2,4,6-Trihydroxyacetophenone
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2,4,6-Trihydroxyacetophenone
2,4,6-Trihydroxyacetophenone (THAP) is a chemical compound that is a derivative of phloroglucinol. In an animal model, THAP was reported to enhance cholesterol 7 alpha-hydroxylase (CYP7A1) activity. THAP is also used as a matrix in matrix-assisted laser desorption/ionization (MALDI) for the analysis of acidic glycans and glycopeptides in negative ion mode. Derivatives THAP is a chemical precursor that can be used to form part of the backbone of 5,7-dihydroxyflavones like noreugenin, apigenin, luteolin, diosmetin, naringenin, and hesperetin. See also *Flopropione Flopropione (Compacsul, Cospanon, Ecapron, Pellegal, Argobyl, Floveton, Saritron, Spamorin, Labrodax, Tryalon, Mirulevatin, Padeskin, Profenon) is a spasmolytic or antispasmodic agent. It acts as a COMT inhibitor. It is synthetized from phloro ... References {{DEFAULTSORT:Trihydroxyacetophenone, 2,4,6- Phloroglucinols Aromatic ketones 3-Hydroxypropenals ...
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Flopropione
Flopropione (Compacsul, Cospanon, Ecapron, Pellegal, Argobyl, Floveton, Saritron, Spamorin, Labrodax, Tryalon, Mirulevatin, Padeskin, Profenon) is a spasmolytic or antispasmodic agent. It acts as a COMT inhibitor. It is synthetized from phloroglucinol in a Hoesch reaction The Hoesch reaction or Houben–Hoesch reaction is an organic reaction in which a nitrile reacts with an arene compound to form an aryl ketone. The reaction is a type of Friedel-Crafts acylation with hydrogen chloride and a Lewis acid catalyst. .... See also * 2,4,6-Trihydroxyacetophenone (THAP) References Phloroglucinols Aromatic ketones Serotonin receptor antagonists 3-Hydroxypropenals {{musculoskeletal-drug-stub ...
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Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction. In the past, derivative also meant a compound that ''can be imagined to'' arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms, but modern chemical language now uses the term structural analog for this meaning, thus eliminating ambiguity. The term "structural analogue" is common in organic chemistry. In biochemistry, the word is used for compounds that at least theoretically can be formed from the precursor compound. Chemical derivatives may be used to facilitate analysis. For example, melting point (MP) analysis can assist in identification of many organic compounds. A crystalline derivative may be prepared, such as a semicarbazone or 2,4-dinitrophenylhydrazone (derived from aldehydes or ketones), as a simple way of verifying the identity of the original compound, assuming that a table of derivative MP values is available ...
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Phloroglucinol
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are unre ...
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Cholesterol 7 Alpha-hydroxylase
Cholesterol 7 alpha-hydroxylase also known as cholesterol 7-alpha-monooxygenase or cytochrome P450 7A1 (CYP7A1) is an enzyme that in humans is encoded by the gene which has an important role in cholesterol metabolism. It is a cytochrome P450 enzyme, which belongs to the oxidoreductase class, and converts cholesterol to 7-alpha-hydroxycholesterol, the first and rate limiting step in bile acid synthesis. The inhibition of cholesterol 7-alpha-hydroxylase (CYP7A1) represses bile acid biosynthesis. Evolution Sequence comparisons indicated a huge similarity between cytochromes P450 identified in man and bacteria, and suggested that the superfamily cytochrome P450 first originated from a common ancestral gene some three billion years ago. The superfamily cytochrome P450 was named in 1961, because of the 450-nm spectral peak pigment that cytochrome P450 has when reduced and bound to carbon monoxide. In the early 1960s, P450 was thought to be one enzyme, and by the mid 1960s it was ...
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Matrix-assisted Laser Desorption/ionization
In mass spectrometry, matrix-assisted laser desorption/ionization (MALDI) is an ionization technique that uses a laser energy absorbing matrix to create ions from large molecules with minimal fragmentation. It has been applied to the analysis of biomolecules ( biopolymers such as DNA, proteins, peptides and carbohydrates) and various organic molecules (such as polymers, dendrimers and other macromolecules), which tend to be fragile and fragment when ionized by more conventional ionization methods. It is similar in character to electrospray ionization (ESI) in that both techniques are relatively soft (low fragmentation) ways of obtaining ions of large molecules in the gas phase, though MALDI typically produces far fewer multi-charged ions. MALDI methodology is a three-step process. First, the sample is mixed with a suitable matrix material and applied to a metal plate. Second, a pulsed laser irradiates the sample, triggering ablation and desorption of the sample and matrix materi ...
