Sandaracopimaric acid

The common pine resin acids based on the pimarane and isopimarane skeletal (pimaric-type acids) are shown in Fig. 9. The pimarane and isopimarane acids series differ only in the methyl group position in the carbon-13 position. Isopimaric and sandaracopimaric acids differ in the location of the carbon-carbon double bond. 

Cupressaceae Juniper, Cupressus, Tetraclinis articulata (sandarac) Pimaradienic acids (sandaracopimaric acid), communic acid, totarol... 

Of the Cupressaceae family, sandarac (from Tetraclinis articulata) has frequently been used as a paint varnish. It contains labdane compounds that account for the polymeric fraction of the resin (about 70%) [31]. The main monomeric diterpenoid present is sandaracopimaric acid, together with smaller amounts of 12-acetoxysandaracopimaric acid. Phenols, including totarol, are also present [31]. 

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.

Pinus monticola. Further studies on the oleoresin of the white cypress, Callitris columellaris, show that it contains cis- and trans-communic acids, communic acid, sandaracopimaric acid, and 7-oxo-4-epidehydroabietic acid. Dundathic acid is a polymer of communic acid containing ca. four diterpenoid units. 

Epimandol has been detected in the neutral extracts of Larix europaea and in the bark of the Sitka spruce. Cupressus resins have been examined by g.l.c. and imbricatolic acid (5) identified in all but Cupressus sempervirens. This acid co-occurs with the cis- and trans-communic acids and with sandaracopimaric acid. A -Communic acid has been isolated as its methyl ester from Callitris columellaris. During this work the thermal isomerisation of the conjugated diene of communic acid was noted. The structures and stereochemistry of some... 

The synthesis of sandaracopimaric acid from the androstane skeleton has been described. In this work there is an interesting contrast between alkylation of the saturated keto-ester (148), which gives the axial product, and of the unsaturated ester (149), which gives the product an equatorial methyl group. Cleavage of the androstane 14,15-bond permitted the contruction of the C-13 methyl vinyl substitution pattern. 

Anticopalic acid has been found in the needles and wood of Pinus strobus and in the wood of Pinus monticola. The diterpenoid constituents of Juniperus phoenica include manoyl oxide, eperuene diol, labd-8-ene-l2-hydroxy-19-oic acid (13), sandaracopimaric acid, and 6a-hydroxysandaracopimaric acid. Imbricatalic acid (14) has been isolatedas its methyl ester from Pinus elliottii. 

Totarol, 3-oxototarol, A -3-oxototarol, 1,3-dioxototarol, xanthoperol, sugiol, sandaracopimaric acid, and isopimaric acid have been isolated from Juniperus conferta ... 

The most common pimarane-type acids are pimaric, isopimaric and sandaracopimaric acids (Fig. 4.3). Compared with the abietic counterparts, not only is the basic skeleton diffa-ent but, more importantly, the double bond system is now not conjugated, a fact which reduces significantly the possible chemical exploitation of these compounds. 

Tricyclic diterpenes fall into four main classes those with the pimarane, abietane, rosane, or cassaine skeleta. Epimers at C-13 exist among many groups of tricyclic diterpenes [e.g., pimaric acid (31) and sandaracopimaric acid (32) (Fig. 22.1)]. 

Neoabietic acid, T32.il Levopimaric acid, T32.il Palustric acid, T32.il Abietic acid, T32.il, T"33, D"4 Pimaric acid, T32.14, T"32 Isopimaric acid, T32.18 Cyathin A2, T 13.7 Isoagatholactone, T 14.2, T"39 Sandaracopimaric acid, T32.18 Trachylobanic acid, T35.6 3-Hydroxy-7-kemp-8-en-6-one, T"37.15 C20H30O3... 

Constit. of Pinus, Juniperus and Cupressus spp. Also from Cryptomera japonica, Tetraclinis articulata, Callitris sp. and Agathus australis. Cryst. (MeOH aq.). Mp 171-173° (softens at 163°). [a]j3 —20° (c, 2.6 in CHCI3). 3P-Hydroxy [35951-45-2]. 3P-Hydroxyisopimara-% 14), 15-dien- %-oic acid. 3 P-Hydroxy sandaracopimaric acid C20H30O3 M 318.455... 

Sandaracopimaric acid, T32 a-santalal. Til Santalenes, Til ct-santalol. Til Santanolide C, T22 Santonins, T21, T22 Sapogenins, T49 Sarkomycin, A36 Sarpagine, Kll Sarsapogenin, T49 Sativene, T28... 

Rosin contains mainly diterpene resin acids including abietic acid (22-50%), dehydroa-bietic acid (6-30%), palustric acid (10-25%), neoabietic acid (4-20%), isopimaric acid (10-17%), and pimaric acid (4- %). Others present include dehydropimaric acid, levopi-maric acid, and sandaracopimaric acid. It also contains small amounts of diterpene alcohols and aldehydes, sterols (mainly sitosterol), and phenolic compounds. ... 

---