Dehydro abietic acid

The principal constituents of rosin (qv) are abietic and related acids. Tall oil (qv) is a mixture of unsaturated fatty and aHcycHc acids of the abietic family. Refined tall oil may be high in rosin acids or unsaturated acids, depending on the refining process. Ethoxylates of rosin acids, eg, dehydro abietic acid, are similar to fatty acid ethoxylates in surfactant properties and manufacture, except for thek stabiHty to hydrolysis. No noticeable decomposition is observed when a rosin ester of this type is boiled for 15 min in 10% sulfuric acid or 25% sodium hydroxide (90). Steric hindrance of the carboxylate group associated with the aHcycHc moiety has been suggested as the cause of this unexpectedly great hydrolytic stabiHty. 

COOH, ndls decomposng at 178—185°, by nitrating dehydro abietic acid, Ci9Ha7.COOH, with fuming nitric or mixed nitric sulfuric acid. This compd was identified as 6,8-dinitrodebydroabietic or pyroabietic acid and had the same props as comp reported by Jo--hansson as dinitroabietic acid... 

Retene is a methyl isopropyl phenanthrene (Fig. 2). As mentioned above, Wakeham [43] was the first to address the natural non-combustion production of retene in relation to lake sediments. The starting material for retene is abietic acid, a diterpenoid found primarily in the resin of coniferous trees. When burned, the abietic acid forms retene. It can also degrade via one of two pathways to retene without combustion (Fig. 5). One pathway is through dehydro abietin and another intermediate to retene. The other proceeds through dehydroabietane, another intermediate to simonellite and finally to retene. These mechanisms can occur in both the atmosphere [44] and in aquatic systems. Therefore, where there is abietic acid, retene can follow. This becomes especially important in areas where there are high densities of conifers, and thus abietic acid. 

Reference Standards. Reference standards for TLC, GC, and MS were obtained as follows. Pure abietic acid (mp 172-173 °C) was used as received. Dehydroabietic acid was prepared by oxidation of abietic acid with selenium dioxide to hydroxy abietic acid and subsequent dehydration with glacial acetic acid (11). 7-Ketodehydroabietic acid was prepared by oxidation of dehydroabietic acid with potassium permanganate and isolation of the product by way of the Girard reagent T (12). Pyroabietic acid (a mixture of dehydro- and dihydroabietic acids) was prepared by heating abietic acid with 10% palladium on charcoal to 250 °C for 1 h (13). 

C-7 Ketones are readily available from the aromatic acids such as dehydro-abietic acid. Epoxidation of the enol-acetate derived from the 7-ketones,... 

Studies aimed at the synthesis of the tetracyclic steroid skeleton from dehydro-abietic acid have centred, in their initial stages, on transformations of the C-13 isopropyl group. The full paper describing the conversion of methyl 12-acetyl-abieta-8,ll,13-trien-18-oate into methyl 13-hydroxypodocarpa-8,ll,13-trien-18-oate by nitrodeacylation and dealkylation reactions, has appeared. Birch reduction of the methyl ether of the phenol afforded the a/5-unsaturated ketone (56) which is a useful synthetic intermediate. Methods for the conversion of podocarpic acid into the a) -unsaturated ketones (57 R = CO2H and CHjOAc) have been investigated reduction of the ester (58 R = C02Me) with lithium in liquid ammonia, which was accompanied by decarboxylation, gave only a... 

L-Abietic acid (124) has been converted (Scheme 7) into the tricyclic ketone 131). a known intermediate which can be transformed into steroids. Dehydro-... 

Abietic type—abietic (32%), neoabietic (4%), palustric (10%), and dehydro-abietic(30%) acids. 

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