Phloxine

Phloxine[1]
Names
Preferred IUPAC name
Disodium 2′,4′,5′,7′-tetrabromo-4,5,6,7-tetrachloro-3-oxo-3H-spiro[[2]benzofuran-1,9′-xanthene]-3′,6′-bis(olate)
Other names
Cyanosin; Cyanosine; Eosine bluish; Eosine Blue; Cyanosin B; Eosin Blue; Phloxine P; Phloxin B; Eosine I Bluish; Acid red 92; C.I. 45410; D & C Red no. 28
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.038.490 Edit this at Wikidata
UNII
  • C1=C2C(=C(C(=C1Br)[O-])Br)OC3=C(C(=C(C=C3C24C5=C(C(=C(C(=C5Cl)Cl)Cl)Cl)C(=O)O4)Br)[O-])Br.[Na+].[Na+]
Properties
C20H2Br4Cl4Na2O5
Molar mass 829.63 g·mol−1
Appearance Red to brown powder
Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phloxine B (commonly known simply as phloxine) is a water-soluble red dye used for coloring drugs and cosmetics in the United States[2] and coloring food in Japan.[3] It is derived from fluorescein, but differs by the presence of four bromine atoms at positions 2, 4, 5 and 7 of the xanthene ring and four chlorine atoms in the carboxyphenyl ring.[4] It has an absorption maximum around 540 nm and an emission maximum around 564 nm.[5] Apart from industrial use, phloxine B has functions as an antimicrobial substance, viability dye and biological stain.[6] For example, it is used in hematoxylin-phloxine-saffron (HPS) staining to color the cytoplasm and connective tissue in shades of red.[7]

  1. ^ Phloxine B (Acid red 92)
  2. ^ Food and Drug Administration (2001). The Code of Federal Regulations of the United States of America, Title 21, Part 74.1328. U S Government Printing Office. p. 296. Retrieved 15 April 2016.
  3. ^ Kamikura, M (1970). "Thin Layer Chromatography of Synthetic Dyes (X)". Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi). 11 (4): 242–248. doi:10.3358/shokueishi.11.242.
  4. ^ Duarte, Paulo; Ferreira, Diana P.; Ferreira Machado, Isabel; Filipe, Luis; Ferreira, Vieira; Rodríguez, Hernan B.; San Román, Enrique (2012). "Phloxine B as a Probe for Entrapment in Microcrystalline Cellulose". Molecules. 17 (2): 1602–1616. doi:10.3390/molecules17021602. PMC 6268435. PMID 22314381.
  5. ^ Coppeta, J.; Rogers, C. (1998). "Dual emission laser induced fluorescence for direct planar scalar behavior measurements". Experiments in Fluids. 25 (1): 1–15. Bibcode:1998ExFl...25....1C. doi:10.1007/s003480050202. S2CID 37649159.
  6. ^ Rasooly, Avraham; Weisz, Adrian (2002). "In Vitro Antibacterial Activities of Phloxine B and Other Halogenated Fluoresceins against Methicillin-Resistant Staphylococcus aureus". Antimicrobial Agents and Chemotherapy. 46 (11): 3650–3653. doi:10.1128/AAC.46.11.3650-3653.2002. PMC 128710. PMID 12384384.
  7. ^ Borgerink, Hermina. "HPS stain". Narkive Mailing List Archive. Retrieved 18 April 2016.