Cinnamic acids benzoic acid from

Definition Oleoresin extracted from Myroxylon pereirae] mixt. of resins and chemicals incl. benzyl benzoate, benzyl cinnamate, cinnamic acid, benzoic acid, and vanillin... 

Benzoe resin (also known as benzoin) comes from Styrax spp. (Styraceae family). In the Sty rax genus the only species that occurs in the Mediterranean is Styrax officinalis, so this was probably the source of the resin in ancient times in that area. Benzoe mainly contains free cinnamic and benzoic acids, and their corresponding esters with cinnamyl, p-coumaryl and coniferyl alcohols. The amounts of these compounds are quite variable and depend on which species the resin was obtained from [129]. 

Benzoic and salicylic acids. Two of the simplest plant acids arising from fraus-cinnamate are benzoic acid, accumulated in plums and cranberries, and salicylic acid, present in all green plants and accumulated as methyl esters or glycosides in some plants, e.g., those of the willow family. Salicylic acid is made by hydroxylation of benzoic acid,177 which can be formed from frans-cinnamate by P oxidation as depicted in Fig. 25-8, but it may also arise from isochoris-mate as shown in Fig. 25-2.178 Salicylic acid plays a central role in resistance of plants to a variety of... 

Balsam Peru. Peruvian balsam Indian balsam China oil Black balsam Honduras balsam Surinam balsam. From Toluifera pereirae (Klotzsch) Bail]. (Myroxylon perei-rae Klotzsch), Leguminosae. Habit. Central America (San Salvador) in forests near Pacific coast. Constit 50-60% cinnamein —esters of cinnamic and benzoic acid about 28% resin, styracine, vanillin Ref Bergemann, Pharmazie 5, 494 (1950) Cortesi, Bull Soc. Pharm. Bordeaux 89, 141 (1951). C.A. 46, 1718b (1952). 

The condensation is analogous to that by which cinnamic acid is prepared from benzoic aldehyde and sodium acetate, although in the latter case a dehydrating agent is required to bring about the elimination of water. Benzalacetone melts at 42°, and possesses the properties of an unsaturated compound and of a ketone. 

The function of the matrix is to transfer energy from the laser beam to the sample, to prevent aggregation of sample molecules, and probably to participate in the ionization process in some unspecified way. A large number of matrix compounds have been described, but selection criteria are not well developed. Typical examples include derivatives of benzoic and cinnamic acids, nicotinic acid, succinic acid, and anilines. 

In roots of Quercus pedunculata, for instance, two forms of PAL were found, one in the mito-chondria-microbody fraction and the other in the microsome fraction, which differed in their sensitivity to cinnamic and benzoic acids and obviously belonged to different metabolic pathways. From the glandular tissue of Aesculus hippocastanum. two PAL species were isolated which were differently inhibited either by cinnamic acid and flavonoids or by benzoic acid derivatives. One of these enzymatic forms is present in plastids, the other in ER. 

Fission of the skeleton to form phenylpropane, phenylethane and phenyl-methane derivatives. Hence the corresponding cinnamic and benzoic acids derive from rings B and C and phloroglucinol carboxylic acid from ring A. 

Fig. 2.7 The effects of pH on the ionic state of a theoretical phenolic acid with a pKa value of 4.5 (a) and estimated pKa values for cinnamic and benzoic acids (b). Where CAF equals caffeic acid, PCO equals p-coumaric acid, FER equals ferulic acid, SIN equals sinapic add, POH equals p-hydroxybenzoic acid, SYR equals syringic acid, and VAN equals vanillic add. A pKa value for caffeic acid was not available. Figure (b) based on data from Blum et al. (1999b). CRC Press LLC, data used with permission of Taylor Francis Ltd, http //www.tandf.co.uk/joumals. Origintil sources of data Al Leo, personal communication, Leo et al. (1971), Nordstrom and Lindbeig (1965), Kenttamaa et al. (1970), Connors and Lipari (1976) Glass (1975)...

Sodium hydroxide solution cannot be used at this stage since it may produce benzoic acid by the Cannizzaro reaction (Section IV,123) from any unchanged benzaldehyde. If, however, the reaction mixture is diluted with 3-4 volumes of water, steam distilled to remove the unreacted benzaldehyde, the residue may then be rendered alkaline with sodium hydroxide solution. A few grams of decolourising carbon are added, the mixture boiled for several minutes, and filtered through a fluted filter paper. Upon acidifying carefully with concentrated hydrochloric acid, cinnamic acid is precipitated. This is collected, washed and purified as above. 

