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

• ChemBase编号: 4132
• 分子式: C6H10O6
• 平均质量: 178.14
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• IUPAC传统名: gluconolactone
• 别名: 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; 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

登记号

• CAS号: 90-80-2
• EC号: 202-016-5
• MDL号: MFCD00006647
• Beilstein号: 83286
• 默克索引号: 144457
• PubChem SID: 24895089; 160967564; 24895381; 46506698; 24895183
• PubChem CID: 7027; 736
• CHEBI ID: 16217
• CHEMBL: 1200829
• Chemspider ID: 6760
• DrugBank ID: DB04564
• KEGG ID: D04332
• 美国药典/FDA物质标识码: WQ29KQ9POT
• 维基百科标题: Glucono_delta-lactone

理论计算性质

JChem

• Acid pKa: 11.618472
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -2.7452736
• LogD (pH = 7.4): -2.7452993
• Log P: -2.745273
• 摩尔折射率: 34.7788 cm^3
• 极化性: 14.633189 Å^3
• 极化表面积: 107.22 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.16
• LOG S: 0.52
• 溶解度: 5.86e+02 g/l

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: White Solid
• 熔点: 154-159°C dec.; 154-162 °C; 160 °C (dec.)(lit.); 160°C; 162-164°C
• 比旋光度: [α]20/D +66.0±1°, c = 4% in H2O; +65 (c=4 in water)
• 疏水性(logP): -2.229

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: LZ5184000
• 德国WGK号: 3
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

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

详细说明

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-lactone1

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.

参考文献

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