Metabolite Card
Formula: C6H10O6 (178.0477)
SMILES: OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Synonyms [en]
D-glucono-1,5-lactone; gluconolactone; Gluconic acid lactone; gluconic lactone; 1,5-Gluconolactone; D-Gluconolactone
Last reviewed on 2024-06-28.
Cite this Page
D-Glucono-1,5-lactone. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000009342). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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.
DBLinks
- CAS Registry Number: 90-80-2
- PubChem CID: 7027
- ChEBI: 16217
- HMDB: HMDB0000150
- LipidMaps:
- KEGG: C00198
- BioCyc: GLC-D-LACTONE
- NCBI MeSH: beta-glucono-1,5-lactone
- Wikipedia: Gluconolactone
Other DBLinks
- CAS Registry Number: 54910-68-8
- CAS Registry Number: 90-80-2
- PubChem: 7027
- PubChem: 736
- ChEBI: ChEBI:16217
- HMDB: HMDB0000150
- KEGG: C00198
- BioCyc: GLC-D-LACTONE
- NCBI MeSH: beta-glucono-1,5-lactone
- Wikipedia: Gluconolactone
- Wikipedia: Glucono_delta-lactone
- DrugBank: DB04564
- RefMet: RM0049636
- MoNA: BAF_UVA_POS000720
- MoNA: BAF_UVA_POS000721
- MoNA: BAF_UVA_POS000722
- MoNA: BAF_UVA_POS000723
- MoNA: BAF_UVA_POS000724
- MoNA: BAF_UVA_POS001596
- MoNA: EMBL-MCF_spec22944
- MoNA: FiehnHILIC000384
- MoNA: FiehnLib000526
- MoNA: FiehnLib000528
- MoNA: HMDB0000150_c_ms_1604
- MoNA: HMDB0000150_ms_ms_227
- MoNA: HMDB0000150_ms_ms_228
- MoNA: HMDB0000150_ms_ms_229
- MoNA: MoNA031917
- MoNA: MoNA031920
- MoNA: MoNA031923
- MoNA: MoNA032317
- MoNA: MoNA032318
- MoNA: MoNA032321
- MoNA: MoNA033798
- MoNA: MoNA033799
- MoNA: MoNA033803
- MoNA: MoNA034319
- MoNA: MoNA034320
- MoNA: MoNA034321
- MoNA: MoNA037088
- MoNA: MoNA037251
- MoNA: MoNA037787
- MoNA: MoNA037973
- MoNA: MoNA_0007281
- MoNA: MoNA_0007282
- MoNA: MoNA_0007283
- MoNA: MoNA_0007284
- MoNA: MoNA_0007362
- MoNA: MoNA_0007363
- MoNA: MoNA_0008784
- MoNA: MoNA_0008785
- MoNA: MoNA_0009470
- MoNA: MoNA_0009471
- MoNA: MoNA_0009685
- MoNA: MoNA_0009686
- MoNA: MoNA_0009687
- MoNA: MoNA_0009688
- MoNA: MoNA_0009689
- MoNA: PS020803
- Metlin: METLIN_353
Class / Ontology
- WishartLab ClassyFire: [Carbohydrates and carbohydrate conjugates] Carbohydrates and carbohydrate conjugates
- RefMet: [Hexoses] Hexoses
- ChEBI: [CHEBI:16217] D-glucono-1,5-lactone
| ID | EC Number | Name |
|---|---|---|
| KEGG:R00300 | 1.1.1.118 | D-glucose:NAD+ 1-oxidoreductase |
| KEGG:R00305 | 1.1.5.9 | D-glucose:quinone 1-oxidoreductase |
| KEGG:R00874 | 1.1.99.28 | D-glucose:D-fructose oxidoreductase |
| KEGG:R01519 | 3.1.1.17 | D-glucono-1,5-lactone lactonohydrolase |
| KEGG:R01520 | 1.1.1.47 | beta-D-glucose:NAD+ 1-oxoreductase |
| KEGG:R01521 | 1.1.1.47 | beta-D-glucose:NADP+ 1-oxoreductase |
| KEGG:R01522 | 1.1.3.4 | beta-D-glucose:oxygen 1-oxidoreductase |
| KEGG:R03861 | 2.3.1.132 | sinapoyl-CoA:glucarolactone O-(hydroxycinnamoyl)transferase |
| KEGG:R06620 | 1.1.5.2 | D-glucose:ubiquinone oxidoreductase |
| KEGG:R07147 | 1.1.1.119 | D-glucose:NADP+ 1-oxidoreductase |
| KEGG:R10411 | 1.1.99.35 | D-glucose:acceptor oxidoreductase |
| BioCyc:RXN0-6373 | 1.1.5.2 | Ubiquinones + Glucopyranose --> Ubiquinols + GLC-D-LACTONE |
| BioCyc:GLUCONOLACT-RXN | 3.1.1.17 | GLC-D-LACTONE + WATER --> PROTON + GLUCONATE |
| BioCyc:RXN0-6372 | GLC-D-LACTONE + 2 E- + 2 PROTON --> Glucopyranose | |
| Rhea:RHEA:10441 | 3.1.1.17 | D-glucono-1,5-lactone + H2O => D-gluconate + H+ |
| Rhea:RHEA:10442 | 3.1.1.17 | D-gluconate + H+ => D-glucono-1,5-lactone + H2O |
| Rhea:RHEA:10443 | 3.1.1.17 | D-glucono-1,5-lactone + H2O <=> D-gluconate + H+ |
| Rhea:RHEA:11429 | 1.1.3.4 | β-D-glucose + O2 => D-glucono-1,5-lactone + H2O2 |
| Rhea:RHEA:11430 | 1.1.3.4 | D-glucono-1,5-lactone + H2O2 => β-D-glucose + O2 |
| Rhea:RHEA:11431 | 1.1.3.4 | β-D-glucose + O2 <=> D-glucono-1,5-lactone + H2O2 |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_PWY-7058 | esculetin modification |
| BioCyc:META_PWY-7091 | linustatin bioactivation |
| BioCyc:META_PWY-6002 | lotaustralin degradation |
| BioCyc:META_PWY-5821 | dalcochinin biosynthesis |
| BioCyc:META_PWY-5530 | sorbitol biosynthesis II |
| BioCyc:ECO_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:ARA_PWY-5530 | sorbitol biosynthesis II |
| BioCyc:SHIGELLA_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:MTBCDC1551_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:AGRO_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:BSUB_GLUCOSE1PMETAB-PWY-1 | glucose and glucose-1-phosphate degradation |
| BioCyc:ECOL316407_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:ECOL413997_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:10403S_RAST_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:PABTQVLC_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |
| BioCyc:META_PWY-7056 | daphnin interconversion |
| BioCyc:META_NPGLUCAT-PWY | Entner-Doudoroff pathway II (non-phosphorylative) |
| BioCyc:META_PWY-116 | coniferin metabolism |
| BioCyc:META_PWY-7165 | L-ascorbate biosynthesis VI (engineered pathway) |
| BioCyc:ARA_GLUCOSE1PMETAB-PWY | glucose and glucose-1-phosphate degradation |