(3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one

• ChemBase ID: 102755
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: O=C([C@@H](O)[C@H](O)[C@@H](O)CO)CO
• Canonical SMILES: OC[C@@H]([C@H]([C@@H](C(=O)CO)O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1
• InChIKey: BJHIKXHVCXFQLS-OTWZMJIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one
• IUPAC Traditional name: L-sorbose
• Synonyms: Sorbinose; L-xylo-Hexulose; Sorbose; L-(-)-SORBOSE; L-(-)-Sorbose

Database IDs

• CAS Number: 87-79-6
• EC Number: 201-771-8
• MDL Number: MFCD00151097
• Beilstein Number: 1724554
• PubChem SID: 162090363; 24888378
• PubChem CID: 6904
• Wikipedia Title: Sorbose

CALCULATED PROPERTIES

• Acid pKa: 9.481385
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2670772
• LogD (pH = 7.4): -3.2706153
• Log P: -3.267032
• Molar Refractivity: 37.5618 cm^3
• Polarizability: 15.251392 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless to very faintly yellow; Highly Soluble in water
• Apperance: Crystalline solid
• Melting Point: 163-165 °C; 165°C; 171-173°C
• Density: 1.65 g/cm^3 (15 °C)
• Optical Rotation: [α]20/D -43±2°, c = 5% in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: WG3195025
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%; ≥98% (HPLC); ≥98.0% (sum of enantiomers, HPLC)
• Grade: for biotechnological purposes
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

MP Biomedicals - 02102939

Purity: ≥98%
Crystalline

Sigma Aldrich - 85541

Application
L-Sorbose is used as a starting reagent for the commercial biosynthesis of ascorbic acid (vitamin C).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 85541.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.