Conduritol

Last updated
Conduritol
Conduritol-generic.png
Names
Preferred IUPAC name
Cyclohex-5-ene-1,2,3,4-tetrol [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H10O4/c7-3-1-2-4(8)6(10)5(3)9/h1-10H
    Key: LRUBQXAKGXQBHA-UHFFFAOYSA-N
  • OC1C=CC(O)C(O)C1O
Properties
C6H10O4
Molar mass 146.142 g·mol−1
log P −2.764
Acidity (pKa)13.325
Basicity (pKb)1.672
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. Conduritol.svg

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

See also

Related Research Articles

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Aromatic compounds or arenes usually refers to organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule. Aromatic compounds have the following general properties:

<span class="mw-page-title-main">Functional group</span> Group of atoms giving a molecule characteristic properties

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

Monosaccharides, also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Simply, this is the structural unit of carbohydrates.

In chemistry, a pentose is a monosaccharide with five carbon atoms. The chemical formula of many pentoses is C
5
H
10
O
5
, and their molecular weight is 150.13 g/mol.

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<span class="mw-page-title-main">Stereoisomerism</span> When molecules have the same atoms and bond structure but differ in 3D orientation

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<span class="mw-page-title-main">Hexose</span> 6-Carbon simple sugar

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

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n
H
2n-x
(OH)
x
or C
n
H
2n
O
x
where 3 ≤ xn.

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14
H
8
O
6
, almost invariably derived from 9,10-anthraquinone by replacing four hydrogen atoms by hydroxyl groups. Only a few of these isomers are commercially significant. These are 1,2,5,8-tetrahydroxyanthraquinone (quinalizarin), 1,4,5,8-tetrahydroxyanthraquinone, and 1,2,3,4-tetrahydroxyanthraquinone.

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<span class="mw-page-title-main">1,2,3,4,5-Cyclopentanepentol</span> Chemical compound

1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5
H
10
O
5
or (–CHOH–)
5
, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.

A cyclohexanetetrol is a chemical compound consisting of a cyclohexane molecule with four hydroxyl groups (–OH) replacing four of the twelve hydrogen atoms. It is therefore a cyclitol. Its generic formula is C
6
H
12
O
4
or C
6
H
8
(OH)
4
.

<span class="mw-page-title-main">1,2,3,4-Cyclohexanetetrol</span> Chemical compound

1,2,3,4-Cyclohexanetetrol (also named cyclohexane-1,2,3,4-tetrol, 1,2,3,4-tetrahydroxycyclohexane, or ortho-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on four consecutive carbon atoms. Its formula can be written C
6
H
12
O
4
, C
6
H
8
(OH)
4
, or (–CH(OH)–)4(–CH
2
–)2.

<span class="mw-page-title-main">1,2,4,5-Cyclohexanetetrol</span> Chemical compound

1,2,4,5-Cyclohexanetetrol (also named cyclohexane-1,2,4,5-tetrol, 1,2,4,5-tetrahydroxycyclohexane, or para-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on two non-adjacent pairs of adjacent carbon atoms. Its formula can be written C
6
H
12
O
4
, C
6
H
8
(OH)
4
, or [–(CH(OH)–)2CH
2
–]2.

References

  1. "cyclohex-5-ene-1,2,3,4-tetrol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 29 January 2012.
  2. (1990) Tetrahedron, Vol 46, No 11, 3715 - 3742.
  3. K. Kübler (1908), Arch. Phann. Ber. Stsch. Pharm. 246,620.