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Encyclopedia > Salicylic acid
Salicylic acid
IUPAC name 2-Hydroxybenzoic acid
Identifiers
CAS number [69-72-7]
EINECS number 200-712-3
SMILES OC(=O)c1ccccc1O
Properties
Molecular formula C7H6O3
Molar mass 138.123 g/mol
Density 1.44 g/cm³ (at 20 °C)
Melting point

159 °C Image File history File links Salicylic-acid-skeletal. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...

Boiling point

211 °C (2666 Pa) Italic text This article is about the boiling point of liquids. ...

Related compounds
Related compounds Methyl salicylate,
Benzoic acid,
Phenol, Aspirin,
4-Hydroxybenzoic acid,
Magnesium salicylate,
Bismuth subsalicylate (Pepto Bismol),
Sulfosalicylic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Salicylic acid (from the Latin word for the willow tree, Salix, from whose bark it can be obtained) is a beta hydroxy acid (BHA) with the formula C6H4(OH)CO2H, where the OH group is adjacent to the carboxyl group. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It is derived from the metabolism of salicin. It is probably best known as a compound that is chemically similar to but not identical to the active component of aspirin (acetylsalicylic acid). In fact, salicylic acid is a metabolite of aspirin, the product of esterase hydrolysis in the liver. Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl-2-hydroxybenzoate) is a natural product of many species of plants. ... Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... This article is about the drug. ... 4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. ... Magnesium salicylate is a common analgesic and non-steroidal anti-inflammatory drug (NSAID) used to treat mild to moderate muscular pain. ... ... Sulfosalicylic acid is used in urine tests to determine urine protein content. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Species About 350, including: Salix alba - White Willow Salix amygdaloides - Peachleaf Willow Salix arbuscula - Mountain Willow Salix aurita - Eared Willow Salix babylonica - Peking Willow Salix caprea- Goat Willow Salix caroliniana - Coastal Plain Willow Salix cinerea - Grey Sallow Salix fragilis - Crack Willow Salix herbacea - Dwarf Willow Salix lanata - Woolly Willow Salix... 3-Hydroxypropanoic acid, a simple beta hydroxy acid A beta hydroxy acid (BHA) is an organic compound which contains a carboxylic acid functional group and hydroxy functional group separated by two carbon atoms. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... For other uses, see acid (disambiguation). ... Organic synthesis is the construction of organic molecules via chemical processes. ... Plant hormones (also known as plant growth regulators (PGRs) and phytohormones) are chemicals that regulate a plants growth. ... Salicylic acid is a colorless, crystalline organic carboxylic acid. ... This article is about the drug. ... This article is about the drug. ...

Contents

Plant Hormone

Salicylic acid (SA) is a phytohormone; and a phenol, ubiquitous in plants generating a significant impact on plant growth and development, photosynthesis, transpiration, ion uptake and transport and also induces specific changes in leaf anatomy and chloroplast structure. SA is recognized as an endogenous signal, mediating in plant defense, against pathogens[1] It plays a role in the resistance of pathogens by inducing the production of 'pathogenesis-related proteins'. It is involved in the systemic acquired resistance [SAR] in which a pathogenic attack on older leaves causes the development of resistance in younger leaves, though whether SA is the transmitted signal is debatable. SA is the calorigenic substance that causes thermogenesis in Arum flowers.[2] Plant hormones (or plant growth regulators, or PGRs) are internally secreted chemicals in plants that are used for regulating their growth. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... Photosynthesis splits water to liberate O2 and fixes CO2 into sugar The leaf is the primary site of photosynthesis in plants. ... Transpiration is the evaporation of excess water from aerial parts and of plants, especially leaves but also stems, flowers and fruits. ... This article is about the electrically charged particle. ... Chloroplasts are organelles found in plant cells and eukaryotic algae that conduct photosynthesis. ... Look up Endogenous in Wiktionary, the free dictionary. ... A pathogen (literally birth of pain from the Greek παθογένεια) is a biological agent that can cause disease to its host. ... In plants, the transpiration stream is the uninterrupted stream of water which is taken up by the roots and, via the xylem vessels, transported to the leaves where it will eventually evaporate at the air/apoplast-interface of the substomatal cavity. ... Thermogenesis is the process of heat production in organisms. ... Species See text. ...


