Connection between taste and constitution of carboxylic hydrazides and their derivatives was written by Blanksma, J. J.;Bakels, H. A.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1939.HPLC of Formula: 18393-54-9 This article mentions the following:
The presence of one CONHNH2 group is insufficient to produce a sweet taste; at least 2 such groups are required and the result is not always a sweet taste, contrary to the conclusion of de Graaf (C. A. 32, 3340.6). The rule of Cohn (Die organische Gesckmackstoffe, Berlin, 1914, p. 731 (C. A. 8, 3605) that the NC group produces a bitter taste is confirmed. Condensation of CH2(CONHNH2)2 (I), (CH2CONHNH2)2 (II), CH2(CONHNH2)C(OH) (CONHNH2)CH2CONHNH2 (III), 2-HOCH2C6H4-CONHNH2 (IV) and 5,2-O2N(HOCH2)C6H3CONHNH2 (V) with the following aldehydes and ketones gave compounds with the m. ps. which follow, resp.: AcH, with I, 188°, with II, 250°; EtCHO, I, 175°, II, 238°; PrCHO, I, 169°, II, 241°; iso-PrCHO, I, 173°, II, 203°; BuCHO, I, 166° II, 221°; Me(CH2)5CHO, I, 157°; BzH, I, 236°, II, 252°, III, 213°, IV, 152°, V, 196°; 4-MeC6H4CHO, I, 222°, II, 235°, III, 200°; piperonal, I, 221°, II, 268°, III, 195° IV, 183°, V, 203°; vanillin, I, 219°, II, 209°; HOC6H4CHO, I, 255°, II, 285° III, 211°; 4-isomer, I, 202°, II, 240°, III, 280°; 2-O2NC6H4CHO, I, 249°, II, 286°, III, 206° IV, 186°, V, 207°; 3-isomer, I, 228°, II, 315°, III, 185° IV, 186°, V, 189°; 4-isomer, I, 256°, II, 292° III, 274°, IV, 213°, V, 217°; 2-ClC6H4CHO, I, 229°, II, 269°, IV, 182°, V, 207°; 3-isomer, I, 210°, II, 254°, IV, 153°, V, 198°; 4-isomer, I, 257°, II, 288°, IV, 175°, V, 202°; PhCH2CHO, I, 170°, II, 228°; 2-furaldehyde, I, 243°, II, 267°, III, 179°, IV, 168°, V, 181°; 5-Me derivative, I, 207°, II, 235°, III, 178°, IV, 183°, V, 161°; 5-HOCH2 derivative, I, 187°, II, 199° III, 166°, IV, 157°, V, 166°; Me2CO, I, 185°, II, 200°, IV, 147°, V, 185°; AcEt, I, 142°, II, 165°; Et2CO, I, 130°, II, 160°; Pr2CO, I, 109°, II, 173°; BzMe, I, 220°, II, 274°, III, 182°. In addition II gave the following condensation product with AcPr, m. 144°. None of the products from III have taste, and from I and II only the products with AcH, Me2CO, AcEt and Et2CO have any taste, bitter in all cases, although I, II and III are sweet. o-C6H4(CONHNHAc)2 (VI) (Davidis, J. prakt. Chem. [2], 54, 66(1896)) has no taste, nor does o-C6H4(CONHAc) CONHNH2, m. 174°, prepared by pouring hot VI with Ac2O into cold H2O. No taste was found for m-C6H4(CONHNH2)2 (VII), m. 227°, or p-C6H4(CONHNH2)2 (VIII), m. 320°. From VII and VIII, resp., the Me2CO derivatives, m. 255° and 310°, were slightly bitter, the BzH derivatives m. 254° and 336°, were tasteless. From VII, a tasteless BzMe derivative, m. 251°, was secured. From VIII the N-Me derivative, m. 239°, and the N,N’-di-Me derivative, m. 175°, were slightly bitter while the Ac derivative, m. 140°, was tasteless. The condensation product of IV with 5-(hydroxymethyl)-2-furaldehyde gave a bitter Ac derivative, m. 143°. The products from V are the most bitter of the whole series. From 5,2-H2N(HOCH2)C6H3CONHNH2 with Me2CO and BzH, tasteless products were secured, m. 179° and 177°, resp. A number of the above compounds which are tasteless have a faint bitter after-taste. The reaction of meconin and various of its substitution products with NH2NH2 and condensation of these products with Me2CO and BzH were reinvestigated (Kleemann, Ber. 20, 875(1887); Anderson, Ann. 98, 47(1856); Tasman, C. A. 21, 3357). These substances were either bitter or tasteless. The following generalizations regarding constitution and taste may be drawn from this work: the condensation products of hydrazides with aldehydes and ketones are bitter when soluble enough to taste; 2 or more CONHNH2 groups located near to each other are required to produce a sweet taste; the introduction of a Ph group favors a bitter taste. In the experiment, the researchers used many compounds, for example, 2-Methyl-2,3-dihydrophthalazine-1,4-dione (cas: 18393-54-9HPLC of Formula: 18393-54-9).
2-Methyl-2,3-dihydrophthalazine-1,4-dione (cas: 18393-54-9) belongs to phthalazine derivatives. Pyridazine and phthalazine have quite different spectroscopic properties compared with their isomers, pyrazine and quinoxaline. Both pyridazine and phthalazine give rise to very good TREPR signals in rigid media at low temperatures.HPLC of Formula: 18393-54-9
Referemce:
Phthalazine – Wikipedia,
Phthalazine | C8H6N2 – PubChem