(2R,3R,4S,5S)-hexane-1,2,3,4,5,6-hexol

• ChemBase ID: 154289
• Molecular Formular: C6H14O6
• Molecular Mass: 182.17176
• Monoisotopic Mass: 182.07903817
• SMILES: C([C@H]([C@H]([C@H]([C@H](CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@H]([C@H](CO)O)O)O)O
• InChI: InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6+
• InChIKey: FBPFZTCFMRRESA-FBXFSONDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S)-hexane-1,2,3,4,5,6-hexol
• IUPAC Traditional name: (2R,3R,4S,5S)-hexane-1,2,3,4,5,6-hexol
• Synonyms: Allodulcit; Allodulcitol; Allitol; Galacto-Hexitol; Dulcose; Dulcite; Melampyrin; Dulcitol; Euonymit; Melampyrum; Galactitol

Database IDs

• CAS Number: 488-44-8; 608-66-2
• MDL Number: MFCD11519461
• PubChem SID: 162248428
• PubChem CID: 120700

CALCULATED PROPERTIES

• Acid pKa: 12.585201
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -3.7300189
• LogD (pH = 7.4): -3.7300217
• Log P: -3.7300189
• Molar Refractivity: 38.4036 cm^3
• Polarizability: 15.776147 Å^3
• Polar Surface Area: 121.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: BA1840000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Inductor of extracellular -galactosidase (Bga1) formation; Stumulates Mg[2+]-ATPase

Product Information

• Purity: ≥98%
• Biological Source: Isol. from various brown algae incl. Himanthalia elongata and Notheia anomala
• Application(s): Shows some antitumour effect
• Empirical Formula (Hill Notation): C6H14O6

DETAILS

Sigma Aldrich - A2858

General description
A rare sugar alcohol (polyol).
Application
Allitol, a water retentive rare sugar alcohol, may be used as a monosaccharide laxative. Allitol may be used as a reference compound during separation and analysis of hexitols such as galactitol, iditol, altritols, sorbitol and mannitol.

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 186D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 290B, (nmr)
• Lespieau, M.R., Bull. Soc. Chim. Fr., 1934, 1374, (synth)
• Lohmar, R., Adv. Carbohydr. Chem., 1949, 4, 211, (rev, derivs)
• Berman, H.M. et al., Acta Cryst. B, 1968, 24, 435, (cryst struct)
• Petersson, G., Tetrahedron, 1969, 25, 4437, (ms)
• Bliss, C.A. et al., Phytochemistry, 1972, 11, 1705, (biosynth)
• Brimacombe, J.S. et al., The Carbohydrates, Academic Press, 1972, 1A, 479, (rev)
• Voelter, W. et al., Tetrahedron, 1973, 29, 3845, (conformn, cmr)
• Angyal, S.J. et al., Carbohydr. Res., 1980, 84, 201, (cmr)
• Shirota, O. et al., Nat. Med. (Tokyo), 1998, 52, 184-186; CA, 129, 193564a, (isol, activity)