Production

Salicylic acid is an organic acid biosynthesized from the amino acid phenylalanine. Biosynthesis is a phenomenon where chemical compounds are produced from simpler reagents. ... Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ...


Sodium salicylate is commercially prepared by treating sodium phenoxide with a high pressure of carbon dioxide at high temperature via the Kolbe-Schmitt reaction. Acidification of the product solution gives salicylic acid: R-phrases , S-phrases , , Autoignition temperature > 250 °C Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sodium salicylate is a sodium salt of salicylic acid. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... Carbon dioxide (chemical formula: ) is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... The Kolbe-Schmitt reaction/Kolbe process (named after Adolph Wilhelm Hermann Kolbe and R. Schmitt) is a carboxylation chemical reaction that proceeds by heating sodium phenolate (the sodium salt of phenol) with carbon dioxide under pressure (100 atm, 125°C), then treating the product with sulfuric acid. ...


It can be prepared by the hydrolysis of Aspirin (acetylsalicylic acid)[3] or methyl salicylate (Oil of Wintergreen) with a strong acid or base. Image File history File links Download high resolution version (1380x279, 10 KB) Summary Diagram of the Kolbe-Schmitt reaction created with ChemDraw. ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... This article is about the drug. ... Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl-2-hydroxybenzoate) is a natural product of many species of plants. ...


Analysis

Salicylic acid is an enol of a β-keto carbonic acid and therefore forms purple complexes with iron(III) salts: Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. ...



This tris(chelate) complex forms more readily in basic solution.


History

Main article: History of aspirin
White willow (Salix alba) is a natural source of salicylic acid
White willow (Salix alba) is a natural source of salicylic acid

The Greek physician Hippocrates wrote in the 5th century BC about a bitter powder extracted from willow bark that could ease aches and pains and reduce fevers. This remedy was also mentioned in texts from ancient Sumer, Lebanon, and Assyria. The Cherokee and other Native Americans used an infusion of the bark for fever and other medicinal purposes for centuries.[4] The medicinal part of the plant is the inner bark and was used as a pain reliever for a variety of ailments. The Reverend Edward (Edmund) Stone, a vicar from Chipping Norton, Oxfordshire, England, noted in 1763 that the bark of the willow was effective in reducing a fever.[5] Ancient Greece is the term used to describe the Greek-speaking world in ancient times. ... For other uses, see Hippocrates (disambiguation). ... Species About 350, including: Salix acutifolia - Violet Willow Salix alaxensis - Alaska Willow Salix alba - White Willow Salix alpina - Alpine Willow Salix amygdaloides - Peachleaf Willow Salix arbuscula - Mountain Willow Salix arbusculoides - Littletree Willow Salix arctica - Arctic Willow Salix atrocinerea Salix aurita - Eared Willow Salix babylonica - Peking Willow Salix bakko Salix barrattiana... Sumer ( Sumerian: KI-EN-GIR, Land of the Lords of Brightness[1], or land of the Sumerian tongue[2][3], Akkadian: Å umeru; possibly Biblical Shinar ), located in southern Mesopotamia, is the earliest known civilization in the world. ... For other uses, see Assyria (disambiguation). ... This page contains special characters. ... Reverend Edward (Edmund) Stone (1702-1768) was a Church of England Reverend who discovered the active ingredient of Aspirin. ... , Chipping Norton is a town in Oxfordshire, England, located north west of Oxford. ... For other uses, see England (disambiguation). ...


The active extract of the bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated in crystalline form in 1828 by Henri Leroux, a French pharmacist, and Raffaele Piria, an Italian chemist. Piria was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid. Salicylic acid is a colorless, crystalline organic carboxylic acid. ... For other uses, see Latins and Latin (disambiguation). ... Binomial name Salix alba L. The White Willow is a willow native to Europe, and western and central Asia. ...


