Spinochrome D

Last updated
Spinochrome D
Spinochrome D.svg
Spinochrome-D-3D-balls.png
Names
Preferred IUPAC name
2,3,5,6,8-Pentahydroxynaphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C10H6O7/c11-2-1-3(12)6(13)5-4(2)7(14)9(16)10(17)8(5)15/h1,11-13,16-17H Yes check.svgY
    Key: HYVDWYISUNRFCU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H6O7/c11-2-1-3(12)6(13)5-4(2)7(14)9(16)10(17)8(5)15/h1,11-13,16-17H
    Key: HYVDWYISUNRFCU-UHFFFAOYAZ
  • O=C(C1=C2C(O)=C(O)C(O)=C1O)C(O)=CC2=O
  • Oc1c(O)cc(O)c2C(=O)C(\O)=C(\O)C(=O)c12
Properties
C10H6O7
Molar mass 238.151 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Spinochrome D (2,3,5,6,8-pentahydroxy-1,4-naphthoquinone) is an organic compound with formula C
10
H
6
O
5
, formally derived from 1,4-naphthoquinone through the replacement of five hydrogen atoms by hydroxyl (OH) groups.

Spinochrome D occurs naturally as a brownish red pigment in the shell and spines of sea urchins such as the Japanese aka-uni ( Pseudocentrotus depressus ). [1] It is soluble in diethyl ether and crystallizes as brownish red needles that sublime at 285−295 °C. [1]

The compound gives a yellowish brown solution when treated with sodium hydroxide, a bluish green solution with ferric chloride, and a violet precipitate with lead acetate. It forms a five-fold acetate ester, C
10
HO
2
(CH
3
COO
)5, that crystallizes from methanol as yellow needles that melt at 185−186 °C. [1]

See also

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.

<span class="mw-page-title-main">Lead(II) iodide</span> Chemical compound

Lead(II) iodide is a chemical compound with the formula PbI
2
. At room temperature, it is a bright yellow odorless crystalline solid, that becomes orange and red when heated. It was formerly called plumbous iodide.

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

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

IARC group 3 substances, chemical mixtures and exposure circumstances are those that can not be classified in regard to their carcinogenicity to humans by the International Agency for Research on Cancer (IARC). This category is used most commonly for agents, mixtures and exposure circumstances for which the level of evidence of carcinogenicity is inadequate in humans and inadequate or limited in experimental animals. Exceptionally, agents (mixtures) for which the evidence of carcinogenicity is inadequate in humans, but sufficient in experimental animals may be placed in this category when there is strong evidence that the mechanism of carcinogenicity in experimental animals does not operate in humans. Agents, mixtures and exposure circumstances that do not fall into any other group are also placed in this category.

<i>Biancaea sappan</i> Species of legume

Biancaea sappan is a species of flowering tree in the legume family, Fabaceae, that is native to tropical Asia. Common names in English include sappanwood and Indian redwood. It was previously ascribed to the genus Caesalpinia. Sappanwood is related to brazilwood, and was itself called brasilwood in the Middle Ages.

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

Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.

<span class="mw-page-title-main">1-Naphthylamine</span> Chemical compound

1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.

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

Lawsone (2-hydroxy-1,4-naphthoquinone), also known as hennotannic acid, is a red-orange dye present in the leaves of the henna plant, for which it is named, as well as in the common walnut and water hyacinth. Humans have used henna extracts containing lawsone as hair and skin dyes for more than 5,000 years. Lawsone reacts chemically with the protein keratin in skin and hair via a Michael addition reaction, resulting in a strong permanent stain that lasts until the skin or hair is shed. Darker colored staining is due to more lawsone–keratin interactions occurring, which evidently break down as the concentration of lawsone decreases and the tattoo fades. Lawsone strongly absorbs UV light, and aqueous extracts can be effective sunless tanning agents and sunscreens. Lawsone is a 1,4-naphthoquinone derivative, an analog of hydroxyquinone containing one additional ring.

In organic chemistry, a homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series. A homologous series is a group of compounds that differ by a constant unit, generally a methylene group. The reactants undergo a homologation when the number of a repeated structural unit in the molecules is increased. The most common homologation reactions increase the number of methylene units in saturated chain within the molecule. For example, the reaction of aldehydes or ketones with diazomethane or methoxymethylenetriphenylphosphine to give the next homologue in the series.

<span class="mw-page-title-main">Tetrahydroxy-1,4-benzoquinone</span> Chemical compound

Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone, is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.

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

Spinochrome E is a polyhydroxylated 1,4-naphthoquinone pigment found in sea urchin shell ("test"), spine, gonads, coelomic fluid, and eggs, of sea urchin commonly known as spinochromes. These natural phenolic compounds are quinones with potential pharmacological properties. The several hydroxyl groups are appropriate for free-radical scavenging, which diminishes ROS and prevents redox imbalance. Mechanisms are described such as scavenging of reactive oxygen species (ROS), interaction with lipid peroxide radicals, chelation of metal ions, inhibition of lipid peroxidation and regulation of the cell redox potential.

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).

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

Spinochrome B (2,3,5,7-tetrahydroxynaphthoquinone) is an organic compound with formula C
10
H
6
O
4
, formally derived from 1,4-naphthoquinone through the replacement of four hydrogen atoms by hydroxyl (OH) groups.

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).

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

Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring 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.

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

Benzoquinonetetracarboxylic dianhydride is an organic compound with formula C
10
O
8
which can be seen as the result of removing two molecules of water H
2
O
from benzoquinonetetracarboxylic acid.

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

1,4-Naphthoquinone or para-naphthoquinone is a quinone 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.

The enzyme 1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28; systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase) catalyses the following reaction:

<span class="mw-page-title-main">Chika Kuroda</span> Japanese chemist (1884–1968)

Chika Kuroda was a Japanese chemist whose research focused on natural pigments. She was the first woman in Japan to receive a Bachelor of Science.

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

Echinochrome A (7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone) is a polyhydroxylated 1,4-naphthoquinone, a type of pigments commonly found in sea urchin shell ("test"), spine, gonads, coelomic fluid, and eggs, of sea urchin. These type of pigments are commonly known as spinochromes and are natural marine phenolic compounds with potential pharmacological effects and modes of action.

References

  1. 1 2 3 Chika KURODA and Masae OKAJIMA (1967), Studies on the Derivatives of Naphthoquinones, XVIII. The pigments of sea urchins, XIII. Proc. Japan Acad., volume 43, pages 41--44. Online version accessed on 2010-02-01.