DMACA reagent

p-Dimethylaminocinnamaldehyde

Names
IUPAC name 3-[4-(Dimethylamino)phenyl]prop-2-enal
Other names DMAC 4-Dimethylaminocinnamaldehyde
Identifiers
CAS Number	20432-35-3 Y
3D model (JSmol)	Interactive image
Abbreviations	DMACA
Beilstein Reference	972369
ChemSpider	4447567 (E) 23646677 (Z) 83262
ECHA InfoCard	100.025.698
EC Number	228-267-0
MeSH	4-Dimethylaminocinnamaldehyde
PubChem CID	5284506 (E) 25310830 (Z) 92224
UNII	9RSI7WZ9F0 Y
InChI 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
SMILES [H]C(=O)C=CC1=CC=C(C=C1)N(C)C
Properties
Chemical formula	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).
Infobox references

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

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. It is also particularly useful for localization of proanthocyanidins compounds in plants, resulting in a blue staining. It has been used for grapevine fruit or for legumes foliage histology.

A colorimetric assay based upon the reaction of A-rings with the chromogen. p-Dimethylaminocinnamaldehyde has been developed for flavanoids in beer that can be compared with the vanillin procedure. The DMACA reagent may be superior to the vanillin procedure for the detection of catechins.

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

The DMACA reagent may also be referred to as the Renz and Loew reagent.