Hexahydroxy-1,4-naphthalenedione
Encyclopedia
2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called hexahydroxynaphthoquinone or spinochrome E, is an organic compound with formula . 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.
The substance forms red micro-needles which
do not melt below 300°C, and can be sublimed in vacuum at about 265°C.
The compound occurs in the shell
("test") and spine
s of the sea urchin
s Paracentrotus lividus
and Psammechinus miliaris
.
The compound can be produced by condensation of 3,4,5,6-tetramethoxyphthalaldehyde with glyoxal
.
Naphthoquinone
Naphthoquinone is a class of natural phenols based on the C6-C4 skeleton.1,4-Naphthoquinone can be viewed as derivatives of naphthalene through the replacement of two hydrogen atoms by two ketone groups....
(1,4-naphtalenedione) through replacement of all six hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atoms by hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
(OH) groups. The numerical prefixes "2,3,5,6,7,8" are superfluous since there is no other hexahydroxy derivative of 1,4-naphthoquinone.
The substance forms red micro-needles which
do not melt below 300°C, and can be sublimed in vacuum at about 265°C.
The compound occurs in the shell
Test (biology)
A test is a term used to refer to the shell of sea urchins, and also the shell of certain microorganisms, such as testate foraminifera and testate amoebae....
("test") and spine
Spine (zoology)
A spine is a hard, thorny or needle-like structure which occurs on various animals. Animals such as porcupines and sea urchins grow spines as a self-defense mechanism. Spines are often formed of keratin...
s of the sea urchin
Sea urchin
Sea urchins or urchins are small, spiny, globular animals which, with their close kin, such as sand dollars, constitute the class Echinoidea of the echinoderm phylum. They inhabit all oceans. Their shell, or "test", is round and spiny, typically from across. Common colors include black and dull...
s Paracentrotus lividus
Paracentrotus lividus
Paracentrotus lividus is a species of sea urchin in the family Parechinidae commonly known as the purple sea urchin. It is the type species of the genus and occurs in the Mediterranean Sea and eastern Atlantic Ocean.-Description:...
and Psammechinus miliaris
Psammechinus miliaris
Psammechinus miliaris is a species of sea urchin in the family Parechinidae. It is sometimes known as the green sea urchin or shore sea urchin. It is found in shallow areas of the eastern Atlantic Ocean and the North Sea.-Description:...
.
The compound can be produced by condensation of 3,4,5,6-tetramethoxyphthalaldehyde with glyoxal
Glyoxal
Glyoxal is an organic compound with the formula OCHCHO. This yellow colored liquid is the smallest dialdehyde . Its tautomer acetylenediol is unstable.-Production:...
.
See also
- Hexahydroxy-2,3-naphthalenedioneHexahydroxy-2,3-naphthalenedioneHexahydroxy-2,3-naphthalenedione is an organic compound with formula . It is formally derived from 2,3-naphthoquinone through replacement of all six hydrogen atoms by hydroxyl groups...
, a structural isomer. - Tetrahydroxybenzoquinone
- OctahydroxyanthraquinoneOctahydroxyanthraquinoneOctahydroxyanthraquinone is an organic compound with formula , formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups....