2-ヒドロキシ安息香酸

2.26

log Kow = 2.26

2.26

2.3

Acrid taste

IT HAS SWEETISH, AFTERWARD ACRID, TASTE

1.44 at 68 °F (USCG, 1999) - Denser than water; will sink

1.443 g/cu cm at 20 °C/4 °C

Relative density (water = 1): 1.4

White crystals, fine needles, or fluffy white crystalline powder

Powder or needles from water

Needles in water; monoclinic prisms in alcohol

2240

Solubility (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, ether

SLIGHTLY SOL IN TOLUENE

In water, 2,240 mg/L at 25 °C

2.24 mg/mL at 25 °C

315 °F (157 °C) (closed cup)

157 °C c.c.

211

211 °C at 20 torr

211.00 °C. @ 20.00 mm Hg

256 °C (sublimes)

211 °C (20 mm Hg)

Danger

H302: 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.

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Commission Regulation (EC) No 1565/2000 (Repealed by Com.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/14544；Status: Active Update: 09-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23278

Salicylic acid: Does not have an individual approval but may be used under an appropriate group standard

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.

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)

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 coma; Topical salicylic acid is keratolytic in concentrations greater than 3%; [HSDB] See Acetylsalicylic acid.

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.

IPCS; Poisons 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, 2008

Cosmetic Ingredient Review (CIR) Expert Panel; Safety 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 Salicylate; Intl J of Toxicology 22 (Suppl 3): 1-108 (2003)

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.

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 water; those 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

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.

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.

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.

WATER, FOAM, CARBON DIOXIDE, DRY CHEM

Water 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 liquid; the foaming action blankets the surface of the liquid and extinguishes the fire by excluding oxygen. This tactic is expecially successful with high viscosity liquids.

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.

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.

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.

Salicylic acid was detected in the breast milk of 2 nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestion; concns 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).

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.

EC50; Species: Daphnia magna (Water flea, <24 hr neonate); Conditions: freshwater, static, 21 °C, pH 7.45; Concentration: 1060 mg/L for 24 hr; Effect: intoxication, immobilization /99.5% purity/

EC50; Species: Daphnia magna (Water flea, <24 hr neonate); Conditions: freshwater, static, 21 °C, pH 7.45; Concentration: 870 mg/L for 48 hr; Effect: intoxication, immobilization /99.5% purity/

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).

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).

EXPERIMENTAL: Salicylic acid was detected in the breast milk of 2 nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestion; concns 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).

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 qualifications

IDENTIFICATION: 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, wa

Salicylic 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.

/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/L; lowest-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.

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/14544；Status: Active Update: 09-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23278

Salicylic acid: Does not have an individual approval but may be used under an appropriate group standard

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.

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.

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.

D - Dermatologicals；D01 - Antifungals for dermatological use；D01A - Antifungals for topical use；D01AE - Other antifungals for topical use；D01AE12 - Salicylic acid

S - Sensory organs；S01 - Ophthalmologicals；S01B - Antiinflammatory agents；S01BC - Antiinflammatory agents, non-steroids；S01BC08 - Salicylic acid

QS - Sensory organs；QS01 - Ophthalmologicals；QS01B - Antiinflammatory agents；QS01BC - Antiinflammatory agents, non-steroids；QS01BC08 - Salicylic acid

QD - Dermatologicals；QD01 - Antifungals for dermatological use；QD01A - Antifungals for topical use；QD01AE - Other antifungals for topical use；QD01AE12 - Salicylic acid

D01AE12

Salicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution 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. 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 even gas. It is also very mildly anti-biotic.

Salicylic acid directly and reversibly inhibits COX-1 and COX-2 to decrease conversion of arachidonic acid to precursors of prostaglandins and thromboxanes. Salicylate's use in rheumatic diseases is due to it's analgesic and anti-inflammatory activity. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. Salicylic acid allows cells of the epidermis to more readily slough off. 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 competitively inhibits oxidation of uridine-5-diphosphoglucose (UDPG) with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of the glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to a phenolic acceptor. Inhibition of mucopoly saccharide synthesis is likely responsible for the slowing of wound healing with salicylates.

Salicylic acid has a potent keratolytic action and a slight antiseptic action when applied topically to the skin. In low concentrations, the drug has keratoplastic activity (correction of abnormal keratinization) and in higher concentrations (i.e., 1% or higher, depending on the vehicle), the drug has keratolytic activity (causes peeling of skin). Salicylic acid softens and destroys the stratum corneum by increasing endogenous hydration (water concentration), probably because of decreased pH, which causes the cornified epithelium (horny layer) of the skin to swell, soften, and then desquamate.