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Glycan
The terms glycans and polysaccharides are defined by IUPAC as synonyms meaning "compounds consisting of a large number of monosaccharides linked glycosidically". However, in practice the term glycan may also be used to refer to the carbohydrate portion of a glycoconjugate, such as a glycoprotein, glycolipid, or a proteoglycan, even if the carbohydrate is only an oligosaccharide. Glycans usually consist solely of O-glycosidic linkages of monosaccharides. For example, cellulose is a glycan (or, to be more specific, a glucan) composed of β-1,4-linked D-glucose, and chitin is a glycan composed of β-1,4-linked ''N''-acetyl-D-glucosamine. Glycans can be homo- or heteropolymers of monosaccharide residues, and can be linear or branched. Glycans and proteins Glycans can be found attached to proteins as in glycoproteins and proteoglycans. In general, they are found on the exterior surface of cells. O- and N-linked glycans are very common in eukaryotes but may also be found, although ...
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Glycopeptide
Glycopeptides are peptides that contain carbohydrate moieties (glycans) covalently attached to the side chains of the amino acid residues that constitute the peptide. Over the past few decades it has been recognised that glycans on cell surface (attached to membrane proteins or lipids) and those bound to proteins (glycoproteins) play a critical role in biology. For example, these constructs have been shown to play important roles in fertilization, the immune system, brain development, the endocrine system, and inflammation. The synthesis of glycopeptides provides biological probes for researchers to elucidate glycan function in nature and products that have useful therapeutic and biotechnological applications. Glycopeptide linkage variety ''N''-Linked glycans ''N''-Linked glycans derive their name from the fact that the glycan is attached to an asparagine (Asn, N) residue, and are amongst the most common linkages found in nature. Although the majority of N-linked glycans tak ...
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Chemical Precursor
In chemistry, a precursor is a compound that participates in a chemical reaction that produces another compound. In biochemistry, the term "precursor" often refers more specifically to a chemical compound preceding another in a metabolic pathway, such as a protein precursor. Illicit drug precursors In 1988, the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances introduced detailed provisions and requirements relating the control of precursors used to produce drugs of abuse. In Europe the Regulation (EC) No. 273/2004 of the European Parliament and of the Council on drug precursors was adopted on 11 February 2004. (European law on drug precursors) Illicit explosives precursors On January 15, 2013, the Regulation (EU) No. 98/2013 of the European Parliament and of the Council on the marketing and use of explosives precursors was adopted. The Regulation harmonises rules across Europe on the making available, introduction, possession and us ...
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Apigenin
Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool. Sources in nature Apigenin is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources. Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids. Dried parsley can contain about 45  mg apigenin/gram of the herb, and dried chamomile flower about 3-5 mg/gram. The apigenin content of fresh parsley is reportedly 215.5 mg/100 grams, which is much higher than the next highest food source, green celery hearts providing 19.1 mg/100 grams. Biosynthesis Apigenin is biosynthetically derived from the general phenylpropanoid pathway and the flavone synthesis pathway. The phenylpropanoid pathway starts from the aromatic a ...
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Luteolin
Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance. Luteolin is the principal yellow dye compound that is obtained from the plant ''Reseda luteola'', which has been used as a source of the dye since at least the first millennium B.C. Luteolin was first isolated in pure form, and named, in 1829 by the French chemist Michel Eugène Chevreul. The luteolin empirical formula was determined by the Austrian chemists Heinrich Hlasiwetz and Leopold Pfaundler in 1864. In 1896, the English chemist Arthur George Perkin proposed the correct structure for luteolin. Perkin's proposed structure for luteolin was confirmed in 1900 when the Polish-Swiss chemist Stanislaw Kostanecki (1860–1910) and his students A. Różycki and J. Tambor synthesized luteolin. Natural occurrences Luteolin is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen. It has also been isolated from the aromatic flowering plant, ''Salvia t ...
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Diosmetin
Diosmetin, also known as 5,7,3′-trihydroxy-4′-methoxyflavone, is an ''O''-methylated flavone, a chemical compound that can be found in the Caucasian vetch. It has been found to act as a weak TrkB receptor agonist. Glycosides Diosmetin is the aglycone of diosmin Diosmin (diosmetin 7-O-rutinoside), a flavone glycoside of diosmetin, is manufactured from citrus fruit peels as a phlebotonic non-prescription dietary supplement used to aid treatment of hemorrhoids or chronic venous diseases, mainly of the le .... See also * Tropomyosin receptor kinase B § Agonists References O-methylated flavones Resorcinols TrkB agonists 3-Hydroxypropenals within hydroxyquinones {{Aromatic-stub ...
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