Veratrate

CgHjoO,. A compound of largely historical interest for its role in establishing the structure of many natural products. Methylation of vanillin gives veratraldehyde which may be oxidized to veratric acid. Veratric acid was identified as a degradation product of the alkaloid papaverine. 

Convolamine, Ci,H2304N. This alkaloid is hydrolysed by boiling alcoholic potash into tropine and veratric acid, and is, therefore, veratroyl-tropine. It has m.p. 114-5° and yields a picrate, m.p. 263-4° (dec.) aurichloride, m.p. 201-2° platinichloride, m.p. 216-7°, and methiodide, m.p. 273-5°. 

Papaverinic acid, CieHjjO N. HjO, crystallises in small tablets, m.p. 233°. It is dibasic, readily forms an anhydride, furnishes an oxime and a phenylhydrazone, contains two methoxyl groups, and on oxidation yields veratric and pyridine-2 3 4-tricarboxylic acids, and hence is represented by the following formula —... 

In a similar attempt, Decker and Eichler reduced A -methylnor-papaverinium phenolbetaine (VIII) with tin and hydrochloric acid and obtained i/i-laudanine, m.p. 112°, pierate, m.p. 162-3°, which was subsequently investigated by Spath and Epstein, who showed that on methylation it furnished dMaudanosine and that the ethyl ether on energetic oxidation yielded veratric acid (3 4-dimethoxybenzoic acid) and the methyl ethyl ether of nor-m-hemipinic acid. This clearly indicated that the free hydroxyl group was in the woquinoline nucleus, and its position was determined by the fact that on mild oxidation 7-methoxy-6-ethoxy-l-keto-2-methyl-l 2 3 4-tetrahydrowoquinoline, m.p. 95-6°, was produced, and on this basis these authors assigned formula (IX R = H R = CH3) to -laudanine. 

By methylation with dimethyl sulphate and potash, it yields methyl-eugenol, boiling at 248° to 249° and which on oxidation yields veratric acid, melting at 179° to 180°. 

The principal derivative for identification purposes is veratric acid, C H.,(C00H)(0CH3)2, which is obtained by oxidising 6 grams of methyl-eugenol with a solution of 18 grams of potassium permanganate in 400 c.c. of water. When recrystallised from alcohol, veratric acid melts at 179° to 180°. 

On oxidation it yields veratric acid melting at 179° to 180°, and by the action of bromine on the phenol-ether dissolved in absolute ether, a dibromide is obtained, which melts at 101° to 102°. It has the constitution—... 

Protocatechualdehyde has been made by a variety of methods, but is usually prepared from catechol by the Reimer-Tiemann method 1 by demethylation of vanillin,2 or veratric aldehyde 3 or from piperonal by the action of phosphorus pentachloride followed by hydrolysis.4... 

Provident MA, JM O Brien, J Ruff, AM Cook, IB Lambert (2006) Metabolism of isovanillate, vanillate, and veratrate by Comamonas testosteroni strain BR6020. J Bacteriol 188 3862-3869. 

Basic hydrolysis of 6 afforded alcohol 19 and methyl veratrate. The H-NMR spectrum of 19 (Table II) revealed the presence of one methylenedioxy, one N-methyl, and two methoxyl groups. The mass spectrum (Table IV) exhibited the most abundant and significant ion peak at m/z 229 indicative of metaphanine-type cleavage. Treatment of an aqueous THF solution of stephavanine (18) with excess sodium hydride and methyl iodide gave N.O-dimethylstephine, a compound identical to alcohol 19. Thus, the structure of the new alkaloid 6 was established by chemical correlation with stephavanine (79). 

Valeraldehyde, p28 Valeric acid, p38 Valeronitrile, p35 Valeryl chloride, p45 Vanillic acid, hi43 Vanillin, hl42 Vanillyl alcohol, hl45 Veratraldehyde, d492 Veratric acid, d496 Veratrole, d493 Veronal, d330... 

Tertiary benzamides whose N-atom is part of a cyclic system can also be hydrolyzed metabolically as shown in the following examples. The hydrolysis of the amide group in 6-[4-(3,4-dimethoxybenzoyl)piperazin-l-yl]-3,4-di-hydro-1 //-quinolin-2-one (OPC-8212, 4.85), an inotropic agent, occurred in rats, mice, dogs, monkeys, and humans [54], After oral administration to rats, both products of hydrolysis, namely 3,4-dimethoxybenzoic acid (veratric acid, 4.86) and piperazine-l//-quinolin-2-one (4.87) were detected in the plasma, urine, and feces. 

Reduction. The reductive capacity of P. chrysosporium has been known for a long time. For example, veratraldehyde, veratric acid, vanillin, vanillic acid and analogous structures were converted into the corresponding... 

In our studies on the lignin peroxidase catalyzed oxidation of veratraldehyde and veratric acid no degradation was observed under the reaction conditions used. However, ligninolytic cultures of P. chrysosporium degraded veratraldehyde and veratric acid via reduction to veratryl alcohol... 

In some of the reductions of veratric acid or vanillic acid 250 /iM ATP was added to the reaction mixture. 

Previously, the quantitative reduction of veratraldehyde and veratric acid to veratryl alcohol by active ligninolytic cultures of P. chrysosporium had been described by Leisola and Fiechter (21). 

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