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

• ChemBase ID: 4132
• Molecular Formular: C6H10O6
• Molecular Mass: 178.14
• Monoisotopic Mass: 178.04773804
• SMILES: OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1OC(=O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: 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
• InChIKey: PHOQVHQSTUBQQK-SQOUGZDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• IUPAC Traditional name: gluconolactone
• Synonyms: D-GLUCONO-delta-LACTONE; D-(+)-Gluconic acid δ-lactone; 1,2,3,4,5-Pentahydroxycaproic acid δ-lactone; D-(+)-Dextronic acid δ-lactone; D-GLUCONO-δ-LACTONE; D-Gluconic acid δ-Lactone; D-Gluconic Acid Lactone; 1,5-Gluconolactone; D-(+)-Gluconic acid δ-lactone; D-(+)-Glucono-1,5-lactone; D-(+)-Glucono-δ-lactone; D-Gluconic acid 1,5-Lactone; D-Glucono-δ-lactone; E 575; Fujiglucon; Gluconolactone; Lysactone; D-Glucono-1,5-lactone; Gluconolactone; δ-Gluconolactone; 1,2,3,4,5-Pentahydroxycaproic acid δ-lactone; D-Glucono-1,5-lactone; Glucono delta-lactone; D-(+)-Gluconic acid δ-lactone; D-(+)-Dextronic acid δ-lactone; Gluconolactone; D-(+)-Gluconic acid delta-lactone; delta-Gluconolactone; D-(+)-Glucono-1,5-lactone; (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one; (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one; D-(+)-葡萄糖酸δ-内酯; δ-葡萄糖酸內酯; 1,2,3,4,5-五羟基己酸δ-内酯; D-(+)-葡萄糖酸δ-内酯; 葡萄糖酸內酯; D-(+)-葡萄糖酸-1,5-内酯

Database IDs

• CAS Number: 90-80-2
• EC Number: 202-016-5
• MDL Number: MFCD00006647
• Beilstein Number: 83286
• Merck Index: 144457
• PubChem SID: 160967564; 24895381; 24895089; 46506698; 24895183
• PubChem CID: 7027; 736
• CHEBI ID: 16217
• CHEMBL: 1200829
• Chemspider ID: 6760
• DrugBank ID: DB04564
• KEGG ID: D04332
• Unique Ingredient Identifier: WQ29KQ9POT
• Wikipedia Title: Glucono_delta-lactone

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.618472
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.7452736
• LogD (pH = 7.4): -2.7452993
• Log P: -2.745273
• Molar Refractivity: 34.7788 cm^3
• Polarizability: 14.633189 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.16
• LOG S: 0.52
• Solubility (Water): 5.86e+02 g/l

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 154-159°C dec.; 154-162 °C; 160 °C (dec.)(lit.); 160°C; 162-164°C
• Optical Rotation: [α]20/D +66.0±1°, c = 4% in H2O; +65 (c=4 in water)
• Hydrophobicity(logP): -2.229

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: LZ5184000
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0%; ≥99.0% (T); 95%; 95+%; 99%; 99-100%
• Grade: purum
• Suitability: meets USP testing specifications; suitable for cell culture
• Empirical Formula (Hill Notation): C6H10O6

DETAILS

MP Biomedicals - 02101780

Purity: 99+%
Crystalline

MP Biomedicals - 05211907

MP Biomedicals Rare Chemical collection

DrugBank - DB04564

• Drug Groups: experimental
• Description: Gluconolactone is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a cyclic ester of D-gluconic acid. Pure gluconolactone is a white odorless crystalline powder.
• External Links: Wikipedia

Sigma Aldrich - G4750

包装
1 kg in poly bottle
100, 500 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G4750.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 49120

Other Notes
Bromination to 2,6-dibromo-2,6-dideoxy-D-mannono 1,4-lactone2
Biochem/physiol Actions
Glucono-d-lactone increased the doubling time and activated enzymes involved in the oxidative pentose phosphate pathway of Saccharomyces cerevisiae. 1

Toronto Research Chemicals - G417475

A lactone (cyclic ester) of D-gluconic acid used as a used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent.

REFERENCES

• Jacob, M. et al.: Food Hydrocoll., 25, 928 (2011)
• Li, J. et al.: J. Sci. Food Agric., 91, 38, 2011;