Conduritol

Conduritol
IUPAC name Cyclohex-5-ene-1,2,3,4-tetrol[1]
Identifiers
CAS number	526-87-4 Y
PubChem	136345, 10290862 2R, 10888045 1R,2R,3R,4R, 10057625 1R,2R,3R,4S, 11008046 1R,2R,3S,4R, 11094760 1R,2R,3S,4S
ChemSpider	120119 Y, 8466331 2R Y, 9063309 1R,2R,3R,4R Y, 8233179 1R,2R,3R,4S Y
ChEMBL	CHEMBL307042 Y
Jmol-3D images	Image 1
SMILES OC1C=CC(O)C(O)C1O
InChI InChI=1S/C6H10O4/c7-3-1-2-4(8)6(10)5(3)9/h1-10H Y Key: LRUBQXAKGXQBHA-UHFFFAOYSA-N
Properties
Molecular formula	C6H10O4
Molar mass	146.14 g mol−1
log P	−2.764
Acidity (pKa)	13.325
Basicity (pKb)	1.672
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Conduritol or 1,2,3,4-cyclohexenetetrol is any of the organic compounds with chemical formula C₆H₁₀O₄, that can be seen as derivatives of cyclohexene with four hydroxyl groups (OH) replacing hydrogen atoms on the four carbon atoms not adjacent to the double bond. They are therefore cyclic polyols or cyclitols.^[2]

The compounds in this group exhibit cis–trans isomerism, with six isomers that differ by the relative positions of the hydroxyls compared to the mean plane of the ring. In addition, some of these can exist as two distinct enantiomers.

Only the A and B isomers have been found in nature. The first conduritol was isolated in 1908 by K. Kübler^[3] from the bark of the vine Marsdenia condurango, hence its name. A number of conduritol derivatives has antifeedant, antibiotic, antileukemic, and growth-regulating activity. Also some conduritol derivatives show interesting biological properties including tumour-inhibitory, antileukaemic, and antibiotic activities.

See also

• Inositol

References