The trans cinnamic acid and phenyl propiolic acid data involve fits of essentially the same precision at o-, m-, and p- positions (SD =. 05 . 02). However, the RMS of these sets is quite low, and consequently, / values of. 200 prevail. The interpretation of these results is therefore uncertain. To the extent that the results of Table VII are meaningful, it is of particular interest that Kj =p°Ip =. 68 for the phenyl propiolic acid, whereas for the tram cinnamic acids, K° = 1.02. These results suggest that in contrast to the ortho substituted benzoic acids, the lines of field forces in the ortho substituted phenyl propiolic acids do (partly at least) penetrate regions of hi dielectric solvent. The results for the tram cinnamic acids would then indicate some (but not complete) exclusion of solvent resulting from the presence of the vinyl hydrogens. These interesting results from the application of eq. (1) clearly need to be confirmed by additional studies. 

Two hypotheses have been proposed to explain how phenolic acids directly increase membrane permeability. The first is that the compounds solubilize into cellular membranes, and thus cause a "loosening" of the membrane structure so that minerals can leak across the membrane (28-30, 42). Support for this hypothesis comes from the fact that the extent of inhibition of electrical potentials correlates with the log P (partition coefficient of a compound between octanol and water) for various benzoic and cinnamic acid derivatives (Figure 5). 

The benzoic acid, the acid moiety found in cocaine (98), is also derived from phenylalanine (141). Feeding of [4-3H]phenylalanine to E. coca led to the benzoyl moiety, where 96% of the 3H was located at the para position (138). The intermediacy of cinnamic, 3-hydroxy-3-phenylpropionic, and benzoylacetic acid in the formation of benzoic acid has been suggested (138). 

Recently, we developed a new matrix based on nanoparticle technologies, which have a completely different chemical structure from benzoic or cinnamic acid derivatives.17 Derivatives of these matrices may enhance specific molecules in IMS. 

Storax resin is extracted from Liquidambar orientalis (Hammamelidiaceae) and Altingia and its major components are cinnamyl cinnamate and 3-phenylpropanyl cinnamate, with significant amounts of benzoic and cinnamic acids, and 3-phenylpropanol and cinnamyl alcohols [130,131]. The volatile content is very low and triterpenes (oleanonic and 3-epioleanolic acids and liquid ambronovic acid) have also been observed [130,132]. 

Simple phenolic compounds include (1) the phenylpropanoids, trans-cinnamic acid, p-coumaric acid and their derivatives (2) the phenylpropanoid lactones called coumarins (Fig. 3.4) and (3) benzoic acid derivatives in which two carbons have been cleaved from the three carbon side chain (Fig. 3.2). More complex molecules are elaborated by additions to these basic carbon skeletons. For example, the addition of quinic acid to caffeic acid produces chlorogenic acid, which accumulates in cut lettuce and contributes to tissue browning (Fig. 3.5). 

Work on the rate of dissolution of regular shaped solids in liquids has been carried out by Linton and Sherwood(1), to which reference is made in Volume 1. Benzoic acid, cinnamic acid, and /3-naphthol were used as solutes, and water as the solvent. For streamline flow, the results were satisfactorily correlated on the assumption that transfer took place as a result of molecular diffusion alone. For turbulent flow through small tubes cast from each of the materials, the rate of mass transfer could be predicted from the pressure drop by using the 1 j-factor for mass transfer. In experiments with benzoic acid, unduly high rates of transfer were obtained because the area of the solids was increased as a result of pitting. 

In addition to the substances cited elsewhere in this section, a variety of natural materials of vegetable origin have been analyzed using RPC. These include benzoic and cinnamic acids from plants (504) and a variety of phenolic compounds from tobacco (505). Alktdoids have been analyzed... 

Simple phenols, phenolic acids derived from benzoic acid, and phenolic acids derived from cinnamic acid have been the most commonly identified... 

It is also important to understand that most allelopathic effects apparently result from the combined actions of several allelochemicals, often with each below a threshold concentration for impact. In allelopathic situations which implicate phenolic acids, soil concentrations have ranged from below 10 to above 1000 ppm for each compound. The lower end of the spectrum is below a concentration required for an effect in current bioassays. Additive and synergistic effects have been demonstrated, however, for combinations of cinnamic acids (102), benzoic acids (103), benzoic and cinnamic acids (10 ). and -hydroxybenzaldehyde with coumarin (105). It appears that such combined interactions may be very important under field conditions. 

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