Isanic Acid
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Isanic Acid
Isanic acid or erythrogenic acid is a linear fatty acid composed of 18 carbon atoms, with two triple bonds in the positions 9≡10 and 11≡12 and a double bond in the position 17=18. This is one of the rare polyacetylenic acids with conjugated triple bonds. Its delta notation is 18:3Δ9a,11a,17. Its structural formula is CH2=CH-(CH2)4–C≡C–C≡C–(CH2)7–COOH. Exocarpic acid is isomeric to isanic acid. The related isanolic acid, unlike isanic acid, contains an additional hydroxyl group. The oxygenated isanic acid is called ketoisanic acid. Discovery Isanic acid was initially isolated in 1937 by researchers A. Steger and J. van Loon in the oil of the seeds of ''Ongokea gore'' or ''Ongokea klaineana'', a plant from equatorial Africa, called in the native language "boleka" or "isane", hence the common name of isanic acid. The oil seeds contain about 60% lipids. Various analyses have revealed the concentration of isanic acid in isane oil from 32% to 51%. Synthesis The synthe ...
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Triple Bond
A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, single bonds or double bond, double bonds, with a bond order of three. The most common triple bond is in a nitrogen N2 molecule; the second most common is that between two carbon atoms, which can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as diphosphorus and carbon monoxide, are also triple bonded. In skeletal formula, skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms. Bonding Triple bonding can be explained in terms of orbital hybridization. In the case of acetylene, each carbon atom has two sp orbital, sp-orbitals and two p-orbitals. The two sp-orbitals are linear, with 180° bond angles, and occupy ...
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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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Conjugated System
In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Resonance (chemistry), conventionally represented as having alternating single and multiple covalent bond, bonds. Lone pairs, radical (chemistry), radicals or carbenium ions may be part of the system, which may be Cyclic molecule, cyclic, acyclic, Linear molecular geometry, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele (chemist), Johannes Thiele. Conjugation is the orbital overlap, overlap of one p-orbital with another across an adjacent Sigma bond, σ bond (in transition metals, d-orbitals can be involved). A conjugated system has a region of overlapping p-orbitals, bridging the interjacent locations that simple diagrams illustrate as not having a π bond. They allow a delocalization of pi el ...
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Exocarpic Acid
Exocarpic acid is an unsaturated, conjugated fatty acid with one double bond and two triple bonds. It is isomeric to isanic acid and belongs to the class of alkyne and alkenoic acids, as well as the diynes and enynes. The acid's delta notation is 18:3-delta-9a,11a,13t. Its structural formula is CH 3(CH2)3-CH=CH-C≡CC≡C-(CH2)7-COOH. The acid was initially isolated in 1959, by H. H. Hatt and co-workers, from the roots of the Australian tree ''Exocarpos cupressiformis''; from this genus they derived the common name of exocarpic acid. Natural occurrence Exocarpic acid is found in various plant species of the order ''Santalales''. In the family ''Olacaceae'', it occurs, among others, in the seed oils of ''Curupira tefeensis'' and ''Olax dissitiflora''. In the family ''Santalaceae'', it occurs in several species of the genus ''Thesium'', such as mountain flax and ''Thesium chinense'', as well as in several species of the genus ''Buckleya'', such as ''Buckleya lanceolata'' and ' ...
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Isanolic Acid
Isanolic acid is a linear fatty acid composed of 18 carbon atoms, with two triple bonds in the positions 9≡10 and 11≡12, a double bond in the position 17=18, and a hydroxyl-OH in the position 8. The acid is one of the rare polyacetylenic acids with conjugated triple bonds. The compound belongs to the family of diynes and enynes, as well as to the alkyne and alkenoic acids. The related compounds are isanic and ketoisanic acids, both containing only one hydroxyl group. Discovery The acid was initially isolated in 1937 by researchers A. Steger and J. van Loon from the seed oilof the tree '' Ongokea gore'' or ''Ongokea klaineana'', a plant from equatorial Africa, called in the native language "boleka" or "isano"; a common name of isanolic acid comes from the latter. They also discovered isanic acid. The oil seeds contain about 60% lipids. Since the compound is hard to isolate, various analyses have revealed non-homogeneous data on the concentration of isanolic acid in isano o ...
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Hydroxyl Group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this ...
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Ketoisanic Acid
Ketoisanic acid is a linear fatty acid composed of 18 carbon atoms, with two triple bonds in the positions 9≡10 and 11≡12, a double bond in the position 17=18, and a ketone substituent in the position 8. This is one of the rare polyacetylenic acids with conjugated triple bonds, the oxygenated isanic acid. Natural occurrence The acid can be detected, at concentrations of 1–3%, together with isanic and isanolic acid, in the seed oil of the tree ''Ongokea gore'' or ''Ongokea klaineana''; both are plants from equatorial Africa, called "isano" in the local language.{{cite journal , last1=Badami , first1=R. C. , last2=Patil , first2=K. B. , title=Structure and occurrence of unusual fatty acids in minor seed oils , journal=Progress in Lipid Research ''Progress in Lipid Research'' is a quarterly peer-reviewed scientific journal that covers research on all aspects of research on lipids. The journal was established in 1973 with Ralph Holman (University of Minnesota) as founding edito ...
