| Salicylic acid | |
|---|---|
 |
 |
| IUPAC name | 2-Hydroxybenzoic acid |
| Identifiers | |
| CAS number | [69-72-7] |
| EINECS number | |
| SMILES | OC(=O)c1ccccc1O |
| Properties | |
| Molecular formula | C7H6O3 |
| Molar mass | 138. 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 They are also referred to The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each Chemical substance commercially available in the A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 123 g/mol |
| Density | 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 44 g/cm³ (at 20 °C) |
| Melting point |
159 °C |
| Boiling point |
211 °C (2666 Pa) |
| 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. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Methyl salicylate ( Chemical formula C6H4(HOCOOCH3 also known as salicylic acid methyl ester, oil of wintergreen, Benzoic acid, C7H6O2 (or C6H5COOH is a colorless crystalline solid and the simplest Aromatic Carboxylic acid Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve 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 Bismuth subsalicylate, with a chemical formula C7H5BiO4 is a drug used to treat Nausea, Heartburn, Indigestion, Sulfosalicylic acid is used in urine tests to determine Urine Protein content In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Willows, sallows and osiers form the Genus Salix, around 400 species of Deciduous Trees and Shrubs found primarily A beta hydroxy acid (BHA is an Organic compound which contains a Carboxylic acid Functional group and hydroxy functional group separated by A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic Plant hormones (also known as phytohormones) are chemicals that regulate plant growth It is derived from the metabolism of salicin. Salicin (C13H18O7 is an alcoholic β- Glycoside that contains D-glucose. It is probably best known as a compound that is chemically similar to but not identical to the active component of aspirin (acetylsalicylic acid). Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve In fact, salicylic acid is a metabolite of aspirin, the product of esterase hydrolysis in the liver. Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve
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. Plant hormones (also known as phytohormones) are chemicals that regulate plant growth Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" Photosynthesis is a Metabolic pathway that converts Light Energy into Chemical energy. Transpiration is the Evaporation of water from the aerial parts of Plants especially leaves but also stems Flowers and Roots An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Chloroplasts are Organelles found in Plant cells and eukaryotic Algae that conduct Photosynthesis. 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'. The word endogenous means "arising from within" the opposite of Exogenous. A pathogen (from Greek πάθος pathos "suffering passion" and γἰγνομαι (γεν- gignomai (gen- "I give birth to" infectious 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. In plants systemic acquired resistance (SAR is a "whole-plant" resistance response that occurs following an earlier localized exposure to a Pathogen. SA is the calorigenic substance that causes thermogenesis in Arum flowers. Thermogenesis is the process of Heat production in organisms It occurs mostly in Warm-blooded animals but a few species of Thermogenic plants exist Arum is a genus of about 25 species of Flowering plants in the family Araceae, native to Europe, northern Africa, and western [2]
Production
Salicylic acid is an organic acid biosynthesized from the amino acid phenylalanine. Biosynthesis is a phenomenon wherein Chemical compounds are produced from simpler Reagents Biosynthesis unlike Chemosynthesis, takes place within living Phe redirects here For the BitTorrent feature see PHE. For the constellation see Phoenix (constellation.
Sodium salicylate is commercially prepared by treating sodium phenoxide with a high pressure of carbon dioxide at high temperature via the Kolbe-Schmitt reaction. Sodium salicylate is a Sodium salt of Salicylic acid. It can be prepared from Sodium phenolate and Carbon dioxide under higher temperature Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single The Kolbe-Schmitt reaction / Kolbe process (named after Adolph Wilhelm Hermann Kolbe and Rudolf Schmitt) is a Carboxylation Chemical reaction Acidification of the product solution gives salicylic 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. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve Methyl salicylate ( Chemical formula C6H4(HOCOOCH3 also known as salicylic acid methyl ester, oil of wintergreen,
Analysis
Salicylic acid is an enol of a β-keto carbonic acid and therefore forms purple complexes with iron(III) salts:
This tris(chelate) complex forms more readily in basic solution. Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. Keto acids are organic Acids containing a Ketone Functional group and a Carboxylic acid group
History
