| Identification | More | [Name]
4-(Dimethylamino)cinnamaldehyde | [CAS]
6203-18-5 | [Synonyms]
(2E)-3-[4-(DIMETHYLAMINO)PHENYL]PROP-2-ENAL
4-DIMETHYLAMINOCINNAMALDEHYDE
4-(DIMETHYLAMINO)-CINNAMALDEHYDE REAGENT
4-(N,N-DIMETHYLAMINO)CINNAMALDEHYDE
DIMETHYLAMINOCINNAMALDEYHDE,4-
DMACA REAGENT
(E)-4-DIMETHYLAMINOCINNAMALDEHYDE
P-DIMETHYLAMINOCINNAMALDEHYDE
(2E)-3-[4-(Dimethylamino)phenyl]-2-propenal
3-(4-(dimethylamino)phenyl)-2-Propenal
3-[4-(dimethylamino)phenyl]-2-propena
4-Dimethylaminocinnamic aldehyde
4-Dimethylcinnamaldehyde
Cinnamaldehyde, p-(dimethylamino)-
p-Dimethylaminocinnamic aldehyde
p-N,N-Dimethylaminocinnamaldehyde
4-Dymethylaminocinnamaldehyde
4-(N,N-DIMETHYLAMINO)-CINNAMIC ALDEHYDE R. G.
P-DimethylAminoCinnamaldehydeGr
4-DIMETHYLAMINO CHINAMALDEHYDE | [EINECS(EC#)]
228-267-0 | [Molecular Formula]
C11H13NO | [MDL Number]
MFCD00007002 | [Molecular Weight]
175.23 | [MOL File]
6203-18-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
138-140 °C(lit.)
| [Boiling point ]
306.53°C (rough estimate) | [density ]
1.0582 (rough estimate) | [refractive index ]
1.5260 (estimate) | [storage temp. ]
−20°C
| [solubility ]
dioxane: 50 mg/mL, clear
| [form ]
Powder | [pka]
4.59±0.24(Predicted) | [color ]
Yellow to orange | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong bases. | [Sensitive ]
Air & Light Sensitive | [BRN ]
972369 | [InChIKey]
RUKJCCIJLIMGEP-ONEGZZNKSA-N | [LogP]
2.630 (est) | [CAS DataBase Reference]
6203-18-5(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Propenal, 3-[4-(dimethylamino)phenyl]-(6203-18-5) | [EPA Substance Registry System]
6203-18-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1789 8/PG 3
| [WGK Germany ]
3
| [F ]
8-10-23 | [TSCA ]
Yes | [HS Code ]
29124990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
4-(Dimethylamino)cinnamaldehyde is a reagent for assay of indole product of apotryptophanase and tryptophanase. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder.
| [Definition]
ChEBI: 4-dimethylaminocinnamaldehyde is a member of cinnamaldehydes. | [General Description]
DMACA is basically a selective staining reagent. It helps identify the flavanols by staining them blue in color. | [Biochem/physiol Actions]
Reagent for assay of indole product of apotryptophanase and tryptophanase. DMAC produces colored adducts with flavanols for subsequent HPLC. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder. | [Synthesis]
General procedure for the synthesis of (E)-3-(4-(dimethylamino)phenyl)acrolein from acetaldehyde and p-dimethylaminobenzaldehyde: A mixture of 4-N,N-dimethylaminobenzaldehyde (5.00 g, 34 mmol) with 25 ml of concentrated sulfuric acid was cooled to 0°C. Subsequently, 1 ml of distilled water was slowly added. Keeping the reaction mixture at 0°C, acetaldehyde (5.6 ml, 102 mmol) was added dropwise, ensuring that the reaction temperature did not exceed 2°C. After the dropwise addition, the dark reaction mixture was continued to be stirred at 0°C for 0.5 hours. Subsequently, the reaction mixture was poured into ice water and neutralized with 10% NaOH solution to pH 7. The resulting brown solution was filtered and the crude product was washed with distilled water and crystallized twice by ethanol to give a final orange solid product. The yield was 56% and the melting point was 134-136 °C. The product was analyzed by FT-IR (KBr, cm^-1 ) showing characteristic peaks: 2921, 2801, 2738, 1662, 1599, 1527, 1456, 1373. 1H NMR (300 MHz, CDCl3, ppm) data were as follows: δ 9.62 (1H, d, J=7.5 Hz), 7.48 (2H, d, J=7.5 Hz), 7.41 (1H, d, J=13.1 Hz), 6.71 (2H, d, J=7.5 Hz), 6.57 (1H, dd, J=7.5 Hz, 13.1 Hz), 3.08 (6H, s). Mass spectrometry (MS) analysis showed the molecular ion peak m/z: 176.2 (M+), consistent with the molecular formula C11H13NO. | [Purification Methods]
The aldehyde crystallises from EtOH or ligroin and is dried in vacuo. The oxime has m 157o (from ligroin). The phenylhydrazone has m 169o (form MeOH). It is used as a reagent for amines (with NH3, UV has max at 630nm). [K.nig et al. Chem Ber 61 2075 2075, Quareshi & Kahn Anal Chim Acta 86 309 1976, Beilstein 14 III 184, 14 IV 197.] | [References]
[1] Dyes and Pigments, 2017, vol. 139, p. 820 - 830
[2] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 8, p. 1254 - 1260
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1803 - 1807 |
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