Abietic acid
Encyclopedia
Abietic acid an organic compound
that occurs widely in trees. It is the primary component of resin acid
, is the primary irritant
in pine
wood and resin, isolated from rosin
(via isomerization) and is the most abundant of several closely related organic acids that constitute most of rosin
, the solid portion of the oleoresin of coniferous trees. Its ester
is called an abietate.
It belongs to the abietane
diterpene
group of organic compounds (compounds derived from four isoprene
units). It is used in lacquer
s, varnish
es, and soap
s, and for the analysis of resin
s and the preparation of metal resinates. It is found in Pinus insularis (Khasi Pine), Pinus kesiya Royle, Pinus strobus (Eastern White Pine), Pinus sylvestris (Scotch Pine).
ships. It is also rubbed on the bows of musical instruments to make them less slippery. In modern times methods have been developed for improving the properties of the rosin acids, which are otherwise soft, tacky, and low-melting and subject to rapid deterioration by oxidation in air. Stability is greatly increased by heat treatment
.
Resin acids are converted into ester gum by reaction with controlled amounts of glycerol
or other polyhydric alcohols. Ester gum has drying properties and is used in paints, varnishes, and lacquers.
prepared from rat prostate. The fraction responsible for this activity was purified, and the active constituent was isolated and identified as abietic acid which exhibited potent testosterone 5α-reductase inhibitory activity
in vitro
.
inventory. Abietic acid is a contact allergen; however, compounds resulting of its oxidation by air elicit stronger response. It is soluble in alcohol
s, acetone
, and ether
s.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
that occurs widely in trees. It is the primary component of resin acid
Resin acid
Resin acids usually refers to mixtures primarily. Abietic acid is the main component but several related carboxylic acids. Nearly all resin acids have the same basic skeleton: three fused ring fused with the empirical formula C19H29COOH. These materials occur in rosin but also occur in fossil...
, is the primary irritant
Irritation
Irritation or exacerbation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant...
in pine
Pine
Pines are trees in the genus Pinus ,in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species.-Etymology:...
wood and resin, isolated from rosin
Rosin
.Rosin, also called colophony or Greek pitch , is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene components. It is semi-transparent and varies in color from yellow to black...
(via isomerization) and is the most abundant of several closely related organic acids that constitute most of rosin
Rosin
.Rosin, also called colophony or Greek pitch , is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene components. It is semi-transparent and varies in color from yellow to black...
, the solid portion of the oleoresin of coniferous trees. Its ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
is called an abietate.
Preparation
Abietic acid is extracted from tree rosin. The pure material is a colourless solid, but commercial samples are usually glassy or partly crystalline yellowish solid that melts at temperatures as low as 85 °C (185 °F).It belongs to the abietane
Abietane
Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid, carnosic acid, and ferruginol which are collectively known as abietanes or abietane diterpenes....
diterpene
Diterpene
Diterpenes are a type of terpenes composed of four isoprene units. They derive from geranylgeranyl pyrophosphate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol...
group of organic compounds (compounds derived from four isoprene
Isoprene
Isoprene , or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH2=CCH=CH2. Under standard conditions it is a colorless liquid...
units). It is used in lacquer
Lacquer
In a general sense, lacquer is a somewhat imprecise term for a clear or coloured varnish that dries by solvent evaporation and often a curing process as well that produces a hard, durable finish, in any sheen level from ultra matte to high gloss and that can be further polished as required...
s, varnish
Varnish
Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss...
es, and soap
Soap
In chemistry, soap is a salt of a fatty acid.IUPAC. "" Compendium of Chemical Terminology, 2nd ed. . Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford . XML on-line corrected version: created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN...
s, and for the analysis of resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...
s and the preparation of metal resinates. It is found in Pinus insularis (Khasi Pine), Pinus kesiya Royle, Pinus strobus (Eastern White Pine), Pinus sylvestris (Scotch Pine).
Uses
Rosin has been used for centuries for caulkingCaulking
Caulking is one of several different processes to seal joints or seams in various structures and certain types of piping. The oldest form of caulking is used to make the seams in wooden boats or ships watertight, by driving fibrous materials into the wedge-shaped seams between planks...
ships. It is also rubbed on the bows of musical instruments to make them less slippery. In modern times methods have been developed for improving the properties of the rosin acids, which are otherwise soft, tacky, and low-melting and subject to rapid deterioration by oxidation in air. Stability is greatly increased by heat treatment
Heat treatment
Heat treating is a group of industrial and metalworking processes used to alter the physical, and sometimes chemical, properties of a material. The most common application is metallurgical. Heat treatments are also used in the manufacture of many other materials, such as glass...
.
Resin acids are converted into ester gum by reaction with controlled amounts of glycerol
Glycerol
Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...
or other polyhydric alcohols. Ester gum has drying properties and is used in paints, varnishes, and lacquers.
In vitro effects
The 50% ethanol extracts from Resina pini of Pinus sp. (Pinaceae) showed inhibitory activity against testosterone 5α-reductase5-alpha reductase
5α-reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in 3 metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism, and prostate cancer....
prepared from rat prostate. The fraction responsible for this activity was purified, and the active constituent was isolated and identified as abietic acid which exhibited potent testosterone 5α-reductase inhibitory activity
Enzyme inhibitor
An enzyme inhibitor is a molecule that binds to enzymes and decreases their activity. Since blocking an enzyme's activity can kill a pathogen or correct a metabolic imbalance, many drugs are enzyme inhibitors. They are also used as herbicides and pesticides...
in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
.
Safety
Abietic acid is considered a "nonhazardous natural substances" in tall oil. In the U.S., it is listed in the Toxic Substances Control ActToxic Substances Control Act
The Toxic Substances Control Act is a United States law, passed by the United States Congress in 1976, that regulates the introduction of new or already existing chemicals. It grandfathered most existing chemicals, in contrast to the Registration, Evaluation and Authorization of Chemicals ...
inventory. Abietic acid is a contact allergen; however, compounds resulting of its oxidation by air elicit stronger response. It is soluble in alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
s, acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
, and ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...
s.