Conduritol or 1,2,3,4-cyclohexenetetrol is any of the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s with

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

C₆H₁₀O₄, that can be seen as derivatives of

cyclohexene Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Prod ...

with four

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

group A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

s (OH) replacing

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atoms on the four

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms not adjacent to the double bond. They are therefore cyclic

polyol In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, th ...

s or

cyclitol In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''. The name is also used for ...

s. The compounds in this group exhibit

cis–trans isomerism ''Cis''–''trans'' isomerism, also known as geometric isomerism, describes certain arrangements of atoms within molecules. The prefixes "''cis''" and "''trans''" are from Latin: "this side of" and "the other side of", respectively. In the cont ...

, 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

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s. Only the A and B isomers have been found in nature. The first conduritol was isolated in 1908 by

K. Kübler K, or k, is the eleventh letter of the English alphabet. K may also refer to: General uses * K, a normal modal logic * K (programming language), an array processing language developed by Arthur Whitney and commercialized by Kx Systems * K ( ...

K. Kübler (1908), Arch. Phann. Ber. Stsch. Pharm. 246,620. from the bark of the vine ''

Ruehssia cundurango ''Ruehssia cundurango'' is a species of plant of the genus '' Ruehssia'' native to Colombia, Ecuador and Peru in South America. It has the common name condurango. The subspecies ''Ruehssia cundurango'' subsp. ''cundurango'' (synonym ''Marsdenia c ...

'' subsp. ''cundurango'' (syn. ''Marsdenia cundurango''), hence its name.

References

{{Reflist Cyclitols Cyclohexenes

See also

References