514-10-3 Usage
Description
Abietic Acid, a major component of resin acid, is a yellowish resinous powder commonly found in rosin. It is an abietane diterpenoid with a carboxy group at position 18, exhibiting potent testosterone 5α-reductase inhibitory activity in vitro. Abietic Acid is also known to be a major allergen of colophony through its oxidation products.
Uses
Used in Chemical Industry:
Abietic Acid is used as a primary component in the production of various esters, such as methyl ester, vinyl, and glyceryl esters, which are utilized in lacquers, varnishes, and soaps. It is also used in the manufacture of metal resinates, soaps, plastics, and paper sizes.
Used in Manufacturing Industry:
Abietic Acid serves as a major component in the production of varnishes, printing inks, paper, soldering fluxes, greases, cutting fluids, glue tackifiers, adhesives, surface coatings, polish, shoes, insulations, and waxes.
Used in Cosmetics and Personal Care:
Abietic Acid is used in cosmetics, such as mascara, rouge, and eye shadow, as well as in the formulation of topical medicaments.
Used in Musical Instruments:
Abietic Acid is utilized in the production of rosin for violin bows and as an athletic grip aid, making musical instruments less slippery and enhancing grip.
Used in Dental Industry:
Abietic Acid is a component in dental impression materials and periodontal packings.
Used in Electronics Industry:
Abietic Acid is used as a deodorizing agent in cooling fluids and as a precursor to natural product synthesis, as well as in the depackaging of integrated circuits from their epoxy coatings.
Used in Agriculture:
Abietic Acid assists in the growth of lactic and butyric acid bacteria, contributing to the agricultural industry.
Used in Pine Oil Production:
Abietic Acid is a component in tall oil, which is used as a deanser in the production of pine oil.
Reactivity Profile
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.
Health Hazard
ACUTE/CHRONIC HAZARDS: Slight fire hazard, slight explosive hazard as dust. Low toxicity.
Fire Hazard
Combustible.
Contact allergens
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
Safety Profile
Poison by intravenous route.Combustible. Slight explosion hazard as dust. Whenheated to decomposition it emits acrid smoke andirritating fumes.
Purification Methods
Filter, dry it in a vacuum (over KOH or CaSO4) and store it in an O2-free atmosphere. It can also be purified via the anhydride, tritylabietate and the potassium, piperidine and brucine salts. max : nm(log ): 2343(4.3), 241(4.4), 2505(4.2), 235(4.34) and 240(4.36) in Et. [Harris & Sanderson Org Synth Coll Vol IV 1 1963, J Am Chem Soc 35 3736 1949, Lambard & Frey Bull Soc Chim Fr 1194 1948, Buchbauer et al. Monatsh Chem 116 1345 1985.] [Beilstein 9 IV 2175.]
Check Digit Verification of cas no
The CAS Registry Mumber 514-10-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 514-10:
(5*5)+(4*1)+(3*4)+(2*1)+(1*0)=43
43 % 10 = 3
So 514-10-3 is a valid CAS Registry Number.
InChI: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)/p-1/t16-,17-,19-,20+/m1/s1
514-10-3Relevant articles and documents
Hessenland,Stephani,Leo
, p. 2473,2479 (1936)
-
Fleck,Palkin
, p. 1230,1232 (1939)
-
In depth analysis of chiroptical properties of enones derived from abietic acid
Masnyk, Marek,Butkiewicz, Aleksandra,Górecki, Marcin,Luboradzki, Roman,Paluch, Piotr,Potrzebowski, Marek J.,Frelek, Jadwiga
, p. 3547 - 3561 (2018/04/14)
With the use of inexpensive commercially available abietic acid, a whole series of abietane enones were prepared in high yields. The structures of all the products obtained were determined by comprehensive spectroscopic analysis with particular emphasis on the use of advanced NMR techniques, comparison with previously reported data and, where possible, by single crystal X-ray diffraction. However, in cases where X-ray crystallography was not applicable or compounds tested were unstable, a final stereochemical assignment could be inferred only by electronic circular dichroism (ECD) supported by vibrational circular dichroism to increase credibility. To reveal the relationship between structure and chiroptical properties, we used combined experimental and theoretical analysis of geometries, structural parameters, and chiroptical properties of all enones synthesized. A thorough analysis of their conformational flexibility by examining the effect of solvent and temperature on the ECD spectra was also used to achieve desired objectives. As a result, the impact of substituents adjacent to the enone chromophore on the conformation was determined by demonstrating that even slight changes in the position of hydroxyl and isopropyl groups attached to carbon C13 may substantially affect ECD curves' pattern, leading in some cases to Cotton effects sign reversal.
Sulphonated dehydrogenated sylvate, the preparation and use
-
Page/Page column 5, (2008/06/13)
This invention relates to salts of sulfodehydroabietic acid with bismuth or zinc, a kind of new salt useful in treating digestive canal ulcer, acute and chronic gastritis, and erosive gastritis etc., as well as its preparation and use. Said salts can be represented by formula (1), wherein R is Bi(OH)++ or Zn++, 2Bio+, 1/2ZnH, n=0-10. The preparation method comprises following steps: (a) sequentially treating the industrial abietic acid calcium salt with acid, base and extracting with organic solvent to give abietic acid with less isomer; (b) reacting said abietic acid with Pd/C to provide dehydroabietic acid, then converting it to pure sulphonic product, namely sulfodehydroabietic acid, via sulphonation and recrystallization; (c) by use of neutralization or salt displacement reaction to convert the sulphonic product of zinc or bismuth salts of sulfodehydroabietic acid. The resultant salts can used to prepare medicine for treating digestive canal ulcer and gastritis.
Investigation of the Allergenic Principles from Colophony: Autoxidation, Synthesis, and Sensitization
Krohn, Karsten,Budianto, Emil,Floerke, Ulrich,Hausen, Bjoern M.
, p. 911 - 920 (2007/10/02)
The autoxidation of abietic acid (1a), levopimaric acid (2a), and dehydroabietic acid (3a) was studied and the compounds 3a as well as (after esterification) 8b, 9b, 10b, 11b (from 1a); 6b (from 2a); and 4b, 5b (from 3a) were isolated for the first time.Some derivatives (6a, 6b, 13b/14b, and 7b) were semi-synthezised.The isolated autoxidation products, the synthetic compounds and some polar fractions of natural colophony were tested for their sensitizing capacity.Compounds 4a, 10b, 16, and 18 as well as the combined polar fraction A-D of colophony show enhanced sensitizing capacity.Methylation of the acids to the ester significantly reduces their activity.Key Words: Resin acids, autoxidation of / Colophony, allergy of / Sensitizing potency