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. The history of Aspirin and the medical use of it and related substances stretches back to antiquity, though pure aspirin ( acetylsalicylic acid or ASA The term ancient Greece refers to the period of Greek history lasting from the Greek Dark Ages ca Hippocrates of Cos II or Hippokrates of Kos ( ca. 460 BC – ca Willows, sallows and osiers form the Genus Salix, around 400 species of Deciduous Trees and Shrubs found primarily This remedy was also mentioned in texts from ancient Sumer, Lebanon, and Assyria. Sumer ( Sumerian: sux-Latn [[Ki (earth ki]]-[[EN (cuneiform en]]-'''ĝir15''', Akkadian: Šumeru; possibly Biblical Shinar Lebanon (ˈlɛbənɒn Arabic: ar لبنان Lubnān) officially the Republic of Lebanon or Lebanese Republic (ar الجمهورية اللبنانية Early history The most Neolithic site in Assyria is at Tell Hassuna, the center of the Hassuna culture The Cherokee and other Native Americans used an infusion of the bark for fever and other medicinal purposes for centuries. The Cherokee (ᎠᏂᏴᏫᏯ a-ni-yv-wi-ya, in the Cherokee language) are a people native to North America, who at the time of European contact [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. 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 the West Oxfordshire Distrcit of Oxfordshire, England, located north west of Oxford. England is a Country which is part of the United Kingdom. Its inhabitants account for more than 83% of the total UK population whilst its mainland [5]
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. Salicin (C13H18O7 is an alcoholic β- Glycoside that contains D-glucose. Latin ( lingua Latīna, laˈtiːna is an Italic language, historically spoken in Latium and Ancient Rome. White Willow redirects here See White Willow (band for the Norwegian band This article is about the country For a topic outline on this subject see List of basic France topics. Italy (Italia officially the Italian Republic, (Repubblica Italiana is located on the Italian Peninsula in Southern Europe, and on the two largest Piria was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.
Salicylic acid was also isolated from the herb meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839. Filipendula is a genus of 12 species of perennial Herbaceous Flowering plants in the family Rosaceae, native to the temperate For the European and west Asian herb see Meadowsweet. Spiraea (Meadowsweet is a genus of about 80-100 species 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. In Human anatomy, the stomach is a J-shaped hollow muscular organ of the Gastrointestinal tract involved in the second phase of Digestion, following In Medicine, diarrhea, also spelled diarrhoea (see spelling differences) is frequent loose or liquid Bowel movements Acute diarrhea
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. α-hydroxy acids, or alpha hydroxy acids ( AHAs) are a class of chemical compounds that consist of a Carboxylic acid substituted with a hydroxy group Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle Psoriasis (səˈraɪəsɪs ( suh-RI-uh-sus) is a non-contagious disorder which affects the Skin and Joints It commonly causes red scaly A callus (or Callosity) is an especially toughened area of Skin which has become relatively thick and hard as a response to repeated contact or pressure A callus (or Callosity) is an especially toughened area of Skin which has become relatively thick and hard as a response to repeated contact or pressure Keratosis pilaris (KP also follicular keratosis is a very common genetic follicular condition that is manifested by the appearance of rough bumps on the skin A wart (also known as verruca) is generally a small rough Tumor, typically on hands and feet but often other locations that can resemble a Cauliflower 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. Epidermis is the outermost layer of the Skin. It forms the waterproof protective wrap over the body's surface and is made up of stratified squamous Epithelium with The sebaceous glands are Glands found in the Skin of Mammals Locations and morphology A branched type of Acinar gland, these Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Shampoo is a Hair care product used for the removal of oils, dirt skin particles Dandruff, environmental pollutants and other contaminant particles that Dandruff (also called scurf and historically termed Pityriasis capitis) is due to the excessive shedding of dead skin cells from the Scalp. Salicylic acid is also used as an active ingredient in gels which remove warts. A wart (also known as verruca) is generally a small rough Tumor, typically on hands and feet but often other locations that can resemble a Cauliflower 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. 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 [6][7]
The medicinal properties of salicylate, mainly for fever relief, have been known since ancient times, and it was used as an anti-inflammatory drug. Fever (also known as pyrexia, from the Greek pyretos meaning fire or a febrile response, from the Latin word Febris Year 1763 ( MDCCLXIII) was a Common year starting on Saturday (link will display the full calendar of the Gregorian calendar (or a [8]
