M-Phthalaldehyde

Yoshimura, T. KamataM, T. Miura, T. Difference between histidine and histamine in the mechanistic pathway of the fluorescence reaction with ort/m-phthalaldehyde. Anal. Biochem. 1990, 188, 132-135. 

Berlin and Breitmaier [188] first synthesized a benzene-containing porphyrin analog 325. The method exploits the ready availability of tri- or tris-pyrroles 326 and their ability to condense with m-phthalaldehyde 327 and related compounds to give the macrocycle 325 (Scheme 6.80a). Owing to the presence of the benzene ring in the ring system, 325 does not exhibit aromatic properties. Soon after, Lash [189] reported that the macrocycle obtained by reaction of 326 with 5-formylsalicylaldehyde 328 exists in the keto form 329 as a fairly stable aromatic compound rather than in the phenolic form 330 (Scheme 6.80b). 

Phthalaldehyde [643-79-8] M 134.1, m 54-56°, 55.5-56°, 58°, b 83-84°/0.8mm. Purified by steam distillation better by using super heated steam (at 175-180°) and efficient cooling. The distillate is saturated with Na2S04 extracted exhaustively with EtOAc, dried (Na2S04), filtered and evaporated. The residue... 

Phenyl thiocarbamide, pi58 a-Phenyl-o-tohiic acid, b84 Phenyl m-tolyl ether, p76 Phloroglucinol, t318 Phorone, d613 Phthalaldehydic acid, 37... 

H Brucker, M Langer, M Lupke, T Westhauser, H Godel. Liquid chromatographic determination of amino acid enantiomers by derivatization with o-phthalaldehyde and chiral thiols. Applications with reference to food science. J Chromatogr A 697 229-245, 1995. 

Method (manual). An aliquot portion (0.1 ml) of effluent containing the amino acid is mixed with 3 ml of a solution containing 1.5 ml of o-phthalaldehyde (10 mg/ml in ethanol), 90 ml of sodium tetraborate buffer (0.05 M, pH 9.5) and 1.5 ml of a solution of 2-mercaptoethanol (5 mg/ml) in ethanol. The latter reagent should be freshly prepared each day. The reaction mixture is permitted to stand for 5 min and the intensity of fluorescence is measured in a fluorimeter (340-nm excitation, 455-nm emission). The buffered reagent may be also useful as a spray reagent for amino acids separated by TLC, although such an investigation has not been reported. 

Phloroglucinol, t305 Phorone, d529 Phthalaldehydic acid, f33 m-Phthalic acid, bl6 p-Phthalic acid, bl7 Phthalonitrile, d236... 

Lehtonen, P., Saarinen, M., Vesanto, M., and Riekkola, M. L. Z. (1992). Determination of wine amines by HPLC using automated precolumn derivatisation with o-phthalaldehyde and fluorescence detection. Lebensm. Unters. Forsch. 194, 434-437. 

Following derivatization with o-phthalaldehyde, TV1 -acetylspermidine, and putrescine are separated on a Beckman Ultrasphere ion-pair column (4.6 mm x 250 mm, 5 /urn). Solvent A was composed of 0.1 M sodium acetate and 10 mM octanesulfonic acid adjusted to pH 4.5 with acetic acid. Solvent B contained 0.2 M sodium acetate (pH 4.5)-acetonitrile (10 3, v/v) with 10 mM octanesulfonic acid. A linear gradient from 35% A and 65% B to 100% B was achieved in 10 minutes, followed by continued flow of solvent B for 15 minutes. The flow rate was 1 mL/min. Postminutes, column derivatization of polyamines with o-phthalaldehyde was accomplished with a pump. Fluorescence detection was used, with excitation and emission wavelengths of 340 and 455 nm. 

When pure 3-bromophthalide is allowed to stand, its melting point is depressed, owing apparently to some decomposition. It may, therefore, be desirable to prepare the compound in smaller quantities than specified here. A sample of 3-bromophthalide, prepared by using 20 g. of phthalide and 26.6 g. of N-bromosuccinimide, amounted to 29.8 g. (93.4%) of crude product. Hydrolysis of the crude material gave phthalaldehydic acid, m.p. 96-98°. 

