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Salicylsäure
2-HYDROXYBENZOIC ACID · SALICYCLIC ACID · 171 · salicylic · Acido salicilico · 380 · FEMA 3985 · O-HYDROXYBENZOIC ACID
Identifikatoren & physikalische Daten
| CAS No. | 69-72-7 |
|---|---|
| Summenformel | C7H6O3 |
| Durchschnittliche Molmasse | 138,12 g/mol |
| Monoisotopische Masse | 138,03169405 g/mol |
| SMILES | O=C(O)c1ccccc1O |
| InChIKey | YGSDEFSMJLZEOE-UHFFFAOYSA-N |
| PubChem CID | 338 |
| ChEMBL | CHEMBL424 |
| ChEBI | CHEBI:16914 |
| EC No. | 200-712-3 |
| DTXSID | DTXSID7026368 |
| Lokaler Name | Salicylsäure |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 133 |
| pH | pH of saturated solution: 2.43.21(1 mM solution)2.57(10 mM solution)2.02(100 mM solution) |
| LogP (Verteilungskoeffizient) | 2.26log Kow = 2.262.3 |
| LogS | -1.82 |
| Geruch | SYNTHETIC ACID IS ODORLESS |
| Geschmack | Acrid tasteIT HAS SWEETISH, AFTERWARD ACRID, TASTE |
| Dichte | 1.44 at 68 °F (USCG, 1999) - Denser than waterwill sink1.443 g/cu cm at 20 °C/4 °CRelative density (water = 1): 1.4 |
| Color/Form | White crystals, fine needles, or fluffy white crystalline powderPowder or needles from waterNeedles in watermonoclinic prisms in alcohol |
| Löslichkeit | 2240Solubility (weight percent): carbon tetrachloride 0.262 (25 °C)benzene 0.775 (25 °C)propanol 27.36 (21 °C)absolute ethanol 34.87 (21 °C)acetone 396 (23 °C)Soluble in oil of turpentine, alcohol, etherSLIGHTLY SOL IN TOLUENEIn water, 2,240 mg/L at 25 °C2.24 mg/mL at 25 °Cethanol: 1 M at 20 °C, clear, colorless1.8 g/L (20 ºC) |
| Corrosivity | Non-corrosive |
| Flammpunkt | 315 °F (157 °C) (closed cup)157 °C c.c. |
| Siedepunkt | 211211 °C at 20 torr211.00 °C. @ 20.00 mm Hg256 °C (sublimes)211 °C (20 mm Hg)211 °C(lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 158-161 °C(lit.) |
| Dampfdichte | 4.8 (vs air) |
| Dampfdruck | 1 mm Hg ( 114 °C) |
| Brechungsindex | 1,565 |
| FEMA | 3985 | 2-HYDROXYBENZOIC ACID |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 2.98(at 25℃) |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| Geruch | at 100.00 %. faint phenolic nutty |
| Geruchsart | nutty |
| Biologische Quelle | synthetic |
| Merck | 14,8332 |
| JECFA Number | 958 |
| BRN | 774890 |
| Henry-Konstante | 1.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Substances to be avoided include oxidizing agents, strong bases, iodine, fluorine. Combustible. Sensitive to light. |
| Hauptanwendungen | Semiconductors, nanoparticles, photoresists, lubricating oils, UV absorbers, adhesive, leather, cleaner, hair dye, soaps, cosmetics, pain medication, analgesics, antibacterial agent, treatment of dandruff, hyperpigmented skin, tinea pedis, onychomycosis, osteoporosis, beriberi, fungicidal skin disease, autoimmune disease |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGANTI-SEBORRHEICFRAGRANCESKIN CONDITIONINGPRESERVATIVEKERATOLYTIC |
| InChI | 1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) |
| InChIKey | YGSDEFSMJLZEOE-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccccc1O |
| LogP (Verteilungskoeffizient) | 2.01 |
| CAS Datenbank | 69-72-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 2-hydroxy-(69-72-7) |
| EPA chemische Informationen | Salicylic acid (69-72-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]H361d: Suspected of damaging the unborn child [Warning Reproductive toxicity]P203, P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P318, P330, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.1% (7 of 4704) of reports. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 2-hydroxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzoic acid, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 2-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 18-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14544Status: Active Update: 09-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23278Salicylic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Salicylic acid and its salts: Human health tier II assessment |
| Brandgefahren | Special Hazards of Combustion Products: Irritating vapors of unburned material and phenol may form in fire.Behavior in Fire: Sublimes and forms vapor or dust that may explode (USCG, 1999)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | SLIGHT WHEN EXPOSED TO HEAT OF FLAMECAN REACT WITH OXIDIZING MATERIALS |
| Gesundheitsgefahren | Inhalation of dust irritates nose and throat. Vomiting may occur spontaneously if large amounts are swallowed. Contact with eyes causes irritation, marked pain, and corneal injury which should heal. Prolonged or repeated skin contact may cause marked irritation or even a mild burn. (USCG, 1999) |
