatite or struvite calculi and fragments after surgery or to achieve partial dissolution of renal calculi to facilitate surgical removal. Renacidin Irrigation is also indicated for dissolution of bladder calculi of the struvite or apatite variety by local intermittent irrigation through a urethral catheter or cystostomy catheter as an alternative or adjunct to surgical procedures. Renacidin Irrigation is also indicated for use as an intermittent irritating solution to prevent or minimize encrustations of indwelling urinary tract catheters. Since many complications are experienced by patients receiving infusions of Renacidin Irrigation into the renal pelvis, considerable caution must be employed. Additionally, hospitalization is prolonged for days to weeks when chemolytic therapy is used in lieu of, or following surgery. For these reasons, use of this therapy should be reserved for selected patients. Renacidin Irrigation is not indicated for dissolution of calcium oxalate, uric acid or cysteine calculi. Launch Date 1990

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-034999	http://www.3bsc.com/index/pro_info.php?id=56932
Aaron Chemicals	AR0037J4	http://www.aaronchem.com/90-80-2
abcr GmbH	AB116915	http://www.abcr.com/shop/en/AB116915
Achemtek	0104-020816	http://www.achemtek.com/90-80-2
Acros Organics	AC271050010	https://www.fishersci.com/shop/products/delta-gluconolactone-99-acros-organics-1/AC271050010
Acros Organics	AC271050051	https://www.fishersci.com/shop/products/delta-gluconolactone-99-acros-organics/AC271050051
Acros Organics	AC271052500	https://www.fishersci.com/shop/products/delta-gluconolactone-99-acros-organics-1/AC271052500
AHH Chemical co.,ltd	MT-49829	http://www.ahhchemical.com/product/MT-49829.html
Alfa Aesar	A13105	https://www.alfa.com/en/catalog/A13105/
Alfa Chemistry	AP90802	https://reagents.alfa-chemistry.com/product/d-gluconic-acid-lactone-cas-90-80-2-18457.html
Alichem	119001671	http://www.alichem.com/en/products/90-80-2.html
Aurora Fine Chemicals LLC	A13.112.201	http://online.aurorafinechemicals.com/info?ID=A13.112.201
Aurum Pharmatech LLC	NE10449	http://www.Aurumpharmatech.com/Product/ProductDetails/NE10449
BioSynth	W-100325	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-100325.html
BLD Pharm	BD123238	http://www.bldpharm.com/products/90-80-2.html
Boerchem	BC205704	http://www.boerchem.com/?product_34663.html
Chem Scene	CS-M3768	http://www.chemscene.com/90-80-2.html
Chemenu	CM100852	http://www.chemenu.com/products/CM100852
ChemMol	30102801	http://www.chemmol.com/chemmol/30102801.html
ChemMol	44002252	http://www.chemmol.com/chemmol/44002252.html
Chemspace	CSSB00000765944	https://chem-space.com/CSSB00000765944
China MainChem Co., Ltd	MS90-80-2	https://www.mainchem.com/product/delta-gluconolactone/
CSNpharm	CSN23445	https://www.csnpharm.com/products/d-(+)-glucono-1,5-lactone.html
eNovation Chemicals	D381156	http://www.enovationchem.com/productDetails.asp?productID=D381156
eNovation Chemicals	D604531	http://www.enovationchem.com/productDetails.asp?productID=D604531
Glentham Life Sciences	GC5247	http://www.glentham.com/products/product/GC5247/
Hairui	HR100863	http://www.hairuichem.com/en/product/4253-68-3.html
Hairui	HR130762	http://www.hairuichem.com/en/product/90-80-2.html
iChemical	EBD71631	http://www.ichemical.com/products/90-80-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00201717	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00201717
LGC Standards	DRE-C14026800	https://www.lgcstandards.com/US/en/p/DRE-C14026800
Matrix Scientific	99798	https://www.matrixscientific.com/099798.html
MedChem Express	HY-I0301	https://www.medchemexpress.com/E_575.html
MuseChem	M046786	https://www.musechem.com/product/M046786.html
MuseChem	M116502	https://www.musechem.com/product/M116502.html
MuseChem	R041226	https://www.musechem.com/product/R041226.html
Oakwood	242801	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=123800&ExtHyperLink=1
Renno Tech	RP23931	http://www.rennotech.com/product_show.asp?id=29586
Sigma-Aldrich	1294150_USP	https://www.sigmaaldrich.com/catalog/product/usp/1294150?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	76139_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/76139?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	G2164_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/g2164?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	G4750_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/g4750?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S566436	https://www.smolecule.com/products/s566436
TCI (Tokyo Chemical Industry)	G0039	http://www.tcichemicals.com/eshop/en/us/commodity/G0039/index.html
THE BioTek	bt-305279	https://www.thebiotek.com/product/others/bt-305279
VladaChem	VL278359-1KG	https://www.vladachem.com/product.php?products=90-80-2
Yuhao Chemical	XJ0182	http://www.chemyuhao.com/90-80-2.html

