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Salicylic acid{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em" ! colspan="2" align=center bgcolor="#cccccc" | Salicylic acid |- | IUPAC nomenclature | 2-Hydroxybenzoic acid |- | Chemical formula | C7H6O3 |- | Molecular mass | 138.12 g/mol |- | Melting point | 159 °C |- | Boiling point | 211 °C at 2666 Pa (reduced pressure) |- | CAS registry number | 69-72-7 |- | Simplified molecular input line entry specification | OC1=CC=CC=C1C(O)=O |- | colspan="2" align="center" | |- |} Salicylic acid is a colorless, crystalline organic carboxylic acid. It is usually prepared by Adolph Wilhelm Hermann Kolbe synthesis (aka Kolbe-Schmitt reaction). Salicylic acid functions as a plant hormone; see Salicylic acid (plant hormone). Salicylic acid is also found in plants, especially in fruit, in the form of its ester methyl salicylate. It is toxic if ingested in large quantities, but in small quantities is used as a food preservative and antiseptic in toothpaste. The carboxyl group (–COOH) can react with alcohol, forming several useful esters. The hydroxyl group (–OH) can react with acetic acid to form acetylsalicylic acid. Salicylic acid can also trap oxygen (O2) and initiate free radical reactions. Salicylic acid is the key additive in many skin-care products for the treatment of acne, keratosis pilaris and warts. It treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. The medicinal properties of salicylate (mainly the lowering of fever) have been known since ancient times. The substance occurs in the bark of willow trees and the name Salicylic acid is derived from the Latin name for the Willow tree - ''Salix''. == Suppliers/Manufacturers == *[http://www.lancastersynthesis.com/homecatsearch.htm Lancaster] (now part of Alfa) *[https://www1.fishersci.com/index.jsp Fisher] *[http://www.vwr.com/index.htm VWR] *[http://www.alfa.com/alf/index.htm Alfa] *[http://www.sigmaaldrich.com Aldrich] *[http://www.aurora-feinchemie.com Aurora Fine Chemicals] == See also == * Benzoic acid * Benzene ring * Phenol * Acetylsalicylic acid Carboxylic acids Phenols Salicylic acidThe "Vitamin S" section needs work. The one reference cited (''European Journal of Nutrition'') seems OK, but are there any corroborating references available? It isn't clear if this is given much credence in the mainstream scientific world or if it is borderline quackery. In any case, the section is too long, poorly written, and so loaded with weasel words it reads more like a plea to accept the author's opinion than a statement of fact. If the Vitamin S stuff is kept, most of it should be moved to vitamin which already has a brief Vitamin S section and only a short pointer to it left here. Currently it's over half the article. (Another problem in passing: ''salicylate'' is used several times throughout the entry without any prior definition.) --User:66.188.84.209 07:14, 20 Jan 2005 (UTC) I agree with the above post. Also, I believe the statement that salicylic acid could be argued as more important than vitamin A or D should be removed. The effects of vitamin A and D deficiency are well documented, and I don't believe I need to explain them here. There is no evidence of a salicylate deficiency related disorder. == Moved from article == I have moved the following section from the article here. Maybe somebody can write a critical/NPOV section for the article: === "Vitamin S" === "Vitamin S" is a proposed alternative name for salicylate, which would have the effect of classifying it as a vitamin. There is no generally agreed definition of what constitutes a vitamin, though salicylate meets at least one of the requirements: * It is present in our natural diet in fruit and vegetables, particularly if they have had to defend themselves against damage or disease * It is not produced by our bodies * Trace amounts, it has been suggested, are required for the maintenance of life This last point is controversial because salicylate deficiency, unlike, say, Vitamin C deficiency, which causes scurvy, does not result in any particular known symptoms. A low salicylate intake seems to be related to longer term problems, resulting in higher risks of age-related chronic diseases. Whereas most vitamins are enzyme cofactors, promoting cellular biochemical reactions - Vitamin C boosts production of collagen - salicylate is not, but then nor is Vitamin E, which is an antioxidant, like salicylate. Lack of salicylate appears to predispose humans to: * Cancer * Myocardial infarction * Stroke * Alzheimer's disease It can be argued that salicylate has a better claim to be called a vitamin than vitamins Vitamin A and vitamin D. Whether or not you choose to call aspirin a vitamin, there is still a case to be made that salicylate is an important micronutrient. There is evidence that salicylates in past ages were much more common in human diets than they are now. Salicylates are produced by fruit as a defense mechanism: inducing damaged and diseased cells to commit suicide. Modern man's predilection for fruit and vegetables in a pristine condition - with shoppers often rejecting fruit with bumps of bruises - means that we eat less salicylates than in the past. A study has shown that organic vegetable soups contain nearly six times as much salicylate as non-organic equivalents (''European Journal of Nutrition'', vol. 40 p 289). See other meanings of words starting from letter: SSB | SC | SD | SE | SF | SG | SH | SI | SJ | SK | SL | SM | SN | SO | SP | SR | SS | ST | SU | SW | SX | SY | SZ |Words begining with Salicylic_acid: Salicylic_acid Salicylic_acid Salicylic_acid_(plant_hormone) |
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