| Gefahrenübersicht | An eye irritant[CAMEO] Symptoms of salicylism after an acute overdose include ringing in the ears, confusion, hyperventilation, vomiting, and in severe cases, seizure and comaTopical salicylic acid is keratolytic in concentrations greater than 3%[HSDB] See Acetylsalicylic acid. |
| FDA-Anforderungen | Salicyclic acid used as a preservative only is an indirect food additive for use only as a component of adhesives.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: salicylic acid is included in topical acne drug products.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: salicylic acid is included in external analgesic drug products.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: salicylic acid is included in skin protectant drug products.For more FDA Requirements (Complete) data for SALICYLIC ACID (11 total), please visit the HSDB record page. |
| Reaktive Gruppe | Acids, CarboxylicPhenols and Cresols |
| Special Reports | IPCSPoisons Information Monograph 642: Salicylic Acid (September 1998). Available at http://www.inchem.org/documents/pims/pharm/pim642.htm#PartTitle:5.%20%20ROUTES%20OF%20ENTRY as of February 13, 2008Cosmetic Ingredient Review (CIR) Expert PanelSafety Assessment of Salicylic Acid, Butyloctyl Salicylate, Calcium Salicylate, C12-15 Alkyl Salicylate, Capryloyl Salicylic Acid, Hexyldodecyl Salicylate, Isocetyl Salicylate, Isodecyl Salicylate, Magnesium Salicylate, MET-Salicylate, Ethylhexyl Salicylate, Potassium Salicylate, Methyl Salicylate, Myristyl Salicylate, Sodium Salicylate, TEA-Salicylate, and Tridecyl SalicylateIntl J of Toxicology 22 (Suppl 3): 1-108 (2003) |
| FIFRA-Anforderungen | Product registrations which once contained active ingredients incl salicyclic acid have previously been amended to remove the ingredient from the formula or have been cancelled for other reasons ... These ingredients will be removed from Reregistration List D effective 90 days after publication of this notice ... and will not be considered further for reregistration. |
| Reactivity Profile | SALICYLIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in waterthose with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (ca |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Salicylic acid is produced, as an intermediate or a final product, by process units covered under this subpart. |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)Use water spray, carbon dioxide, powder. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer immediately for medical attention. |
| Erste Hilfe | INHALATION: move to fresh air.INGESTION: induce vomiting and get medical attention promptly.EYES: promptly flush with water for 15 min. and get medical attention.SKIN: wash with soap and water. (USCG, 1999) |
| Sichere Lagerung | Separated from incompatible materials. See Chemical Dangers. |
| Brandbekämpfungsverfahren | WATER, FOAM, CARBON DIOXIDE, DRY CHEMWater or foam may case frothing ... to liquids having flash points above 212 °F (100 °C) ... It does not indicate that water or fire fighting foam should not be used. The frothing may be violent and could endanger any fire fighters located too close to the burning liquid, particularly when solid streams of water are directed onto the hot, burning liquid. On the other hand, a carefully applied water spray has frequently been used to achieve extinguishment by deliberately causing frothing only on the surface of the liquidthe foaming action blankets the surface of the liquid and extinguishes the fire by excluding oxygen. This tactic is expecially successful with high viscosity liquids. |
| Lagerbedingungen | Salicylic acid should be stored in well-closed containers. Salicylic acid collodion should be stored in tight containers at 15-30 °C. Because the collodion is flammable, it should not be stored near heat or an open flame. Salicylic acid plaster should be stored in well-closed containers, preferably at 15-30 °C. The Trans-Ver-Sal plaster should be stored at a temperature less than 37.8 °C. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Salicyclic acid is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance, protective clothing, protective gloves and safety goggles. If appropriate, moisten first to prevent dusting. Sweep spilled substance into covered containers. Then store and dispose of according to local regulations. |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached when dispersed. |
| Skin Prevention | Protective gloves. |
