ABIETIC ACID

Abietic acid is probably a major allergen of colophony, by way of oxidation products.
Abietic acids detection in a material indicates that allergenic components of colophony are present.
Abietic acid is a naturally occurring organic compound that belongs to the class of diterpene resin acids, and it is one of the primary components found in rosin, which is obtained from the resin of various pine trees. 

CAS Number: 514-10-3
Molecular Formula: C20H30O2
Molecular Weight: 302.45
EINECS Number: 208-178-3

Synonyms: ABIETIC ACID, 514-10-3, Sylvic acid, l-Abietic acid, 7,13-Abietadien-18-oic acid, Kyselina abietova, 13-Isopropylpodocarpa-7,13-dien-15-oic acid, CCRIS 3183, Abietic acid, technical, Abietinic acid, EINECS 208-178-3, NSC 25149, UNII-V3DHX33184, (-)-Abietic acid, CHEBI:28987, AI3-17273, V3DHX33184, NSC-25149, DTXSID7022047, Podocarpa-7,13-dien-15-oic acid, 13-isopropyl-, (1R,4aR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid, (1R,4AR,4BR,10AR)-1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-1-PHENANTHRENECARBOXYLIC ACID, DTXCID202047, 1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-, (1R-(1ALPHA,4ABETA,4BALPHA,10A.ALPHA)).-, 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl-)-, 208-178-3, Abietate, Rosin Acid, MFCD03423567, Abieta-7,13-dien-18-oic acid, Abietic Acid, >95%, (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, 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aR,4bR,10aR)-, NSC25149, (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid, Abietic Acid, 75%, NCGC00166273-01, Colophonium, abieta-7,13-dien-18-oate, Kyselina abietova [Czech], Abietic acid dimer, 15522-12-0, Kolophonium, Highrosin, Shiragiku rosin, Yellow resin, Rondis R, WW Wood rosin, Rosin WW, Hongkong rosin WW, Levamisole resinate, AbietinsA currencyure, Rosin [USP], Bandis G100, Abietic acid, 90%, Caswell No. 667, BALS 3A, DSSTox_CID_2047, ABIETIC ACID [MI], DSSTox_RID_82575, DSSTox_GSID_47831, SCHEMBL28888, CHEMBL71893, Podocarpa-7, 13-isopropyl-, EM 3, UNII-88S87KL877, RSWGJHLUYNHPMX-ONCXSQPRSA-, AAA51410, BCP14376, MSK40139, EINECS 232-475-7, Tox21_112386, BDBM50442901, KE 709, NSC154789, Podocarpa-7, 13-isopropyl-, dimer, s5122, AKOS016036412, 88S87KL877, Abietic acid, technical, ~75% (GC), CCG-267495, EPA Pesticide Chemical Code 067205, LMPR0104050001, NSC-154789, (5beta)-abieta-7,13-dien-18-oic acid, 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl- ), AS-35301, DA-50090, NCI60_002007, NS00075578, 10248-55-2, C06087, EC 232-475-7, EN300-1699654, Q321068, WLN: L B666 EU GUTJ A1 EY1&1 KVQ K1, C32BF2BB-9F97-4AF5-8F5E-06BC0EA97E83, F8881-8980, Z1954802293, Abietic acidColeonol; colforsina; colforsine; colforsinum; Boforsin, 1-Phenanthrenecarboxylic acid,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, [1R-(1.alpha.,4a.beta.,4b.alpha.,10a.alpha.)]-, A9H, InChI=1/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1, ABIETIC ACID;(1R,4AR,4BR,10AR)-7-ISOPROPYL-1,4A-DIMETHYL-1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-PHENANTHRENE-1-CARBOXYLIC ACID;13-isopropyl-podocarpa-13-dien-15-oicacid;13-isopropylpodocarpa-7,13-dien-15-oicacid;ABIETIC ACID, TECH., 70%;ABIETIC ACID MELTING POINT 153-167 C;ABIETIC ACID, 90-95%;Abieticacid,TechnicalGrade

Abietic acid is a tricyclic carboxylic acid with the molecular formula C₂₀H₃₀O₂, and its structure includes a phenanthrene-like ring system with an isopropyl group and a carboxylic acid functional group.
Abietic acid is typically yellowish and appears as a solid at room temperature, although it can be melted and purified for industrial or laboratory use. 
Abietic acid is moderately soluble in organic solvents such as ethanol and acetone, but sparingly soluble in water. 

