Rosocyanine: Difference between revisions
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{{chembox |
{{chembox |
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| verifiedrevid = |
| verifiedrevid = 451289962 |
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| ImageFile = Rosocyanine. |
| ImageFile = Rosocyanine.svg |
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| ImageSize = 300px |
| ImageSize = 300px |
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| IUPACName = 2-methoxy-4-[(E)-2-[2,4,10-tris[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,5,7,11-tetraoxa-6-boroniaspiro[5.5]undecan-8-yl]ethenyl]phenol;chloride |
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| IUPACName = |
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| OtherNames = Rosocyanine |
| OtherNames = Rosocyanine |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 21106498 |
| ChemSpiderID = 21106498 |
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| PubChem = 57473111 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C42H44BO12.ClH/c1-48-39-21-27(9-17-35(39)44)5-13-31-25-32(14-6-28-10-18-36(45)40(22-28)49-2)53-43(52-31)54-33(15-7-29-11-19-37(46)41(23-29)50-3)26-34(55-43)16-8-30-12-20-38(47)42(24-30)51-4;/h5-24,31-34,44-47H,25-26H2,1-4H3;1H/q+1;/p-1/b13-5+,14-6+,15-7+,16-8+; |
| StdInChI = 1S/C42H44BO12.ClH/c1-48-39-21-27(9-17-35(39)44)5-13-31-25-32(14-6-28-10-18-36(45)40(22-28)49-2)53-43(52-31)54-33(15-7-29-11-19-37(46)41(23-29)50-3)26-34(55-43)16-8-30-12-20-38(47)42(24-30)51-4;/h5-24,31-34,44-47H,25-26H2,1-4H3;1H/q+1;/p-1/b13-5+,14-6+,15-7+,16-8+; |
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| InChI = 1S/C42H44BO12.ClH/c1-48-39-21-27(9-17-35(39)44)5-13-31-25-32(14-6-28-10-18-36(45)40(22-28)49-2)53-43(52-31)54-33(15-7-29-11-19-37(46)41(23-29)50-3)26-34(55-43)16-8-30-12-20-38(47)42(24-30)51-4;/h5-24,31-34,44-47H,25-26H2,1-4H3;1H/q+1;/p-1/b13-5+,14-6+,15-7+,16-8+; |
| InChI = 1S/C42H44BO12.ClH/c1-48-39-21-27(9-17-35(39)44)5-13-31-25-32(14-6-28-10-18-36(45)40(22-28)49-2)53-43(52-31)54-33(15-7-29-11-19-37(46)41(23-29)50-3)26-34(55-43)16-8-30-12-20-38(47)42(24-30)51-4;/h5-24,31-34,44-47H,25-26H2,1-4H3;1H/q+1;/p-1/b13-5+,14-6+,15-7+,16-8+; |
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| InChIKey1 = XZWTYNUGOWPDCM-JWMINOHISA-M |
| InChIKey1 = XZWTYNUGOWPDCM-JWMINOHISA-M |
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| CASNo_Ref = {{cascite|correct|PubChem}} |
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| CASNo = 37204-72-1 |
| CASNo = 37204-72-1 |
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|Section2={{Chembox Properties |
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| Formula = [B(C<sub>21</sub>H<sub>19</sub>O<sub>6</sub>)<sub>2</sub>]Cl (as chloride) |
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| MolarMass = 781.013 g/mol |
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| Appearance = dark-green colored solid |
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| Density = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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'''Rosocyanine''' and [[ |
'''Rosocyanine''' and [[rubrocurcumin]] are two red colored materials, which are formed by the reaction between [[curcumin]] and [[borate]]s. |
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==Application== |
==Application== |
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The [[color reaction]] between [[borate]]s and [[curcumin]] is used |
The [[color reaction]] between [[borate]]s and [[curcumin]] is used for the [[spectrophotometrical|spectrophotometric]] determination and quantification of [[boron]] present in food or materials. [[Curcumin]] is a yellow coloring [[natural pigment]] found in the root stocks of some ''[[Curcuma]]'' species, especially [[turmeric|''Curcuma longa'']] (turmeric), in concentrations up to 3%. In the so-called curcumin method for [[boron quantification]] it serves as reaction partner for [[boric acid]]. The reaction is very sensitive and so the smallest quantities of [[boron]] can be detected. The maximum absorbance at 540 nm for rosocyanine is used in this [[colorimetry|colorimetric]] method. The formation of rosocyanine depends on the reaction conditions. The reaction is carried out preferentially in acidic solutions containing hydrochloric or sulfuric acid. The color reaction also takes place under different conditions; however, in [[alkaline]] solution, gradual decomposition is observed. The reaction might be disturbed at higher [[pH]] values, interfering with other compounds.{{citation needed|date=April 2024}} |