PubMed

Title	Date	PubMed
Purification and partial characterization of polygalacturonase from Streptomyces lydicus.	2008-09	17996445
Fabrication of novel core-shell hybrid alginate hydrogel beads.	2008-03-03	17964745
Improvement of P450(BM-3) whole-cell biocatalysis by integrating heterologous cofactor regeneration combining glucose facilitator and dehydrogenase in E. coli.	2008-02	18057930
Co-ordinated regulation of gluconate catabolism and glucose uptake in Corynebacterium glutamicum by two functionally equivalent transcriptional regulators, GntR1 and GntR2.	2008-01	18047570
Acid gelation properties of heated skim milk as a result of enzymatically induced changes in the micelle/serum distribution of the whey protein/kappa-casein aggregates.	2007-12-26	18038987
Remarkable beta-selectivity in the synthesis of beta-1-C-arylglucosides: stereoselective reduction of acetyl-protected methyl 1-C-arylglucosides without acetoxy-group participation.	2007-12-07	17997568
A low perfusion rate microreactor for continuous monitoring of enzyme characteristics: application to glucose oxidase.	2007-11	17909761
Expedited struvite-stone dissolution using a high-flow low-pressure irrigation system.	2007-10	17949316
Short syntheses of gabosine I and gabosine G from delta-D-gluconolactone.	2007-08-17	17637067
pH oscillations and bistability in the methylene glycol-sulfite-gluconolactone reaction.	2007-07-28	17622405
Crystal structure of Saccharomyces cerevisiae 6-phosphogluconate dehydrogenase Gnd1.	2007-06-14	17570834
[The drug release properties of poly (acrylamide-co-itaconate-vinylbenzylglycosylallylamide) hydrogels].	2007-06	17713271
Solubilized micellar calcium induced low methoxyl-pectin aggregation during milk acidification.	2007-06	17517709
Acid gelation in heated and unheated milks: interactions between serum protein complexes and the surfaces of casein micelles.	2007-05-16	17439142
Crystal structure of intracellular family 1 beta-glucosidase BGL1A from the basidiomycete Phanerochaete chrysosporium.	2007-04-03	17376440
Effect of components extracted from okara on the physicochemical properties of soymilk and tofu texture.	2007-03	17995824
An organic-based pH oscillator.	2007-02-01	17249741
Ultrasonic monitoring of yoghurt formation by using AT-cut quartz: lighting of casein micelles interactions process during the acidification.	2006-12-22	16797636
Mechanisms responsible for poor oral bioavailability of paeoniflorin: Role of intestinal disposition and interactions with sinomenine.	2006-12	17063398
Cellobiase from Termitomyces clypeatus: activity and secretion in presence of glycosylation inhibitors.	2006-11	16912924
A novel technique for differentiation of proteins in the development of acid gel structure from control and heat treated milk using confocal scanning laser microscopy.	2006-11	16834815
Adsorption and aggregation properties of heterogemini surfactants containing a quaternary ammonium salt and a sugar moiety.	2006-10-24	17042528
Study of the effect of soy proteins on the acid-induced gelation of casein micelles.	2006-10-18	17032034
Starter bacteria are the prime agents of lipolysis in cheddar cheese.	2006-10-18	17032033
Soluble aldose sugar dehydrogenase from Escherichia coli: a highly exposed active site conferring broad substrate specificity.	2006-10-13	16864586
Addition of pectin and soy soluble polysaccharide affects the particle size distribution of casein suspensions prepared from acidified skim milk.	2006-08-23	16910714
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	16903719
Functional and structural properties of 2S soy protein in relation to other molecular protein fractions.	2006-08-09	16881715
Divergent synthesis of L-sugars and L-iminosugars from D-sugars.	2006-07-24	16718730
Complex coacervation between beta-lactoglobulin and Acacia gum: a nucleation and growth mechanism.	2006-07-15	16530214
Formation of stable nanoparticles via electrostatic complexation between sodium caseinate and gum arabic.	2006-06-05	16453308
Potentially implantable miniature batteries.	2006-06	16538459
Redox polymer and probe DNA tethered to gold electrodes for enzyme-amplified amperometric detection of DNA hybridization.	2006-04-15	16615783
Testing electrostatic complementarity in enzyme catalysis: hydrogen bonding in the ketosteroid isomerase oxyanion hole.	2006-04	16602823
Discovering functional gene expression patterns in the metabolic network of Escherichia coli with wavelets transforms.	2006-03-08	16524469
Investigations on foamability of surface-chemically pure aqueous solutions of functionalized alkylaldonamides.	2006-02-15	16154577
Redox mediation at 11-mercaptoundecanoic acid self-assembled monolayers on gold.	2006-02-09	16471810
Effect of insulin on small intestinal transit in normal mice is independent of blood glucose level.	2006-02-01	16448577
Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris.	2005-12	16417459
Stabilization of caseinate-covered oil droplets during acidification with high methoxyl pectin.	2005-11-02	16248559
Microwave activation of the electro-oxidation of glucose in alkaline media.	2005-10-21	16294230
Effects of two types of emulsifying salts on the functionality of nonfat pasta filata cheese.	2005-10	16162514
The effects of various organic acids on phytate phosphorus utilization in chicks.	2005-09	16206555
Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond.	2005-09	16141538
Enzyme-assisted reforming of glucose to hydrogen in a photoelectrochemical cell.	2005-06-18	15960593
Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition.	2005-05-09	15882454
Adsorption behavior of surface chemically pure N-cycloalkylaldonamides at the air/water interface.	2005-04-26	15835969
Inhibitory effect of naturally occurring flavonoids on the formation of advanced glycation endproducts.	2005-04-20	15826074
Adsorption behavior of surface-chemically pure N-alkyl-N-(2-hydroxyethyl)aldonamides at the air/water interface.	2004-03-02	15801414
Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia.	1991-10-04	1797843