Abietic acid is chemically reactive, especially due to the presence of its carboxylic acid group, which allows it to form salts, esters, and other derivatives.
Abietic acid (also known as abietinic acid or sylvic acid) is a diterpenoid found in coniferous trees. 
It is supposed to exist to defend the host plant from insect attack or various wounds.

Abietic acid 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 commercially important. 
Historically speaking, it was a major component of naval stores. 

Abietic acid 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.

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).
Abietic acid is soluble in alcohols, acetone, and ethers. 
Its esters and salts are called an abietates, e.g. ethyl abietate and sodium abietate.

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.

Abietenes are synthesized from geranylgeranyl diphosphate via a copalyl diphosphate intermediate by class 2 diterpene cyclases and class 1 diterpene syntheses.
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.
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.

Abietic acid (also known as abietinic acid or sylvic acid) is an organic compound that occurs widely in trees.
Abietic Acid 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.

Abietic Acid belongs to the abietane diterpene group of organic compounds derived from four isoprene units.
Abietic Acid is used in lacquers, varnishes, and soaps, and for the analysis of resins and the preparation of metal resinates.
Abietic Acid is found in Pinus insularis (Khasi Pine), Pinus kesiya Royle, Pinus strobus (Eastern White Pine), and Pinus sylvestris (Scots Pine).

Abietic acid is an organic abietane diterpenoid and the primary component of resin acid. 
Extracted from tree rosin, abietic acid's applications include use in lacquers, varnishes, soaps, the analysis of resins, and the preparation of metal resinates.

In nature, abietic acid plays a protective role for coniferous trees, acting as a defense compound against insects and pathogens by contributing to the stickiness and antimicrobial properties of tree resins. 
Industrially, it is used in the production of varnishes, adhesives, and sealing waxes, and also as a precursor for making soaps, inks, and synthetic resins.

Melting point: 139–142 °C (lit.), 150–165 °C  
Boiling point: 440 °C  
alpha: D24 -106° (c = 1 in abs alc)  
Density: 1.06  
Refractive index: 1.4800 (estimate)  
Flash point: 208 °C  
Storage temp.: 2–8 °C  
Solubility: Soluble in alcohols, acetone, and ethers  
pKa: pK1: 7.62 (25 °C)  
Form: Crystals and Chunks  
Color: Yellow-brownish  
Odor: at 100.00 %: mild acetic  
Optical activity: [α]20/D 85±10°, c = 1% in ethanol  
Water solubility: Soluble in acetone, petroleum ether, diethyl ether, and ethanol. Insoluble in water.  
Sensitive: Air Sensitive  
Merck: 14,7  
BRN: 2221451  
Exposure limits: NIOSH: TWA 0.1 mg/m³  
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.  
LogP: 6.460  

An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.
Abietic acid reacts exothermically with bases, both organic (for example, the amines) and inorganic. 
Can react with active metals to form gaseous hydrogen and a metal salt. 

Such reactions are slow if the solid acid remains dry. 
Can react with cyanide salts to generate gaseous hydrogen cyanide. 
The reaction is slow for dry, solid carboxylic acids. 

Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. 
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. 
Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.

Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. 
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. 
These reactions generate heat. A wide variety of products is possible. 

Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Abietic acid is probably the major allergen of colophony, along with dehydroabietic acid, by way of oxidation products. 
Its detection in a material indicates that allergenic components of colophony are present

Abietic acid is an irritant in resin and pine wood. 
Abietic acid is found in lacquers, varnishes, and soaps.
Abietic acid, the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. 