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[[Image:Rosocyanine-3D-vdW.png|thumb|Space filling model]] |
[[Image:Rosocyanine-3D-vdW.png|thumb|Space filling model]] |
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Rosocyanine is formed as |
Rosocyanine is formed as a 2:1 complex from curcumin and boric acid in acidic solutions. The boron complexes formed with rosocyanine are [[dioxaborines]] (here a 1,3,2-dioxaborine). Curcumin possesses a 1,3-[[diketone]] structure and can therefore be considered as a [[chelating agent]]. Unlike the simpler 1,3-diketone–containing compound [[acetylacetone]] (which forms [[metal acetylacetonates|acetylacetonate complexes]] with metals), the entire skeleton of curcumin is in [[resonance (chemistry)|resonance]] with the 1,3-dicarbonyl section, making the backbone an extended [[conjugated system]]. Investigations of the structure have shown that the positive charge is distributed throughout the molecule. In rosocyanine, the two curcumin moieties are not coplanar but rather perpendicular relative to one another (as seen in the 3D model), as a result of the tetrahedral geometry of tetracoordinate boron. The same applies to rubrocurcumin. |
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In order to exclude the |
In order to exclude the presence of other materials during the boron quantification using the curcumin method, a variant of the process was developed. In this process, [[2,2-dimethyl-1,3-hexanediol]] or [[2-ethyl-1,3-hexanediol]] are added, in addition to curcumin, to a neutral solution of the boron-containing solution. The complex formed between boron and the 1,3-hexanediol derivative is removed from the aqueous solution by extraction in an organic solvent. Acidification of the organic phase yields rubrocyanine, which can be detected by colorimetric methods. The reaction of curcumin with borates in presence of oxalic acid produces the coloring compound [[rubrocurcumin]]. |
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==Characteristics== |
==Characteristics== |
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Rosocyanine is a dark |
Rosocyanine is a dark green solid with a glossy, metallic shine that forms red colored solutions. It is almost insoluble in water and some organic solvents, very slightly soluble (up to 0.01%) in [[ethanol]], and somewhat soluble (approximately 1%) in [[pyridine]], [[sulfuric acid]], and [[acetic acid]]. An alcoholic solution of rosocyanine temporarily turns deeply blue on treatment with [[alkali]]. |
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In rubrocurcumin one molecule curcumin is replaced with [[oxalic acid]]. Rubrocurcumin produces a similar red colored solution. Rosocyanine is an ionic compound, while rubrocurcumin is a neutral complex. |
In rubrocurcumin one molecule of curcumin is replaced with [[oxalic acid]]. Rubrocurcumin produces a similar red colored solution. Rosocyanine is an ionic compound, while rubrocurcumin is a neutral complex. |
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==See also== |
==See also== |
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==References== |
==References== |
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{{Refbegin|30em}} |
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* M. E. Schlumberger: Sur la réaction de l'acide borique sur la curcumine. In: ''Bulletin de la Société Chimique de Paris'' N.S. 5, p. 194-202 (1866), ISSN: 0991-6504. |
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* {{ cite journal | last = Schlumberger | first = M. E. | title = Sur la réaction de l'acide borique sur la curcumine | trans-title = On the reaction of boric acid upon curcumin | journal = Bulletin de la Société Chimique de Paris | volume = 5 | issue = 1 | pages = 194–202 | date = 1866 | issn = 0991-6504 | url = https://books.google.com/books?id=gPBGAQAAIAAJ&pg=PA194 }} |
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* L. Clarke and C. L. Jackson: Rosocyanine. In: ''American Chemical Journal'' Vol. 39, p. 696-719 (1908); ISSN: 0096-4085, [[CODEN]]: ACJOAZ. |
