Names | |
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IUPAC name Abieta-7,13-dien-18-oic acid | |
Systematic IUPAC name (1R,4aR,4bR,10aR)-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid | |
Other names Abietinic acid; Sylvic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.436 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C20H30O2 | |
Molar mass | 302.458 g·mol−1 |
Appearance | Yellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water). Colorless solid when pure. |
Density | 1.06 g/mL |
Melting point | 172–175 °C (342–347 °F; 445–448 K) [1] |
Boiling point | 250 °C; 482 °F; 523 K |
Insoluble [1] | |
Solubility in other solvents | Very soluble in acetone, petroleum ether, Et2O, and ethanol |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Irritant |
GHS labelling: | |
Warning | |
H317 | |
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501 | |
NFPA 704 (fire diamond) | |
Safety data sheet (SDS) | MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Abietic acid (also known as abietinic acid or sylvic acid) is a diterpenoid found in coniferous trees. It is supposed to exist as a defend the host plant from insect attack or various wounds. Chemically, it is a complicated molecule featuring two alkene groups and a carboxylic acid within a chiral tricyclic framework. As the major component of rosin, it is a commercially important. Historically speaking, it was a major component of naval stores. It is the most common of the resin acids. Another common resin acid is pimaric acid, which converts to abietic acid upon heating.
Abietic acid is found in rosin obtained from pine trees. [2] Pure abietic acid is a colorless solid, but commercial samples are usually a glassy or partly crystalline yellowish solid that melts at temperatures as low as 85 °C (185 °F). [3] Abietic acid is soluble in alcohols, acetone, and ethers. Its esters and salts are called an abietates, e.g. ethyl abietate and sodium abietate. [4]
The ancient presence of abietic acid (and other resin acids), being abundant and resilient, can inferred by analysis of rocks and archeological samples. Through the process of diagenesis, abietic acid changes into a collection of simpler compounds called abietanes.
Abietic acid is derived from the diterpene abietadiene, which in turn is made from copalyl pyrophosphate (CPP), which is derived from geranylgeranyl pyrophosphate ( GGPP), the precursor to many diterpenoids. In air and in the presence of certain cytochrome P450 enzymes, abietadiene is oxidized to abietic acid. An entire family of so-called resin acids form similarly. Together with abietic acid, these resin acids are a major portion of rosin, the solid portion of the oleoresin of coniferous trees.
The conformation of the GGPP molecule dictates the stereochemistry of the CPP intermediate after cyclization. The stereochemistry of the typical abietane skeleton suggests a GGPP precursor with its fused cyclohexyl rings in a chair-chair ("normal") conformation, although some abietanes with alternative stereochemistry may be cyclized from CCP isomers containing alternative combinations of boat and chair cyclohexane conformers. After the initial cyclization to CPP, which forms rings A and B in the abietane skeleton, the C ring is formed with the help of a class I diterpene synthase enzyme. Subsequent methyl migration and dehydrogenation steps yield the abietene isomers. [5]
Abietic acid is extracted from tree rosin. Laboratory procedures illustrate the nature of the extraction, which is the basis of a substantial industry, formerly known as naval stores. [6]
As a component of rosin and one of the principal resin acid]]s, abietic acid has many uses, e.g. in some paints, soaps, foods, soldering flux,
A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, and predominantly terpenes. Well known resins include amber, hashish, frankincense, myrrh and the animal-derived resin, shellac. Resins are commonly used in varnishes, adhesives, food additives, incenses and perfumes.
Turpentine is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Principally used as a specialized solvent, it is also a source of material for organic syntheses.
Rosin, also known as colophony or Greek pitch (Latin: pix graeca), is a resinous material obtained from pine trees and other plants, mostly conifers. The primary components of rosin are diterpenoids, i.e., C20 carboxylic acids. Rosin consists mainly of resin acids, especially abietic acid. Rosin often appears as a semi-transparent, brittle substance that ranges in color from yellow to black and melts at stove-top temperatures.
In metallurgy, a flux is a chemical reducing agent, flowing agent, or purifying agent. Fluxes may have more than one function at a time. They are used in both extractive metallurgy and metal joining.
Dihydrotestosterone is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.
Diterpenes are a class of terpenes 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 a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and anti-inflammatory.
5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes of 5α-reductase encoded by the genes SRD5A1, SRD5A2, and SRD5A3.
Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common (-)-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.
Resin acid refers to any of several related carboxylic acids found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids occur in nature as tacky, yellowish gums consisting of several compounds. They are water-insoluble. A common resin acid is abietic acid. Resin acids are used to produce soaps for diverse applications, but their use is being displaced increasingly by synthetic acids such as 2-ethylhexanoic acid or petroleum-derived naphthenic acids.
Pimaric acid is a carboxylic acid that is classified as a resin acid. It is a major component of the rosin obtained from pine trees.
Tall oil, also called liquid rosin or tallol, is a viscous yellow-black odorous liquid obtained as a by-product of the kraft process of wood pulp manufacture when pulping mainly coniferous trees. The name originated as an anglicization of the Swedish tallolja. Tall oil is the third largest chemical by-product in a kraft mill after lignin and hemicellulose; the yield of crude tall oil from the process is in the range of 30–50 kg / ton pulp. It may contribute to 1.0–1.5% of the mill's revenue if not used internally.
Ferruginol is a natural phenol with a terpenoid substructure. Specifically, it is a diterpene of the abietane chemical class, meaning it is characterized by three fused six-membered rings and alkyl functional groups. Ferruginol was first identified in 1939 by Brandt and Neubauer as the main component in the resin of the Miro tree and has since been isolated from other conifer species in the families Cupressaceae and Podocarpaceae. As a biomarker, the presence of ferruginol in fossils, mainly resin, is used to describe the density of these conifers in that particular biosphere throughout time.
Taxodone is a naturally occurring diterpenoid found in Taxodium distichum, Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.
Abietane is an organic compound with the formula C20H36. It is a tricyclic, saturated hydrocarbon with an elaborate stereochemistry. It is a colorless solid. It is of little biochemical interest except as a reference structure of the abietanes,
Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. Levopimaric acid accounts for about 18 to 25% of pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.
This article is about the discovery and development of 5α-reductase inhibitors (5-ARIs), also known as dihydrotestosterone (DHT) blockers.
Spruce resin salve is a traditional wound treatment method that has gained new popularity again after clinical studies in the 21st century. The pure coniferous resin from Norway spruce is antimicrobial against a wide range of bacteria and fungi and positively associates with progressive healing of the wound. The improvement is not limited to the healing of the infected wounds only, suggesting that the resin has positive influences on mechanisms that play a role in wound repair.
Sugiol is a phenolic abietane derivative of ferruginol and can be used as a biomarker for specific families of conifers. The presence of sugiol can be used to identify the Cupressaceae s.1., podocarpaceae, and Araucaraiaceae families of conifers. The polar terpenoids are among the most resistant molecules to degradation besides n-alkanes and fatty acids, affording them high viability as biomarkers due to their longevity in the sedimentary record. Significant amounts of sugiol has been detected in fossil wood dated to the Eocene and Miocene periods, as well as a sample of Protopodocarpoxylon dated to the middle Jurassic.
Palustric acid is an organic compound with the formula C20H30O2. It is classified as a diterpenoid and a resin acid. Palustric acid is an isomer of abietic acid: the location of the two C=C bonds differ in these two compounds. It is a colorless solid that is soluble in polar organic solvents. In terms of biological function palustric acid protects its host trees, especially conifers, against insects, an example of plant defense against herbivory. It is biosynthesized from the C20 precursor geranylgeranyl diphosphate.