Pimaric acid

Pilocarpine [92-32-7] Piloted airblast atomizer Pilot-plant Pilot plants Pilsner Pimaric acid [127-27-5]... 

Fig. 1. Abietic-type acids include abietic acid [514-10-3] (1), levopimaiic acid [79-54-9] (2), neoabietic acid [471-77-2] (3), palustiic acid [1945-53-5] (4), and dehydroabietic acid [1740-19-8] (5). Pimaric-type acids are pimaric acid [127-27-5] (6) and isopimaric acid [5835-26-7] (7).

Pine oleoresin [1 kg. containing 260 g. (0.86 mole) of levo-pimaric acid] (Notes 1 and 2) is dissolved in 2 1. of acetone in a 4-1. beaker. A solution of 200 g. (2.2 moles) of 2-amino-2-methyl-1-propanol (Note 3) in 200 ml. of acetone is added as rapidly as possible with stirring. The pasty precipitate which forms almost immediately is collected by suction filtration and is pressed as dry as possible using a rubber dam (Note 4). The crude moist precipitate is returned to a 2-1. beaker and is dissolved in the minimum volume ( 1 1.) of boiling methanol. The methanolic solution is cooled to 5° in a refrigerator and stirred occasionally to expedite crystallization. When the crystallization is completed, the solid is collected by suction filtration. The precipitate is redissolved in a minimum volume of boiling methanol ( l 1.) (Note 5), the solution concentrated to two-thirds its original volume (Note 6), cooled to 5°, and the amine salt allowed to... 

There are several materials that make up this category, including wood-derived tall oil rosins and pine stump extracts sold under the well known VinsoH trade mark. They consist of complicated mixtures containing greater or lesser amounts of abietic acid (Fig 3.2) together with pimaric acid, and phenolic compounds such as phlobaphenes. 

Head-to-tail rearrangement of four isoprene units results in the formation of diterpenes (C20H32), as seen also in Fig. 4.2. Diterpenes are generally found in resins, e.g. pimaric acid and abietic acid. Some diterpenoids are also constituents of essential oils, e.g. phytol [3, 7-14, 37, 52, 53]. Like sesquiterpenes, diterpenes are heavier than monoterpenes therefore, they require more energy to go to the vapour phase. For this reason, longer distillation times are necessary for their recovery. The DNP lists 118 different structural types for diterpenoids [37]. Important diterpenes found in essential oils will be detailed. Some representatives of volatile diterpenes are as in Structure 4.32. 

Fig. 5-5. Examples of resin acids. 1, Pimaric acid 2, sandaracopimaric acid 3, isopimaric acid 4, abietic acid 5, levopimaric acid 6, palustric acid 7, neoabietic acid 8, dehydroabietic acid.

Ultraviolet irradiation of the polycyclic cyclohexa-1,3-diene, levo-pimaric acid (12), yields photolevopimaric acid (13), the structure of which is considered to be the 6,14-bridged valence tautomer. ... 

Beckman rearrangement of the oxime of 7-ketodehydroabietate with phosphoric acid gives the expected lactam (50) and a decarbonylated amine (51). The dihalocarbene adduct of methyl abietate is formed " across the 7(8) double bond. The photo-oxidation of methyl isopimarate, which has a A -double bond, gives 7a-hydroxysandaracopimaric acid methyl ester. However, in the pimaric acid series both the 7a- and 14a-allylic alcohols are formed. 

Naturally Occurring Substances.-A -isomer of pimaric acid has been isolated" from Othona cylindrica and O. floribunda (Compositae). ent-Pimara-8(14),15-dien-19-oic acid and thermarol (en/-pimara-15-en-8/8,19-diol) were isolated from... 

Pimaric acid (6) and isopimaric acid (7) differ in carbon skeleton from abietic acid, and the amounts initially present in rosin are lost in the process described for the preparation of dehydroabietic acid. In the step of dehydrogenation with palladium the two acids act as hydrogen acceptors and are converted into a mixture of dihydro-pimaric and dihydroisopimaric acids. Note that pimaric acid and isopimaric acid have been shown to be rearranged to abietic acid by concentrated sulfuric acid. 

Phthalazinedione, 331-332 Phthaldehyde, 156, 157 Phthalaldehydic acid, 157 Phthalhydrazide, 332, 399 Phthalic acid, 190, 373 Phthalic anhydride, 427, 441 Picrolonic acid, 213 Pimaric acid, 190 Pinacolone, 79 Pinacolone, 79 10a-Pinane-2/5-ol, 169, 170 a-Pinene, 343 0-Pinene, 239, 362 a-Pinene oxide, 344 rra/w-Pinocarveol, 362 Piperidine, 28, 332 Pivalic acid, 353 Platinous chloride, 272 Platinum catalysts, 332-333 Podocarpic acid, 342... 

Levopimaric Acid. UR)-l,2,3,4,4a,4b-abietadienoic acid i-pimaric acid 0-pimaric acid /-sapietic acid. C HjjOj mol wt 302.44. C 79.42%, H [0.00%. O [0.58%. Isolation from American pine oleoresin Palkin, Harris, J. Am. Chem. Soc. 55, 3677 (1933) from French galipot, from Pinos maritima Ruzicka, Bacon, Heh. Chim. Acta 20, 1542 (1937) from Pittas paiustris Harris, Sanderson, J. Am. Chem. Soc. 70, 334, 3671 (1948). Structure Ruzicka, Kaufmann, Helv. 

Sandarac. Resin from Callitris quadrivatvis Vent.. Pinaceae. Habit. Morocco. Constit. About 80% pimaric acid, about 10% callitrolic acid sandaricinic acid. 

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