Login
Login

p-Dimethylaminocinnamaldehyde

{{DISPLAYTITLE: p-Dimethylaminocinnamaldehyde}}

{{Chembox

| Name = p-Dimethylaminocinnamaldehyde

| Watchedfields = changed

| ImageFile = Dimethylaminocinnamaldehyde.svg

| ImageSize = 200px

| IUPACName = 3-[4-(Dimethylamino)phenyl]prop-2-enal

| OtherNames = DMAC

4-Dimethylaminocinnamaldehyde

|Section1={{Chembox Identifiers

| Abbreviations = DMACA

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 20432-35-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9RSI7WZ9F0

| PubChem = 5284506

| PubChem_Comment = (E)

| PubChem1 = 25310830

| PubChem1_Comment = (Z)

| PubChem2 = 92224

| PubChem2_Comment =

| ChemSpiderID = 4447567

| ChemSpiderID_Comment = (E)

| ChemSpiderID1 = 23646677

| ChemSpiderID1_Comment = (Z)

| ChemSpiderID2 = 83262

| ChemSpiderID2_Comment =

| EINECS = 228-267-0

| MeSHName = 4-Dimethylaminocinnamaldehyde

| SMILES = [H]C(=O)C=CC1=CC=C(C=C1)N(C)C

| InChI = 1/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+

| InChIKey = RUKJCCIJLIMGEP-ONEGZZNKBZ

| StdInChI = 1S/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+

| StdInChIKey = RUKJCCIJLIMGEP-ONEGZZNKSA-N

| Beilstein = 972369}}

|Section2={{Chembox Properties

| Formula = C11H13NO

| MolarMass = 175.22 g/mol

| Appearance = white to light yellow crystal powder

| Density = 1.057 g/mL

| MeltingPtC = 138

| BoilingPtC = 329

| SolubleOther = 50 g/L

| Solvent = dioxane

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

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

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{{Cite journal | last1 = Porubsky | first1 = P. | last2 = Scott | first2 = E. | last3 = Williams | first3 = T. | doi = 10.1016/j.abb.2008.03.035 | title = P-Dimethylaminocinnamaldehyde derivatization for colorimetric detection and HPLC–UV/vis–MS/MS identification of indoles | journal = Archives of Biochemistry and Biophysics | volume = 475 | issue = 1 | pages = 14–17 | year = 2008 | pmid = 18423367| pmc =2504418 }}
  • 1 g DMACA, 1 mL conc. hydrochloric acid and 99 mL water{{cite web | url = http://www.sigmaaldrich.com/catalog/product/fluka/49825?lang=en®ion=GB | title = DMACA Reagent for microbiology | access-date = 2013-10-29 | author = Sigma-Aldrich Co. LLC}}
  • 1 g DMACA in 99 mL conc. hydrochloric acid.{{Cite journal | last1 = Chung | first1 = K. R. | last2 = Shilts | first2 = T. | last3 = Ertürk | first3 = Ã. M. | last4 = Timmer | first4 = L. W. | last5 = Ueng | first5 = P. P. | title = Indole derivatives produced by the fungusColletotrichum acutatumcausing lime anthracnose and postbloom fruit drop of citrus | doi = 10.1016/S0378-1097(03)00605-0 | journal = FEMS Microbiology Letters | volume = 226 | issue = 1 | pages = 23–30 | year = 2003 | pmid = 13129603| doi-access = free }}

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|date=October 2013}} It is also particularly useful for localization of proanthocyanidins compounds in plants, resulting in a blue staining. It has been used for grapevine fruit{{Cite journal | last1 = Bogs | first1 = J. | last2 = Jaffe | first2 = F. W. | last3 = Takos | first3 = A. M. | last4 = Walker | first4 = A. R. | last5 = Robinson | first5 = S. P. | title = The Grapevine Transcription Factor VvMYBPA1 Regulates Proanthocyanidin Synthesis during Fruit Development | doi = 10.1104/pp.106.093203 | journal = Plant Physiology | volume = 143 | issue = 3 | pages = 1347–1361 | year = 2007 | pmid = 17208963| pmc =1820911 }} or for legumes foliage{{Cite journal | last1 = Li | first1 = Y. G. | last2 = Tanner | first2 = G. | last3 = Larkin | first3 = P. | title = TheDMACA-HCl Protocol and the Threshold Proanthocyanidin Content for Bloat Safety in Forage Legumes | doi = 10.1002/(SICI)1097-0010(199601)70:1<89::AID-JSFA470>3.0.CO;2-N | journal = Journal of the Science of Food and Agriculture | volume = 70 | pages = 89–101 | year = 1996 }} histology.

A colorimetric assay based upon the reaction of A-rings{{clarify|date=October 2013}} with the chromogen. p-Dimethylaminocinnamaldehyde has been developed for flavanoids in beer that can be compared with the vanillin procedure.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}} The DMACA reagent may be superior to the vanillin procedure for the detection of catechins.{{Cite journal | doi = 10.1016/j.chroma.2009.03.026| pmid = 19339019| title = Densitometric determination of (+)-catechin and (−)-epicatechin by 4-dimethylaminocinnamaldehyde reagent| journal = Journal of Chromatography A| volume = 1216| issue = 20| pages = 4485–91| year = 2009| last1 = Glavnik | first1 = V. | last2 = Simonovska | first2 = B. | last3 = Vovk | first3 = I. }}

The DMACA reagent changes color over several days when exposed to air but when refrigerated can be stored for up to two weeks.{{Cite journal | doi = 10.1104/pp.42.10.1395| title = Studies on the Oxidation of Indole-3-Acetic Acid by Peroxidase Enzymes. I. Colorimetric Determination of Indole-3-Acetic Acid Oxidation Products| year = 1967| last1 = Meudt | first1 = W. J.| last2 = Gaines | first2 = T. P.| journal = Plant Physiology| volume = 42| issue = 10| pages = 1395–9 | pmid=16656668 | pmc=1086736}}

The DMACA reagent may also be referred to as the Renz and Loew reagent.{{Cite journal | last1 = Ehmann | first1 = A. | title = The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives | doi = 10.1016/S0021-9673(00)89300-0 | journal = Journal of Chromatography A | volume = 132 | issue = 2 | pages = 267–276| year = 1977 | pmid = 188858| url = https://erowid.org/psychoactives/testing/testing_field_article2.pdf}}

See also

References

{{reflist|2}}

External links

  • [http://www.bd.com/ds/productCenter/261187.asp DMACA on www.bd.com]

{{DEFAULTSORT:Dimethylaminocinnamaldehyde, p-}}

Category:Conjugated aldehydes

Category:Anilines

Category:Drug testing reagents

Category:Histology

Category:Staining dyes