P-Dimethylaminocinnamaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
p-Dimethylaminocinnamaldehyde (DMACA) is an aromatic hydrocarbon. It is used in an acidic solution to detect indoles.
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| Names | |
|---|---|
| IUPAC name
3-[4-(Dimethylamino)phenyl]prop-2-enal | |
| Other names
DMAC 4-Dimethylaminocinnamaldehyde | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | DMACA |
| 972369 | |
| ChemSpider | |
| EC Number |
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| MeSH | 4-Dimethylaminocinnamaldehyde |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C11H13NO | |
| Molar mass | 175.22 g/mol |
| Appearance | white 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 dioxane | 50 g/L |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Use as a testing reagent
The DMACA is any of a number of acidified DMACA solutions:
- 0.117 g of DMACA, 39 mL of ethanol, 5 mL of conc hydrochloric acid and diluted to 50mL with water[1]
- 1 g DMACA, 1 mL conc. hydrochloric acid and 99 mL water[2]
- 1 g DMACA in 99 mL conc. hydrochloric acid.[3]
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
- Ehrlich's reagent, a simple spot-test to presumptively identify alkaloids