4-Aminobenzoic acid
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4-Aminobenzoic acid
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CAS No:
150-13-0
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Formula:
C7H7NO2
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Chemical Name:
4-Aminobenzoic acid
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Synonyms:
Benzoic acid,4-amino-;Benzoic acid,p-amino-;4-Aminobenzoic acid;Amben;p-Aminobenzoic acid;Anticanitic vitamin;Chromotrichia factor;Anti-Chromotrichia factor;PABA;Paraminol;Trichochromogenic factor;Vitamin BX;Vitamin H';p-Carboxyaniline;Paranate;p-Carboxyphenylamine;4-Carboxyaniline;PAB;Hachemina;Pabacyd;Pabafilm;Pabamine;Romavit;Aniline-4-carboxylic acid;Sunbrella;Antichromotrichia factor;Anticantic vitamin;Bacterial vitamin H1;NSC 7627;4-Carboxyphenylamine;Actipol;4-Aminobenzenecarboxylic acid;p-Aminobenzenecarboxylic acid;para-Aminobenzoates;8014-65-1
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CAS No:
Description
White to off white crystalline powderChEBI: An aminobenzoic acid in which the amino group is para to the carboxy group.4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA because the number 4 carbon in the benzene ring is also known as the para position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and a carboxyl groups.
P-aminobenzoic acid appears as colorless crystals that discolor on exposure to light and air. (NTP, 1992)|Solid
P-aminobenzoic acid appears as colorless crystals that discolor on exposure to light and air. (NTP, 1992)|4-aminobenzoic acid is an aminobenzoic acid in which the amino group is para to the carboxy group. It has a role as an Escherichia coli metabolite, a plant metabolite and an allergen. It derives from a benzoic acid. It is a conjugate acid of a 4-aminobenzoate.|A member of the vitamin B complex. It used to be common in sunscreening agents until found to also be a sensitizer. The potassium salt is used therapeutically in fibrotic skin disorders.|Aminobenzoic acid is a Vitamin B Complex Member.|Aminobenzoic Acid is an organic acid with UV absorption and antifibrotic properties. When exposed to light, aminobenzoic acid (para-aminobenzoic acid or PABA) absorbs UV light and emits excess energy via a photochemical reaction that may cause damage to DNA. Because DNA defects contribute to skin cancer, aminobenzoic acid is no longer widely used in sunscreen formulations. Aminobenzoic acid may also increase oxygen uptake at the tissue level and may enhance monoamine oxidase (MAO) activity to promote the degradation of serotonin, which in excess, may lead to fibrotic changes.|An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.
4-Aminobenzoic acid Basic Attributes
137.14
137.14
471605
205-753-0
TL2TJE8QTX
7627
DTXSID6024466
C61634
Monoclinic prisms from dilute alcohol|Light buff crystals; white when pure|Yellowish to red crystals or prisms|White or slightly yellow crystals or crystalline powder
D - Dermatologicals
29224995
Characteristics
63.3
0.8
White to light yellow Crystalline Powder
1.37 (NTP, 1992)
188.5 °C
200 °C @ Press: 10 Torr
250 °C
1.5323 (estimate)
H2O: 4.7 g/L (20 ºC);95% ethanol: soluble 5%, clear to slightly hazy, colorless to yellow
2-8°C
4.5X10-6 mm Hg at 25 deg C /Extrapolated from measurements at higher temperatures/
Oral-mouse LD50: 2850 mg/kg; Oral-rabbit LD50: 1000 mg/kg
Flammable; burning produces toxic nitrogen oxide fumes
Odorless
pH (0.5% solution): 3.5
2.38(at 25 °C)
Henry's Law constant = 1.5X10-10 atm-cu m/mole at 25 °C (est)
2.38 (at 25 °C)|pKa1 = 2.38 at 25 °C|pKa2 = 4.85 at 25 °C
131 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|127.3 Ų [M+H]+
May turn slightly yellow on prolonged exposure to light and air|Hydroxyl radical reaction rate constant = 4.0X10-11 cu cm/molecule sec at 25 °C (est)
No rapid reaction with air. No rapid reaction with water.
Acids, Carboxylic
P-AMINOBENZOIC ACID is incompatible with ferric salts and oxidizing agents. (NTP, 1992)
Safety Information
NONH for all modes of transport
3
22-36/37/38-43
26-36-37/39
DG1400000
Xn,Xi
Warehouse ventilated, low temperature and dry
Stable. Incompatible with strong oxidizing agents. Combustible. Sensitive to light and air. May discolour on exposure to light.