Aspirin (acetylsalicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid. Cotton is a soft staple Fibre that grows around the seeds of the cotton plant ( Gossypium sp Exfoliation involves the removal of the oldest dead Skin cells on the skin's outermost surface and has been used for many years to help maintain the skin Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve Esterification is the general name for a Chemical reaction in which two reactants (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. Bismuth (ˈbɪzməθ is a Chemical element that has the symbol Bi and Atomic number 83 Bismuth subsalicylate, with a chemical formula C7H5BiO4 is a drug used to treat Nausea, Heartburn, Indigestion, When combined, the two key ingredients help control diarrhea, nausea, heartburn, and gas. In Medicine, diarrhea, also spelled diarrhoea (see spelling differences) is frequent loose or liquid Bowel movements Acute diarrhea It is also a very mild antibiotic. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa
Choline salicylate is used topically to relieve the pain of aphthous ulcers. Choline is an Organic compound, classified as a water-soluble Essential nutrient and usually grouped within the Vitamin B complex
Other uses
- Although toxic in large quantities, salicylic acid is used as a food preservative and antiseptic in toothpaste. A preservative is a natural or synthetic chemical that is added to products such as foods pharmaceuticals paints biological samples wood etc Antiseptics (from Greek αντί - anti, '"against" + σηπτικός - septikos, "putrefactive" are antimicrobial Toothpaste is a Paste or Gel Dentifrice used to clean and maintain the aesthetics and health of Teeth. For some people with salicylate sensitivity even these small doses can be harmful. Salicylate sensitivity, also known as salicylate intolerance, is any Adverse effect that occurs when a normal amount of salicylate ( Salicylic acid) is introduced
- Sodium salicylate is a useful phosphor in the vacuum ultraviolet with nearly flat quantum efficiency for wavelengths between 10 to 100 nm. A phosphor is a substance that exhibits the phenomenon of Phosphorescence (sustained glowing after exposure to energized particles such as Electrons Ultraviolet ( UV) light is Electromagnetic radiation with a Wavelength shorter than that of Visible light, but longer than X-rays [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. Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound
- Methyl Salycilate is used an a liniment, to soothe joint and muscle pain. Liniment, (or embrocation from the Latin linere, to Anoint, is a medicated topical preparation for application to the skin
Safety
Salicylic acid has an ototoxic effect by inhibiting prestin. Ototoxicity is damage of the Ear ( oto) specifically the Cochlea or auditory nerve and sometimes the Vestibulum, by a Toxin Prestin is the Motor protein of the outer hair cells of the inner ear of the Mammalian Cochlea. [10] It can induce transient hearing loss in zinc-deficient individuals. Zinc (ˈzɪŋk from Zink is a Metallic Chemical element with the symbol Zn and Atomic number 30
This finding is based on clinical studies with rats. Rats are various medium sized long-tailed Rodents of the superfamily Muroidea 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. Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 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. Reye's 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 any Adverse effect that occurs when a normal amount of salicylate ( Salicylic acid) is introduced
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]
Footnotes
- ^ S. Hayat, A. Ahmad (2007). Salicylic acid - A Plant Hormone. Springer. Springer Science+Business Media or Springer (ˈʃpʁɪŋɐ is a worldwide Publishing company based in Germany, which publishes textbooks academic ISBN 1402051832.
- ^ Davies, Peter J. (2004). Plant Hormones: Biosynthesis, Signal Transduction, Action!. Springer, 13. Springer Science+Business Media or Springer (ˈʃpʁɪŋɐ is a worldwide Publishing company based in Germany, which publishes textbooks academic ISBN 1402026846.
- ^ Hydrolysis of ASA to SA. Retrieved on July 31, 2007.
- ^ 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.
- ^ Stone, E (1763). "An Account of the Success of the Bark of the Willow in the Cure of Agues". Philosophical Transactions 53: 195–200.
- ^ Grimes P. E. (1999). "The Safety and Efficacy of Salicylic Acid Chemical Peels in Darker Racial-ethnic Groups". Dermatologic Surgery 25: 18–22. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ Roberts W. E. (2004). "Chemical peeling in ethnic/dark skin". Dermatologic Therapy 17 (2): 196. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ Philip A. Mackowiak (2000). "Brief History of Antipyretic Therapy". Clinical Infectious Diseases, 31: 154–156. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ JAR Samson Techniques of Vacuum Ultraviolet Spectroscopy
- ^ Wecker, H. ; Laubert, A. (2004). "Reversible hearing loss in acute salicylate intoxication" (in German). HNO 52 (4): 347–51. Nitroxyl (HNO/NO− or hyponitrous acid, in Chemistry is the reduced form of Nitric oxide (NO PMID 15143764.
- ^ Beta Hydroxy Acids in Cosmetics. Retrieved on 2007-11-23. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 800 - Charlemagne arrives at Rome to investigate the alleged crimes of
Dictionary
salicylic acid
-noun
- (organic chemistry) A white crystalline organic acid, 2-hydroxy-benzoic acid, C6H4(OH)(COOH), used in the production of aspirin and other industrial chemicals.
Dapyx Software network: MP3 Explorer | Ebook Manager | Zenithic