Patents

Sample Use Guides

In Vivo Use Guide

For dissolution of bladder calculi, 30 mL (one container) of Renacidin should be instilled into the bladder via a urethral catheter or cystostomy tube. For prevention of encrustations in urethral catheters and cystostomy tube, 30 mL (one container) of Renacidin should be instilled into the urethral catheter or cystostomy tube. As a food additive, gluconolactone is administered orally.

Route of Administration: Other

In Vitro Use Guide

Chemolysis rate was tested using an in-vitro urinary-tract model. A laboratory-proved large human struvite stone was divided into 3.5-g fragments, which were placed in the model. In the experimental group, Renacidin irrigation was performed through the high-flow low-pressure irrigation system. In the control group, Renacidin solution was infused at 120 mL/hour through a nephrostomy tube. The overall chemolysis rates with the high-flow low-pressure irrigation and control systems were 0.12 g/hr and 0.06 g/hr, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:29:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:29:46 GMT 2025`
Record UNII	WQ29KQ9POT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Gluconolactone

Official Name

English

Glucono delta-lactone

Preferred Name

English

GLUCONO .DELTA. LACTONE

Common Name

English

GLUCONOLACTONE [MART.]

Common Name

English

LYSACTONE

Common Name

English

D-(+)-Glucono-?-lactone

Common Name

English

RIKEN LACTONE

Common Name

English

GLUCONO-DELTA-LACTONE [VANDF]

Common Name

English

NSC-758238

Code

English

NSC-34393

Code

English

INS-575

Code

English

GDL

Common Name

English

(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one

Systematic Name

English

DELTA-GLUCONOLACTONE

Common Name

English

RENACIDIN COMPONENT GLUCONOLACTONE

Common Name

English

D-GLUCONIC ACID DELTA-LACTONE

Common Name

English

FUJIGLUCON

Common Name

English

(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

Systematic Name

English

D-GLUCONIC ACID .DELTA.-LACTONE

Common Name

English

GLUCONOLACTONE [MI]

Common Name

English

Gluconolactone [WHO-DD]

Common Name

English

INS NO.575

Code

English

GLUCONOLACTONE [USP-RS]

Common Name

English

GLUCONOLACTONE [ORANGE BOOK]

Common Name

English

GLUCONO .DELTA.-LACTONE

Common Name

English

E-575

Code

English

GLUCONO DELTA-LACTONE [FCC]

Common Name

English

D-GLUCONO-1,5-LACTONE

Common Name

English

GLUCONOLACTONE [USP MONOGRAPH]

Common Name

English

.DELTA.-D-GLUCONOLACTONE

Common Name

English

GLUCONOLACTONE [II]

Common Name

English

GLUCONOLACTONE [HSDB]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

INS-575