化工社化工社 化学情報印刷レポート · 研究参考用
2-ヒドロキシ安息香酸
2-ヒドロキシ安息香酸 · サリシル酸 · 2-ヒドロキシベンゼンカルボン酸 · o-ヒドロキシ安息香酸 · スピール膏 · サリチル酸 · 2-ヒドロキシ安息香酸 [生化学用] · サリチル酸2-ヒドロキシ安息香酸
識別子と物理属性
| CAS No. | 69-72-7 |
|---|---|
| 分子式 | C7H6O3 |
| 平均分子量 | 138.12 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 2-ヒドロキシ安息香酸 |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 57.5 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 133 |
| pH | pH of saturated solution: 2.43.21(1 mM solution)2.57(10 mM solution)2.02(100 mM solution) |
| LogP（分配係数） | 2.26log Kow = 2.262.3 |
| LogS | -1.82 |
| 臭い | SYNTHETIC ACID IS ODORLESS100.00%で。かすかなフェノールナッツのような |
| 味 | Acrid tasteIT HAS SWEETISH, AFTERWARD ACRID, TASTE |
| 密度 | 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 |
| 溶解度 | 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 °Cエタノール：20℃で1M 無色透明1.8g/L(20℃) |
| Corrosivity | Non-corrosive |
| 引火点 | 315 °F (157 °C) (closed cup)157 °C c.c. |
| 沸点 | 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. |
| 融点 | 158-161 °C(lit.) |
| 蒸気密度 | 4.8 (vs air) |
| 蒸気圧 | 1 mm Hg ( 114 °C) |
| 屈折率 | 1,565 |
| FEMA | 3985 | 2-HYDROXYBENZOIC ACID |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 2.98(at 25℃) |
| 外観・状態 | 個体 |
| 色 | ホワイトからオフホワイト |
| においのタイプ | ナッティ |
| 由来生物 | synthetic |
| Merck | 14,8332 |
| JECFA Number | 958 |
| BRN | 774890 |
| ヘンリー定数 | 1.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。避けるべき物質には、酸化剤、強塩基、ヨウ素、フッ素などがあります。可燃性。光に敏感。 |
| 主な用途 | 半導体、ナノ粒子、フォトレジスト、潤滑油、紫外線吸収剤、接着剤、皮革、洗浄剤、染毛剤、石鹸、化粧品、鎮痛剤、鎮痛薬、抗菌剤、フケの治療、色素沈着皮膚、白癬、爪真菌症、骨粗鬆症、脚気、皮膚真菌症、自己免疫疾患 |
| 化粧品成分の機能 | ヘアコンディショニング抗脂漏性香料スキンコンディショニング防腐剤角質溶解性 |
| 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（分配係数） | 2.01 |
| CAS データベース | 69-72-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, 2-hydroxy-(69-72-7) |
| EPAの化学物質情報 | Salicylic acid (69-72-7) |
化学的特性
サリチル酸C7H6O3は芳香族の有機酸であり植物由来の化合物であることが多いですこの物質は特に白樺から抽出されることで知られていますが多くの植物や果物野菜にも自然に存在しますサリチル酸は医薬品や化粧品の製造に広く利用されており抗炎症抗菌角質溶解の効果があるためにきび治療薬や肌の角質を取り除く製品などに使用されます
化学的特性
Salicylic acid has the formula C6H4(OH) COOH, where the OH group is ortho to the carboxyl group. It is also known as 2- hydroxybenzoic acid. It is poorly soluble in water (2 g / L at 20 °C). Aspirin (acetyl salicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride.
