P-methoxy benzoic acid

Anisic acid is p-methoxy-benzoic acid, C, H. COCHg. COOH.. It is found in aniseed oil, and also in Tahiti vanillas. It is a crystalline body-melting at 184°. 

Anethole, C H O, a major constituent of the oil of anise, has the lH NMR spectrum shown. On oxidation with Na2Cr207, anethole yields p-methoxy-benzoic acid. What is the structure of anethole Assign all peaks in the NMR spectrum, and account for the observed splitting patterns. 

A new type of pyrrolizidine alkaloid has been isolated from the leaves of Ehretia aspera Willd. by Suri et al.n The structure (39) for ehretinine was established by spectroscopic evidence and by hydrolysis to give retronecanol and p-methoxy-benzoic acid. Confirmation of the structure (39) was obtained by synthesis of ehretinine from retronecanol and pmethoxybenzoyl chloride. This is the first reported occurrence of a retronecanol ester, although it should be pointed out that retronecanol esters can be produced by hydrogenolysis of retronecine diesters. The authors do not appear to have considered the possibility that ehretinine could have been formed by hydrogenolysis of the common type of ester (40) on treatment with the zinc and sulphuric acid that are used in their extraction procedure. 

Alternatively, the synthesis was initiated with an electrophilic initiator core such as p-(methoxy)benzoic acid. This reagent was allowed to react with ethylene diamine, followed by sequencing to give a mono-dendron where Y = p-MeO — C6H4 — CONH — CH2CH2 — (see Fig. 19). 

Thus while the phenolic ester, methyl p-hydroxybenzoate does not react with NaHCOs/ the carboxylic acid p-methoxy-benzoic acid will and this is the basis of their separation. 

Fushiya S, Kabe Y, Ikegaya Y, Takano F (1998) (-t)-rhododendrol and epi-rhododendrin suppress the NO production by activated macrophages in vivo. Plemta Med 64(7) 598-602 Gadgoli C, Mishra SH (1999) Antihepatotoxic activity of p-methoxy benzoic acid from Capparis spinosa. J Ethnopharmacol 66(2) 187-192... 

The rates of Tl(lll)-oxidation of benzoic, p-chlorobenzoic acid, and p-methoxy benzoic acid hydrazides in acidic medium increased with [H+] and decreased with [Cl ]. The participation of a Tl(lll)-substrate complex had been proposed. ... 

Preparation by reaction of p-methoxy-benzoic acid (p-anisic acid) with resorcinol monomethyl ether in the presence of boron trifluoride [650]. 

Vitamin D2 3,5-dinitrobenzoate Ergocalciferol, 3,5-dinitrobenzoate (8,9) (4712-11-2) Ethyl p-dimethylaminobenzoate Benzoic acid, p-(dimethylamino)-, ethyl ester (8) Benzoic acid, 4-(dimethylamino)-, ethyl ester (9) (10287-53-3) tert-Butyl methyl ether Ether, tert-butyl methyl (8) Propane, 2-methoxy-2-methyl-(9) (1634-04-4)... 

The liquid crystalline side chain polymers investigated have either a polysiloxane (compounds SiCl and SIGN) or a polyacrylic (compound AcCN) polymer chain. These are coupled via flexible spacers with the mesogenic p-substituted benzoic acid phenylester groups. SiCl and SiCN are copolymers with p-methoxy components in excess. 

Table 11.1 Overview of studies for profiling human pathogens with MALDI-TOF MS at the strain level Examples of strain categorization (A), strain differentiation (B), and strain identification (C). MRSA methicillin-resistant Staphylococcus aureus, MSSA methicillin-sensitive S. aureus, L library-based approach, P proteomics-based approach, CHCA a-cyano-4-hydroxycinnamic acid, CMBT 5-chloro-2-mercaptobenzothiazole, DHB 2-hydroxy-5-methoxy benzoic acid, FA ferulic acid, HABA 2,4-hydroxyphenylazobenzoic acid, SA 3,5-dimethoxy-4-hydroxycinnamic acid (sinapinic acid), THAP 2,4,6-trihydroxyacetophenon. Adapted and modified from Sandrin et al. (2013)... 

Rhizonic acid, 4-0-Metbyl-p-orcinolcarboxylic acid, 2-Hydroxy,3,6-dimethyl-4-methoxy-benzoic acid (Rbizoninsaure, 4-0-Metbyl-P-orcinolcarbonsaure, 2-Hydroxy-3,6-dimetbyl-4-metboxybenzoesaure)... 

Benzoic acid, /(-chloro-Benzoic acid, m-hydroxy-Benzoic acid, o-hydroxy-Benzoic acid, p-hydroxy-Benzoic acid, mercapto-Benzoic acid, methoxy-Benzoic acid, methyl-Benzoic acid, o-, m-, and... 

