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. Th ...

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 (biology), family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanic ...

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 ...

s that constitute most of

, 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 ...

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 ...

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 quant ...

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

. 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, macros ...

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 c ...

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 variou ...

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 us ...

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 nat ...

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, Ph ...

'' (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 or ...

'' (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 ...

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 ...

in air. Stability is greatly increased by

heat treatment Heat treating (or heat treatment) is a group of industrial process, industrial, thermal and metalworking, metalworking processes used to alter the physical property, physical, and sometimes chemical property, chemical, properties of a material. ...

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, and ...

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. 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 ...

es, and

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 tin ...

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 a ...

''.

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 An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical terms ...

; 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 ...

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 miscibl ...

, 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 ...

References

External links

Abietic acid MS Spectrum

Wolfram Alpha Page
{{Authority control Carboxylic acids Diterpenes Phenanthrenes