Commercial abietic acid is usually a glassy or partly crystalline, yellowish solid that melts at temperatures as low as 85° C (185° F). 
Abietic acid belongs to the diterpene group of organic compounds (compounds derived from four isoprene units).
Abietic acid can be an allergen and is known to cause skin irritation or contact dermatitis in sensitive individuals. 

Therefore, proper handling and safety precautions are necessary when working with it in concentrated forms.
Abietic acid is a naturally derived organic compound that primarily exists in the resin of coniferous trees, especially pine species, and it serves as one of the chief constituents of colophony, more commonly known as rosin. 

Abietic acid is classified as a diterpenoid resin acid, meaning it is composed of four isoprene units and contains 20 carbon atoms, giving it the molecular formula C₂₀H₃₀O₂. 
Structurally, it consists of a complex, tricyclic ring system with a carboxylic acid group at one end, and it exists in nature as part of a mixture of related resin acids.
In its pure form, abietic acid is a pale yellow solid with a faint characteristic odor, and it melts at around 173°C, making it relatively easy to purify and manipulate for industrial uses. 

Abietic acid is sparingly soluble in water, but readily dissolves in organic solvents like ethanol, ether, and acetone, which makes it suitable for various chemical reactions, especially in esterification and salt formation. 
Because of its carboxylic acid group, abietic acid can react with alkalis to form metallic soaps that are widely used in the production of paints, inks, and emulsifiers.

In industrial and commercial applications, abietic acid plays a vital role in the formulation of varnishes, adhesives, synthetic rubber, lubricants, and sealing materials, due to its sticky, film-forming, and chemically modifiable nature. 
Abietic acid is also used in the manufacture of rosin-based fluxes in soldering processes, especially in electronics, where it helps clean metal surfaces and promote proper solder adhesion.
Abietic acid has drawn interest for its anti-inflammatory, antibacterial, and cytotoxic properties in recent research, although its therapeutic potential is still under investigation and not yet widely utilized in clinical settings.

On the downside, abietic acid is known to be a skin sensitizer, and repeated exposure, especially in the workplace (e.g., among musicians handling rosin or workers in varnish industries), may lead to contact dermatitis, skin irritation, or allergic reactions. 
Because of this, products containing unmodified abietic acid are often labeled with safety warnings, and protective equipment is recommended during handling.
Abietic acid is considered biodegradable, but it can be moderately toxic to aquatic organisms in high concentrations, particularly in its free acid form or when present in industrial effluents, so care must be taken during disposal.

Uses Of Abietic acid:
Abietic Acid is the primary component of resin acid found commonly in rosin. 
Abietic Acid exhibited potent testosterone 5α-reductase inhibitory activity in vitro.
Abietic acid, e.g., methyl ester, vinyl and glyceryl esters for use in lacquers and varnishes; manufacture of "metal resinates", soaps, plastics, and paper sizes; assists growth of lactic and butyric acid bacteria; component in tall oil used as deodorizing agent in cooling fluids; major component of rosin used in the production of varnishes, printing inks, paper, soldering fluxes, greases, cutting fluids, glue tackifiers, adhesives, surface coatings, polish, shoes, insulations, waxes, cosmetics (mascara, rouge, eye shadow), topical medicaments, violin bow rosin, day, athletic grip aid, pine oil deansers; component in dental impression materials and periodontal packings

Abietic acid is used to make ester gums in lacquers, varnishes and soaps. 
It is also used in metal resonates and plastics. 
Further, it is utilized in musical instruments to make them less slippery. 

