Naphthazarin

Last updated
Naphthazarin
Naphthazarin.svg
Naphthazarin-3D-balls.png
Names
Preferred IUPAC name
5,8-Dihydroxynaphthalene-1,4-dione
Other names
Dihydroxynaphthoquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.816 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-495-4
KEGG
PubChem CID
UNII
  • InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H Yes check.svgY
    Key: RQNVIKXOOKXAJQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H
    Key: RQNVIKXOOKXAJQ-UHFFFAOYAN
  • C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O
  • O=C\2c1c(O)ccc(O)c1C(=O)/C=C/2
Properties
C10H6O4
Molar mass 190.154 g·mol−1
Melting point 228–232 °C (442–450 °F; 501–505 K)
Hazards
GHS pictograms GHS-pictogram-exclam.svg
GHS Signal word Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring [1] [2] organic compound with formula C
10
H
6
O
4
, formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.

Naphthazarin is soluble in 1,4-dioxane from which it crystallizes as deep red needles that melt at 228−232 °C. [3]

Synthesis

Naphtharazin can be prepared by condensation of 1,4-dimethoxybenzene with 2,3-dichloromaleic anhydride followed by reductive dechlorination and reoxidation. [4] [5]

Naphtharazin can also be obtained by oxidation of 5,8-dihydroxy-1-tetralone with manganese dioxide (MnO2). [3]

Related Research Articles

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

Anthraquinone Chemical compound

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone, however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It 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.

Copper(II) chloride Chemical compound

Copper(II) chloride is the chemical compound with the chemical formula CuCl2. The anhydrous form is yellowish brown but slowly absorbs moisture to form a blue-green dihydrate.

Tin(IV) oxide Chemical compound known as stannic oxide, cassiterite and tin ore

Tin(IV) oxide, also known as stannic oxide, is the inorganic compound with the formula SnO2. The mineral form of SnO2 is called cassiterite, and this is the main ore of tin. With many other names, this oxide of tin is an important material in tin chemistry. It is a colourless, diamagnetic, amphoteric solid.

1,2-Naphthoquinone Chemical compound

1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C
10
H
6
O
2
. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.

1,4-Benzoquinone Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

Juglone Chemical produced by walnut trees

Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is an organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the staining compound in the henna leaf.

In enzymology, juglone 3-monooxygenase (EC 1.14.99.27) is an enzyme that catalyzes the chemical reaction

1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.

Hexahydroxy-1,4-naphthalenedione Chemical compound

2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called hexahydroxynaphthoquinone or spinochrome E, is an organic compound with formula C
10
H
6
O
8
. It is formally derived from naphthoquinone (1,4-naphtalenedione) through replacement of all six hydrogen atoms by hydroxyl (OH) groups. The numerical prefixes "2,3,5,6,7,8" are superfluous, since there is no other hexahydroxy derivative of 1,4-naphthoquinone.

A dihydroxyanthraquinone is any of several isomeric organic compounds with formula C
14
H
8
O
4
, 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.

A hydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

A dihydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms (H) by hydroxyl groups (OH).

Hydroxyquinone

Hydroxyquinone often refers to a hydroxybenzoquinone, any organic compound with formula C
6
H
4
O
3
which can be viewed as a derivative of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). When unqualified, the terms usually mean specifically the compound 2-hydroxy-1,4-benzoquinone, derived from 1,4-benzoquinone or para-benzoquinone.

Hydroxyanthraquinone

A hydroxyanthraquinone (formula: C14H9O2(OH)) is any of several organic compounds that can be viewed as derivatives of an anthraquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

A hydroxybenzoquinone is any of several organic compounds that can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

1,4-Naphthoquinone Chemical compound

1,4-Naphthoquinone or para-naphthoquinone is an organic compound derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.

1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28) is an enzyme with systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase. This enzyme catalyses the following chemical reaction

1-Tetralone Chemical compound

1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.

Homoisoflavonoid

Homoisoflavonoids (3-benzylidenechroman-4-ones) are a type of phenolic compounds occurring naturally in plants.

References

  1. Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
  2. Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.
  3. 1 2 J. Khalafy and J.M. Bruce (2002), Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.
  4. Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.
  5. Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted by Khalafy and Bruce.