Auricolic Acid
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Auricolic Acid
Auricolic acid is a linear fatty acid composed of 20 carbon atoms, with two double bonds at the position 11=12 and 17=18 and a hydroxyl-OH at the position 14. The compound's delta notation is 14-OH-20: 2Δ. The acid is found in '' Lesquerella auriculata'' seed oil. Also, the compound has been isolated from '' Lesquerella ludoviciana'', ''Lesquerella calcicola'', ''Physaria saximontana'' and others from the genera ''Lesquerella'' and ''Physaria'' (Bladderpod oil Bladderpod oil is a seed oil, extracted from the seeds of the ''Physaria fendleri'' and other species of genus ''Physaria'', Native to the plains and mesas of southwestern United States, eastward to Kansas and southward into northern Mexico. Bladder ...). Discovery The acid was initially isolated in 1937 by researchers Kleiman, Spencer, Earle, Nieschlag, Barclay in the oil of '' Lesquerella auriculata'' and ''Lesquerella densiflora'' with the concentration of auricolic acid being between 30% and 40% of the total fatty acids ...
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Fatty Acid
In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an Branched chain fatty acids, unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids (up to 70% by weight) in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important diet (nutrition), dietary sources of fuel for animals and important structural components for cell (biology), cells. History The concept of fatty acid (''acide gras'') was introduced in 1813 by Michel Eugène Chevreul, though he initially used some variant terms: ''graisse acide'' and ''acide huileux'' ("acid fat" and "oi ...
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Double Bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were introduced in chemical notation by Russian chemist Alexander Butlerov. Double bonds involving carbon are stronger and shorter than single bonds. The bond order is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions of the halogens). File:Ethene structural.svg, ...
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John Wiley & Sons
John Wiley & Sons, Inc., commonly known as Wiley (), is an American Multinational corporation, multinational Publishing, publishing company that focuses on academic publishing and instructional materials. The company was founded in 1807 and produces books, Academic journal, journals, and encyclopedias, in print and electronically, as well as online products and services, training materials, and educational materials for undergraduate, graduate, and continuing education students. History The company was established in 1807 when Charles Wiley opened a print shop in Manhattan. The company was the publisher of 19th century American literary figures like James Fenimore Cooper, Washington Irving, Herman Melville, and Edgar Allan Poe, as well as of legal, religious, and other non-fiction titles. The firm took its current name in 1865. Wiley later shifted its focus to scientific, Technology, technical, and engineering subject areas, abandoning its literary interests. Wiley's son Joh ...
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Lesquerella Auriculata
''Lesquerella'' is the former name of a genus of flowering plants in the family Brassicaceae.Genus: ''Lesquerella'' S. Watson
USDA GRIN Taxonomy for Plants
Recent work has shown that ''Lesquerella'' is indistinct from the genus '''' and both genera have been united under ''Physaria''. In addition, the former ''Lesquerella'' of the southeastern United States have been moved to the genus '' Paysonia'' since 2002. The genus ''Lesquerella'' is now no longer applied to any species and is considered defunct. The genus is named in honor of

Springer Publishing
Springer Publishing Company is an American publishing company of academic journals and books, focusing on the fields of nursing, gerontology, psychology, social work, counseling, public health, and rehabilitation (neuropsychology). It was established in 1951 by Bernhard Springer, a great-grandson of Julius Springer, and is based in Midtown Manhattan, New York City. History Springer Publishing Company was founded in 1950 by Bernhard Springer, the Berlin-born great-grandson of Julius Springer, who founded Springer Science+Business Media, Springer-Verlag (now Springer Science+Business Media). Springer Publishing's first landmark publications included ''Livestock Health Encyclopedia'' by R. Seiden and the 1952 ''Handbook of Cardiology for Nurses''. The company's books soon branched into other fields, including medicine and psychology. Nursing publications grew rapidly in number, as Modell's ''Drugs in Current Use'', a small annual paperback, sold over 150,000 copies over several edi ...