Groups of 3 and 25 month old male Fischer 344 rats were dosed iv with 5 or 50 mg/kg(14)C-salicylic acid ... . The half life value s in 3 month old animals were 4.08 and 30.1 hr with doses of 5 and 50 mg/kg, respectively; these values were 21.3 and 21.9 hr, respectively, in 25 month old animals.

Salicylic acid is extensively metabolized.

At low dosage, approximately 80% of salicylic acid is metabolized in the liver. Conjugation with glycine, forms salicyluric acid and when conjugated with glucuronic acid, acyl and phenolic glucuronide are formed. Small amounts of salicylic acid are also hydroxylated to gentisic acid. With large doses, the kinetics switch from first order to zero order.

Dogs were dosed intravenously with 1 g (14)C-salicylic acid (containing 10 uCi) in sodium bicarbonate solution. Urine was collected for 30 to 36 hours. Urinary metabolite recovery from one animal, which was representative of all the dosed animals, was 50% unchanged salicylic acid, 25% glucuronates, 10% salicyluric acid, and 4% to 5% gentisic acid. Total recovery was > 90% of the dose.

The major urinary metabolites identified after topical administeration differ from those after oral salicylate adminisration; those derived from percutaneous absorption contain more salicylate glucuronides (42%) and less salicyluric (52%) and salicylic acid (6%).

YIELDS O-CARBOXYPHENYL-B-D-GLUCURONIDE IN MAN; IN RABBIT; YIELDS O-CARBOXYPHENYL SULFATE IN RAT. /FROM TABLE/

For more Metabolism/Metabolites (Complete) data for SALICYLIC ACID (6 total), please visit the HSDB record page.

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.

About 10% is excreted unchanged in the urine.

The volume of distribution is about 170 mL/kg of body weight.

A single-center, single-sequence, two-period crossover study was performed to compare the systemic exposure to salicylic acid following facial application of a 30% salicylic acid cosmetic skin peel formulation applied for 5 min and an oral dose of 650 mg aspirin in nine healthy male and female subjects. The mean (SD) maximum salicylic acid concentration (C(max)) was 0.81 (0.32) ug/mL and 56.4 (14.2) ug/mL. The AUC-based safety margin ratio was 50:1. A depot effect was observed during topical application of the skin peel solution as the absorption of salicylic acid continued beyond the 5-min application period. Plasma salicylic acid C(max) values were achieved from 1.4 to 3.5 hr after topical application and from 0.5 to 1.5 hr after oral aspirin. The plasma concentrations in the present study (30%; 5 min) were similar to that of a low concentration (2%) applied in a leave-on product to the same body surface area.

The absorption of reagent-grade salicylic acid through abdominal guinea pig skin was examined. The abdominal area was shaved and a recirculation apparatus was applied to determine the rate of absorption. Salicylic acid, pH 3.0, had a constant rate of absorption (approximately 4%) at concentrations of 250, 400, and 1000 ug/mL. Salicylic acid at a concentration of 500 ug/mL was used to examine the absorption as a function of pH. The percent absorbed from 1 to 6 hours was 6.1, 3.3, 0.6, and 0 at pH 2, 3, 4, and 5, respectively, and 0, 1.8, 8.0, and 15.5 at pH 7, 8, 9, and 10, respectively.

Salicylic acid is rapidly absorbed from the intact skin, especially when applied in oily liniments or ointments, ... .

The percutaneous absorption of salicylic acid through damaged guinea pig skin was studied using a recirculation apparatus. After the abdominal skin of male guinea pigs was clipped and the stratum corneum removed, a glass vessel was attached and used for continuous recirculation and the amount of salicylic acid, 500 ug/mL and pH 3.0, absorbed was calculated from the concentration remaining in the solution. Also, concentrations of 250, 500, and 1000 ug/mL salicylic acid at pH 3.0 and 500 ug/ml at a pH of 2, 3, 4, 5, or 6 were used to determine the effect of concentration and pH, respectively, on absorption. The absorption rate of 500 ug/ml salicylic acid from the recirculating solution was 79.4% for damaged skin; the disappearance of salicylic acid from the solution was linear from the start of exposure. (This was 10 times the rate through intact skin; disappearance from intact skin was linear 1 hour after the start of exposure.) The rate of absorption from the recirculating solution was independent of concentration, but it did increase with an increasing fraction of un-ionized form. The amount of drug retained in damaged guinea pig skin after various exposure times was then determined. The animals were exposed to 500 ug/mL salicylic acid, pH 3.0, for 0.5, 1.0, 3.0, 4.5, or 6.0 hours, and then killed. The test area was wiped and the skin isolated to the corium. A peak in the amount of salicylic acid reserved in the skin was observed after 0.5 to 1 hour. ... These results were attributed to an increase in percutaneous absorption and rapid decrease in concentration in the test solution due to removal of the stratum corneum and a rapid decrease in skin concentration because of the decrease of salicylic acid in the solution. Varying the concentration of salicylic acid from 250 to 1000 ug/mL resulted in similar patterns of retention. Varying the pH from 3 to 6, the peak of the amount reserved became lower and broader with a decreasing fraction of unionized salicylic acid,

