Revision as of 12:21, 6 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,083 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit |
Latest revision as of 05:37, 20 November 2024 edit undo2600:1700:60bb:c810:a871:628e:4f46:e44f (talk) It was not the first azo dye, that would be aniline yellow, discovered about 20 years prior.Tags: Mobile edit Mobile web edit |
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{{chembox |
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{{chembox |
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| ImageFile = Para Red.png |
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| verifiedrevid = 476994415 |
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| IUPACName = 1--2-naphthol |
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| ImageFile = Para Red Formula V.1.svg |
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| OtherNames = 1-((4-Nitrophenyl)azo)-2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1-((p-nitrophenyl)azo)-2-naphthalenol, 1-((p-nitrophenyl)azo)-2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS |
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| ImageSize = 250px |
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| Section1 = {{Chembox Identifiers |
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| PIN = 1-naphthalen-2-ol |
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| ChemSpiderID = 13544963 |
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| OtherNames = <nowiki>1--2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1--2-naphthalenol, 1--2-naphthol, 1--2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS</nowiki> |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13544963 |
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| InChI = 1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+ |
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| InChI = 1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+ |
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| InChIKey = WOTPFVNWMLFMFW-ISLYRVAYBR |
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| InChIKey = WOTPFVNWMLFMFW-ISLYRVAYBR |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+ |
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| StdInChI = 1S/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WOTPFVNWMLFMFW-ISLYRVAYSA-N |
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| StdInChIKey = WOTPFVNWMLFMFW-ISLYRVAYSA-N |
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| CASNo_Ref = {{cascite|correct|PubChem}} |
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| CASNo = 6410-10-2 |
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| CASNo = 6410-10-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 229-093-8 |
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| PubChem = |
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| UNII = D54Q24K2EI |
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| EINECS = 229-093-8 |
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| SMILES = O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O |
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| PubChem = 22917 |
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| ChEMBL = 1967257 |
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| SMILES = O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=16 |
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| Formula = C<sub>16</sub>H<sub>11</sub>N<sub>3</sub>O<sub>3</sub> |
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| H=11 |
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| MolarMass = |
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| Appearance = Red solid |
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| N=3 |
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| O=3 |
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| Appearance = Red solid |
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| Density = |
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| Density = |
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| MeltingPt = 248 - 252 °C |
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| MeltingPtC = 248 to 252 |
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| BoilingPt = |
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| Solubility = |
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| BoilingPt = |
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| Solubility = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| RPhrases = {{R36/37/38}} |
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| SPhrases = {{S26}}, {{S36}} |
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| FlashPt = |
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| Autoignition = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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'''Para Red''' ('''paranitraniline red''', '''Pigment Red 1''', '''C.I. 12070''') is a chemical ]. Chemically, the dye is similar to ]. The dye was discovered in 1880 by von Gallois and Ullrich, and was the first ]. It dyes cellulose fabrics a brilliant red, but is not very fast. The dye can be washed away easily from cellulose fabrics if not dyed correctly. Throughout making Para Red, the solution will become acidic and basic. Small amounts of byproducts may be left over after the Para Red dye is made that may be acidic or basic, but if made correctly there are little of these and the byproducts have no effect. |
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'''Para red''' ('''paranitraniline red''', '''Pigment Red 1''', '''C.I. 12070''') is a ]. Chemically, it is similar to ]. It was discovered in 1880 by von Gallois and Ullrich. It dyes cellulose fabrics a brilliant red color, but is not very ]. The dye can be washed away easily from ] fabrics if not dyed correctly. Acidic and basic stages both occur during the standard formation of Para Red, and acidic or basic byproducts may be present in the final product. |
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==Synthesis== |
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==Synthesis== |
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Para Red is prepared by ] of ] at ice-cold temperatures, followed by coupling with ]:<ref>{{cite book |
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Para red is prepared by ] of ] at ice-cold temperatures, followed by coupling with ]:<ref>{{cite book |
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| last = Williamson |
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| last = Williamson |
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| first = Kenneth L. |
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| first = Kenneth L. |
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| title = Macroscale and Microscale Organic Experiments, Fourth Edition |
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| title = Macroscale and Microscale Organic Experiments, Fourth Edition |
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| publisher = ] |
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| publisher = ] |
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| year = 2002 |
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| year = 2002 |
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| isbn = 0618197028}} |
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| isbn = 0-618-19702-8 |
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| url-access = registration |
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| url = https://archive.org/details/macroscalemicros00will_0 |
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}} |
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</ref> |
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</ref> |
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] |
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:]{{clear-left}} |
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==UK food alert== |
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==Regulation== |
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In the ], the dye is not permitted in food. The UK's ] (FSA) stated that "''the Agency’s independent scientific experts have advised that, although there are very limited data available, it would be prudent to assume that it could be a genotoxic carcinogen''". <ref name=fsa>{{cite news | url = http://www.food.gov.uk/news/newsarchive/2005/apr/oldelpaso | title = Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye | publisher = ] | format = press release | date = 21 April 2005}}</ref> |
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Para red is not approved for use in food in any jurisdiction. In 2005, ] dinner kits were found to be contaminated with the dye and removed from supermarket shelves.<ref name=fsa>{{cite news | url = http://www.food.gov.uk/news/newsarchive/2005/apr/oldelpaso | title = Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye | publisher = ] | format = press release | date = 21 April 2005}}</ref><ref>{{cite news | url = http://news.bbc.co.uk/1/hi/health/4518139.stm | title = Banned dye found in more products | publisher = ] | date = 5 May 2005}}</ref> |
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On 21 April 2005, the FSA announced that some batches of ] dinner kits had been contaminated with the dye, and issued an alert.<ref name=fsa/> Also, reported on the 5 May 2005, the dye was found in 35 products which have now been taken off supermarket shelves. The products were mainly cooking sauces, though some are also spices.<ref>{{cite news | url = http://news.bbc.co.uk/1/hi/health/4518139.stm | title = Banned dye found in more products | publisher = ] | date = 5 May 2005}}</ref> |
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==References== |
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==References== |
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