P261-P280-P305 + P351 + P338
H315-H317-H319-H335-H413
Product: Offer surplus and nor-recyclable solutions ot a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.|SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incompatible materials: Strong oxidizing agents.|Incompatible with ferric salts and oxidizing agents.
Sunscreen active ingredients. The active ingredient of the product consists of any of the following, within the concentration specified for each ingredient, and the finished product provides a minimum SPF value of not less than 2 as measured by the testing procedures established in subpart D of this part: Aminobenzoic acid (PABA) up to 15 percent is included on this list.
|Warning|H302 (57.89%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 224 companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (USA) or EN 166(EU).|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx).
Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.|Environmental precautions: Do not let product enter drains.|Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle is accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of the workday.|Skin protection: ... Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/
4-Aminobenzoic acid was detected in ammunition plant wastewater (concn unspecified)(1).
Toxicity
moderately
Sulfonamides act by competitive inhibition of PABA in the microorganism. PABA administration in sufficient doses thus antagonized the antibacterial effect of the sulfonamides.|PABA appears to block the formatin of salicyluric acid from salicylic acid, resulting in increased salicylate blood levels.|Aminosalicylic acid appears to act on tubercle bacilli in a manner similar to that of sulfonamides on other organisms (by competing with PABA). Thus the administration of PABA may be expected to inhibit the antimicrobial activity of aminosalicylic acid.|Interferon titers induced by 0.007% PABA and poludan were compatible after both injections in the conjunctiva but not in the anterior chamber humor.|For more Interactions (Complete) data for 4-AMINOBENZOIC ACID (14 total), please visit the HSDB record page.
LD50 Rabbit iv 2000 mg/kg|LD50 Rabbit oral 1830 mg/kg|LD50 Dog oral 1000 mg/kg|LD50 Mouse oral 2850 mg/kg|LD50 Rat oral 6,000 mg/kg bw
Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/
4-Aminobenzoic acid is widely distributed in nature as a B complex factor(1). Baker's yeast contains 5 to 6 ppm 4-aminobenzoic acid(1); brewer's yeast contains from 10 to 100 ppm 4-aminobenzoic acid(1). 4-Aminobenzoic acid (PABA) is a chemical found in the folic acid vitamin and also in several foods including grains, eggs, milk, and meat(2).
4-Aminobenzoic acid's production and use in the manufacturer of various esters, folic acid, azo dyes(1), as a cross-linking agent for polyurethane resins(2) and as UV absorber in suntan lotions(3) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: According to a classification scheme(1), measured Koc values ranging from 19.9 to 316(2-4) suggest that 4-aminobenzoic acid is expected to have very high to moderate mobility in soil. The pKa values of 4-aminobenzoic acid are 2.38 (acid group)(5) and 4.85 (amino group)(6), indicating that this compound will exist almost entirely 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(7). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 4-aminobenzoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 4.5X10-6 mm Hg(10), and water solubility, 5390 mg/L(11). 4-Aminobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. An 82% of theoretical BOD using activated sludge in the Japanese MITI test classifies 4-aminobenzoic acid as readily biodegradable(12). Results of other screening studies(13,14) also suggest that biodegradation may be an important fate process(SRC).|AQUATIC FATE: According to a classification scheme(1), measured Koc values ranging from 19.9 to 316(2-4) indicate that 4-aminobenzoic acid may have no to moderate adsorption to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 4.5X10-6 mm Hg(6), and water solubility, 5390 mg/L(7). According to a classification scheme(8), an estimated BCF of 3(SRC), from its log Kow of 0.83(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An 82% of theoretical BOD using activated sludge in the Japanese MITI test classifies 4-aminobenzoic acid as readily biodegradable(11). Results of other screening studies(12,13) also suggest that biodegradation may be an important fate process(SRC). 4-Aminobenzoic acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(5). Using simulated solar irradiation in aqueous solutions, the direct photolysis of 4-aminobenzoic acid followed pseudo-first order kinetics with the rate constant increasing with increasing pH(14); the direct photolysis rate constants were determined to be 3.46X10-6/sec, 12.57X10-6/sec and 14.96X10-6/sec at respective pH values of 4.8, 7.8 and 9.2(14) which correspond to respective half-lives of 2.32 days, 15.3 hours and 12.9 hours(SRC); it was determined that direct photolysis was the dominant phototransformation process in sunlit natural water with sensitized photolysis occurring at a much slower rate(14); p-hydroxybenzoic acid was identified as a photodegradation product with the photodegradation pathway including di(tri)-polymerization(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-aminobenzoic acid, which has a vapor pressure of 4.5X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-aminobenzoic 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 9.5 hours(SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 4-aminobenzoic acid may be removed from the air by wet and dry deposition(SRC). 4-Aminobenzoic acid has been shown to degrade through direct photolysis in the sunlight spectrum(4,5), therefore, photolysis may have some importance as a fate process in the atmosphere(SRC).
