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Revision as of 09:29, 30 November 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 18:42, 12 December 2024 edit undoMarbletan (talk | contribs)Extended confirmed users5,452 editsNo edit summary 
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{{chembox {{chembox
| verifiedrevid = 399692179 | verifiedrevid = 399693280
|ImageFile=Biebrich scarlet.png | ImageFile=Biebrich scarlet.png
|ImageSize=200px | ImageSize=200px
|IUPACName=2--5-(4-sulfophenyl)diazenyl-benzenesulfonic acid | IUPACName=2--5-(4-sulfophenyl)diazenyl-benzenesulfonic acid
|OtherNames=Croceine scarlet | OtherNames=Croceine scarlet; C.I. 26905
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| index1_label = (Sodium salt)
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4757734 | ChemSpiderID = 4757734
| InChI = 1/C22H16N4O7S2.2Na/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30;;/h1-13,27H,(H,28,29,30)(H,31,32,33);;/q;2*+1/p-2 | InChI1 = 1/C22H16N4O7S2.2Na/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30;;/h1-13,27H,(H,28,29,30)(H,31,32,33);;/q;2*+1/p-2
| InChIKey = VVAVKBBTPWYADW-NUQVWONBAJ | InChIKey1 = VVAVKBBTPWYADW-NUQVWONBAJ
| InChI1 = 1/C22H16N4O7S2/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30/h1-13,25H,(H,28,29,30)(H,31,32,33)/b24-23+,26-22- | InChI = 1/C22H16N4O7S2/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30/h1-13,25H,(H,28,29,30)(H,31,32,33)/b24-23+,26-22-
| InChIKey1 = VJULFVPZZZJPDJ-PUNVMFJJBJ | InChIKey = VJULFVPZZZJPDJ-PUNVMFJJBJ
| SMILES1 = O=S(=O)(O)c4ccc(/N=N/c1ccc(c(c1)S(=O)(=O)O)N/N=C2/c3ccccc3\C=C/C2=O)cc4 | SMILES = O=S(=O)(O)c4ccc(/N=N/c1ccc(c(c1)S(=O)(=O)O)N/N=C2/c3ccccc3\C=C/C2=O)cc4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C22H16N4O7S2/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30/h1-13,25H,(H,28,29,30)(H,31,32,33)/b24-23+,26-22- | StdInChI = 1S/C22H16N4O7S2/c27-20-12-5-14-3-1-2-4-18(14)22(20)26-25-19-11-8-16(13-21(19)35(31,32)33)24-23-15-6-9-17(10-7-15)34(28,29)30/h1-13,25H,(H,28,29,30)(H,31,32,33)/b24-23+,26-22-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VJULFVPZZZJPDJ-PUNVMFJJSA-N | StdInChIKey = VJULFVPZZZJPDJ-PUNVMFJJSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo=4196-99-0
| CASNo=25317-38-8
⚫ | PubChem=5940755
⚫ | CASNo1=4196-99-0
⚫ | SMILES = ..S(=O)(=O)c1ccc(cc1)/N=N/c4ccc(/N=N/c2c3ccccc3ccc2O)c(c4)S()(=O)=O
⚫ | PubChem=20171
⚫ | MeSHName=Biebrich+scarlet
| PubChem1=20170
| EINECS = 224-084-5
⚫ | SMILES1 = ..S(=O)(=O)c1ccc(cc1)/N=N/c4ccc(/N=N/c2c3ccccc3ccc2O)c(c4)S()(=O)=O
⚫ | MeSHName=Biebrich+scarlet
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=22 | H=16 | N=4 | O=7 | S=2
| Formula=C<sub>22</sub>H<sub>16</sub>N<sub>4</sub>O<sub>7</sub>S<sub>2</sub>
| Appearance=
| MolarMass=512.517
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|315|319|332|335}}
| PPhrases = {{P-phrases|}}
}} }}
}} }}


'''Biebrich scarlet''' (C.I. 26905) is a molecule used in ].<ref>{{cite journal |last1=Lillie |first1=R. D. |date=1940 |title=Further Experiments with the Masson Trichrome Modification of Mallory's Connective Tissue Stain |journal=] |volume=15 |issue=1 |pages=17–22 |doi=10.3109/10520294009110327}}</ref> It is an anionic mono-azo dye, which is an important pigmenting agent in the textile and paper industries, used to color wool, silk, cotton, and papers. The dye was created in 1878 by the German chemist ].<ref>{{cite book |last=Schwarz |first=Holm-Dietmar |title=Neue Deutsche Biographie |year=1999 |volume=19 |language=de |chapter=Nietzki, Rudolf Hugo |access-date=2015-10-12 |chapter-url=http://www.deutsche-biographie.de/pnd117585262.html}}</ref> He was employed by ] and completed his contributions on August of 1880, where he claimed to be the inventor of Biebrich scarlet. The name, Biebrich scarlet, originated from the location where a company, Kalle & Co., marketed the dye in ] (Wiesbaden). <ref name=":03">Cooksey, C. (2020). Quirks of dye nomenclature. 13. Biebrich scarlet. ''Biotechnic & Histochemistry'', ''95''(3), 194–197. <nowiki>https://doi.org/10.1080/10520295.2019.1662945</nowiki></ref>
'''Biebrich scarlet''' (C.I. 26905) is a molecule used in ].