Salicylic acid was also isolated from the herb meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as gastric irritation, bleeding, diarrhea, and even death when consumed in high doses. This article is about the Eurasian plant, introduced in some parts of America. ... Binomial name Filipendula ulmaria (L.) Maxim. ... Species About 80-100, see text Wikimedia Commons has media related to: Category Spiraea Spiraea is a genus of about 80-100 species of shrubs in the Rosaceae, subfamily Spiraeoideae. ... In anatomy, the stomach (in ancient Greek στομάχι) is an organ in the alimentary canal used to digest food. ... In medicine, diarrhea, also spelled diarrhoea (see spelling differences), refers to frequent loose or liquid bowel movements. ...


Medicinal and cosmetic uses

Also known as 2-hydroxybenzoic acid, one of several beta hydroxy acids (compare to AHA), salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove warts. Use of concentrated solutions of salicylic acid may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock.[6][7] α-Hydroxy Acids (AHAs) are naturally occurring carboxylic acids which are well-known for their use in the cosmetics industry. ... This article is about calluses and corns of human skin. ... This article is about calluses and corns of human skin. ... Keratosis pilaris (KP) is a very common genetic follicular condition that is manifested by the appearance of rough bumps on the skin and hence colloquially referred to as chicken skin. It most often appears on the back and outer sides of the upper arms (though the lower arms can also... For the Nintendo character, see Wart (Nintendo). ... Cross-section of all skin layers Optical coherence tomography tomogram of fingertip, depicting stratum corneum (~500µm thick) with stratum disjunctum on top and stratum lucidum (connection to stratum spinosum) in the middle. ... Schematic view of a hair follicle with sebaceous gland. ... Shampoo is a common hair care product used for the removal of oils, dirt, skin particles, dandruff, environmental pollutants and other contaminant particles that gradually build up in hair. ... For the album by Ivor Cutler, see Dandruff (album). ... For the Nintendo character, see Wart (Nintendo). ... In dermatology, hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin. ... The Fitzpatrick Scale (aka Fitzpatrick skin typing test or Fitzpatrick phototyping scale) is a numerical classification schema for the color of skin. ...


The medicinal properties of salicylate, mainly for fever relief, have been known since ancient times, and it was used as an anti-inflammatory drug.[8] An analogue medical thermometer showing the temperature of 38. ... 1763 was a common year starting on Saturday (see link for calendar). ...

Cotton pads soaked in salicylic acid can be used to chemically exfoliate skin

Aspirin (acetylsalicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid. Image File history File linksMetadata Download high resolution version (2048x1536, 581 KB) Licensing I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... Image File history File linksMetadata Download high resolution version (2048x1536, 581 KB) Licensing I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... For other uses, see Cotton (disambiguation). ... This article or section does not cite its references or sources. ... This article is about the drug. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ...


Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined, the two key ingredients help control diarrhea, nausea, heartburn, and gas. It is also a very mild antibiotic. General Name, Symbol, Number bismuth, Bi, 83 Chemical series poor metals Group, Period, Block 15, 6, p Appearance lustrous pink Standard atomic weight 208. ... ... In medicine, diarrhea, also spelled diarrhoea (see spelling differences), refers to frequent loose or liquid bowel movements. ... Staphylococcus aureus - Antibiotics test plate. ...


Choline salicylate is used topically to relieve the pain of aphthous ulcers. Choline is an organic compound, classified as an essential nutrient and usually grouped within the Vitamin B complex. ... An aphthous ulcer or canker sore is a type of mouth ulcer which presents as a painful open sore inside the mouth, caused by a break in the mucous membrane. ...


Other uses

  • Although toxic in large quantities, salicylic acid is used as a food preservative and antiseptic in toothpaste. For some people with salicylate sensitivity even these small doses can be harmful.
  • Sodium salicylate is a useful phosphor in the vacuum ultraviolet with nearly flat quantum efficiency for wavelengths between 10 to 100 nm.[9] It fluoresces in the blue at 420 nm. It is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.
  • Methyl Salycilate is used an a liniment, to soothe joint and muscle pain.