化学性质
ガリ酸はフェノール類の一種でありその分子構造には3つのヒドロキシ基OHが結合していますこれらのヒドロキシ基はガリ酸が強い抗酸化作用を持つ理由の一つです抗酸化物質としてガリ酸は自由ラジカルを中和し細胞の酸化的ストレスを減少させることができますこの性質は食品保存剤や化粧品における防腐剤としてガリ酸が利用される理由を説明しています
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | IMAP assessments - Salicylic acid and its salts: Human health tier II assessment |
| 火災危険 | 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. |
| 火災の可能性 | SLIGHT WHEN EXPOSED TO HEAT OF FLAMECAN REACT WITH OXIDIZING MATERIALS |
| 健康有害性 | 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) |
| 有害性の概要 | 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 要件 | 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. |
| 反応性グループ | 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 要件 | 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 |
| 大気基準 | 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. |
| 消火 | 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. |
| 応急処置措置 | 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. |
| 応急処置 | 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) |
| 安全保管 | Separated from incompatible materials. See Chemical Dangers. |
| 消火手順 | 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. |
| 保管条件 | 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. |
| 処分方法 | 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. |
| 漏出処分 | 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. |
| 体内負荷 | 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). |
| 相互作用 | 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. |
| 健康影響 | Investigated as a mutagen and reproductive effector. |
| 生態毒性値 | 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 |
| 環境中動態 | 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). |
| 食品調査値 | 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). |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 暴露経路 | 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). |
| 毒性の概要 | 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). |
| 生態毒性抜粋 | /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. |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | VO0525000 |
| 輸送番号（UN） | UN 1648 3 / PGII |
| 毒性 | LD50 i.v. in mice: 500 mg/kg (Sota) |
| 税関コード | 29182100 |
| 危険文句（R） | 22-41-36/37/38-36-20/21/22-11 |
| 化審法 | (3)-1640 |
| 危険表示 | Xn,F |
| 安全措置（S） | 26-39-37/39-36-36/37-16 |
| 自然発火温度 | 500 °C |
| 危険等級 | Acute Tox. 4 OralEye Dam. 1Repr. 2 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 69-72-7(Hazardous Substances Data) |
用途
解説
o-hydroxybenzoic acid．C7H6O3(138.12)．種々の植物中にこのまま，または誘導体の形で存在し，とくに冬緑油中にはメチルエステルとして含まれている．サリチル酸は，工業的には，フェノールと二酸化炭素からのコルベ-シュミット反応により合成される．無色の結晶．融点159 ℃，沸点約211 ℃(2.6 kPa)．減圧下に昇華し，また水蒸気蒸留される．エタノール，エーテル，アセトンに易溶，水，ベンゼンに可溶．Ka 1.06×10－3(25 ℃)．塩化鉄(Ⅲ)で紫色を呈する．清酒，果実酒，酢などの食品の防腐剤として用いられ，また染料，とくに媒染アゾ染料の中間物としても用途がある．また，サリチル酸の誘導体はアスピリンをはじめとして医薬品に供されるものが多い．LD50 1.3 g/kg(ウサギ，経口)．森北出版「化学辞典（第2版）
用途
角質剥離、抗かび剤
用途
オルトヒドロキシ安息香酸の別名。無色の結晶。融点159℃，沸点211℃（20mmHg）。水に可溶，エチルアルコール，エーテルに易溶。塩化第二鉄塩水溶液で紫色を呈する。フェノールのナトリウム塩に二酸化炭素を加圧下で反応させてつくる。防腐剤，染料中間体，医薬原料などとして重要。たとえば，アセチル化すればアセチルサリチル酸（商品名アスピリン）。清酒，酢などの食品防腐剤として使用されていたが，現在は食品添加物としての使用は禁止。殺菌剤、角質軟化剤として用いる。解熱鎮痛消炎作用をもつが、内服や注射にはサリチル酸ナトリウムが用いられ、サリチル酸そのものは消化器障害が著しいため内服には用いられず、外用のみである。うおのめ、いぼとりに用いられるサリチル酸絆創膏(ばんそうこう)には50％含有され、白癬(はくせん)（水虫）や乾癬など皮膚糸状菌症には2～10％の軟膏や塗布液が用いられる。また脱毛症や腋臭(えきしゅう)症（わきが）、汗疹(かんしん)（あせも）などの治療剤にも配合されている。
説明
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.
天然物の起源
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.
来歴
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.
使用
Salicylic Acid is an Impurity of Acetylsalicylic Acid (A187780). Acetylsalicylic acid Impurity B.
一般的な説明
Odorless white to light tan solid. Sinks and mixes slowly with water.
使用用途
サリチル酸には、殺菌作用、消炎鎮痛作用、皮膚の角質軟化作用があります。そのため、医薬の分野で主に皮膚疾患の外用薬として利用される場合が多いです。また、サリチル酸の誘導体であるアセチルサリチル酸は、サリチル酸の鎮痛効果を保ちつつ、内服時の副作用が軽減されているので、鎮痛内服薬として広く使用可能です。 さらに、角質除去を目的として洗顔料などにも配合されているほか、染料中間物や防腐剤としても利用されています。かつては食品にも防腐剤として使われていましたが、現在は食品添加物としての使用はできません。
製法・合成法
調製方法
Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana it can also be synthesized via a phenylalanine - independent pathway. Sodium salicylate is commercially prepared by treating sodium phenolate ( the sodium salt of phenol ) with carbon dioxide at high pressure (100 atm ) and high temperature (390K) -a method known as the Kolbe-Schmitt reaction. Acidification of the product with sulfuric acid gives salicylic acid : It can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid) or methyl salicylate (oil of winter green) with a strong acid or base.
製造方法
Prepared by heating sodium phenolate with carbon dioxide under pressure
純化方法
It has been purified by steam distillation, by recrystallisation from H2O (solubility is 0.22% at room temperature and 6.7% at 100o), absolute MeOH, or cyclohexane and by sublimation in a vacuum at 76o. The acid chloride (needles) has m 19-19.5o, b 92o/15mm, the amide has m 133o (yellow needles from H2O), the O-acetyl derivative has m 135o (rapid heating and the liquid resolidifies at 118o), and the O-benzoyl derivative has m 132o (aqueous EtOH). [IR: Hales et al. J Chem Soc 3145 1954, Bergmann et al. J Chem Soc 2351 1950]. [Beilstein 10 IV 125.]