The rate constant for the vapor-phase reaction of 4-aminobenzoic acid with photochemically-produced hydroxyl radicals has been estimated as 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Using simulated solar irradiation in aqueous solutions, the direct photolysis of 4-aminobenzoic acid was observed to follow pseudo-first order kinetics with the rate constant increasing with increasing pH(2); the direct photolysis rate constants were determined to be 3.46X10-6/sec, 12.57X10-6/sec and 14.96X10-6/sec at respective pH values of 4.8, 7.8 and 9.2(2) which correspond to respective half-lives of 2.32 days, 15.3 hours and 12.9 hours(SRC); it was determined that direct photolysis was the dominant phototransformation process in sunlit natural water with sensitized photolysis occurring at a much slower rate(2); p-hydroxybenzoic acid was identified as a photodegradation product with the photodegradation pathway including di(tri)-polymerization(2). 4-Aminobenzoic acid was observed to directly photolysis when spread on quartz sand and two topsoil samples(3). 4-Aminobenzoic acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4).
An estimated BCF of 3 was calculated in fish for 4-aminobenzoic acid(SRC), using a log Kow of 0.83(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
316.23 L/kg|In a Chernozem soil of pH 7.5, the Koc of 4-aminobenzoic acid was determined to be 19.9(1). Using OECD Guideline 106 and three different soils of pH values of 2.8, 6.7 and 7.1, 4-aminobenzoic acid was found to have respective Koc values of 239, 46 and 55(2). A measured log Koc of 2.5 has been reported for 4-aminobenzoic acid(3) which corresponds to a Koc of 316. According to a classification scheme(4), these Koc values suggests that 4-aminobenzoic acid is expected to have very high to moderate mobility in soil. The pKa values of 4-aminobenzoic acid are 2.38 (acid group)(5) and 4.85 (amino group)(6), indicating that this compound will exist almost entirely 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(7). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), suggesting that mobility may be much lower in some soils(SRC).
The Henry's Law constant for 4-aminobenzoic acid is estimated as 1.5X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 4.5X10-6 mm Hg at 25 °C(1), and water solubility, 5390 mg/L(2). This Henry's Law constant indicates that 4-aminobenzoic acid is expected to be essentially nonvolatile from water surfaces(3). 4-Aminobenzoic acid's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 4-Aminobenzoic acid is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).
4-Aminobenzoic acid (PABA) is a chemical found in the folic acid vitamin and also in several foods including grains, eggs, and meat(1). It may also occur in Brewer's yeast, liver, molasses, mushrooms, and spinach(2).
4-Aminobenzoic acid (PABA) is a chemical found in the folic acid vitamin and also in several foods including milk(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,227 workers (6,397 of these are female) are potentially exposed to 4-aminobenzoic acid in the US(1). Occupational exposure to 4-aminobenzoic acid may occur through dermal contact with this compound at workplaces where 4-aminobenzoic acid is produced or used(SRC). The general population may be exposed to 4-aminobenzoic acid via dermal contact with consumer products (e.g. suntan lotion) containing 4-aminobenzoic acid and through ingestion of foods containing 4-aminobenzoic acid(SRC).