| Körperbelastung | Salicylic acid was detected in the breast milk of 2 nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestionconcns ranged from 0.2-1.5 and 0.27-1.0 mg/L(1). The salicylate ion was also detected in breast milk from 6 nursing mothers between the ages of 24 and 32 who ingested aspirin(1). Salicylic acid was measured in the serum of South Indians (0.05-0.64 umol/L), vegetarians (0.04-2.47 umol/L), nonvegetarians (0.02-0.20 umol/L), and aspirin takers (0.23-25.40 umol/L)(2). Salicylates, including salicylic acid, readily cross the placental barrier(3). |
| Wechselwirkungen | PERCUTANEOUS ABSORPTION OF HYDROCORTISONE & SALICYLIC ACID WAS FOUND TO BE GREATER WHEN DIMETHYL SULFOXIDE WAS PRESENT. HOWEVER, EFFECT ON ... ACID WAS GREATER @ LOW PH VALUES, & POSITIVE ACTION OF DIMETHYL SULFOXIDE APPEARED TO BE DUE PARTLY TO ITS ABILITY TO INCR SOLUBILITY OF UN-IONIZED DRUG.PENTOBARBITAL /SRP: CNS DEPRESSION/ IN MICE WAS ENHANCED AFTER PRE-TREATMENT WITH ... SALICYLIC ACID ... SALICYLIC ACID ... SHOWN TO DECR PLASMA-PROTEIN BINDING OF DIPHENYLHYDANTOIN IN MAN ... .The anti-inflammatory properties of salicylates and prednisolone were investigated using inhibition of in vitro phytohemagglutinin-stimulated lymphocyte proliferation in human whole blood from healthy male and female subjects. Steroids and salicylates are used in conjunction for the treatment of inflammatory disorders such as rheumatoid arthritis and inhibit the proinflammatory transcription factor, NFKB, by different mechanisms. Data generated using various combinations of these drugs were analyzed using isobolograms and the universal surface response approach based on the Loewe additivity principle. The interaction between aspirin and prednisolone was mildly antagonistic while that between salicylic acid and prednisolone was modestly synergistic at therapeutic concentrations. Further, aspirin was slightly more potent in males, but the nature of the steroid-salicylate interaction was similar across genders. This study helps rationalize part of the beneficial effects of steroids and salicylates in treatment of inflammatory disorders.In rats, magnesium deficiency caused a moderate hearing loss, measured by means of evoked potentials at 10 and 20 kHz, which was repaired after refeeding a normal diet. Application of 700 mg/kg salicylic acid or injection of 5 x 100 mg/kg gentamicin also caused a reversible hearing loss in normally fed rats. Treatment of zinc deficient rats with salicylic acid produced a stronger although reversible hearing loss than in normally fed salicylate treated rats. Treatment of magnesium-deficient rats with gentamicin induced a strong hearing loss that was nearly complete and irreversible in 9 of 25 rats.For more Interactions (Complete) data for SALICYLIC ACID (7 total), please visit the HSDB record page. |
| Gesundheitliche Auswirkungen | Investigated as a mutagen and reproductive effector. |
| Ökotoxizitätswerte | EC50Species: Daphnia magna (Water flea, <24 hr neonate)Conditions: freshwater, static, 21 °C, pH 7.45Concentration: 1060 mg/L for 24 hrEffect: intoxication, immobilization /99.5% purity/Concentration: 870 mg/L for 48 hr |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 404(SRC), determined from a log Kow of 2.26(2) and a regression-derived equation(3), indicates that salicylic acid is expected to have moderate mobility in soil(SRC). The pKa of salicylic acid is 2.98(4), indicating that this compound will exist primarily in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil surfaces is not expected to be an important fate process because anions do not volatilize. Salicylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.2X10-5 mm Hg(6). Salicylic acid has been observed to biodegrade quickly under differing sets of agricultural practices in Pahokee muck soil(7), suggesting that biodegradation in soil is an important fate process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 404(SRC), determined from a log Kow of 2.26(2) and a regression-derived equation(3), indicates that salicylic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 2.98(4) indicates salicylic acid will exist almost entirely in anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In aqueous biodegradation screening tests, salicylic acid reached 88.1% of its theoretical biological oxygen demand after 14 days(8), suggesting that biodegradation in water is an important fate process(SRC).AQUATIC FATE: Half-lives of 30 to 142 days have been calculated(SRC) for the photochemical reaction of salicylic acid and the salicylate with hydroxyl radicals in full intensity sunlit natural waters(1-3). Limited evidence suggests that salicylic acid, via photochemical processes, is involved in polymerization of fulvic acids in natural waters(4). The pseudo-first order rate constant for the direct photolysis of aqueous salicylic acid has been reported to be <0.02 hr-1(5).