Diterpene acid from pine tree

Wood is the raw material of the naval stores iadustry (77). Naval stores, so named because of their importance to the wooden ships of past centuries, consist of rosin (diterpene resin acids), turpentine (monoterpene hydrocarbons), and associated chemicals derived from pine (see Terpenoids). These were obtained by wounding the tree to yield pine gum, but the high labor costs have substantially reduced this production in the United States. Another source of rosin and turpentine is through extraction of old pine stumps, but this is a nonrenewable resource and this iadustry is in decline. The most important source of naval stores is spent sulfate pulpiag Hquors from kraft pulpiag of pine. In 1995, U.S. production of rosin from all sources was estimated at under 300,000 metric tons and of turpentine at 70,000 metric tons. Distillation of tall oil provides, in addition to rosin, nearly 128,000 metric tons of tall oil fatty acids annually (78). 

More than 200 diterpenes with an abietane skeleton are reported to exist naturally Numerous representatives oeeur in conifers. Selected examples include palustra-diene, also referred to as (-)-8,13-abietadiene, from the pine tree Pintds palustris, from the so-called berries of the sade tree Juniperus sabina (Cupressaceae) and other species of juniper trees, (-)-abietenol from the pine Pinus silvestris and the fir Abies sibirica, (-)-abietic aeid belonging to the resin acids of turpentine and wide-spread in conifers such as various pines Pinus), larch trees Larix) and firs Abies), as well as (+)-palustric acid from the balm and the roots of Pinus palustris, isolated from gum rosin. 

For thousands of years, turpentine has been obtained from conifers by a process known as tapping. A cut is made in the bark which prompts the tree to exude an oil which can be drained off into vessels attached to the tree. Turpentine thus obtained is referred to as gum turpentine. Nowadays, another form of turpentine is available in large quantities as a by-product of paper manufacture. When softwood (pine, fir, spruce) is converted into pulp in the Kraft paper process, the water insoluble liquids which were present in it are freed and can be removed by physical separation from the process water. This material is known as crude sulfate turpentine (CST). Fractional distillation of CST gives a number of products as shown in Table 9.2. (Dipentene is the name given to racemic limonene.) The residue from the distillation is known as tall oil and contains diterpenes such as abietic acid. 

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