From Ammonium Betaine

Berberine, 162, 169, 170, 171, 287, 328, 329, 331, 344, 345, 631 Berberine, quaternary ammonium bases from tetrahydro-derivative, 337 Berberine and related bases, pharmacological action, 345 syntheses, 334 Berberineacetone, 333 cptBerberine, 297 profoBerberine, 336 4-Berberines, 335 Berberinium hydroxide, 333 Berberinol, 333 Berberis spp., 328, 331, 346 Berberoline, 332 Berberonic acid, 507 Berberrubine, 329, 343 Berbine, 336 Betaine, 518 Bicucine, 170, 209... 

The least studied of these two cycles are the tetra-chalcogen compounds [P(E)(EH)(/i-NR)]2 for which only the sulfur analogue (E = S) 37 has been reported. It can be prepared as its ammonium salt from reaction of di-thiophosphonic acid chloride betaine (py.PS2Cl py = pyridine) and one equivalent of primary amine in the presence of NEt3 (Equation 54).66,67... 

Ergothioneine is the betaine derived from 2-thiol histidine (i.e. the trimethyl-ammonium derivative). It can be written as a thiol 40 or thione 41 42 the... 

Therefore, a C13-AE, a cationic (quaternary ammonium) surfactant (quat), an amphoteric Ci2-alkylamido betaine, and the non-ionic fatty acid diethanol amide (FADA) as presented with their FIA-MS spectra in Fig. 2.5.12(a)-(d) were analysed as pure blends and as mixtures always obtained from two blends in FIA-MS multiple ion detection mode (MID). Mixtures as well as pure blends contained identical concentrations of surfactant homologues. For AE quantitation the mass traces of all A m/z 44 equally spaced homologues (m/z 306-966) of the C13-AE were recorded. The cationic (quaternary ammonium) surfactant, the amphoteric Ci2-alkylamido betaine, and the non-ionic FADA were quantified recording the mass traces at m/z 214 and 228, or 184, 212, 240, 268, 285, 296, 313, 324 and 341, or 232,260, 288, 316 and 344, respectively. 

Fig. 2.5.12. APCI-FIA-MS(+) overview spectra of industrial surfactant blends used as pure blends or mixtures in the examination of ionisation interferences, (a) C13-AE, (b) cationic (alkyl benzyl dimethyl ammonium quat) surfactant, (c) amphoteric C12-alkylamido betaine, and (d) non-ionic FADA all recorded from methanolic solutions. 

An improved specificity was observed when FIA-MS-MS in product or parent ion mode was used to perform quantification of the surfactants in the methanolic mixtures. The ions selected for quantitation in product or parent ion mode were C13-AE m/z 71, 85, 99, 113, and 127 from alkyl chain together with 89, 133, and 177 from PEG chain generated from parent ions m/z 394, 526, 658, 790 and 922 alkylbenzyl dimethyl ammonium quat m/z 91 and 58 generated from parent ion m/z 214 FADA m/z 88, 106 and 227 generated from parent ions m/z 232, 260, 288, 316, 344 and 372 while the alkylamido betaine was quantified generating the parent ion m/z 343 obtained from product ion at m/z 240. 

It is possible to remove a proton from the methyl group of a trialkylmethylammonium halide with strong bases. Thereby, a betaine (see Section 4.7.4) is produced with the structure R3N+—CH2. A betaine in which the positive and the negative charges are located on adjacent atoms as in R3N+—CH2 is called an ylide. The yl part of the name ylide refers to the covalent bond in the substructure N+—CH2. The ide part indicates that it also contains an ionic bond. When one wants to distinguish the ylide R3N+—CH2 from other ylides, it is called an ammonium ylide or an N ylide. 

Quaternary ammonium compounds are important as osmoprotectants in times of water deficiency and cold stress, as well as being constituents of membrane phospholipids, p-Alanine and phosphoethanolamine are each methylated three times on their nitrogens to produce the products P-alanine betaine and phosphocholine, respectively (Fig. ll.l).24"27 An example of O-methylation and N-methylation occurring on the same molecule can be found in the indole alkaloid vindoline from Catharanthus roseus (Fig. 11.1) 28,29... 

Chloro-3-hydroxy-5(and 6)-methylpyrazine with ammonium hydroxide, copper, and cupric chloride at 125° for 15 hours gave 2-amino-3-hydroxy-5(and 6)-methylpyrazine (373, 835), but 2-chloro-5-hydroxy-3,6-dimethylpyrazine was recovered unchanged after treatment with alcoholic ammonia under drastic conditions (312) and 2-chloro-3-hydroxy-5,6-diphenylpyrazine with pyridine and its hydrochloride at reflux gave the betaine (33) from 2-hydroxy-5,6-diphenyl-3-pyridiniopyrazine chloride (863). Replacement of the chloro substituent occurred... 

Many types of superabsorbents have been prepared from various materials, by various methods, and in different shapes. They are modified natural hydrophilic polymers such as starch, cellulose, alginic acids, etc. and synthetic hydrophilic polymers such as poly (acrylic acid) and poly(sodium acrylate). Most of them have anionic moieties such as poly(sodium acrylate) and poly(vinyl sulfonate). Now, many types of superabsorbents having not only anionic groups but also cationic groups such as ammonium groups, phospho-nium groups, or betaine have been prepared from both... 

Treatment of the quaternary ammonium salt PhC=CCH2NMe2CH2COPh Br" with sodium hydroxide gives, inter alia, the betaine (98). Controlled-potential electrolysis of 7-nitro-ketones on a mercury cathode yields 1-pyrroline 1-oxides, pyrrolines, or pyrrolidines, according to conditions thus the oxide (99) is obtained from the compound 02NCMe2CHPhCH2C0Ph. The pyrrolinone (101) results from autoxidation of the furan derivative (100). Irradiation of the amide (102) leads to the pyrrolidinone (103) by an unprecedented [1,6] shift of hydrogen. " ... 

The basic nitrogen atom (Nb) of strychnine is tertiary for quaternary alkylstrychninium salts result from reaction with molar proportions of alkyl halides (18, 208). The alkylstrychnines (2, 4, 47, 208, 256) result from fission of the lactam grouping and betaine formation with the quaternary ammonium hydroxide grouping. The secondary amine (NgH) of methylstrychnine (C2oH220(Nb CH3) (NaH) (CO2") may be further methylated with the formation of dimethylstrychnine (C20H22O) (NaCHa) (Nb CHa) (C02 ) (2, 47), or if it is heated with mineral acid lactamization results in the formation of methylstrychninium salts (47). 

Taking into account the unsurpassed mildness of all these surfactants, promising sphere of their application is "no-more-tears" child shampoos and products for intimate hygiene. In various combinations phosphobetaines and phosphatobetaines are patented in a range of personal care products by Johnson Johnson [44, 45, 111]. Zwitter-ionic 3-amidopropyldimethylammonio-l-propane-3-sulphonate derived from cholic acid (ChAPS) has been used as selective membrane protein solubiliser in the biochemical practice. All surface-active betaines are compared favourably with quaternary ammonium compounds in respect to their moderate toxicity, low mucous membrane irritation and better biodegradation. 

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