Natural Phenol
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Natural Phenol
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants. Classification Various classification schemes can be applied. A commonly used scheme is based on the number of carbons and was devised by Jeffrey Harborne and Simmonds in 1964 and published in 1980: C6-C7-C6 Diarylheptanoids are not included in this Harborne classification. They can also be classified on the basis of their number of phenol groups. They can therefore be called ''simple phenols'' or ...
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Biochemistry
Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and metabolism. Over the last decades of the 20th century, biochemistry has become successful at explaining living processes through these three disciplines. Almost all areas of the life sciences are being uncovered and developed through biochemical methodology and research. Voet (2005), p. 3. Biochemistry focuses on understanding the chemical basis which allows biological molecules to give rise to the processes that occur within living cells and between cells, Karp (2009), p. 2. in turn relating greatly to the understanding of tissues and organs, as well as organism structure and function.Miller (2012). p. 62. Biochemistry is closely related to molecular biology, which is the study of the molecular mechanisms of biological phenomena.Ast ...
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Acetophenone
Acetophenone is the organic compound with the chemical formula, formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement reaction, rearrangement of the intermediate: :C6H5C(CH3)2O2H -> C6H5C(O)CH3 + CH3OH The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities. Acetophenone is also generated from ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone ...
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Xanthonoid
A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids. Xanthonoid biosynthesis in cell cultures of '' Hypericum androsaemum'' involves the presence of a benzophenone synthase condensing a molecule of benzoyl-CoA with three malonyl-CoA yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone. Some examples are tomentonone, zeyloxanthonone and calozeyloxanthone isolated from the bark of '' Calophyllum tomentosum'', apetalinone A, B, C and D from ''Calophyllum apetalum'', gaudichaudione A, B, C, D, E, F, G, H, gaudichaudiic acid A, B, C, D, E, morellic acid and forbesione from '' Garcinia gaudichaudii'', methylswertianin and bellidifolin from '' Swertia punicea'' or psorospermin obtained from ''Psorospermum febr ...
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Naphthoquinone
Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone Natural products * Alkannin * Hexahydroxy-1,4-naphthalenedione * Juglone * Lapachol * Lawsone * Menatetrenone * 2-Methoxy-1,4-naphthoquinone, a compound found in ''Impatiens'' species * Nigrosporin B * 2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione * Phylloquinone * Plumbagin * 2,3,5,7-Tetrahydroxy-1,4-naphthalenedione * Vitamin K and related compounds Synthetic naphthoquinones * Menadione (2-Methyl-1,4-naphthoquinone), a vitamin K mimic * 5,8-Dihydroxy-1,4-naphthoquinone and dihydroxynaphthoquinones * Atovaquone * Buparvaquone, an antiprotozoal drug used in veterinary medicine * Diazonaphthoquinone, a diazo derivative of naphthoquinone * 1,2-Naphthoquinone, from the biodegradation of naphthalene. See also * Hydroxynaphthoquinone A hydroxynaphthoquinone (formula: ) is any of several ...
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Chromone
Chromone (or 1,4-benzopyrone) is a derivative of benzopyran with a substituted keto group on the pyran ring. It is an isomer of coumarin. Derivatives of chromone are collectively known as ''chromones''. Most, though not all, chromones are also phenylpropanoids. Examples * 6,7-dimethoxy-2,3-dihydrochromone has been isolated from '' Sarcolobus globosus''. * Eucryphin, a chromone rhamnoside, can be isolated from the bark of '' Eucryphia cordifolia''. * Cromolyn (disodium cromoglicate) was found to inhibit antigen challenge as well as stress induced symptoms.HOWELL, J.B. & ALTOUNYAN, R.E. (1967). A double-blind trial of disodium cromoglycate in the treatment of allergic bronchial asthma. Lancet, 2, 539–542Abstract/ref> Cromoglicate is used as a mast cell stabilizer in allergic rhinitis, asthma and allergic conjunctivitis. * Nedocromil sodium was found to have a somewhat longer half-life than cromolyn; however, production was discontinued in the US in 2008. * Xanthone with a ...
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Isocoumarin
Isocoumarin (1''H''-2-benzopyran-1-one; 3,4-benzo-2-pyrone) is a lactone, a type of natural organic compound. Known natural compounds * Thunberginol A and B ; dihydroisocoumarins * Hydrangenol * Phyllodulcin * Thunberginol C, D, E and G * The derivative 3-acetyl-3,4-dihydro-5,6-dimethoxy-1''H''-2-benzopyran-1-one can be found in Huáng bǎi (''Phellodendron chinense''), one of the fifty fundamental herbs of traditional Chinese medicine. See also * Coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered h ... References {{heterocyclic-stub ...
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Coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. By inhibiting synthesis of vitamin K, a related compound is used as the prescription drug warfarin – an anticoagulant – to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism. Etymology Coumarin is derived from ''coumarou'', the French word for the tonka bean. The word ''tonka'' for the tonka bean is taken from the Galibi (Carib) tongue spoken by natives of French Gui ...
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Phenylpropene
Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene. In plant biochemistry, the phenylpropene skeleton is the parent (simplest representation) of the phenylpropanoids. Prominent derivatives include eugenol, safrole Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among oth ..., and many others. References External links * {{Phenylpropene ...
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Hydroxycinnamic Acid
Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid. In the category of phytochemicals that can be found in food, there are : * α-Cyano-4-hydroxycinnamic acid * Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple * Cichoric acid * Cinnamic acid – aloe * Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries * Diferulic acids * Coumaric acid * Ferulic acid (3-methoxy-4-hydroxycinnamic acid) – oats, rice, artichoke, orange, pineapple, apple, peanut * Sinapinic acid (3,5-dimethoxy-4-hydroxycinnamic acid or sinapic acid) Hydroxycinnamoyltartaric acids * Caftaric acid – grapes and wine, mainly the ''trans'' isomer * Coutaric acid – grapes and wine, both ''trans'' and ''cis'' isomers * Fertaric acid Fertaric acid is a hydroxycinnamic acid found in wine and grapes. It is an ester f ...
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Homogentisic Acid
Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid usually found in ''Arbutus unedo'' (strawberry-tree) honey. It is also present in the bacterial plant pathogen ''Xanthomonas campestris'' pv. ''phaseoli'' as well as in the yeast ''Yarrowia lipolytica'' where it is associated with the production of brown pigments. It is oxidatively dimerised to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses. It is less commonly known as melanic acid, the name chosen by William Prout. Human pathology Accumulation of excess homogentisic acid and its oxide, named alkapton, is a result of the failure of the enzyme homogentisic acid 1,2-dioxygenase (typically due to a mutation) in the degradative pathway of tyrosine, consequently associated with alkaptonuria. Intermediate It is an intermediate in the catabolism of aromatic amino acids such as phenylalanine and tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylal ...
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P-Hydroxyphenylacetic Acid
4-Hydroxyphenylacetic acid is a chemical compound found in olive oil and beer. Synthesis 4-Hydroxyphenylacetic acid is obtained by reducing 4-hydroxymandelic acid with elemental phosphorus and iodine. Uses In industry, 4-hydroxyphenylacetic acid is an intermediate used to synthesize atenolol Atenolol is a beta blocker medication primarily used to treat high blood pressure and heart-associated chest pain. Atenolol, however, does not seem to improve mortality in those with high blood pressure. Other uses include the prevention of mi ..., 3,4-dihydroxyphenylacetic acid, and coclaurine. References {{DEFAULTSORT:Hydroxyphenylacetic Acid, 4- Phenols Acetic acids Hydroxy acids ...
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