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| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 413897454
| verifiedrevid = 413897454
| Name = Bicinchoninic acid
| Name = Bicinchoninic acid
| ImageFile = Structure of bicinchoninic acid.png
| ImageFile = Structure of bicinchoninic acid.png
| ImageSize = 200px
| ImageName =
| PIN = [2,2′-Biquinoline]-4,4′-dicarboxylic acid
| ImageName =
⚫
| OtherNames = Bicinchoninic acid<br>4,4′-Dicarboxy-2,2′-biquinoline<br>2,2'-Biquinoline-4,4'-dicarboxylic acid
| IUPACName = 2-(4-Carboxyquinolin-2-yl)quinoline-4-carboxylic acid
⚫
|Section1={{Chembox Identifiers
⚫
| OtherNames = Bicinchoninic acid<br>4,4'-Dicarboxy-2,2'-biquinoline
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| Section1 = {{Chembox Identifiers
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64223
| ChemSpiderID = 64223
| InChI = 1/C20H12N2O4/c23-19(24)13-9-17(21-15-7-3-1-5-11(13)15)18-10-14(20(25)26)12-6-2-4-8-16(12)22-18/h1-10H,(H,23,24)(H,25,26)
| SMILES = O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O
| SMILES = O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O
| InChIKey = AFYNADDZULBEJA-UHFFFAOYAF
| PubChem = 71068
| PubChem = 71068
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 1245-13-2
| CASNo = 1245-13-2
| CASNo_Comment = (free acid)
⚫
| RTECS =
| CASNo2_Ref = {{cascite|unknown|CAS}}
| CASNo2 = 979-88-4
| CASNo2_Comment = (disodium salt)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CX56TX9Y1I
⚫
| RTECS =
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=20|H=12|N=2|O=4
| C=20|H=12|N=2|O=4
| Appearance = Cream colored powder
| Appearance = Cream colored powder
| Odor = Characteristic odor{{vague|date=October 2013}}
| Odor = Characteristic odor{{vague|date=October 2013}}
| Density =
| Density =
| Solubility = Partially soluble in cold water, hot water{{vague|date=October 2013}}
| Solubility = Partially soluble in cold water, hot water{{vague|date=October 2013}}
| MeltingPtCL = 365
| MeltingPtC = 352
| MeltingPt_notes = decomposes
| MeltingPtCL = 367
| BoilingPt =
| BoilingPt =
| pKa =
| pKa =
}}
}}
| Section3 = {{Chembox Structure
|Section3={{Chembox Structure
| CrystalStruct =
| CrystalStruct =
| Dipole =
| Dipole =
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| ExternalMSDS = [http://www.gfschemicals.com/Search/MSDS/381MSDS.PDF External MSDS]
| ExternalSDS = [http://www.gfschemicals.com/Search/MSDS/381MSDS.PDF External MSDS]
| MainHazards = Will irritate eyes and mucous membranes.
| MainHazards = Will irritate eyes and mucous membranes.
| NFPA-H = 1
| NFPA-H = 1
| NFPA-R =
| NFPA-R =
| NFPA-F =
| NFPA-F =
| FlashPt =
| FlashPt =
}}
}}
}}
}}


'''Bicinchoninic acid''' ({{IPAc-en|b|aɪ|s|ɪ|n|k|ɔː|n|ɪ|n|ɪ|k}}) or '''BCA''' is a [[weak acid]] composed of two [[carboxyl]]ated [[quinoline]] rings. It is an organic compound with the formula (C<sub>9</sub>H<sub>5</sub>NCO<sub>2</sub>H)<sub>2</sub>. The molecule consists of a pair of [[quinoline]] rings, each bearing a [[carboxylic acid]] group. Its [[conjugate base|sodium salt]] forms a purple complex with [[Copper|cuprous]] ions.<ref>{{Cite journal|year=1985|title=Measurement of Protein Using Bicinchoninic Acid|journal=Analytical Biochemistry|volume=150|issue=1|pages=76–85|doi=10.1016/0003-2697(85)90442-7|last1=Smith |first1=P.K. |last2=Krohn |first2=R.I. |last3=Hermanson |first3=G.T. |last4=Mallia |first4=A.K. |last5=Gartner |first5=F.H. |last6=Provenzano |first6=M.D. |last7=Fujimoto |first7=E.K. |last8=Goeke |first8=N.M. |last9=Olson |first9=B.J. |last10=Klenk |first10=D.C. |pmid=3843705 }}</ref><ref>{{cite journal |doi=10.1016/0003-2697(89)90101-2|title=Protein measurement using bicinchoninic acid: Elimination of interfering substances |year=1989 |last1=Brown |first1=Rhoderick E. |last2=Jarvis |first2=Kari L. |last3=Hyland |first3=Kristi J. |journal=Analytical Biochemistry |volume=180 |issue=1 |pages=136–139 |pmid=2817336 }}</ref><ref>{{cite book |doi=10.1016/S0076-6879(09)63008-1|chapter=Chapter 8 Quantitation of Protein |title=Guide to Protein Purification, 2nd Edition |series=Methods in Enzymology |year=2009 |last1=Noble |first1=James E. |last2=Bailey |first2=Marc J.A. |volume=463 |pages=73–95 |pmid=19892168 |isbn=9780123745361 }}</ref>
'''Bicinchoninic acid''' is a weak acid composed of two [[carboxyl]]ated [[quinoline]] rings.


