(2R,3R,4R,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 132622
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C([C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6-/m1/s1
• InChIKey: WQZGKKKJIJFFOK-QZABAPFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: β-D-allose
• Synonyms: β-D-Allose; All; β-D-Allopyranose; β-D-Allose; D-Allose; beta-D-Allose; β-D-别吡喃糖; β-D-阿洛糖; β-D-阿洛糖; D-阿洛糖

Database IDs

• CAS Number: 2595-97-3; 7283-09-2
• EC Number: 219-994-4
• MDL Number: MFCD00063268
• Beilstein Number: 1724623
• Merck Index: 14280
• PubChem SID: 24891083; 24857188; 24845870; 162226899
• PubChem CID: 448388

CALCULATED PROPERTIES

• Acid pKa: 11.298101
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.93254
• LogD (pH = 7.4): -2.932594
• Log P: -2.9325392
• Molar Refractivity: 35.9234 cm^3
• Polarizability: 15.155883 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 141-146 °C; 143-146°C; 148-150 °C(lit.)
• Optical Rotation: [α]19/D +15°, c = 3.8 in H2O; [α]20/D +15±1°, 2 hr, c = 10% in H2O

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 98%
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - A6390

包装
10 mg in autosmp vl
Application
β-D-Allose (β-D-Allose), a rare sugar member of the aldohexose family and a C3 epimer of glucose, is used as an inhibitor of fruiting body formation and sporulation in Myxococcus xanthus.
Biochem/physiol Actions
D-Allose is a rare aldohexose sugar that has demonstrated anti-cancer, antitumor, anti-inflammatory, anti-oxidative, antihypertensive, cryoprotective, and immunosuppressant activities.1 D-Allose upregulates thioredoxin-interacting protein (TXNIP) gene expression and was found to induce G1 cell cycle arrest in hepatocellular carcinoma cells.2 It inhibited transcriptional activity of the activator protein 1, nuclear factor-κB, and nuclear factor of activated T cells.3 D-Allose decreases transport of 2-deoxy-D-glucose and 3-O-methyl-D-glucose in V79 Chinese hamster lung fibroblast cells.4

Sigma Aldrich - 285005

Packaging
100, 250 mg in glass bottle