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Ongokea Gore
''Ongokea'' is a genus of flowering plants, with one species ''Ongokea gore'' (Boleko). In the APG IV system, the genus is placed in the family Olacaceae. Other sources place it in the segregate family Aptandraceae. Its native range is Western Tropical Africa to Angola, and is notable for the seeds of its edible fruits containing an industrially-useful oil that can undergo explosive polymerization reactions at elevated temperatures. This oil is curious for being rich in diacetylenic and hydroxy-diacetylenic fatty acids, primarily isanic and bolekic acid—that is, instead of a typical single-bonded fatty acid backbone, these acids contain multiple (thermally unstable) triple bonds. Description ''Ongokea gore'' is a medium to large size tree that can reach 40 m tall with a diameter than reach 1.2 m and often has basal root swellings. It has a fairly open crown that is usually in the upper canopy of the forest. The bark is thick, dark brown, grey or black in color, it is commo ...
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Springer Science & Business Media
Springer Science+Business Media, commonly known as Springer, is a German multinational publishing company of books, e-books and peer-reviewed journals in science, humanities, technical and medical (STM) publishing. Originally founded in 1842 in Berlin, it expanded internationally in the 1960s, and through mergers in the 1990s and a sale to venture capitalists it fused with Wolters Kluwer and eventually became part of Springer Nature in 2015. Springer has major offices in Berlin, Heidelberg, Dordrecht, and New York City. History Julius Springer founded Springer-Verlag in Berlin in 1842 and his son Ferdinand Springer grew it from a small firm of 4 employees into Germany's then second-largest academic publisher with 65 staff in 1872.Chronology
". Springer Science+Business Media.
In 1964, Springer expanded its business internationally, ...
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Journal Of The Chemical Society (Resumed)
The ''Journal of the Chemical Society'' was a scientific journal established by the Chemical Society in 1849 as the ''Quarterly Journal of the Chemical Society''. The first editor was Edmund Ronalds. The journal underwent several renamings, splits, and mergers throughout its history. In 1980, the Chemical Society merged with several other organizations into the Royal Society of Chemistry. The journal's continuity is found in ''Chemical Communications'', ''Dalton Transactions'', ''Faraday Transactions'', and ''Perkin Transactions'', all of which are published by the Royal Society of Chemistry. History ;''Proceedings of the Chemical Society'' * ''Memoirs of the Chemical Society of London'' (1841) * ''Proceedings of the Chemical Society of London'' (1842–1843) * ''Memoirs and Proceedings of the Chemical Society'' (1843–1848) * ''Proceedings of the Chemical Society, London'' (1885–1914) * Published as a supplement to ''Journal of the Chemical Society'' from 1914 to 1956 * ''Proce ...
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Boletic Acid
Fumaric acid or ''trans''-butenedioic acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the ion (in solution). Fumaric acid is the ''trans'' isomer of butenedioic acid, while maleic acid is the ''cis'' isomer. Biosynthesis and occurrence It is produced in eukaryotic organisms from succinate in complex 2 of the electron transport chain via the enzyme succinate dehydrogenase. Fumaric acid is found in fumitory (''Fumaria officinalis''), bolete mushrooms (specifically ''Boletus fomentarius var. pseudo-igniarius''), lichen, and Iceland moss. Fumarate is an intermediate in the citric acid cycle used by cells to produce energy in the form of adenosine triphosphate (ATP) from food. It is formed by the oxidation of succinate by the enzyme succinate dehydrogenase. ...
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Exocarpic Acid
Exocarpic acid is an unsaturated, conjugated fatty acid with one double bond and two triple bonds. It is isomeric to isanic acid and belongs to the class of alkyne and alkenoic acids, as well as the diynes and enynes. The acid's delta notation is 18:3-delta-9a,11a,13t. Its structural formula is CH 3(CH2)3-CH=CH-C≡CC≡C-(CH2)7-COOH. The acid was initially isolated in 1959, by H. H. Hatt and co-workers, from the roots of the Australian tree ''Exocarpos cupressiformis''; from this genus they derived the common name of exocarpic acid. Natural occurrence Exocarpic acid is found in various plant species of the order ''Santalales''. In the family ''Olacaceae'', it occurs, among others, in the seed oils of ''Curupira tefeensis'' and ''Olax dissitiflora''. In the family ''Santalaceae'', it occurs in several species of the genus ''Thesium'', such as mountain flax and ''Thesium chinense'', as well as in several species of the genus ''Buckleya'', such as ''Buckleya lanceolata'' and ' ...
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