Anisic acid, methyl ester [Benzoic acid, 4-methoxy-, methyl ester], 55, 40, 41 o-Amsidine [Benzenamine, 2-methoxy-], p-bromination of, 55, 23 [10] ANNULFNE, [ 1 l-Oxablcyclo[4 4 1]-undeca-l,3,5,7,9-pentaene], 55, 86 Anthramhc acid [Benzoic acid, 2-amino-], p-brominahon of, 55, 23 Apparatus, distillation of benzocyclopro-pene for, 55,13... 

C,2oH2iiN20 61380-02-7) see Alfentanil iV-(4-methoxymethyl-4-piperidyl)propionaniIide (C15H24N2O2 61086-18-8) see Alfentanil Sufentanil 2-methoxy-5-(methylsulfonyl)benzoic acid (CgHioOjS 50390-76-6) see Tiapride 2-methoxy-10-[2-methyl-3-(p-toluenesulfonyloxy)propyi]-phenothiazine... 

Sodium in liquid ammonia and ethanol reduced benzoic acid to 1,4-dihy-drobenzoic acid. Reduction of p-toluic acid was more complicated and afforded a mixture of cis- and rranj-l,2,3,4-tetrahydro-p-toluic acid and cis-and tra j-l,4-dihydrotoluic acid. m-Methoxybenzoic acid yielded 1,2,3,4-tetrahydro-5-methoxybenzoic acid, and 3,4,5-trimethoxybenzoic acid gave l,4-dihydro-3,5-dimethoxybenzoic acid in 87% yield (after hydrogenolysis of the methoxy group para to carboxyl) [984. In the case of 4 -methoxy-biphenyl-4-carboxylic acid, sodium in isoamyl alcohol at 130° reduced completely only the ring with the carboxylic group, thus giving 92% yield of 4-(p-methoxyphenyl)cyclohexanecarboxylic acid [955]. 

P-D-Glucopyranosyloxy-2-methoxy-6-hydroxy-benzoic acid-2 -p-D-glucopyranosyl-oxybenzylester Leiocarposide... 

Ai/12(dimerization in benzene) in kcal/mole dimer, o-methoxy benzoic add 3 4 0 2 p-mefcho r. f1) n> ei-r acid ... 

Substituent effects on the A,u I reaction have been studied by Bender and Chen55. These authors measured the rates of hydrolysis of a series of 4-substituted 2,6-dimethylbenzoates in 9.70 M sulphuric acid at 25°C, and found that the values for the first-order coefficients with 4-methoxy, 4-methyl, 4-unsubstituted and 4-bromo-compounds (5.0, 0.37, 0.033 and 0.01 x I0 4 sec-1, respectively) are satisfactorily correlated by the Hammett equation, following cr+ with a slope p = —3.22. Since the esters are not fully protonated in 9.70 M H2SOj, part of this factor is due to the effects of the 4-substituent on the protonation equilibrium, p for the protonation of substituted benzoic acids is about — l35, but is likely to be considerably smaller for di-ortho-substituted compounds, since the conjugative interaction of the p-substituents with the protonated carboxyl group requires coplanarity with the ring. 

Benzohydroxamic acid dioxouranium complexes, 507 metal complexes, 506, 507 as metal precipitant, 506 Benzohydroxamic acid, iV-methyl-metal complexes, 506 Benzohydroxamic acid, N-phenyl-metal complexes, 507 reactions with carboxylic acids, 507 as metal precipitant, 506 titanium complexes, 506 Benzohydroxamic acid, A -(o-tolyl)-as metal precipitant, 506 Benzohydroxamic acid, N-wi-tolyl-p-methoxy-metal complexes, 506 Benzoic acid, dihydroxy-beryllium(II) complexes, 481 Benzoic acid, o-mercapto-esters... 

Compound retention during RP-HPLC depends on the relative hydrophobicity of the sample compounds. As expected, the elution of phenolics for reversed-phase HPLC is in the order of decreasing polarity. Polarity is increased most by hydroxyls at the 4-position, followed by those at the 2- and 3-positions. Availability of the methoxy group and the acrylic substitution reduces polarity and increases retention times (4). Loss of polar hydroxy groups and/or addition of methoxy groups can decrease the polarity within each class of benzoic and cinnamic acid. Also, the presence of the ethylenic side chain in the cinnamic acids can reduce their polarity compared with similarly substituted benzoic acids (6). The elution order for benzoic acids is as follows (Table 1) gallic > a-resorcylic > protocatechuic > y-resorcylic > gentisic > p-hydroxyben-... 

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