Abietic acid acts as a precursor to natural product synthesis. 
In addition to this, it is used to depackage integrated circuits from their epoxy coatings.
As a component of rosin and one of the principal resin acids, abietic acid has many uses, e.g. in some paints, soaps, foods, soldering flux,

Abietic acid has a wide range of industrial, chemical, and functional uses, owing to its unique chemical structure, natural abundance, and reactivity, especially its carboxylic acid group and hydrophobic tricyclic ring system. 
One of the most common uses of abietic acid is in the manufacture of metallic soaps, such as sodium, calcium, and potassium abietates, which are formed by neutralizing abietic acid with metal hydroxides. 
These soaps are widely employed as emulsifiers, stabilizers, and dispersing agents in a variety of industrial formulations, including paints, varnishes, adhesives, and lubricants, where they contribute to texture, film formation, and durability.

Abietic acid is a primary ingredient in rosin fluxes used in electronics and metal soldering, where it helps by cleaning oxide layers from metal surfaces during the soldering process. 
Its mildly acidic and tacky nature allows it to both promote metal adhesion and protect solder joints from oxidation while being non-corrosive to the surrounding components when properly removed.
Because of its excellent film-forming properties, abietic acid and its derivatives are used in the preparation of oil-modified alkyd resins, which are the base for many wood finishes, protective coatings, and clear varnishes. 

These resins create a glossy, durable, and water-resistant finish, making them highly suitable for protecting furniture, floors, and musical instruments.
Abietic acid is often employed as a plasticizer or softening agent in the rubber and plastics industries, where it improves the flexibility and processability of various synthetic materials.
Abietic acid can also be used to modify the thermal and mechanical properties of synthetic polymers, particularly those based on styrene or acrylates.

Due to its sticky, resinous nature and ability to form strong, tacky bonds, abietic acid is a valuable raw material in the formulation of pressure-sensitive adhesives and sealants, which are used in products like labels, tapes, packaging materials, and glues.
Abietic acid is sometimes included in rosin-based soaps, which were historically common in laundry applications. 
These soaps exhibit excellent wetting and foaming characteristics, though today they are used more in specialty soaps or traditional soap making rather than commercial detergents.

Abietic acid serves as a starting material or precursor in the synthesis of a wide range of chemical compounds, including resin esters, amides, and hydrogenated derivatives. 
These compounds are used in pharmaceuticals, perfumes, and specialty chemicals.
Although not yet widely commercialized, abietic acid is being studied for its anti-inflammatory, antimicrobial, and anticancer properties in biomedical research. 

Its structure shows activity against certain pathogens and cancer cell lines, making it a promising lead compound for future drug development.
Rosin modified with abietic acid is used in printing inks, particularly those that require rapid drying, strong adhesion, and color retention. 
The resin improves the viscosity and film strength, contributing to the overall print quality on paper and packaging materials.

Safety Profile Of Abietic acid:
Abietic acid is known to be a skin sensitizer, meaning that repeated or prolonged contact can cause allergic contact dermatitis in sensitive individuals. 
Even a small amount of the compound may trigger redness, itching, swelling, or blistering on the skin, particularly in people who have developed sensitivity over time — such as musicians who frequently handle rosin or industrial workers who come into contact with resin-based products.

When abietic acid is heated, especially during soldering or in resin production, it can release vapors or fumes that may irritate the respiratory tract. 
Inhalation of these fumes can lead to symptoms such as coughing, throat discomfort, shortness of breath, or a burning sensation in the nose or lungs. 
In poorly ventilated areas, these effects can be more severe, and repeated inhalation might contribute to chronic respiratory sensitization.

Poison by intravenous route combustible slight explosion hazard as dust. 
Whenheated to decomposition it emits acrid smoke andirritating fumes.
As the chief component of rosin, abietic acid is approved by the US FDA as a miscellaneous food additive.

Abietic acid is considered a "nonhazardous natural substance" in tall oil ("liquid rosin").
In the U.S., abietic acid is listed in the inventory of the Toxic Substances Control Act.
Abietic acid is the primary irritant in pine wood and resin. 

Abietic acid as a contact allergen it is the cause of abietic acid dermatitis. 
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 inhibitory activity against testosterone 5α-reductase in vitro.