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), salicylic acid, which has a vapor pressure of 8.2X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase salicylic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 30 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase salicylic acid may be removed from the air by wet or dry deposition(SRC). Salicylic acid contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight.(4). |
| Lebensmitteluntersuchungswerte | Salicylic acid occurs in common fruits such as apples, oranges, plums, and grapes, which accounts for its presence in most wines(1). Salicylic acid has been quantitatively detected in many foods, including whole tomatoes, cinnamon, oregano, thyme, red wine, beer, honey, licorice, and raisins(2). A salicylic acid concentration of 1474.7 mg/100 g was measured in cumin, while other common spices contained up to 23.3 mg/100 g salicylic acid(3). Salicylic acid has also been detected in the blueberry Vaccinium arctostaphylos(4) and barley(5). A survey of vegetable soup found that the organic soup tested had a median salicylic acid concentration of 117 ng/g salicylic acid, while the non-organic soup had a median concentration of 20 ng/g(6). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Expositionspfade | The substance can be absorbed into the body by inhalation, by ingestion and through the skin. |
| Milk Concentrations | EXPERIMENTAL: Salicylic acid was detected in the breast milk of 2 nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestionconcns ranged from 0.2-1.5 and 0.27-1.0 mg/L(1). The salicylate ion was also detected in breast milk from 6 nursing mothers between the ages of 24 and 32 who ingested aspirin(1). |
| Toxizitätsübersicht | The Panel concluded that the following ingredients are safe in cosmetics in the present practices of use and concentration described in the safety assessment, when formulated to be non-irritating and non-sensitizing, which may be based on a quantitative risk assessment (QRA)...Salicylic Acid...Safe for use in cosmetics, with qualificationsIDENTIFICATION: Salicylic acid is an analgesic and antipyretic medication. Salicylic acid in the form of esters was found in several plants, notably in wintergreen leaves and the bark of sweet birch. It was made synthetically by heating sodium phenolyate with carbon dioxide under pressure and microbial oxidation of naphthalene. Salicylic acid is colorless or white crystals. Colourless acicular crystals or a white crystalline powder. The synthetic form is white but if prepared from natural methyl salicylate, it may have a slightly yellow or pink tint. Salicylic acid is a white crystalline powder with a sweetish acrid taste. If prepared from natural methyl salicylate, it may have a faint mint like odor. It is available in forms of ointments, cream, gel, transdermal patches, liquids and plaster. Salicylic acid is soluble in water, boiling water, alcohol, ether and chloroform. Salicylic acid has keratinolytic properties and is applied topically in the treatment of hyperkeratotic and scaling conditions such as dandruff, ichthyosis and psoriasis. Initially a concentration of 2% is used increasing to about 6% if necessary. It is often used in conjunction with many other agents, such as benzoic acid, coal tar, resorcinol and sulfur. Salicylic acid is also used in the form of paint and in the form of collodion basis (10 to 17%) or as a plaster (20 to 50%) to destroy warts and corns. It also possesses fungicidal properties and is used topically in the treatment of fungal skin infections such as tinea. HUMAN EXPOSURE: Main risks and target organs: The toxic effects of salicylic acid and salicylates are complex. Main risks with oral therapeutic doses are mostly gastrointestinal irritation. Hepatic encephalopathy (Reye's Syndrome) has been reported in children who had taken aspirin for treatment of viral infections such as influenza. Toxic doses of salicylate stimulate the respiratory centre leading to respiratory alkalosis. In severe intoxication, metabolic acidosis, waSalicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. 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 verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis. |