Drug Information
Sunscreening Agent|Used orally in the treatment of conditions such as scleroderma, dermatomyositis, and Peyronie's disease, and topically as a sunscreen and protectant.|Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.|PABA has long been an accepted objective marker to verify completeness of 24 hour urine sampling as PABA is rapidly and almost completely eliminated with the urine. For this reason PABA has been used clinically for long as the indicator substance in pancreas and liver function tests.|Sunscreen preparations should be applied uniformly and generously to all exposed skin surfaces, including lips, before exposure to UVB radiation. Two applications of the sunscreen may be needed for maximum protection. PABA-containing sunscreens are most effective when applied 1-2 hours before exposure to sunlight. Sunscreen products that are not water resistant should be reapplied after swimming, towel-drying, or profuse sweating and, because most sunscreens are easily removed from the skin, reapplication every 1-2 hours or according to the manufacturer's directions usually is required to provide adequate protection from UVB light. /Sunscreens/
PABA has been shown in vitro to displace methotrexate from plasma protein binding, thus increasing the free methotrexate concentrations.|PABA derivatives reportedly have weak sensitization potential, but the incidence of allergic and photoallergic contact dermatitis associated with their use is increasing. Contamination of PABA derivatives with benzocaine which may cause allergic reactions has been reported. In patients allergic to compounds that are structurally similar to PABA (e.g., ester-type anesthetics, aniline dyes, thiazides, sulfonylurea and paraphenylenediamine drugs), cross-sensitivity to PABA derivatives has been reported occasionally; therefore, sunscreens containing PABA derivatives may be contraindicated in patients with a history of hypersensitivity to these chemicals.|The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/|Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/|For more Drug Warnings (Complete) data for 4-AMINOBENZOIC ACID (13 total), please visit the HSDB record page.
The toxicokinetics of PABA is characterized by fast oral absorption, biotransformation by the major routes acetylation and glycine conjugation, the minor route by glucuronidation in the liver and kidney, and a fast and almost complete elimination via the urine within 24 hrs. PABA is extensively acetylated during percutaneous absorption in humans. Studies have shown that PABA can cross the placenta rapidly. Furthermore, the results of one study indicate that the human placenta has a significant capacity for acetylation of PABA.|Of an oral dose of 1 g para-aminobenzoic acid, 82% was excreted in the urine of 3 male volunteers within 4 hr; para-aminohippuric acid and acetyl-para- aminohippuric acid were the principal metabolites. Concurrent administration of sodium benzoate totally abolished the excretion of these glycine conjugates.|The percutaneous absorption and metabolism of three structurally related compounds, benzoic acid, p-aminobenzoic acid (PABA), and ethyl aminobenzoate (benzocaine), were determined in vitro through hairless guinea pig skin. Benzocaine was also studied in human skin. Absorption of benzocaine was rapid and similar through both viable and nonviable skin. The absorption of the two acidic compounds, benzoic acid and PABA, was greater through nonviable skin. A small portion (6.9%) of absorbed benzoic acid was conjugated with glycine to form hippuric acid. Although N-acetyl-benzocaine had not been observed as a metabolite of benzocaine when studied by other routes of administration, both PABA and benzocaine were extensively N-acetylated during percutaneous absorption. Thus, the metabolism of these compounds should be considered in an accurate assessment of absorption after topical application.|Skin absorption of PABA corresponding to 1.6 to 9.6% of the applied amount of PABA was measured in the urine of six male volunteers after application of PABA in three different preparations. No significant difference where observed between the three preparations.|For more Absorption, Distribution and Excretion (Complete) data for 4-AMINOBENZOIC ACID (10 total), please visit the HSDB record page.
The two major metabolic pathways in a variety of species (guinea-pigs, rabbits and rats, but not dogs) are acetylation of the amino group and conjugation of the carboxy group, either with glycine or with glucuronic acid. Acetylation occurs in liver, heart, lung, blood and kidneys of rats and in the mucous membranes of the gastrointestinal tract of cattle. N-Acetyl-transferase activity in the presence of para-aminobenzoic acid is similar in liver and lung tissue of rabbits. Acetylation not only of para-aminobenzoic acid (30-40%) but also of para-aminohippuric acid (70%) takes place in the kidney of rabbits; acetylation of para-aminohippurate also occurs in the kidney of guinea-pigs.|Acetylation is dose-dependent. In rats given up to 5 mg/kg bw, 75% of the metabolites were acetylated; with higher doses, the extent of acetylation decreased down to 40%. An inverse relationship exists between acetylation and glycine conjugation: when acetylation decreases, glycine conjugation increases; such a decrease is seen in pantothenic acid-deficient rats. . Male rats excreted a larger amount of acetylated conjugates in the urine than females.|Following ingestion /in man/ of 1.0 g, ...main metabolites were p-aminohippuric acid and acetyl-p-aminohippuric acid.|... PABA is predominantly metabolized by acetylation and glycine conjugation to form p-acetamidobenzoic acid (PAABA), p-aminohippuric acid (PAHA), and p-acetamidohippuric acid (PAAHA). ... The half-lives of PABA were 7.01 +/- 0.32 min in rapid acetylation rabbits and 7.08 +/- 0.78 min in slow acetylation rabbits. Significant differences were obtained in formation of PAABA and PAHA formed from PABA in both acetylation phenotype rabbits.|For more Metabolism/Metabolites (Complete) data for 4-AMINOBENZOIC ACID (9 total), please visit the HSDB record page.
