P-Dimethylaminocinnamaldehyde

Last updated
p-Dimethylaminocinnamaldehyde
Dimethylaminocinnamaldehyde.svg
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
MeSH 4-Dimethylaminocinnamaldehyde
PubChem CID
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 mass 175.22 g/mol
Appearancewhite to light yellow crystal powder
Density 1.057 g/mL
Melting point 138 °C (280 °F; 411 K)
Boiling point 329 °C (624 °F; 602 K)
Solubility in dioxane50 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

Contents

Use as a testing reagent

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

It is primarily used as a histological dye used to detect indoles, particularly for production in cells. It is used for the rapid identification of bacteria containing tryptophanase enzyme systems.[ citation needed ] It is also particularly useful for localization of proanthocyanidins 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 for flavanoids in beer that can be compared with the vanillin procedure. [6] The DMACA reagent may be superior to the vanillin procedure for the detection of catechins. [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

Related Research Articles

Flavonoid Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in diets.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Catechin Type of natural phenol and antioxidant. A plant secondary metabolite

Catechin is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols, part of the chemical family of flavonoids.

Proanthocyanidins are a class of polyphenols found in a variety of plants such as blueberry. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

Thearubigins are polymeric polyphenols that are formed during the enzymatic oxidation and condensation of two gallocatechins with the participation of polyphenol oxidases during the fermentation reactions in black tea. Thearubigins are red in colour and are responsible for much of the staining effect of tea. Therefore, a black tea often appears red while a green or white tea has a much clearer appearance. The colour of a black tea, however, is affected by many other factors as well, such as the amount of theaflavins, another oxidized form of polyphenols.

Procyanidin

Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

Vanillic acid Chemical compound

Vanillic acid is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid.

The Duquenois reagent is used in the Rapid Modified Duquenois–Levine test, is an established screening test for the presence of cannabis. The test was initially developed in the 1930s by the French Medical Biochemist, Pierre Duquénois (1904–1986), and was adopted in the 1950s by the United Nations as the preferred test for cannabis, and originally claimed to be specific to cannabis. After several modifications, it became known as the Duquenois–Levine test. However, in the 1960s and 70s various studies showed that the test was not specific to cannabis. In 1973 the Supreme Court of Wisconsin ruled the D–L test insufficient evidence for demonstrating that a substance was cannabis, specifically noting that the D–L tests used "are not exclusive or specific for marijuana."

Phenolic content in wine

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Ehrlich's reagent or Ehrlich reagent is a reagent that contains p-dimethylaminobenzaldehyde (DMAB) and thus can act as an indicator to presumptively identify indoles and urobilinogen. Several Ehrlich tests use the reagent in a medical test; some are drug tests and others contribute to diagnosis of various diseases or adverse drug reactions. A very common Ehrlich test is a simple spot test to identify possible psychoactive compounds such as tryptamines and ergoloids. It gives a negative test-result for 25I-NBOMe and many other non-indole-related psychoactives. The reagent will also give a positive result for opium, because of the presence of tryptophan in natural opium. It is named after Nobel Prize winner Paul Ehrlich who used it to distinguish typhoid from simple diarrhoea.

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.

Leucocyanidin Chemical compound

Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, polyphenols, condensed tannins, and OPCs. Proanthocyanidins were first popularized by French scientist Jacques Masquelier.

Procyanidin A2 Chemical compound

Procyanidin A2 is an A type proanthocyanidin.

Epicatechin gallate Chemical compound

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape.

DMACA may refer to:

Condensed tannin

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

Tryptophol Chemical compound

Tryptophol is an aromatic alcohol that induces sleep in humans. It is found in wine as a secondary product of ethanol fermentation. It was first described by Felix Ehrlich in 1912. It is also produced by the trypanosomal parasite in sleeping sickness.

Dragendorffs reagent

Dragendorff's reagent is a color reagent to detect alkaloids in a test sample or as a stain for chromatography plates. Alkaloids, if present in the solution of sample, will react with Dragendorff's reagent and produce an orange or orange-red precipitate. This reagent was invented by the German pharmacologist, Johann Georg Dragendorff (1836–1898) at the University of Dorpat.

References

  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" . Retrieved 2013-10-29.
  3. 1 2 Chung, 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.