| Average Daily Intake | Using food intake data from the Dutch Food Consumption Survey and measurements of salicylic acid in foods, the average daily intake of salicylic acid has been estimated to be 0-5 mg/day(1). |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Ten acidic and two neutral pharmaceuticals were detected in the effluents of eight sewage treatment plants (STPs) from across Atlantic Canada. ...Six compounds (caffeine, naproxen, salicylic acid, carbamazepine, metoprolol, and sotolol) were found to persist in a small stream for a distance of at least 17 km, suggesting that small stream exposure to pharmaceutically active residues may be relatively greater than that in large bodies of water. Bioassays assessing acute and chronic effects on four organisms were conducted on four high-use drugs: Acetaminophen, ibuprofen, naproxen, and salicylic acid (metabolite of acetyl salicylic acid). Results indicated no negative effects except for the chronic algal (Selanastrum capricornutum) growth test on ibuprofen (no-observed-effect concentration, 10 ug/Llowest-observed-effect concentration, 32 ug/L). Effects of these four compounds on invertebrates and plants in the receiving environments are unlikely based on the concentrations measured./AQUATIC SPECIES/ Metabolic products are often more toxic than their pharmacological parent compounds. Therefore, the acute and chronic effects of the main metabolites--salicylic acid (SAL), gentisic acid (GEN), and o-hydroxyhippuric acid (HDP)--of acetylsalicylic acid (ASA), the active ingredient in Aspirin and many other pharmaceuticals, were assessed using standard (Daphnia magna) and autochthonous (Daphnia longispina) cladocerans. The sequence of decreasing levels of acute and chronic toxicity of ASA metabolites to daphnids was GEN > SAL > HDP. HDP did not present acute toxicity, but chronic exposures enabled the production of abnormal neonates and, in particular, egg abortion. Thus, reproduction was the end point most susceptible to HDP. On the other hand, SAL and GEN induced changes in the normal patterns of reproduction and growth of both species. In general, D. longispina was more sensitive than was D. magna, although the population growth of the autochthonous species was superior under SAL exposures than that of the standard test species. Although the concentrations that were determined to have a toxic effect were above the levels detected in aquatic environmental samples, exposure to low levels of pharmacologically active substances for a duration longer than the test period may induce changes in nontarget organisms. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1648 3 / PGII |
| Zollcode | 29182100 |
| RTECS-Nr. | VO0525000 |
| R-Sätze (R) | 22-41-36/37/38-36-20/21/22-11 |
| Toxizität | LD50 i.v. in mice: 500 mg/kg (Sota) |
| Gefahrensymbole | Xn,F |
| Sicherheitshinweise (S) | 26-39-37/39-36-36/37-16 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 69-72-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralEye Dam. 1Repr. 2 |
| Selbstentzündungstemperatur | 500 °C |
Anwendungen & Verwendung
Beschreibung
Salicylic acid (from Latin salix, willow tree, from the bark of which the substance used to be obtained) is a mono hydroxy benzoic acid, a type of phenolic acid and a beta hydroxy acid. 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. In addition to being an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prod rug to salicylic acid, it is probably best known for its use in anti-acne treatments. The salts and esters of salicylic acid are known as salicylates.
Occurrence
Unripe fruits and vegetables are natural sources of salicylic acid, particularly blackberries, blueberries, cantaloupes, dates, raisins, kiwi fruits, guavas, apricots, green pepper, olives, tomatoes, radish and chicory; also mushrooms. Some herbs and spices contain quite high amounts, although meat, poultry, fish, eggs and dairy products all have little to no salicylates. Of the legumes, seeds, nuts, and cereals, only almonds, water chestnuts and peanuts have significant amounts.
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 . This remedy was also mentioned in texts from ancient Sumer , Lebanon , and As syria . The active extract of the bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated and named by the German chemist Johann Andreas Buchner in 1826. Raffaele Piria, an Italian chemist 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. 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.
Verwenden
Salicylic Acid is an Impurity of Acetylsalicylic Acid (A187780). Acetylsalicylic acid Impurity B.
Herstellung & Synthese
synthetische
Prepared by heating sodium phenolate with carbon dioxide under pressure