A mixture of 400 g. (0.95 mole) of powdered a,a,a, a -tetrabromo-o-xylene (p. 269), 360 g. of powdered potassium oxalate, 2.5 1. of water, and 2.5 1. of ethanol is heated under reflux for 40 hours. The resulting clear solution is distilled until 2.1 1. of ethanol has been collected. The distillate may be redistilled to collect a small amount of phthalaldehyde coming over with it. To the combined residues is added 700 g. of sodium phosphate. The mixture is steam-distilled, and the ethanol coming over first is collected separately and added to another batch. About 10 1. of distillate is collected it is saturated with sodium sulfate and extracted thoroughly with acid-free ethyl acetate. The extracts are dried over sodium sulfate, and the solvent is removed by distillation through a column. The residue is recrystallized from petroleum ethet to give a 90% yield of phthalaldehyde, m.p. 56 6.5 . 

QACs and organomercurials. Phenols may or may not be mycobactericidal. Alkaline glutaralde-hyde exerts a lethal effect but more slowly than against other non-sporulating bacteria, but MAI is more resistant than M. tuberculosis. Recently, glu-taraldehyde-resistant M. chelonae strains have been isolated from endoscope washers. These strains remain sensitive to a new disinfectant used in endoscopy, the aromatic dialdehyde ortho-phthalaldehyde. 

Figure 2. Upper Gradient separation of o-phthalaldehyde derivatives of 11 thiols and sodium sulfite according to Mopper and Delmas Peaks (1) sodium sulfite (100 pmol) (2) glutathione (7 pmol) (3) thloglycollate (200 pmol) (4) N-acetylcysteine (7 pmol) (5) 2-mercaptoethanesulfonate (Co-M) (10 pmol) (6) 3-mercaptoproplonate (10 pmol) (8) monothloglycerol (10 pmol) (9) 2 mercaptoethanol (10 pmol) (10) methanethiol (15 pmol) (11) ethanethlol (10 pmol) (12) 2-propanethlol (15 pmol) (13) 1 propanethlol (15 pmol). Middle Thiols In porewater in reducing sediment slurry from Biscayne Bay. Porewater water was filter-sterilized prior to derlvatlzatlon. Peak 7 sulfide (Note response factor is about 200 times lower than for thiols). Lower reagent blank in porewater matrix.

Figure 18.9 tobramycin is an aminoglycoside. It was derivatized with o-phthalaldehyde in a 1.83 m X 0.38 mm i.d. capillary after passing through the column. Fluorescent products result from a combination of this reagent and amines after a reaction period of 6 s. 

Acetaldehyde 83>, chloral 84>, isovaleralde-hyde 83)f benzaldehyde 83,100,128,140) >-isopropylbenzaldehyde 1S°J, anisaldehyde 84,loo) 2,4-dimethoxybenzaldehyde 150>, sahcylaldehyde 84>, furfural 84>, p-chlorobenz-aldehyde 14 >, phthalaldehyde 10 ), isoph-thalaldehyde 10 >, terephthalaldehyde 106>, cinnamaldehyde 84>, 2-methoxy-l-naphth-aldehyde 150>, 2-formylquinoline 105>, 9-anthraldehyde 105>, 3-pyrenealdehyde 10 > p-tolualdehyde 172>, p-nitrobenzaldehyde l72>, m-nitrobenzaldehyde 172>, />-cyanobenzaldehyde 172>... 

Min, J. K., Yoo, H. S., Lee, E. Y., Lee, W J., Lee, Y.M. Simultaneous quantitative analysis of sphingoid base 1-phosphates in biological samples by o-phthalaldehyde precolumn deri-vatization after dephosphorylation with alkaline phosphatase. Anal Biochem 303 (2002) 167-175. 

Zhao, M. Bada, J. L. Determination of a-Dialkylamino Acids and Their Enantiomers in Geological Samples by High Performance Liquid Chromatography After Derivatization with a Chiral Adduct of O-Phthalaldehyde. J. Chromat. A 1995, 690, 55-63. 

Detector F ex 302 em 412 following post-column reaction. The column effluent mixed with reagent 1 pumped at 0.25 mL/min and with reagent 2 pumped at 0.25 mL/min and this mixture flowed through a 2.5 m x 0.8 mm i.d. PTFE coil at 40° to the detector. (Reagent 1 was 10 mM o-phthalaldehyde in EtOH 700 mM phosphoric acid 2 98. Reagent 2 was 20 mM fl-mercaptoethanol in EtOH 700 mM phosphoric acid 2 98.)... 

---