A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... An antiseptic solution of Povidone-iodine applied to an abrasion Antiseptics (Greek αντί, against, and σηπτικός, putrefactive) are antimicrobial substances that are applied to living tissue/skin to reduce the possibility of infection, sepsis, or putrefaction. ... Modern toothpaste gel Toothpaste is a paste or gel dentifrice used to clean and improve the aesthetic appearance and health of teeth. ... Salicylate sensitivity, also known as salicylate intolerance, is a chemical reaction that occurs when too much salicylate (salicylic acid) is introduced into a persons system. ... Green screen A phosphor is a substance that exhibits the phenomenon of phosphorescence (sustained glowing after exposure to light or energised particles such as electrons). ... UV redirects here. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula CH3OH (often abbreviated MeOH). ... Liniment, from the Latin linere, to anoint, is a medicinal preparation meant for external use, but one that is thinner in consistency than an ointment. ...

Safety

Salicylic acid has an ototoxic effect by inhibiting prestin.[10] It can induce transient hearing loss in zinc-deficient individuals. Ototoxicity is damage of the ear (oto), specifically the cochlea or auditory nerve and sometimes the vestibulum, by a toxin (often medication). ... Prestin is the motor protein of the outer hair cells of the inner ear of the mammalian cochlea. ... General Name, symbol, number zinc, Zn, 30 Chemical series transition metals Group, period, block 12, 4, d Appearance bluish pale gray Standard atomic weight 65. ...


This finding is based on clinical studies with rats. An injection of salicylic acid induced hearing loss in zinc-deficient rats, while a simultaneous injection of zinc reversed the hearing loss. An injection of magnesium in the zinc-deficient rats did not reverse the salicylic acid-induced hearing loss. This article is about rats. ... General Name, symbol, number magnesium, Mg, 12 Chemical series alkaline earth metals Group, period, block 2, 3, s Appearance silvery white solid at room temp Standard atomic weight 24. ...


Salicylic acid is toxic in large amounts. Pregnant women are advised not to use products containing salicylic acid due to the danger of Reye's syndrome. Reyes syndrome is a potentially fatal disease that causes numerous detrimental effects to many organs, especially the brain and liver. ...


Some people are hypersensitive to salicylic acid and related compounds. Salicylate sensitivity, also known as salicylate intolerance, is a chemical reaction that occurs when too much salicylate (salicylic acid) is introduced into a persons system. ...


The United States Food and Drug Administration recommends the use of sun protection when using skincare products containing salicylic acid (or any other BHA) on sun-exposed skin areas.[11] FDA redirects here. ...


