Octahydroxyanthraquinone

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Octahydroxyanthraquinone
Skeletal formula of octahydroxyanthraquinone Octahydroxyanthraquinone.png
Skeletal formula of octahydroxyanthraquinone
Ball and stick model of octahydroxyanthraquinone Octahydroxyanthraquinone-3D-balls.png
Ball and stick model of octahydroxyanthraquinone
Names
Preferred IUPAC name
1,2,3,4,5,6,7,8-Octahydroxyanthracene-9,10-dione
Other names
Octahydroxyanthracenedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C14H8O10/c15-5-1-2(8(18)12(22)11(21)7(1)17)6(16)4-3(5)9(19)13(23)14(24)10(4)20/h17-24H X mark.svgN
    Key: KOWBNNJAGJIIJW-UHFFFAOYSA-N X mark.svgN
  • OC1=C(O)C(O)=C2C(=O)C3=C(O)C(O)=C(O)C(O)=C3C(=O)C2=C1O
  • OC1=C(O)C(O)=C(O)C2=C1C(C3=C(O)C(O)=C(O)C(O)=C3C2=O)=O
Properties
C14H8O10
Molar mass 336.208 g·mol−1
log P -0.291
Acidity (pKa)5.358
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Octahydroxyanthraquinone is an organic compound with formula C
14
H
8
O
10
, formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups.

The compound was obtained in 1911 by Georg von Georgievics [1] [2] and can be obtained through oxidation of rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) with boric acid and mercuric oxide in sulfuric acid at 250 °C (482 °F). [3]

Esters of octahydroxyanthraquinone, where all eight hydroxyls are replaced by straight-chain 1-alkanecarboxylate groups H
3
C
-(CH
2
)n-COO-, with n between 6 and 14, are liquid crystals and have been studied for possible LCD applications. [3]

Octahydroxyanthraquinone is active against the malaria parasite, but rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) is 22 times more potent. [4]

Related Research Articles

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In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Hydroxy group</span> Chemical group (–OH)

In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula −OH and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion HO, called hydroxide, and the neutral radical HO·, known as the hydroxyl radical, consist of an unbonded hydroxy group.

<span class="mw-page-title-main">Hydrogen peroxide</span> Chemical compound

Hydrogen peroxide is a chemical compound with the formula H2O2. In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution in water for consumer use and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or "high-test peroxide", decomposes explosively when heated and has been used as both a monopropellant and an oxidizer in rocketry.

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979.

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<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

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Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
2
. Several isomers exist but these terms usually refer to 9,10-anthraquinone wherein the keto groups are located on the central ring. It is used as a digester additive to wood pulp for papermaking. Many anthraquinone derivatives are generated by organisms or synthesised industrially for use as dyes, pharmaceuticals, and catalysts. Anthraquinone is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

<span class="mw-page-title-main">Hydroquinone</span> Chemical compound

Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.

<span class="mw-page-title-main">2-Iodoxybenzoic acid</span> Chemical compound

2-Iodoxybenzoic acid (IBX) is an organic compound used in organic synthesis as an oxidizing agent. This periodinane is especially suited to oxidize alcohols to aldehydes. IBX is most often prepared from 2-iodobenzoic acid and a strong oxidant such as potassium bromate and sulfuric acid, or more commonly, oxone. One of the main drawbacks of IBX is its limited solubility; IBX is insoluble in many common organic solvents. IBX is an impact- and heat-sensitive explosive (>200°C). Commercial IBX is stabilized by carboxylic acids such as benzoic acid and isophthalic acid.

<span class="mw-page-title-main">Dakin oxidation</span> Organic redox reaction that converts hydroxyphenyl aldehydes or ketones into benzenediols

The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.

Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

<span class="mw-page-title-main">Boronic acid</span> Organic compound of the form R–B(OH)2

A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.

The Fleming–Tamao oxidation, or Tamao–Kumada–Fleming oxidation, converts a carbon–silicon bond to a carbon–oxygen bond with a peroxy acid or hydrogen peroxide. Fleming–Tamao oxidation refers to two slightly different conditions developed concurrently in the early 1980s by the Kohei Tamao and Ian Fleming research groups.

A dihydroxyanthraquinone is any of several isomeric organic compounds with formula (C12H62)(CO)2, formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl oxygens (=O) of the underlying anthraquinone.

<span class="mw-page-title-main">Rufigallol</span> Chemical compound

Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula C
14
O
8
H
8
. It one of several hydroxyanthraquinones. It occurs naturally being derived from gallic acid.

<span class="mw-page-title-main">2-Methylanthraquinone</span> Chemical compound

2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone, is an organic compound which is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes. It is present in the wood of the teak tree, where it gives the tree resistance to insects.

<span class="mw-page-title-main">Fallacinol</span> Chemical compound found in some lichens

Fallacinol (teloschistin) is an organic compound in the structural class of chemicals known as anthraquinones. It is found in some lichens, particularly in the family Teloschistaceae, as well as a couple of plants and non lichen-forming fungi. In 1936, Japanese chemists isolated a pigment named fallacin from the lichen Oxneria fallax, which was later refined and assigned a tentative structural formula; by 1949, Indian chemists had isolated a substance from Teloschistes flavicans with an identical structural formula to fallacin. Later research further separated fallacin into two distinct pigments, fallacin-A and fallacin-B (fallacinol). The latter compound is also known as teloschistin due to its structural match with the substance isolated earlier.

References

  1. Georgievics, G. v. (1911). "Darstellung und Eigenschaften des Octooxyanthrachinons". Monatshefte für Chemie. 32 (5): 347–352. doi:10.1007/BF01518160. S2CID   97848374.
  2. Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 22 January 2010.
  3. 1 2 Kumar, Sandeep (2008). "Rufigallol-based self-assembled supramolecular architectures". Phase Transitions. 81: 113–128. doi:10.1080/01411590701601610. S2CID   59445187.
  4. Winter, R (1995). "Hydroxy-anthraquinones as antimalarial agents". Bioorganic & Medicinal Chemistry Letters. 5 (17): 1927–1932. doi:10.1016/0960-894X(95)00326-O.