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

• ChemBase ID: 132108
• Molecular Formular: C5H10O5
• Molecular Mass: 150.1299
• Monoisotopic Mass: 150.05282342
• SMILES: C1[C@H]([C@H]([C@@H](C(O1)O)O)O)O
• Canonical SMILES: O[C@@H]1COC([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m1/s1
• InChIKey: SRBFZHDQGSBBOR-ZRMNMSDTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-oxane-2,3,4,5-tetrol
• IUPAC Traditional name: D-arabinopyranose
• Synonyms: (3S,4R,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetraol; D-(-)-Arabinose; D-(-)-阿拉伯糖

Database IDs

• CAS Number: 10323-20-3; 28697-53-2
• EC Number: 233-708-5
• MDL Number: MFCD00064361; MFCD00135608
• Beilstein Number: 1723079
• PubChem SID: 24890486; 162226385; 24891053; 24891451
• PubChem CID: 6902

CALCULATED PROPERTIES

• Acid pKa: 11.310624
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.3022048
• LogD (pH = 7.4): -2.3022575
• Log P: -2.3022044
• Molar Refractivity: 29.9609 cm^3
• Polarizability: 12.6405 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 M at 20 °C, clear, colorless to faintly yellow
• Melting Point: 154-158°C; 162-164 °C(lit.)
• Optical Rotation: [α]20/D -104±2.0°, 24 hr, c = 10% in H2O; -104 (c=10 in water, 24h)

Safety Information

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

Product Information

• Purity: ≥98%; ≥99.0%; ≥99.0% (sum of enantiomers, HPLC); 95+%; 99%
• Grade: for microbiology
• Suitability: suitable for component for culture media
• Ignition Residue: ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; As: ≤0.1 mg/kg; Ca: ≤0.001%; Ca: ≤500 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤25 mg/kg; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Mg: ≤0.0005%; Mg: ≤10 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.005%; Na: ≤50 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Zn: ≤0.001%; Zn: ≤15 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV)
• Empirical Formula (Hill Notation): C5H10O5

DETAILS

Sigma Aldrich - A6085

Biochem/physiol Actions
D-阿拉伯糖是一种还原糖。它是一种 D-核糖的戊糖类似物，是组成分支杆菌细胞壁阿拉伯半乳聚糖的成分。也是酵母中 D-红抗坏血酸合成的底物。

Sigma Aldrich - A3131

Biochem/physiol Actions
D-阿拉伯糖是一种还原糖。它是一种 D-核糖的戊糖类似物，是组成分支杆菌细胞壁阿拉伯半乳聚糖的成分。也是酵母中 D-红抗坏血酸合成的底物。
包装
10, 25, 100 g in poly bottle
Application
D-(-)-Arabinose is a D-ribose analogue present in sugar polymers such as the arabinogalatans of mycobacterial cell walls and plant tissues. D-Arabinose is a substrate used to identify, differentiate and characterize arabinose isomerase(s) that have commercial value in the production of tagatose, a low calorie sweetener.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A3131.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - A9432

Biochem/physiol Actions
D-阿拉伯糖是一种还原糖。它是一种 D-核糖的戊糖类似物，是组成分支杆菌细胞壁阿拉伯半乳聚糖的成分。也是酵母中 D-红抗坏血酸合成的底物。
Quality
针对重金属污染进行筛选。

Sigma Aldrich - 10850

Biochem/physiol Actions
D-Arabinose is a reducing sugar. It is a pentose analog of D-ribose that is a constituent of mycobacterial cell wall arabinogalactans. It is also a substrate for D-erythroascorbic acid synthesis in yeast.

REFERENCES

• Chiral building block. For use in the synthesis of a chiral quinuclidine-3,5-diol, see: J. Chem. Soc., Perkin 1, 1065 (1989).