(3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol

• ChemBase ID: 118960
• Molecular Formular: C6H10O4
• Molecular Mass: 146.1412
• Monoisotopic Mass: 146.0579088
• SMILES: [C@@H]12[C@H](OC[C@@H]2O)[C@@H](CO1)O
• Canonical SMILES: O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O
• InChI: InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
• InChIKey: KLDXJTOLSGUMSJ-JGWLITMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
• IUPAC Traditional name: isosorbide; (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
• Synonyms: (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol; 1,4:3,6-Dianhydro-D-sorbitol; D-Isosorbide; Dianhydro-D-glucitol; Isobide. Isorgen G; Sorbide (obsol.); Isosorbide; 1,4:3,6-Dianhydro-D-glucitol; 1,4:3,6-Dianhydro-sorbitol; (+)-D-Isosorbide; Devicoran; Hydronol; Ismotic; Isobide; NSC 40725; Isosorbide; 1,4:3,6-二脱水-D-山梨醇; D-异山梨醇; 异山梨醇

Database IDs

• CAS Number: 652-67-5
• EC Number: 211-492-3
• MDL Number: MFCD00064827
• Beilstein Number: 80510
• PubChem SID: 162107241; 24859776; 24860074
• PubChem CID: 12597

CALCULATED PROPERTIES

• Acid pKa: 13.034376
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.4066117
• LogD (pH = 7.4): -1.4066128
• Log P: -1.4066117
• Molar Refractivity: 31.3834 cm^3
• Polarizability: 13.101962 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Low Melting Yellow Solid
• Melting Point: 60-63 °C; 60-63 °C(lit.)
• Optical Rotation: [α]20/D +45.2°, c = 3 in H2O; [α]20/D +45±1°, c = 3% in H2O

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Mechanism of Action: Guanylate cyclase stimulator

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: purum
• Salt Data: Free Base
• Biological Source: Isol. from the fruit of Cotoneaster microphylla
• Application(s): Diuretic; Hypotensive
• Empirical Formula (Hill Notation): C6H10O4

DETAILS

Sigma Aldrich - 329207

Packaging
100, 500 g in glass bottle

Sigma Aldrich - 33426

Other Notes
Chiral building block1; Chiral doping compound having high helical twisting power used as coloring liquid crystals2

Toronto Research Chemicals - I901680

Reagent used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators.

REFERENCES

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