Footnotes

  1. ^ S. Hayat, A. Ahmad (2007). Salicylic acid - A Plant Hormone. Springer. ISBN 1402051832. 
  2. ^ Davies, Peter J. (2004). Plant Hormones: Biosynthesis, Signal Transduction, Action!. Springer, 13. ISBN 1402026846. 
  3. ^ Hydrolysis of ASA to SA. Retrieved on July 31, 2007.
  4. ^ Paul B. Hemel and Mary U. Chiltoskey, Cherokee Plants and Their Uses -- A 400 Year History, Sylva, NC: Herald Publishing Co. (1975); cited in Dan Moerman, A Database of Foods, Drugs, Dyes and Fibers of Native American Peoples, Derived from Plants.[1] A search of this database for "salix AND medicine" finds 63 entries.
  5. ^ Stone, E (1763). "An Account of the Success of the Bark of the Willow in the Cure of Agues". Philosophical Transactions 53: 195–200. 
  6. ^ Grimes P.E. (1999). "The Safety and Efficacy of Salicylic Acid Chemical Peels in Darker Racial-ethnic Groups". Dermatologic Surgery 25: 18–22. doi:10.1046/j.1524-4725.1999.08145.x. 
  7. ^ Roberts W. E. (2004). "Chemical peeling in ethnic/dark skin". Dermatologic Therapy 17 (2): 196. doi:10.1111/j.1396-0296.2004.04020.x. 
  8. ^ Philip A. Mackowiak (2000). "Brief History of Antipyretic Therapy". Clinical Infectious Diseases, 31: 154–156. doi:10.1086/317510. 
  9. ^ JAR Samson Techniques of Vacuum Ultraviolet Spectroscopy
  10. ^ Wecker, H.; Laubert, A. (2004). "Reversible hearing loss in acute salicylate intoxication" (in German). HNO 52 (4): 347-51. PMID 15143764. 
  11. ^ Beta Hydroxy Acids in Cosmetics. Retrieved on 2007-11-23.
Clonidine is a direct-acting adrenergic agonist prescribed historically as an anti-hypertensive agent. ... Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ... Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. ... Categories: Possible copyright violations ... Orphenadrine (Norflex®, Disipal®, Banflex®, Flexon® and others) is an anticholinergic and NMDA receptor antagonist [1]drug belonging to the ethanolamine class of antihistamines. ... Trazodone (Desyrel®, Trittico®, Thombran®, Trialodine®) is a psychoactive compound with sedative, anxiolytic, and antidepressant properties. ... Ziconotide is a non-opioid, non local anesthetic used for the amelioration of chronic pain. ... Plant hormones (also known as plant growth regulators (PGRs) and phytohormones) are chemicals that regulate a plants growth. ... Abscisic Acid (ABA), also known as abscisin II and dormin, is a plant hormone. ... IAA appears to be the most active auxin in plant growth. ... Zeatin is named after the genera of corn, Zea as it was first discovered in corn. ... Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... GA1 GA3 ent-Gibberellane ent-Kauren Gibberellins (GAs) are plant hormones involved in promotion of stem elongation, mobilization of food reserves in seeds and other processes. ... Brassinolide appears to be the most common Brassinosteroid. ... Jasmonic Acid is released by plants when wounded and helps organize healing and defense. ... The polyamines are organic compounds having two or more primary amino groups - such as putrescine, cadaverine, spermidine, and spermine - that are growth factors in both eucaryotic and procaryotic cells. ...

  Results from FactBites:
 
Salicylic Acid - LoveToKnow 1911 (1887 words)
SALICYLIC ACID (ortho-hydroxybenzoic acid), an aromatic acid, C 6 H 4 (OH)(CO 2 H), found in the free state in the buds of Spiraea Ulmaria and, as its methyl ester, in gaultheria oil and in the essential oil of Andromeda Leschenaultii.
Phenyl salicylate, C6H4(OH) C 02C6H5, or salol, is obtained by heating salicylic acid, phenol and phosphorus oxychloride to 120-125° C.; by heating salicylic acid to 2 =0° C.; or by heating salicyl metaphosphoric acid and phenol to 140-150° C. (German Patent 85,565).
Salicylic acid and salicin (q.v.) share the properties common to the group of aromatic acids, which, as a group, are antiseptic without being toxic to man - a property practically unique; are unstable in the body; are antipyretic and analgesic; and diminish the excretion of urea by the kidneys.
Acidum Salicylicum (U. S. P.)—Salicylic Acid. | Henriette's Herbal Homepage (3477 words)
It is inodorous, but the crude salicylic acid in course of preparation, from wintergreen oil, possesses, from the presence of foreign matters, the peculiar odor of fresh willow bark, an odor familiar to those who have visited willow plantations, and have become impressed with the exhalation from freshly-stripped willows.
Salicylic acid imparts to the urine a characteristic olive-green tint.
Letzerich states that upon the addition of salicylic acid to the diphtheritic organisms in the urine of children affected with severe diphtheria, and which consisted of bacteria, micrococci, and protoplasmic masses, the bacteria were destroyed, and the corpuscles of the plasmic substance became dim, presented a double margin, and apparently contained air-bubbles.
  More results at FactBites »

 
 

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