Naphthazarine

Structural formula
General
Surname	Naphthazarine
other names	5,8-dihydroxy-1,4-naphthoquinone; CI57010;
Molecular formula	C 10 H 6 O 4
Brief description	dark brown solid
External identifiers / databases
EC number	207-495-4
ECHA InfoCard	100.006.816
PubChem	10141
ChemSpider	9735
Wikidata	Q4639550
properties
Molar mass	190.15 g mol −1
Physical state	firmly
Melting point	220-230 ° C
solubility	slightly soluble in water (5520 mg / l at 25 ° C) and ether; soluble in ethanol; soluble in alkalis;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-280-305 + 351 + 338-304 + 340-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naphthazarin is a chemical compound from the group of quinone dyes . It was discovered by François-Zacharie Roussin in 1861 .

Occurrence

Naphthazarin some representatives who could in the roots Borage Family (including in the onosma ) are found.

Extraction and presentation

Naphthazarine can be obtained by reacting 2,3-dichloronaphthazarine with tin (II) chloride , followed by oxidation.

It can also be prepared in 45% yield by reacting 40% oleum , a little sulfur and 1,5-dinitronaphthalene .

properties

Naphthazarin is a lipophilic, dark brown solid that is in the form of greenish, shiny needles.

Naphthazarin occurs in different crystal structures, the C-form in the space group Pc (space group no. 7) at 60 K and space group P 2 ₁ / c (space group no. 14) at 300 K. Template: room group / 7 Template: room group / 14

use

Naphthazarin is a mordant dye , in the wool dyeing and textile printing is used (usually as Hydrogensulfitverbindung ). Naphthazarine can also be used as an acaricide . Some dyes derived from naphthazarin are also important.

Medical use

There is evidence that low doses of naphthazarine could protect the brain of the model organism C57BL / C from Parkinson's disease . It appears that naphthazarine makes the cells of the nervous system more resistant to stress through hormesis . A lower loss of dopaminergic neurons and an improved mobility of C57BL / C could be determined.

Individual evidence

↑ ^a ^b ^c ^d data sheet 5,8-dihydroxy-1,4-naphthoquinone, technical grade from Sigma-Aldrich , accessed on September 27, 2017 ( PDF ).
↑ ^a ^b ^c ^d data sheet 5,8-dihydroxy-1,4-naphthoquinone, 97% from AlfaAesar, accessed on September 27, 2017 ( PDF )(JavaScript required) .
↑ ^a ^b ^c ^d Lexicon of Chemistry: 5,8-Dihydroxy-1,4-naphthoquinone - Lexicon of Chemistry , accessed on September 27, 2017.
↑ WLF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 1142 ( limited preview in Google Book search).
↑ ^a ^b ^c Hans R. Schweizer: Artificial organic dyes and their intermediate products . Springer-Verlag, 2013, ISBN 978-3-642-87245-7 , pp. 299 ( limited preview in Google Book search).
↑ ^a ^b Seon Young Choi, Tae Gen Son, Hee Ra Park, Young Jung Jang, Shin Bi Oh: Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model . In: Journal of Neuroscience Research . tape 90 , no. 9 , September 1, 2012, ISSN 1097-4547 , p. 1842–1849 , doi : 10.1002 / jnr.23061 ( wiley.com [accessed October 6, 2017]).
↑ John R. Lewis, John Paul: A Convenient Synthesis of Naphthazarin and Naphthopurpurin. In: Zeitschrift für Naturforschung B. 32, 1977, doi : 10.1515 / znb-1977-1220 .
^ Fritz Mayer: Chemistry of organic dyes . Springer-Verlag, 2013, ISBN 978-3-662-02246-7 , pp. 173 ( limited preview in Google Book search).
↑ FH Herbstein, M. Kapon, GM Reisner, MS Lehman, RB Kress, RB Wilson, W. -I. Shiau, EN Duesler, IC Paul, DY Curtin: Polymorphism of Naphthazarin and its Relation to Solid-State Proton Transfer. Neutron and X-Ray Diffraction Studies on Naphthazarin C. In: Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences. 399, 1985, p. 295, doi : 10.1098 / rspa.1985.0059 .
↑ PD Cradwick, D. Hall: A further investigation of the crystal structures of naphthazarin. In: Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27, p. 1990, doi : 10.1107 / S0567740871005223 .

[Sigma-1] ta sheet 5,8-dihydroxy-1,4-naphthoquinone, technical grade from Sigma-Aldrich , accessed on September 27, 2017 ( PDF ).

[Alfa-2] ta sheet 5,8-dihydroxy-1,4-naphthoquinone, 97% from AlfaAesar, accessed on September 27, 2017 ( PDF )(JavaScript required) .

[Lexikon_der_Chemie-3] Lexicon of Chemistry: 5,8-Dihydroxy-1,4-naphthoquinone - Lexicon of Chemistry , accessed on September 27, 2017.

[W.L.F._Armarego-4] WLF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 1142 ( limited preview in Google Book search).

[Hans_R._Schweizer-5] Hans R. Schweizer: Artificial organic dyes and their intermediate products . Springer-Verlag, 2013, ISBN 978-3-642-87245-7 , pp. 299 ( limited preview in Google Book search).

[NaphthazarinProtective-6] Seon Young Choi, Tae Gen Son, Hee Ra Park, Young Jung Jang, Shin Bi Oh: Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model . In: Journal of Neuroscience Research . tape 90 , no. 9 , September 1, 2012, ISSN 1097-4547 , p. 1842–1849 , doi : 10.1002 / jnr.23061 ( wiley.com [accessed October 6, 2017]).

[DOI10.1515/znb-1977-1220-7] John R. Lewis, John Paul: A Convenient Synthesis of Naphthazarin and Naphthopurpurin. In: Zeitschrift für Naturforschung B. 32, 1977, doi : 10.1515 / znb-1977-1220 .

[Fritz_Mayer-8] Fritz Mayer: Chemistry of organic dyes . Springer-Verlag, 2013, ISBN 978-3-662-02246-7 , pp. 173 ( limited preview in Google Book search).

[DOI10.1098/rspa.1985.0059-9] FH Herbstein, M. Kapon, GM Reisner, MS Lehman, RB Kress, RB Wilson, W. -I. Shiau, EN Duesler, IC Paul, DY Curtin: Polymorphism of Naphthazarin and its Relation to Solid-State Proton Transfer. Neutron and X-Ray Diffraction Studies on Naphthazarin C. In: Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences. 399, 1985, p. 295, doi : 10.1098 / rspa.1985.0059 .

[DOI10.1107/S0567740871005223-10] PD Cradwick, D. Hall: A further investigation of the crystal structures of naphthazarin. In: Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27, p. 1990, doi : 10.1107 / S0567740871005223 .