CIR ingredient: Salicylic Acid

Source: bark of the white willow and wintergreen leaves; also produced by organic synthesis; Used medicinally for its bacteriostatic, fungicidal, and keratolytic properties; the salts are used as analgesics (aspirin); [ChemIDplus]

Salicylic acid is used mainly in the synthesis of acetylsalicylic acid, the most commonly dispensed pharmaceutical product. In the form of esters, amides, and salicylic acid salts it serves as a starting material for other pharmaceutical products. Technical-grade salicylic acid is used primarily as an intermediate in the production of agrochemical products, dyes, and colorants, as well as in the rubber industry and in the manufacture of phenolic resins.

In the manufacture of aspirin, methyl salicylate, and other salicylates. Coupling agent for azo dyes. Has been used as food preservative. Keratolytic. Sodium salt as anti-inflammatory, analgesic, antipyretic.

Manufacture of resins, prevulcanization inhibitor, analytical reagent, /formerly as a/ fungicide

Acanthosis nigricans can be dealt with by using lotions or creams containing salicylic acid

(1972) NEGLIGIBLE

(1975) 2.02X10+8 GRAMS (TECH GRADE)

2023: 1,000,000 - <5,000,000 lb；2022: 5,000,000 - <10,000,000 lb；2021: 1,000,000 - <2,500,000 lb；2020: 1,000,000 - <2,500,000 lb

(1972) 2.53X10+10 GRAMS

(1975) 1.39X10+10 GRAMS (TECH GRADE)

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1949]

Benzoic acid, 2-hydroxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

During the late 1980s and early 1990s, approximately 60% of the salicylic acid produced in the United States has been consumed in the manufacture of aspirin

The distribution of salicylic acid in terms of application can be estimated as follows: acetylsalicylic acid 55%, esters and salts 18%, resins 10%, dyes and colorants 10%

CHEMICAL PROFILE: Salicylic Acid. Aspirin, 65%; salicylate esters and salts, 20%; foundry resins, 7%; miscellaneous, including rubber retarder and dystuffs intermediate, 8%.

CHEMICAL PROFILE: Salicylic acid. Demand: 1986: 35.5 million lb; 1987: 35.8 million lb; 1991 /projected/: 37.0 million lb.

For more Consumption Patterns (Complete) data for SALICYLIC ACID (6 total), please visit the HSDB record page.

Salicylic acid is prepared on an industrial scale by the Kolbe-Schmitt synthesis from dry sodium phenoxide in a stream of carbon dioxide at 150-160 °C and a pressure of 5 bar. The use of pressure results in a yield of about 90%, whereas without pressure the yield does not exceed 50% because disodium salicylate and phenol are formed in equivalent amounts.

Technical-grade salicylic acid obtained from the Kolbe-Schmitt process is already extremely pure: salicylic acid content 99.5%; phenol, p-hydroxybenzoic acid, or 4-hydroxyisophthalic acid 0.05 - 0.1% (as impurity); ash < 0.1%; water 0.2%. An even higher quality acid (pharmaceutical grade) can be obtained by crystallizing the sodium salicylate from water at a temperature not exceeding 20 °C, or by sublimation of the acid at 20 mbar and a temperature of 154 °C or with the aid of a carrier gas. A more modern process achieves sublimation directly by utilizing the heat of neutralization from the reaction of sodium salicylate with hydrogen chloride.

REACTION OF DRY, POWDERED SODIUM PHENATE WITH EXCESS CARBON DIOXIDE TO PRODUCE SODIUM SALICYLATE SOLUTION, WHICH IS ACIDIFIED TO OBTAIN SALICYLIC ACID

Manufactured by heating sodium phenolate with carbon dioxide under pressure.

SOME IS ... MADE BY SAPONIFYING CERTAIN NATURAL OILS SUCH AS BIRCH OR GAULTHERIA.

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Food Additives -> PRESERVATIVE -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Keratolytic; Preservative