ChemFOnt: Showing chemical card for Gluconolactone (CFc000000097)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:24 UTC

Chemfont ID

CFc000000097

Molecule Identification

Common Name

Gluconolactone

Definition

Gluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one	ChEBI
1,5-D-Gluconolactone	ChEBI
1,5-Gluconolactone	ChEBI
D-Aldonolactone	ChEBI
D-Gluconic acid delta-lactone	ChEBI
D-Gluconic acid lactone	ChEBI
D-Gluconolactone	ChEBI
D-threo-aldono-1,5-Lactone	ChEBI
delta-D-Gluconolactone	ChEBI
delta-Gluconolactone	ChEBI
Glucarolactone	ChEBI
Gluconic acid lactone	ChEBI
Gluconic delta-lactone	ChEBI
Gluconic lactone	ChEBI
D-Gluconate delta-lactone	Generator
D-Gluconate δ-lactone	Generator
D-Gluconic acid δ-lactone	Generator
D-Gluconate lactone	Generator
δ-D-gluconolactone	Generator
δ-Gluconolactone	Generator
Gluconate lactone	Generator
Gluconic δ-lactone	Generator
1,5-delta-Gluconolactone	HMDB
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one	HMDB
D-(+)-Gluconic acid D-lactone	HMDB
D-(+)-Gluconic acid-delta lactone	HMDB
D-delta-Gluconolactone	HMDB
D-Gluconic acid 1,5-lactone	HMDB
D-Gluconic acid D-lactone	HMDB
D-Gluconic acid-1,5-lactone	HMDB
D-Gluconic acid-delta-lactone	HMDB
D-Gluconic delta-lactone	HMDB
D-Glucono-1,5-lactone	HMDB
D-glucono-D-Lactone	HMDB
delta-(+)-Gluconic acid D-lactone	HMDB
delta-Aldonolactone	HMDB
delta-Gluconic acid 1,5-lactone	HMDB
delta-Gluconic acid D-lactone	HMDB
delta-Gluconic acid lactone	HMDB
delta-Gluconic acid-1,5-lactone	HMDB
delta-Glucono-1,5-lactone	HMDB
Fujiglucon	HMDB
Gluconate, lactone	HMDB
Glucono 1,5-lactone	HMDB
Glucono delta lactone	HMDB
Glucono delta-lactone	HMDB
GDL (Gluconate)	MeSH, HMDB
Glucono-delta-lactone	MeSH
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one	HMDB
D-(+)-Gluconic acid delta-lactone	HMDB
D-(+)-Gluconic acid δ-lactone	HMDB
D-(+)-Glucono-1,5-lactone	HMDB
D-(+)-Glucono-delta-lactone	HMDB
D-(+)-Glucono-δ-lactone	HMDB
D-(+)-Glucose delta-lactone	HMDB
D-(+)-Glucose δ-lactone	HMDB
D-Glucono-delta-lactone	HMDB
D-Glucono-δ-lactone	HMDB
Glucono-δ-lactone	HMDB
Gluconolactone	HMDB
Lysactone	HMDB

Chemical Formula

C₆H₁₀O₆

Average Molecular Weight

178.14

Monoisotopic Molecular Weight

178.047738052

IUPAC Name

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

Traditional Name

gluconolactone

CAS Registry Number

90-80-2

SMILES

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

InChI Identifier

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

InChI Key

PHOQVHQSTUBQQK-SQOUGZDYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Gluconolactones

Alternative Parents

Substituents

Gluconolactone
Delta valerolactone
Delta_valerolactone
Oxane
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

aldono-1,5-lactone (CHEBI:16217 )
gluconolactone (CHEBI:16217 )

Functional Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19212411)

Excreta

Biofluid or Excreta

Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0000150)

Source

Exogenous

Exogenous (HMDB: HMDB0000150)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000150)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Transaldolase Deficiency (PathBank: SMP0120804)
Glucose-6-phosphate Dehydrogenase Deficiency (PathBank: SMP0120583)
Ribose-5-phosphate Isomerase Deficiency (PathBank: SMP0120803)

Metabolic pathway

Pentose Phosphate Pathway (PathBank: SMP0087246)
Pentose Phosphate Pathway (HMDB: HMDB0000150)

Prostate cancer (HMDB: HMDB0000150)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000150)

Food and nutrition

Food additive

Food preservative

Sequestrant (HMDB: HMDB0000150)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	586 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.7	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.78 m³·mol⁻¹	ChemAxon
Polarizability	15.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon