2- -5-dimethylaminobenzoic

Perfumes, Flavors, Cosmetics, and Soap. Many naturally occurring esters in essential oils and some synthetic esters are important fragrance and flavor compounds (61,62). They are used in perfumes, flavors, cosmetics, soaps, detergents, and air fresheners. Benzyl, butyl, ethyl, methyl, and phenyl esters of benzoic acid are used as flavors, perfumes, and food preservatives. Glyceryl 4-aminobenzoate [136-44-7] and 2-ethyUiexyl 4-dimethylaminobenzoate [21245-02-3] are used in cosmetic sunscreen preparations. Alkyl esters of 4-hydroxybenzoic acid, called parabens, have been used under various names for fungus infections of the skin, and as preservatives in lotions and creams (101). Soap and cosmetic fragrances use large amounts of amyl and benzyl saHcylate. Benzyl saHcylate [118-58-1] is also used in deodorant sprays. 2-Ethylhexyl saHcylate [118-60-5] and 2-ethylhexyl 4-methoxycinnamate [5466-77-3] are used in sunscreen formulations (102). 

The rearrangement has been extended to other 4-substituted benzofuroxans of type 61, giving 62 i30-i32. although in no ease to date has the benzofuroxan been isolated, they are presumed intermediates in the formation of 63 and 64 from 5-dimethylaminobenzo-furoxan with 2,4-dinitrobenzenediazonium chloride and nitrous acid, respectively, and of 66 from 6, 68 from 67,and 70 from 69.132... 

Dimethylamine, reaction with phosphorus trichloride, 46, 42 f-Dimethylami nobenzaldehyde, conversion to 0,/9-dichloro- -dimethyl-aminostyrene, 46, 34 tn-Dimethylaminobenzoic acid, 47, 71 /5-Dimethylaminobenzoic acid, 47, 71 6.(Dimethylamino)fulvene, 47, 52 -Dimethylaminophenylacetic acid, 47, 71... 

In chemically-cured materials, one example of an initiator/activator system is hydrogen peroxide as initiator, ascorbic acid as activator and cupric sulphate as co-activator. In light-cured materials, camphorquinone is used as a visible-light photochemical initiator, sodium p-toluene-sulphinate as activator and ethyl 4-dimethylaminobenzoate as photoaccelerator. 

Molecular rotors with a dual emission band, such as DMABN or A/,A/-dimethyl-[4-(2-pyrimidin-4-yl-vinyl)-phenyl]-amine (DMA-2,4 38, Fig. 13) [64], allow to use the ratio between LE and TICT emission to eliminate instrument- and experiment-dependent factors analogous to (10). One example is the measurement of pH with the TICT probe p-A,A-dimethylaminobenzoic acid 39 [69]. The use of such an intensity ratio requires calibration with solvent gradients, and influences of solvent polarity may cause solvatochromic shifts and adversely influence the calibration. Probes with dual emission bands often have points in their emission spectra that are independent from the solvent properties, analogous to isosbestic points in absorption spectra. Emission at these wavelengths can be used as an internal calibration reference. 

Fig. 13 Self-calibrating dyes DMA-2,4 and p-A,A-dimethylaminobenzoic acid. Compound 40 is an engineered ratiometric dye composed of a viscosity-sensitive molecular rotor and a nonviscosity-sensitive reference dye [70]...

Jiang Y (1994) pH Dependence of the twisted intramolecular charge transfer(TICT) of p-N, N-dimethylaminobenzoic acid in aqueous solution. J Photochem Photobiol A Chem 78 (3) 205-208... 

For oxalate detection, authors proposed a similar detection approach for recognition of oxalate via an immobilized oxalate oxidase/peroxidase couple and dye precursors MBTH (3-methyl-2-benzothiazolinone hydrazone) and DMAB (3-dimethylaminobenzoic acid). The peroxide generated by oxidation of oxalate to CO2 reacted with the dye precursors in a peroxidase-catalyzed reaction to yield an indamine dye with absorption maximum at 590 nm. The concentration of oxalate was correlated with increased absoiption from dye. 

The configuration of the 4R,5R-dihydrodiol was established by application of the exciton chirality method (6). To minimize undesired interactions between the electric transition dipoles of the two j>-N,N-dimethylaminobenzoate chromophores and the dihydrodiol chromo-phore, a 4,5-dihydrodiol enantiomer was first reduced to 1,2,3,3a,4,5,7,8,9,10-decahydro and 4,5,7,8,9,10,11,12-octahydro derivatives (6). We found that it is not necessary to reduce the chrysene chromophore of a BaP 4,5-dihydrodiol enantiomer (Figure 2). Similarly, the absolute configurations of the K-region dihydrodiol enantiomers of BA (7), 7-bromo-BA (8), 7-fluoro-BA (9), 7-methyl-BA (10). and 7,12-dime thy 1-BA (DMBA) (7 ) can also be determined by the exciton chirality method without further reduction. 

More recently, the esterification of oxadiazolinone 89 by 4-dimethylaminobenzoic acid in dry CH2CI2 in the presence of dicyclohexylcarbodiimide (DCC) was described to afford compound 90 (70%). The structure of the product was based on NMR, IR, and MS spectra <2000JLR545>. No other similar reaction was found. 

The need to consider the effect of zwitter-ion formation applied also to Me2N. For aqueous solutions there appear to be no data relevant to obtaining a precise value of am, but van de Graaf and colleagues have examined p-dimethylaminobenzoic acid236. They obtained values of pK and pK2 (water, 25 °C) of 2.568 and 4.996, respectively, and calculated a value of pK of 4.90 for the ionization of the neutral acid. (The ratio of zwitter-ion to neutral acid is 19.4 80.6.) From this pK value and 4.21 for the pKtl value of benzoic acid, ap for Me2N is —0.69. 

Ion exchanger colorimetry has been used as a sensitive and rapid method for vanadium analysis by immobilization of 2[2-(3-5-dibromopyri-dyl)azo]-5-dimethylaminobenzoic acid onto an ion exchanger resin AG 1X2 [75]. Solid phase fluorimetry can be useful for the analysis of very dilute solutions in water analysis or trace metal determination thus a chelating 8-(benzene-sulfonamido)quinoline, immobilized on Amberlite XAD2 support, has been used for the spectrofluorimetric determination of Zn(II) and Cd(II) [76]. 

Nakajima M, Kawakami T, Niino T, Takahashi Y, Onodera S (2009) Aquatic fate of sunscreen agents octyl-4-methoxycinnamate and octyl-4-dimethylaminobenzoate in model swimming pools and the mutagenic assays of their chlorination byproducts. J Health Sci 55(3) 363-372... 

There are two main synthetic routes to Crystal Violet Lactone (CVL) and its analogues (Figure 1.23). The first involves the condensation of 4,4 -bismethyhydrol (1.73), also called Michler s Hydrol, with 3-dimethylaminobenzoic acid in dilute acid to give the leuco CVL, which is then oxidised to CVL. A wide variety of oxidants can be used but the preferred method uses hydrogen peroxide in basic solution. The oldest, and most versatile route starts by reacting 4-dimethylaminobenzaldehyde... 

Dimethylaminobenzoates have also been used to establish the absolute configuration of diols in the presence of an aromatic chromophore, including metabolites of benzo[a]pyrene163 and precocene I164, as well as the cis-dihydrodiol derived from 12-methylbenz[a]anthracene165 and diastereomeric 2,2 -spirobiindane-l,l -diols166. 

Dimethylaminobenzoic acid and derivs 5 D1308 2,5-dinitro-2-dimethylaminobenzoic acid 5 D1308... 

In most of these studies, hydroxyl has been the typical resident functional group, which is derivatized with appropriate acids containing chromophores suitable for exciton coupling. The ideal chromophore would have a very intense UV-visible transition, located in a convenient spectral window, and with the orientation of its electric transition moment being well-defined relative to alcohol R—OH bond. One of the most successful has been p-dimethylaminobenzoate, which has an intense (s ca 30, 000) transition in an... 

TABLE 9. Conformational structures (a) and Newman projection diagrams (b) of (IS,25)- and (IR,2ft)-cyclohexane diol. Bis-p-dimethylaminobenzoate derivatives (c), bisignate CD Cotton effect data and torsion angles (d)14... 

Fig. 2.4. Absorption A, fluorescence F, and degree of polarization of fluorescence P of DMABN and DMABEE (p-dimethylaminobenzoic acid ethylester) in n-hexane at room temperature, c = 5 x 10 M, and ethyl alcohol at 140 K, c = 1 x 10 4Af, respectively. Arrows indicate excitation wavenumber for measurements of P.6 Subscripts A and B refer to final and initial emission, respectively.

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