... The half-lives of PABA were 7.01 +/- 0.32 min in rapid acetylation rabbits and 7.08+/-0.78 min in slow acetylation rabbits.
Radiation is absorbed by chemical sunscreens when the electron energy level of the drug is raised from its ground state to a higher energy level or excited state. Chromophore groups (C=C, C=O, O-N=O) with loosely held electrons are easily excited by radiation. Compounds which have several chromophore groups in optimal positions have high absorbance over a broad range of wavelengths. Chemical sunscreens are usually agents that absorb not less than 85% of UVB radiation (thus preventing burning) but may permit transmission of UVA radiation (thus allowing tanning). Some sunscreens may absorb wavelengths over a range that is slightly wider or narrower than that of UVB. All PABA derivatives absorb wavelengths of approximately 290-320 nm, benzophenone derivatives absorb wavelengths of approximately 250-360 nm, cinnamic acid derivatives absorb wavelengths of 280-320 nm, and salicylate derivatives and other miscellaneous chemical sunscreens absorb wavelengths of about 270-320 nm.|The wavelength to which the skin is maximally sensitive had been accepted for many years to be 296.7 nm; however, recent evidence suggests that the most erythemogenic UVB wavelength may be slightly lower (e.g., somewhere in the range of 292-295 nm). In addition, of the stronger burning wavelengths that reach the earth's surface, most are approximately 310 nm. Therefore, sunscreens that maximally absorb UVB radiation near either of these wavelengths are particularly effective at preventing sunburn. Maximum absorbance occurs at about 290 nm for PABA, at about 295 nm for glyceryl-p-aminobenzoate, and at about 310 nm for the remaining PABA derivatives. Maximum absorbance occurs at 280-290 nm for benzophenone derivatives, at 310 nm for cinnamic acid derivatives with the exception of diethanolamine-p-methoxycinnamate which has its maximum absorbance at 290 nm, and at 300-305 nm for salicylate derivatives and other miscellaneous sunscreens.|Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/
SYMPTOMS: Large doses by mouth can cause nausea, vomiting, skin rash, methemoglobimemia and possibly toxic hepatitis. ACUTE/CHRONIC HAZARDS: Toxic. Hazardous decomposition products. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ In a dermatological clinic in Norway 23 patients with reactions to sunscreen preparations were seen during the years 1980-1982. The symptoms were eczema, redness, stinging or burning of the face following sun exposure. Patch tests and photopatch tests were carried out on the patients. Allergy to PABA was demonstrated in 11 patients (48%), of which 6 had plain contact allergy (26%) (PABA on non irradiated test sites) and 5 (21.7%) reacted to PABA only after irradiation.|/SIGNS AND SYMPTOMS/ Applications of 5% PABA in sunscreen formulation on human skin have shown that irritation is negligible.|/CASE REPORTS/ Human tests performed on patients contacting a dermatological clinic with a suspected skin disease shows that PABA has a potential to cause photo allergy reactions. Considering the fact that the results are based on patients with suspected dermatological problems rather than the general population, the prevalence is likely to be lower in the general population than in the studied groups. The highest photo allergy reaction to PABA was found in a Norwegian study from 1980 - 82 on 23 patients where 21.7% reacted. In most ... /studies/ the reaction to PABA was in the range 0 - 3%.|/CASE REPORTS/ A case report described that the potassium salt of PABA (administered orally 4 g three times a day for about 2 months) to a 64-year-old woman led to hepatotoxicity in a patient with scleroderma, as evidenced by elevated serum alanine aminotransferase and aspartate aminotransferase. /Potassium salt of PABA/|For more Human Toxicity Excerpts (Complete) data for 4-AMINOBENZOIC ACID (13 total), please visit the HSDB record page.