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CRC Press
The CRC Press, LLC is an American publishing group that specializes in producing technical books. Many of their books relate to engineering, science and mathematics. Their scope also includes books on business, forensics and information technology. CRC Press is now a division of Taylor & Francis, itself a subsidiary of Informa. History The CRC Press was founded as the Chemical Rubber Company (CRC) in 1903 by brothers Arthur, Leo and Emanuel Friedman in Cleveland, Ohio, based on an earlier enterprise by Arthur, who had begun selling rubber laboratory aprons in 1900. The company gradually expanded to include sales of laboratory equipment to chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a graduated scientist trained in the study of chemistry, or an officially enrolled student in the field. Chemists study the composition of ...s. In 1913 the CRC offered a short (116-page) manual called the ''Rubber Handboo ...
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Lesquerella Ludoviciana
''Physaria ludoviciana'' is a species of flowering plant in the mustard family Brassicaceae, with the common names of bladder pod, silver bladderpod, louisiana bladderpod, and foothill bladderpod. It used to be ''Lesquerella ludoviciana'' which is now a synonym. The plant is a source of auricolic acid, a rare fatty acid. Description ''Physaria ludoviciana'' is a taprooted perennial, growing 6-16 inches tall. The flowers have four sepals and four yellow petals and six stamens. The leaves are simple, narrow, and covered with stellate-pilose hairs. The basal leaves are produced in a rosette. The two locule A locule (: locules) or loculus (; : loculi) is a small cavity or compartment within an organ or part of an organism (animal, plant, or fungus). In angiosperms (flowering plants), the term ''locule'' usually refers to a chamber within an ovary ...d fruits are a globe-like silicle with dense pilose hairs. Flowering occurs in early spring to mid/late summer, and some plants a ...
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Lesquerella
''Lesquerella'' is the former name of a genus of flowering plants in the family Brassicaceae.Genus: ''Lesquerella'' S. Watson
USDA GRIN Taxonomy for Plants
Recent work has shown that ''Lesquerella'' is indistinct from the genus ''
Physaria ''Physaria'' is a genus of flowering plants in the family Brassicaceae. Many species are known generally as twinpods, bladderpods, or lesquerella. They are native to the Americas, with many species endemic to western North America. They are dense ...
'' and both genera have been united under ''Physaria''. In addition, the former ''Lesquerella'' of the southeastern United States have been moved to the genus ''
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Physaria
''Physaria'' is a genus of flowering plants in the family Brassicaceae. Many species are known generally as twinpods, bladderpods, or lesquerella. They are native to the Americas, with many species endemic to western North America. They are densely hairy annual and perennial herbs often growing prostrate or decumbent, along the ground in patches or clumps. They bear inflorescences of bright yellow flowers. The fruit is often notched deeply, dividing into twin sections, giving the genus its common name. Bladderpod oil is extracted from the seeds of '' Physaria fendleri'' and certain other species in the genus.
U.S. Fish and Wildlife Service: Missouri Bladderpod 5-Year Review (2008)
Due to the presence of both annual and perennial herbaceous members, this genus has been used as a model for allocation pattern comparison ...
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Bladderpod Oil
Bladderpod oil is a seed oil, extracted from the seeds of the ''Physaria fendleri'' and other species of genus ''Physaria'', Native to the plains and mesas of southwestern United States, eastward to Kansas and southward into northern Mexico. Bladderpod oil is rich in lesquerolic acid (C20:1-OH), a rare hydroxycarboxylic acid. The only commercial source of hydroxycarboxylic acids is ricinoleic acid (C18:1-OH), found in castor oil. Essentially all castor oil production in the U.S. has been eliminated by a combination of economic factors, excessive allergenic reactions of field and processing workers, and toxicity of the seed meal. The fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ... composition of bladderpod oil is: Other species of bladderpod that yield similar oils in ...
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Lipids (journal)
The American Oil Chemists' Society (AOCS) is an international professional organization based in Urbana, Illinois dedicated to providing the support network for those involved with the science and technology related to fats, oils, surfactants, and other related materials. Founded in 1909, AOCS has approximately 2,000 members in 90 countries who are active in a total of ten divisions and six sections, of which only one of the sections is within the United States. History The AOCS was started in May 1909 under the name ''Society of Cotton Products Analysts'' as a group that promoted recommended methods for chemical processes focused on the cottonseed industry. In 1920, the name was changed to American Oil Chemists' Society.National Academy of Sciences - National Research Council (1961), ''Scientific and Technological Societies of the United States and Canada, 7th ed.''; National Academy of Sciences, National Research Council, Washington D.C. In 1976, AOCS hosted the first World C ...
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