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p-Dimethylaminocinnamaldehyde

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(Redirected fromDMACA reagent)
p-Dimethylaminocinnamaldehyde
Names
IUPAC name
3-[4-(Dimethylamino)phenyl]prop-2-enal
Other names
DMAC
4-Dimethylaminocinnamaldehyde
Identifiers
3D model (JSmol)
AbbreviationsDMACA
972369
ChemSpider
EC Number
  • 228-267-0
MeSH4-Dimethylaminocinnamaldehyde
UNII
  • InChI=1S/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+
    Key: RUKJCCIJLIMGEP-ONEGZZNKSA-N
  • InChI=1/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+
    Key: RUKJCCIJLIMGEP-ONEGZZNKBZ
  • [H]C(=O)C=CC1=CC=C(C=C1)N(C)C
Properties
C11H13NO
Molar mass175.22 g/mol
Appearancewhite to light yellow crystal powder
Density1.057 g/mL
Melting point138 °C (280 °F; 411 K)
Boiling point329 °C (624 °F; 602 K)
Solubility in dioxane50 g/L
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

p-Dimethylaminocinnamaldehyde (DMACA) is an aromatic hydrocarbon. It is used in an acidic solution to detect indoles.

Use as a testing reagent

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The DMACA is any of a number of acidified DMACA solutions:

  • 0.117 g of DMACA, 39 mL ofethanol, 5 mL of conchydrochloric acid and diluted to 50mL with water[1]
  • 1 g DMACA, 1 mL conc. hydrochloric acid and 99 mLwater[2]
  • 1 g DMACA in 99 mL conc. hydrochloric acid.[3]

It is primarily used as a histological dye used to detectindoles, particularly for production in cells. It is used for the rapid identification of bacteria containingtryptophanase enzyme systems.[citation needed] It is also particularly useful for localization ofproanthocyanidins compounds in plants, resulting in a blue staining. It has been used for grapevine fruit[4] or for legumes foliage[5] histology.

A colorimetric assay based upon the reaction of A-rings[clarification needed] with the chromogen.p-Dimethylaminocinnamaldehyde has been developed forflavanoids in beer that can be compared with thevanillin procedure.[6] The DMACA reagent may be superior to the vanillin procedure for the detection ofcatechins.[7]

The DMACA reagent changes color over several days when exposed to air but when refrigerated can be stored for up to two weeks.[8]

The DMACA reagent may also be referred to as the Renz and Loew reagent.[3][9]

See also

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References

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  1. ^Porubsky, P.; Scott, E.; Williams, T. (2008)."P-Dimethylaminocinnamaldehyde derivatization for colorimetric detection and HPLC–UV/vis–MS/MS identification of indoles".Archives of Biochemistry and Biophysics.475 (1):14–17.doi:10.1016/j.abb.2008.03.035.PMC 2504418.PMID 18423367.
  2. ^Sigma-Aldrich Co. LLC."DMACA Reagent for microbiology". Retrieved2013-10-29.
  3. ^abChung, K. R.; Shilts, T.; Ertürk, Ã. M.; Timmer, L. W.; Ueng, P. P. (2003)."Indole derivatives produced by the fungusColletotrichum acutatumcausing lime anthracnose and postbloom fruit drop of citrus".FEMS Microbiology Letters.226 (1):23–30.doi:10.1016/S0378-1097(03)00605-0.PMID 13129603.
  4. ^Bogs, J.; Jaffe, F. W.; Takos, A. M.; Walker, A. R.; Robinson, S. P. (2007)."The Grapevine Transcription Factor VvMYBPA1 Regulates Proanthocyanidin Synthesis during Fruit Development".Plant Physiology.143 (3):1347–1361.doi:10.1104/pp.106.093203.PMC 1820911.PMID 17208963.
  5. ^Li, Y. G.; Tanner, G.; Larkin, P. (1996). "TheDMACA-HCl Protocol and the Threshold Proanthocyanidin Content for Bloat Safety in Forage Legumes".Journal of the Science of Food and Agriculture.70:89–101.doi:10.1002/(SICI)1097-0010(199601)70:1<89::AID-JSFA470>3.0.CO;2-N.
  6. ^A new colourimetric assay for flavonoids in pilsner beers. Jan A. Delcour and Didier Janssens de Varebeke, Journal of the Institute of Brewing, January–February 1985, Volume 91, Issue 1, pages 37–40,doi:10.1002/j.2050-0416.1985.tb04303.x
  7. ^Glavnik, V.; Simonovska, B.; Vovk, I. (2009). "Densitometric determination of (+)-catechin and (−)-epicatechin by 4-dimethylaminocinnamaldehyde reagent".Journal of Chromatography A.1216 (20):4485–91.doi:10.1016/j.chroma.2009.03.026.PMID 19339019.
  8. ^Meudt, W. J.; Gaines, T. P. (1967)."Studies on the Oxidation of Indole-3-Acetic Acid by Peroxidase Enzymes. I. Colorimetric Determination of Indole-3-Acetic Acid Oxidation Products".Plant Physiology.42 (10):1395–9.doi:10.1104/pp.42.10.1395.PMC 1086736.PMID 16656668.
  9. ^Ehmann, A. (1977)."The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives"(PDF).Journal of Chromatography A.132 (2):267–276.doi:10.1016/S0021-9673(00)89300-0.PMID 188858.

External links

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