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* {{ cite journal | last1 = Clarke | first1 = L. | last2 = Jackson | first2 = C. L. | title = Rosocyanine | journal = American Chemical Journal | volume = 39 | pages = 696–719 | date = 1908 | issn = 0096-4085 | id = CODEN: ACJOAZ | url = https://books.google.com/books?id=woIFAQAAIAAJ&pg=PA696 | lccn = 14006052 }} |
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* Spicer, G. S.; Strickland, J. D. H. Compounds of Curcumin and Boric acid. Part I. The structure of rosocyanin ''Journal of the Chemical Society (London),'' '''1952''', 4644-4650. ISSN: 0368-1769, CODEN: JCSOA9. |
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* |
* {{ cite journal | last1 = Spicer | first1 = G. S. | last2 = Strickland | first2 = J. D. H. | title = Compounds of Curcumin and Boric acid. Part I. The Structure of Rosocyanin | journal = Journal of the Chemical Society | date = 1952 | volume = 1952 | issue = article 906 | pages = 4644–4650 | issn = 0368-1769 | doi = 10.1039/JR9520004644 | id = CODEN: JCSOA9 }} |
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* {{ cite journal | last1 = Bellamy | first1 = L. J. | last2 = Spicer | first2 = G. S. | last3 = Strickland | first3 = J. D. H. | title = Compounds of Curcumin and Boric acid. Part III. Infra-red Studies of Rosocyanine and Allied Compounds | journal = Journal of the Chemical Society | date = 1952 | volume = 1952 | issue = article 908 | pages = 4653–4656 | issn = 0368-1769 | id = CODEN: JCSOA9 | doi = 10.1039/JR9520004653 }} |
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* G. S. |
* {{ cite journal | last1 = Spicer | first1 = G. S. | last2 = Strickland | first2 = J. D. H. | title = Determination of microgram and submicrogram amounts of boron. I. Absorptiometric determination with curcumin | journal = Analytica Chimica Acta | volume = 18 | pages = 231–239 | date = 1958 | issn = 0003-2670 | id = CODEN: ACACAM | doi = 10.1016/S0003-2670(00)87133-0 }} |
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* H. J. Roth and B. Miller: Zur Kenntnis der Farbreaktion zwischen Borsaeure und Curcumin, I. In: ''Archiv der Pharmazie, Berichte der Deutschen Pharmazeutischen Gesellschaft'' Vol. 297, No. 10, p. 617-623 (1964); ISSN: 0376-0367, CODEN: APBDAJ. |
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* H. J. |
* {{ cite journal | last1 = Roth | first1 = H. J. | last2 = Miller | first2 = B. | title = Zur Kenntnis der Farbreaktion zwischen Borsäure und Curcumin. I. Borinsäure-Curcumin-Komplexe | trans-title = On the understanding of the dye reaction between boric acid and curcumin. I. Borinate–curcumin complexes | journal = [[Archiv der Pharmazie]] | volume = 297 | issue = 10 | pages = 617–623 | date = 1964 | issn = 0376-0367 | id = CODEN: APBDAJ | doi = 10.1002/ardp.19642971007 | pmid = 14341926 | s2cid = 86246794 }} |
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* {{ cite journal | last1 = Roth | first1 = H. J. | last2 = Miller | first2 = B. | title = Zur Kenntnis der Farbreaktion zwischen Borsäure und Curcumin. II. Zur Konstitution des Rosocyanins und Rubrocurcumins | trans-title = On the understanding of the dye reaction between boric acid and curcumin. II. On the structure of rosocyanine and rubrocurcumin | journal = [[Archiv der Pharmazie]] | volume = 297 | issue = 11 | pages = 660–673 | date = 1964 | issn = 0376-0367 | id = CODEN: APBDAJ | doi = 10.1002/ardp.19642971104 | pmid = 5212809 | s2cid = 93540059 }} |
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* Fritz Umland, Detlef Thierig and Gunther Mueller: Photometrische Bestimmung von Bor im Picogram-Bereich. In: ''Fresenius Journal of Analytical Chemistry'' Vol. 215, No. 5, p. 401-406 (1966); ISSN: 0937-0633, CODEN: FJACEP. |
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* {{ cite journal | last1 = Umland | first1 = F. | last2 = Thierig | first2 = D. | last3 = Mueller | first3 = G. | title = Photometrische Bestimmung von Bor im Picogram-Bereich | trans-title = Photometric determination of boron in the picogram region | journal = Fresenius' Journal of Analytical Chemistry | volume = 215 | issue = 5 | pages = 401–406 | date =1966 | issn = 0937-0633 | id = CODEN: FJACEP | doi = 10.1007/BF00510442 | s2cid = 93038447 }} |
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* P. Quint and F. Umland: On the composition of the (1 2)-boron-curcumin-chelate »rosocyanine«. In: ''Fresenius Journal of Analytical Chemistry'' Vol. 295, No. 4, p. 269-270 (1979); ISSN: 0937-0633, CODEN: FJACEP. |
