Abietic acid (also known as ''abietinic acid'' or ''sylvic acid'') is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
that occurs widely in trees. It is the primary component of
resin acid Resin acid refers to mixtures of several related carboxylic acids, primarily abietic acid, found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids are tack ...
, is the primary
irritant in
pine
A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanical Garden accep ...
wood and resin, isolated from
rosin
Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), 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 comp ...
(via
isomerization
In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomeriz ...
) and is the most abundant of several closely related
organic acid
An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are rel ...
s that constitute most of
rosin
Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), 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 comp ...
, the solid portion of the
oleoresin Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvents used for their production. The oleoresin of conifers is known as crude turpentine or gum turpentine, which consists of oil of ...
of
coniferous trees
Conifers are a group of cone-bearing seed plants, a subset of gymnosperms. Scientifically, they make up the division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a single extant class, Pinopsida. All extan ...
. Its
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
or
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantitie ...
is called an ''abietate''.
[Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.]
Preparation
Abietic acid is extracted from tree
rosin
Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), 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 comp ...
. The pure material is a colorless solid, but commercial samples are usually a glassy or partly
crystalline
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macrosc ...
yellowish solid that melts at temperatures as low as .
[
It belongs to the ]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.
Abietanes are found in the ...
diterpene
Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...
group of organic compounds derived from four isoprene
Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...
units. It is used in lacquer
Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity.
Asian lacquerware, which may be ca ...
s, varnish
Varnish is a clear transparent hard protective coating or film. It is not a stain. It usually has a yellowish shade from the manufacturing process and materials used, but it may also be pigmented as desired, and is sold commercially in various ...
es, and soap
Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...
s, and for the analysis of resin
In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...
s and the preparation of metal resinates. It is found in ''Pinus insularis
''Pinus kesiya'' (Khasi pine, Benguet pine or three-needled pine) is one of the most widely distributed pines in Asia. Its range extends south and east from the Khasi Hills in the northeast Indian state of Meghalaya, to northern Thailand, Philipp ...
'' (Khasi Pine), ''Pinus kesiya
''Pinus kesiya'' (Khasi pine, Benguet pine or three-needled pine) is one of the most widely distributed pines in Asia. Its range extends south and east from the Khasi Hills in the northeast Indian state of Meghalaya, to northern Thailand, Philipp ...
'' Royle, ''Pinus strobus
''Pinus strobus'', commonly called the eastern white pine, northern white pine, white pine, Weymouth pine (British), and soft pine is a large pine native to eastern North America. It occurs from Newfoundland, Canada west through the Great Lake ...
'' (Eastern White Pine), and ''Pinus sylvestris
''Pinus sylvestris'', the Scots pine (UK), Scotch pine (US) or Baltic pine, is a species of tree in the pine family Pinaceae that is native to Eurasia. It can readily be identified by its combination of fairly short, blue-green leaves and orang ...
'' (Scots Pine).
Uses
Rosin has been used for centuries for caulking
Caulk or, less frequently, caulking is a material used to seal joints or seams against leakage in various structures and piping.
The oldest form of caulk consisted of fibrous materials driven into the wedge-shaped seams between boards on w ...
ships
A ship is a large watercraft that travels the world's oceans and other sufficiently deep waterways, carrying cargo or passengers, or in support of specialized missions, such as defense, research, and fishing. Ships are generally distinguished ...
. It is also rubbed on the bows of musical instruments
A musical instrument is a device created or adapted to make musical sounds. In principle, any object that produces sound can be considered a musical instrument—it is through purpose that the object becomes a musical instrument. A person who pl ...
to make them less slippery.[ In modern times methods have been developed for improving the properties of the ]rosin acids Resin acid refers to mixtures of several related carboxylic acids, primarily abietic acid, found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids are tacky, ...
, which are otherwise soft, tacky, and low-melting and subject to rapid deterioration by oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
in air. Stability is greatly increased by heat treatment
Heat treating (or heat treatment) is a group of industrial, thermal 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 ...
.
Resin acids Resin acid refers to mixtures of several related carboxylic acids, primarily abietic acid, found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids are tacky, ...
are converted into ester gum
Glycerol ester of wood rosin (or gum rosin), also known as glyceryl abietate or ester gum, is an oil-soluble food additive ( E number E445). The food-grade material is used in foods, beverages, and cosmetics to keep oils in suspension in water, a ...
by reaction with controlled amounts of glycerol
Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
or other polyhydric alcohols
Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble soli ...
. Ester gum has drying properties and is used in paint
Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
s, varnish
Varnish is a clear transparent hard protective coating or film. It is not a stain. It usually has a yellowish shade from the manufacturing process and materials used, but it may also be pigmented as desired, and is sold commercially in various ...
es, and lacquer
Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity.
Asian lacquerware, which may be ca ...
s.[
Rosin has been used to depackage ]integrated circuits
An integrated circuit or monolithic integrated circuit (also referred to as an IC, a chip, or a microchip) is a set of electronic circuits on one small flat piece (or "chip") of semiconductor material, usually silicon. Large numbers of tiny ...
from their epoxy coatings. It is also used as a core for tin solder wire in order to increase the flow of the melted tin when heat is applied.
''In vitro'' effects
The 50% ethanol extracts from ''Resina pini'' of Pinus sp. (Pinaceae) showed inhibitory activity against testosterone 5α-reductase 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
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...
''.
Safety
Abietic acid is considered a "nonhazardous natural substance" in tall oil.[ In the U.S., it is listed in the ]Toxic Substances Control Act
The Toxic Substances Control Act (TSCA) is a United States law, passed by the 94th United States Congress in 1976 and administered by the United States Environmental Protection Agency (EPA), that regulates chemicals not regulated by other U. ...
inventory. Abietic acid is a contact allergen; however, compounds resulting from its oxidation by air elicit stronger responses. It is soluble in alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
s, acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
, and ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...
s.
References
External links
Abietic acid MS Spectrum
Wolfram Alpha Page
{{Authority control
Carboxylic acids
Diterpenes
Phenanthrenes