Bicinchoninic acid is most commonly employed by biochemists in the [[bicinchoninic acid assay|bicinchoninic acid (BCA) assay]], which is used to determine the total level of protein in a solution. In this assay, two molecules of bicinchoninic acid [[chelate]] a single [[Copper|Cu]]<sup>+</sup> ion, forming a purple water-soluble complex that strongly absorbs light at 562 [[nanometer|nm]].<ref>[http://www.piercenet.com/instructions/2161296.pdf Pierce BCA Protein Assay Kit]</ref>
Bicinchoninic acid is most commonly employed in the [[bicinchoninic acid assay|bicinchoninic acid (BCA) assay]], which is used to determine the total concentration of [[protein]] in a solution. Bicinchoninic acid is used to detect the presence of cuprous ions, due to its purple coloration via a [[Biuret test|biuret reaction]]. In this assay, two molecules of bicinchoninic acid [[chelate]] a single [[Copper|Cu]]<sup>+</sup> ion, forming a purple water-soluble complex that strongly absorbs light at 562 [[nanometer|nm]].<ref>[http://www.piercenet.com/instructions/2161296.pdf Pierce BCA Protein Assay Kit]</ref>


==References==
==References==
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[[Category:Dicarboxylic acids]]
[[Category:Dicarboxylic acids]]
[[Category:Aromatic acids]]
[[Category:Aromatic acids]]
[[Category:Dimers (chemistry)]]

Latest revision as of 10:10, 12 August 2024

Bicinchoninic acid
Names
Preferred IUPAC name
[2,2′-Biquinoline]-4,4′-dicarboxylic acid
Other names
Bicinchoninic acid
4,4′-Dicarboxy-2,2′-biquinoline
2,2'-Biquinoline-4,4'-dicarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.628 Edit this at Wikidata
UNII
  • InChI=1S/C20H12N2O4/c23-19(24)13-9-17(21-15-7-3-1-5-11(13)15)18-10-14(20(25)26)12-6-2-4-8-16(12)22-18/h1-10H,(H,23,24)(H,25,26) checkY
    Key: AFYNADDZULBEJA-UHFFFAOYSA-N checkY
  • O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O
Properties
C20H12N2O4
Molar mass 344.326 g·mol−1
Appearance Cream colored powder
Odor Characteristic odor[vague]
Melting point 352 °C (666 °F; 625 K) decomposes
Partially soluble in cold water, hot water[vague]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Will irritate eyes and mucous membranes.
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
1
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Bicinchoninic acid (/baɪsɪnkɔːnɪnɪk/) or BCA is a weak acid composed of two carboxylated quinoline rings. It is an organic compound with the formula (C9H5NCO2H)2. The molecule consists of a pair of quinoline rings, each bearing a carboxylic acid group. Its sodium salt forms a purple complex with cuprous ions.[1][2][3]

Bicinchoninic acid is most commonly employed in the bicinchoninic acid (BCA) assay, which is used to determine the total concentration of protein in a solution. Bicinchoninic acid is used to detect the presence of cuprous ions, due to its purple coloration via a biuret reaction. In this assay, two molecules of bicinchoninic acid chelate a single Cu+ ion, forming a purple water-soluble complex that strongly absorbs light at 562 nm.[4]

References

[edit]
  1. ^ Smith, P.K.; Krohn, R.I.; Hermanson, G.T.; Mallia, A.K.; Gartner, F.H.; Provenzano, M.D.; Fujimoto, E.K.; Goeke, N.M.; Olson, B.J.; Klenk, D.C. (1985). "Measurement of Protein Using Bicinchoninic Acid". Analytical Biochemistry. 150 (1): 76–85. doi:10.1016/0003-2697(85)90442-7. PMID 3843705.
  2. ^ Brown, Rhoderick E.; Jarvis, Kari L.; Hyland, Kristi J. (1989). "Protein measurement using bicinchoninic acid: Elimination of interfering substances". Analytical Biochemistry. 180 (1): 136–139. doi:10.1016/0003-2697(89)90101-2. PMID 2817336.
  3. ^ Noble, James E.; Bailey, Marc J.A. (2009). "Chapter 8 Quantitation of Protein". Guide to Protein Purification, 2nd Edition. Methods in Enzymology. Vol. 463. pp. 73–95. doi:10.1016/S0076-6879(09)63008-1. ISBN 9780123745361. PMID 19892168.
  4. ^ Pierce BCA Protein Assay Kit
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