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20-September-2008 09:29:06 - Phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group -O H attached to an aromatic hydrocarbon group. The simplest of the class is phenol C6H5OH. Phenol - the simplest of the phenols. Phenol - the simplest of the phenols. Although similar to alcohols, phenols have unique properties and are not classified as alcohols since the hydroxyl group is not bonded to a saturated carbon atom. They have relatively higher acidities due to the aromatic ring's tight coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids their pKa is usually between 10 and 12. Loss of a positive hydrogen ion H+ from the hydroxyl group of a phenol forms a negative phenolate ion. Some phenols are germicidal and are used in formulating disinfectants. Others possess estrogenic or endocrine disrupting activity. Contents 1 Synthesis of phenols 2 Reactions of phenols 3 Phenolic compounds 3.1 Medicinals 4 References 5 External links Synthesis of phenols Several laboratory methods for the synthesis of phenols: by an ester rearrangement in the Fries rearrangement by a rearrangement of N-phenylhydroxylamines in the Bamberger rearrangement by hydrolysis of phenolic esters or ethers by reduction of quinones by replacement of an aromatic amine by an hydroxyl group with water and sodium bisulfide in the Bucherer reaction by hydrolysis of diazonium salts by oligomerisation with formaldehyde + base catalysed reaction with epichlorohydrine to epoxi resin components by reaction with acetone/ketones to e.g. Bisphenol A, an important monomer for resins, e.g. polycarbonatePC, epoxi resins by a rearrangement reaction of dienones 1 in the dienone phenol rearrangement 2: The dienone phenol rearrangement Reactions of phenols Phenols react in a wide variety of ways. Esterfication reactions and ether formation Electrophilic aromatic substitutions as the hydroxyl group is activating, for example synthesis of calixarenes 3 Reaction of naphtols and hydrazines and sodium bisulfite in the Bucherer carbazole synthesis Oxidative cleavage, for instance cleavage of 1,2-dihydroxybenzene to the monomethylester of 2,4 hexadienedioic acid with oxygen, copper chloride in pyridine 4 Oxidative de-aromatization to quinones also known as the Teuber reaction. Oxidizing reagents are Fremy's salt 5 and oxone 6. In reaction depicted below 3,4,5-trimethylphenol reacts with singlet oxygen generated from oxone/sodium carbonate in an acetonitrile/water mixture to a para-peroxyquinole. This hydroperoxide is oxidized to the quinole with sodium thiosulfate. Oxone Phenol Dearomatization Phenols are oxidized to benzenediols in the Elbs persulfate oxidation Phenolate anions deriving from phenols by the loss of H+ can act as ligands towards metal cations Phenolic compounds For a full list, see Category:Phenols Phenol the parent compound, used as an disinfectant and for chemical synthesis BHT butylated hydroxytoluene - a fat-soluble antioxidant and food additive Capsaicin the pungent compound of chilli peppers Bisphenol A and other bisphenols produced from ketones and phenol / cresol Chavibetol from betel, used as a flavouring Cresol found in coal tar and creosote Estradiol estrogen - hormones Eugenol the main constituent of the essential oil of clove Gallic acid found in galls Guaiacol 2-methoxyphenol - has a smokey flavor, and is found in roasted coffee, whisky, and smoke 4-Nonylphenol a breakdown product of detergents and nonoxynol-9 Orthophenyl phenol a fungicide used for waxing citrus fruits Picric acid trinitrophenol - an explosive material Phenolphthalein pH indicator Polyphenol e.g. flavonoids and tannins Raspberry ketone a compound with an intense raspberry smell Serotonin / dopamine / adrenaline / noradrenaline natural neurotransmitters Thymol 2-Isopropyl-5-methyl phenol - an antiseptic that is used in mouthwashes Tyrosine an amino acid Xylenol -used in antiseptics disinfecticides Medicinals Cannabinoids the active constituents of cannabis Diethylstilbestrol a synthetic estrogen with a stilbene structure L-DOPA a synthetic estrogen with a stilbene structure Methyl salicylate the major constituent of the essential oil of wintergreen Propofol a short-acting intravenous anesthetic agent Psilocin a hallucinogenic alkaloid of Psilocybe mushrooms Salicylic acid a plant hormone used for its analgesic, antipyretic, and anti-inflammatory properties, also a precursor compound to Aspirin Trichlorophenylmethyliodosalicyl the main component of TCP, an antiseptic. References ^ related to quinones, see for example the Zincke-Suhl reaction ^ Advanced organic Chemistry, Reactions, mechanisms and structure 3ed. page Jerry March ISBN 0-471-85472-7 ^ p-tert-butylcalix8arene, Organic Syntheses, CV 8, 80 Article ^ 2,4-Hexadienedioic acid, monomethyl ester, Z,Z- Organic Syntheses, Coll. Vol. 8, p.490 1993; Vol. 66, p.180 1988 Article ^ 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl Organic Syntheses, Coll. Vol. 6, p.1010 1988; Vol. 52, p.83 1972 Abstract. ^ Oxidative De-aromatization of para-Alkyl Phenols into para-Peroxyquinols and para-Quinols Mediated by Oxone as a Source of Singlet Oxygen M. Carmen Carreño, Marcos González-López, Antonio Urbano Angewandte Chemie International ion Volume 45, Issue 17 , Pages 2737 - 2741 2006 Abstract External links Special Issue on Phenolics flavonoids and non-flavonoids Retrieved from http://en..org/wiki/Phenols Categories: Phenols | Organic chemistry | Disinfectants Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Bosanski ÄŒesky Dansk Deutsch Eesti Español Français í•œêµì–´ Italiano עברית МакедонÑ?ки 日本語 Polski РуÑ?Ñ?кий SlovenÄ?ina ä¸æ–‡ This page was last modified on 4 August 2008, at 09:1
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