== Properties ==
Biebrich scarlet has two alternative structures: the keto form, with the ] of 2--5-benzene-1-sulfonate, and the ] form, with the ] of 2--5-benzene-1-sulfonic acid.<ref name=":03" /> The dye has the molecular weight formula of C<sub>22</sub>H<sub>16</sub>N<sub>4</sub>Na<sub>2</sub>O<sub>7</sub>S<sub>2</sub>, molecular weight of 512.52 grams per mol, and has the maximum absorption of 510 nm.<ref>Bose, S., & Genwa, K. R. (2018). Fabrication of DSSCs with biebrich scarlet, alizarine cyanine green and evans blue dyes as new organic photosensitizers. ''Materials Science Poland'', ''36''(4), 655–661. <nowiki>https://doi.org/10.2478/msp-2018-0077</nowiki></ref>

== Environmental impacts and applications ==
Biebrich scarlet dyes are used to color hydrophobic materials like fats and oils.<ref name=":02">{{Cite journal |last1=Priya |last2=Sharma |first2=Amit Kumar |last3=Kaith |first3=Balbir Singh |last4=Vipula |last5=Chandel |first5=Kajal |last6=Singh |first6=Anoop |last7=Isha |display-authors=3|year=2020 |title=Chemically modified chitosan‑sodium alginate as chemo-sensor adsorbent for the detection of picric acid and removal of biebrich scarlet |journal=] |volume=147 |pages=582–594 |doi=10.1016/j.ijbiomac.2020.01.090 |pmid=31945433 |s2cid=210699599}}</ref> It's also one of the most often used dyes for plasma staining.<ref name=":0">{{Cite journal |last=Begum |first=Shamima |last2=Mishra |first2=Soumya Ranjan |last3=Ahmaruzzaman |first3=Md. |date=December 2022 |title=Fabrication of ZnO–SnO2 nanocomposite and its photocatalytic activity for enhanced degradation of Biebrich scarlet |url=https://link.springer.com/10.1007/s11356-022-21851-1 |journal=Environmental Science and Pollution Research |language=en |volume=29 |issue=58 |pages=87347–87360 |doi=10.1007/s11356-022-21851-1 |issn=0944-1344}}</ref> The dye is an illegal dye for food additives because of its ] properties. Biebrich scarlet can have harmful effects on living and non-living organisms in natural water. This dye is strongly pigmented, and its presence in water bodies, even at low quantities (10-50 mg/L), can be detected, reducing the transparency of the water ecosystem.<ref>{{cite journal | doi = 10.1590/S1517-83822005000300008 | author = Kátia M. G. Machado, Dácio R. Matheus, and Vera L. R. Bononi | title = Ligninolytic enzymes production and Remazol brilliant blue R decolorization by tropical brazilian basidiomycetes fungi | date = 2005 | journal = Braz. J. Microbiol. | volume = 36 | issue = 3 }}</ref> It also hinders the entry of sunlight into the water, affecting both zooplankton and phytoplankton in the water ecosystem,<ref name=":0" /> therefore the pollutant must be removed. Removal of the pollutant involves absorption, ], precipitation, ], fungal detachment, and electrochemical separation.<ref name=":02" /> ] absorbents have active sites to which the dye is held using electrostatic interactions. ] allows for almost total degradation of Biebrich scarlet ] bonds in less than 10 hours.<ref>{{Cite journal |last1=Chebli |first1=D. |last2=Fourcade |first2=F. |last3=Brosillon |first3=S. |last4=Nacef |first4=S. |last5=Amrane |first5=A. |display-authors=3|date=12 January 2010 |title=Supported photocatalysis as a pre-treatment prior to biological degradation for the removal of some dyes from aqueous solutions; Acid Red 183, Biebrich Scarlet, Methyl Red Sodium Salt, Orange II |journal=] |doi=10.1002/jctb.2342}}</ref> Degradation of Biebrich scarlet is also observed using ] enzyme from ] in the presence of mediators like 2-chloro-1,4-dimethoxybenzene.<ref>{{cite journal |last1=Cooksey |first1=C J |date=2019-10-08 |title=Quirks of dye nomenclature. 13. Biebrich scarlet |url=https://www.tandfonline.com/doi/full/10.1080/10520295.2019.1662945 |journal=] |language=en |location= |publisher=] |volume=95 |issue=3 |pages=194&ndash;197 |doi=10.1080/10520295.2019.1662945 |issn=1052-0295 |lccn=91641272 |oclc=8270589858 |pmid=31592687 |access-date=}}</ref>

With such a significant impact on the environment and surrounding resources, researchers are working to reduce the dye's presence in water bodies. Studies have shown techniques to remove the red dye Biebrich Scarlet (BS) from water using UV light and nanophotocatalysts like TiO₂, ZnO, CdS, and ZnS. Among these, ZnO performed the best in dye removal. To enhance the process, researchers adjusted factors such as catalyst concentration (0.25-1.25 g/L), solution pH (3-11), and dye concentration (5-100 mg/L). Precipitation was used to form the ZnO nanoparticles, which were then studied utilizing advanced technologies (XRD, FT-IR, TGA, SEM, and TEM) to confirm their characteristics. Experiments revealed that, under optimal conditions, these produced ZnO particles beat commercial ZnO powders in dye breakdown. Furthermore, the study found that the produced ZnO could be reused well, making it a suitable material for ] applications.<ref>{{Cite journal |last=Kansal |first=Sushil Kumar |last2=Hassan Ali |first2=Ahmed |last3=Kapoor |first3=Seema |date=2010-09-15 |title=Photocatalytic decolorization of biebrich scarlet dye in aqueous phase using different nanophotocatalysts |url=https://linkinghub.elsevier.com/retrieve/pii/S0011916410002298 |journal=Desalination |volume=259 |issue=1 |pages=147–155 |doi=10.1016/j.desal.2010.04.017 |issn=0011-9164}}</ref>


==See also== ==See also==
* ] * ]

==References==
{{reflist}}


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