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* {{ cite journal | last1 = Quint | first1 = P. | last2 = Umland | first2 = F. | title = Über die Zusammensetzung des (1:2)-Bor-Curcumin-Chelates "Rosocyanin" | trans-title = On the composition of the (1:2) boron–curcumin chelate "rosocyanine" | journal = Fresenius' Journal of Analytical Chemistry | volume = 295 | issue = 4 | pages = 269–270 | date = 1979 | issn = 0937-0633 | id = CODEN: FJACEP | doi = 10.1007/BF00481491 | s2cid = 102246426 }} |
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* David W. Dyrssen, Yu. P. Novikov and Leif R. Uppstrom: Chemistry of the determination of boron with curcumin. In: ''Analytica Chimica Acta'' Vol. 60, No. 1, p. 139-151 (1972); ISSN: 0003-2670, CODEN: ACACAM. |
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* {{ cite journal | last1 = Dyrssen | first1 = D. W. | last2 = Novikov | first2 = Yu. P. | last3 = Uppstrom | first3 = L. R. | title = Studies on the chemistry of the determination of boron with curcumin | journal = Analytica Chimica Acta | volume = 60 | issue = 1 | pages = 139–151 | date = 1972 | issn = 0003-2670 | id = CODEN: ACACAM | doi = 10.1016/S0003-2670(01)81893-6 }} |
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* C. G. Kowalenko and L. M. Lavkulich: A modified curcumin method for boron analysis of soil extracts. In: ''Canadian Journal of Soil Science'' Vol. 56, No. 4, p. 537-539 (1976); ISSN: 0008-4271, CODEN: CJSSAR. |
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* {{ cite journal | last1 = Kowalenko | first1 = C. G. | last2 = Lavkulich | first2 = L. M. | title = A modified curcumin method for boron analysis of soil extracts | journal = Canadian Journal of Soil Science | volume = 56 | issue = 4 | pages = 537–539 | date = 1976 | issn = 0008-4271 | id = CODEN: CJSSAR | doi = 10.4141/cjss76-068 | url = http://pubs.aic.ca/doi/pdf/10.4141/cjss76-068 | format = pdf }} |
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* Ulrike de la Chevallerie-Haaf, Axel Meyer and Guenter Henze: Photometrische Bestimmung von Bor im Grund- and Oberflächenwasser. In: ''Fresenius Journal of Analytical Chemistry'' Vol. 323, No. 3, P. 266-270 (1986); ISSN: 0937-0633, CODEN: FJACEP. |
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* {{ cite journal | last1 = Chevallerie-Haaf | first1 = U. | last2 = Meyer | first2 = A. | last3 = Henze | first3 = G. | title = Photometrische Bestimmung von Bor im Grund- and Oberflächenwasser | trans-title = Photometric determination of boron in ground and surface water | journal = Fresenius' Journal of Analytical Chemistry | volume = 323 | issue = 3 | pages = 266–270 | date = 1986 | issn = 0937-0633 | id = CODEN: FJACEP | doi = 10.1007/BF00464089 }} |
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* Elsie M. Donaldson: Spectrophotometric determination of boron in iron and steel with curcumin after separation by 2-ethyl-1,3-hexanediol-chloroform extraction. In: ''Talanta'' Vol. 28, No. 11, p. 825-831 (1981); ISSN: 0039-9140, CODEN: TLNTA2. |
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* |
* {{ cite journal | last = Donaldson | first = E. M. | title = Spectrophotometric determination of boron in iron and steel with curcumin after separation by 2-ethyl-1,3-hexanediol-chloroform extraction | journal = Talanta | volume = 28 | issue = 11 | pages = 825–831 | date = 1981 | issn = 0039-9140 | id = CODEN: TLNTA2 | pmid = 18963014 | doi = 10.1016/0039-9140(81)80024-0 }} |
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* {{ cite journal | last = Wikner | first = B. | title = Boron determination in natural waters with curcumin using 2,2-dimethyl-1,3-hexanediol to eliminate interferences | journal = Communications in Soil Science and Plant Analysis | volume = 12 | issue = 7 | pages = 697–709 | date = 1981 | issn = 0010-3624 | id = CODEN: CSOSA2 | doi = 10.1080/00103628109367185 }} |
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{{Refend}} |
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[[Category:Curcuminoid dyes]] |
[[Category:Curcuminoid dyes]] |
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[[Category: |
[[Category:Tetrahydroxyborate esters]] |
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[[Category:Complexometric indicators]] |
[[Category:Complexometric indicators]] |
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[[Category:Oxycations]] |
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[[de:Rosocyanin]] |