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652-67-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:118960 http://www.chembase.cn/molecule-118960.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
652-67-5
EC Number
211-492-3
MDL Number
MFCD00064827
Beilstein Number
80510
PubChem SID
24859776
24860074
162107241
PubChem CID
12597

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.034376  H Acceptors
H Donor LogD (pH = 5.5) -1.4066117 
LogD (pH = 7.4) -1.4066128  Log P -1.4066117 
Molar Refractivity 31.3834 cm3 Polarizability 13.101962 Å3
Polar Surface Area 58.92 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Low Melting Yellow Solid expand Show data source
Melting Point
60-63 °C expand Show data source
60-63 °C(lit.) expand Show data source
Optical Rotation
[α]20/D +45.2°, c = 3 in H2O expand Show data source
[α]20/D +45±1°, c = 3% in H2O expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
Others expand Show data source
Mechanism of Action
Guanylate cyclase stimulator expand Show data source
Purity
≥98.0% (sum of enantiomers, GC) expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
Isol. from the fruit of Cotoneaster microphylla expand Show data source
Application(s)
Diuretic expand Show data source
Hypotensive expand Show data source
Empirical Formula (Hill Notation)
C6H10O4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 329207 external link
Packaging
100, 500 g in glass bottle
Sigma Aldrich - 33426 external link
Other Notes
Chiral building block1; Chiral doping compound having high helical twisting power used as coloring liquid crystals2
Toronto Research Chemicals - I901680 external link
Reagent used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hastwell, P., et al.: Mutagen., 24, 455 (2009)
  • • Guillarme, S., et al.: Bioorg. Chem., 38, 43 (2009)
  • • Dillon, G., et al.: Bioorg. Med. Chem., 18, 1045 (2009)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 406C, (nmr)
  • • Hockett, R.C. et al., J.A.C.S., 1946, 68, 927
  • • Wiggins, L.F., Adv. Carbohydr. Chem., 1950, 5, 191, (rev, props)
  • • Cope, A.C. et al., J.A.C.S., 1956, 78, 3177, (stereochem)
  • • Hopton, F.J. et al., Can. J. Chem., 1969, 47, 2395, (pmr)
  • • Soltzberg, S., Adv. Carbohydr. Chem. Biochem., 1970, 25, 229, (rev)
  • • Silvieri, L.A. et al., Anal. Profiles Drug Subst., 1975, 4, 225, (deriv)
  • • Hirao, A. et al., J.O.C., 1979, 44, 1720, (use)
  • • van Koningsveld, H. et al., Acta Cryst. C, 1984, 40, 519, (cryst struct)
  • • Bock, K. et al., Acta Chem. Scand., 1989, 43, 264, (L-form)
  • • Defraye, J. et al., Carbohydr. Res., 1990, 205, 191, (synth)
  • • Stoss, P. et al., Adv. Carbohydr. Chem. Biochem., 1991, 49, 93, (rev)
  • • Chandrasekaran, S. et al., Synthesis, 1994, 1032, (nitrates, synth)
  • • Duclos, A. et al., Synthesis, 1994, 1087, (synth, cmr)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCK125; HID350; ISC500
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PATENTS

PATENTS

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INTERNET

INTERNET

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