4 Aminobenzoic Acid
4-Aminobenzoic acid Use and Manufacturing
Add water, sodium chloride, and hydrochloric acid in sequence to the reaction pot. Start stirring and heat up to 50-60℃, add 9/10 amount of iron powder, continue to heat up to 98-102℃, keep warm for 1h, stop heating, slowly add p-nitrobenzoic acid at 95℃, about 1-1.5h After the addition, add iron powder, keep it at 98-102℃ for 1h, let cool to 80℃, add 30% liquid alkali to adjust pH=8.5-9, filter press, wash with a little water, the filtrate and a small amount of washing liquid are combined, press in Pickling pot, cool to 30-34℃, add safety powder to decolorize, filter. Add acid to the filtrate to adjust pH=3.5-4, continue to cool to below 10℃, spin water and dry to get the finished product. The yield is 84-88%. (2) From catalytic hydrogenation of p-nitrobenzoic acid, add industrial p-nitrobenzoic acid and water to a 1000ml beaker, adjust pH=6-7 with 22% sodium hydroxide under stirring, and then add Raney Nickel, pump the liquid into the rocking autoclave with stirring, replace with hydrogen and nitrogen twice, and recharge to 3.43MPa, and react for about 5h at a pressure of 3.43-2.54MPa and a temperature of 134-140℃. Until the hydrogen pressure does not drop as the end point. After the reaction, the product is filtered and dried to obtain a finished product. The yield is over 80%.
Used as pharmaceuticals, dye intermediates, dyes and pharmaceutical intermediates. It is used to produce reactive red M-80, M-10B, reactive red purple X-2R and other dyes, and to produce cyanobenzoic acid to produce p-carboxybenzylamine. P-Aminobenzoic acid can be used as a sunscreen. Its derivative, octyl p-dimethylcarbamate, is an excellent sunscreen. Its trade name is PadimateO. Used as a reagent for determining copper. Used in the synthesis of esters, folic acid and azo dyes. Used as analytical reagent, sunscreen agent, also used in pharmaceutical and dye industry
Polymeric Colorant
< 25,000 lb|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#6349]|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzoic acid, 4-amino-. National Production Volume: Withheld.
Sunscreens are available in a variety of dosage forms and formulations. ... Because these formulations frequently change and the manufacturers often are reluctant to reveal specific ingredients in their formulations, a listing of commercially available sunscreens is not included in this monograph.|Technical, National Formulary|Capsules and tablets (as the potassium salt), 500 mg; Packets (as the potassium salt) 2 g; Powder
All other basic organic chemical manufacturing|Benzoic acid, 4-amino-: ACTIVE|Commercially available as the calcium, potassium, and sodium salts.|p-Aminobenzoic acid is also known as anti-gray hair factor (in rats only).|Absorbs UV light of wavelengths in the region of 260 to 313 nm; its molar absorptivity at 288.5 nm is 18,300. However, it does not absorb throughout the near UV range ... Nevertheless, in the 260 to 313 nm range, it has the highest protection index of current sunscreen agents.|The drug occurs as white or slightly yellow, odorless crystals or crystalline powder. The drug is slightly soluble in water and freely soluble in alcohol. PABA is incompatible with ferric salts and oxidizing agents and darkens on exposure to air or light; preparations of the drug should be stored in light-resistant containers.
Method: AOAC 964.28, p-Aminobenzoic acid in feeds using spectrophotometric method; Analyte: 4-aminobenzoic acid; Matrix: animal feeds; Detection Level: not provided.|... Aromatic amines, including p-aminobenzoic acid have been detected in solution or on TLC plates by determining the fluorescence spectra of their fluorescamine derivatives. Method has a detection limit of 3 ug/L when in solution and 0.2 ug on chromatographic plates.|HPLC has been used for determining p-aminobenzoic acid and its metabolites in urine and serum, with a limit of detection of 5 ng. ... p-Aminobenzoic acid may be determined colorimetrically.
Aniline derivetives, including p-aminobenzoic acid, have been determined in blood and urine by titration with N-bromosuccinimide. The relative error was less than 2% for 0.1-10 mg samples.
Cosmetics -> Uv absorber; Uv filter
Computed Properties
Molecular Weight:137.14
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:63.3
Heavy Atom Count:10
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
The L-cystine in this product is an amino acid drug that can promote the redox function of cells, make the liver function vigorous, neutralize toxins, promote leukocyte proliferation, and prevent the development of pathogens; vitamin B1 combines with adenosine triphosphate to form vitamin B1 pyrophosphate (thiamine diphosphate, cocarboxylase), which is a coenzyme required for carbohydrate metabolism; vitamin B1 can inhibit the activity of cholinesterase. When it is deficient, the activity of cholinesterase is enhanced, and the hydrolysis of acetylcholine is accelerated, causing nerve impulse conduction disorders and affecting gastrointestinal and myocardial function; calcium pantothenate is a precursor of coenzyme A and is a necessary substance for multiple metabolic links (including carbohydrates, proteins and lipids). It can participate in the synthesis of substances such as steroids, porphyrins, acetylcholine, and can maintain normal epithelial function.
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