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Propyl-4-hydroxybenzoat
Propyl parahydroxybenzoate · Parabens · PROPYL 4-HYDROXYBENZOATE · PROPYL P-HYDROXYBENZOATE · Nipazol · Nipasol · PROPYLPARABENE · Nipasol M
Identifikatoren & physikalische Daten
| CAS No. | 94-13-3 |
|---|---|
| Summenformel | C10H12O3 |
| Durchschnittliche Molmasse | 180,2 g/mol |
| Monoisotopische Masse | 180,07864424 g/mol |
| SMILES | CCCOC(=O)c1ccc(O)cc1 |
| InChIKey | QELSKZZBTMNZEB-UHFFFAOYSA-N |
| PubChem CID | 7175 |
| ChEMBL | CHEMBL194014 |
| ChEBI | CHEBI:32063 |
| EC No. | 202-307-7 |
| DTXSID | DTXSID4022527 |
| Lokaler Name | Propyl-4-hydroxybenzoat |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 160 |
| LogP (Verteilungskoeffizient) | log Kow = 3.04 |
| Geruch | Odorless or has faint odor |
| Dichte | 1.28 at 77 °F (NTP, 1992) - Denser than waterwill sink1.287 g/cu cm at 20 °CDensity: 1.0630 g/cu cm at 102 °C |
| Color/Form | White crystalsPrisms from ether |
| Löslichkeit | less than 1 mg/mL at 54 °F (NTP, 1992)In water, 5.00X10+2 mg/L at 25 °CSoluble in 2000 parts waterslightly soluble in boiling waterIn water, 463 mg/L at 20 °CSoluble in ethanol, ethyl etherslightly soluble in chloroformFor more Solubility (Complete) data for PROPYLPARABEN (6 total), please visit the HSDB record page.ethanol: soluble0.1M, clear, colorless<0.1 g/100 mL at 12 ºC |
| Siedepunkt | 271 °F at 1 mmHg (NTP, 1992)294.00 to 295.00 °C. @ 760.00 mm Hg133°C |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| Schmelzpunkt | 203 to 208 °F (NTP, 1992)96.1 °C96 - 97 °C95-98 °C(lit.) |
| Dampfdruck | 0.000555 [mmHg]0.67 hPa (122 °C) |
| Brechungsindex | Index of refraction: 1.5050 at 102 °C/DIndex of refraction: 1.5161 at 20 °C |
| Physical Description | Propyl-4-hydroxybenzoate appears as colorless crystals or white powder or chunky white solid. Melting point 95-98 °C. Odorless or faint aromatic odor. Low toxicity, Tasteless (numbs the tongue). pH: 6.5-7.0 (slightly acidic) in solution.LiquidOther SolidDry PowderColorless or white solid[Hawley] White powder[MSDSonline] |
| Stability/Shelf Life | Stable under recommended storage conditions.Parabens are stable against hydrolysis during autoclaving & resist saponification /Parabens/Calcium salts /are/ stablesodium salts /are/ unstable. /Parabens/ |
| FEMA | 2951 | PROPYL P-HYDROXYBENZOATE |
| Flammpunkt | 180°(356°F) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pKa 8.4 (Uncertain) |
| Farbe | White |
| Wichte | 0.789 (20/4℃) |
| pH | 6-7 (H2O, 20°C) (saturated solution) |
| Geruch | at 100.00 %. sweet smoky burnt woody hawthorn |
| Geruchsart | smoky |
| Biologische Quelle | synthetic |
| Merck | 14,7866 |
| BRN | 1103245 |
| Henry-Konstante | 1.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGPRESERVATIVE |
| InChI | 1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3 |
| InChIKey | QELSKZZBTMNZEB-UHFFFAOYSA-N |
| SMILES | CCCOC(=O)c1ccc(O)cc1 |
| LogP (Verteilungskoeffizient) | 2.8 at 20℃ |
| CAS Datenbank | 94-13-3(CAS DataBase Reference) |
| NIST chemische Informationen | N-propyl-p-hydroxy-benzoate(94-13-3) |
| EPA chemische Informationen | Propylparaben (94-13-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 22.8% (644 of 2829) of reports.WarningH315 (63.6%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (63.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2829 reports by companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 644 of 2829 reports by companies.There are 27 notifications provided by 2185 of 2829 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 4-hydroxy-, propyl esterHazard Traits - Endocrine ToxicityReproductive ToxicityAuthoritative List - CECBP - Priority ChemicalsReport - if used as a fragrance or flavor ingredientDirective (EC) No 114/2003Benzoic acid, 4-hydroxy-, propyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-hydroxy-, propyl ester 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: 28-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13890Propylparaben: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Parabens: Human health tier II assessmentIMAP assessments - Parabens: Environment tier II assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include eye and respiratory irritation, allergies and respiratory diseases. Prolonged or repeated skin exposure may result in irritation. It may also cause contact dermatitis.ACUTE/CHRONIC HAZARDS: This compound will cause skin irritation on prolonged or repeated contact. It may also cause eye irritation. Inhalation of the concentrated dust could cause mild respiratory irritation. When heated to decomposition it emits acrid smoke, phenolic vapors, carbon dioxide and carbon monoxide. (NTP, 1992) |
| Gefahrenübersicht | Parabens are an uncommon cause of allergic contact dermatitis[Marks, p. 115] A moderate eye irritant (saturated aqueous solution)Parabens may cause skin sensitization in a small percentage of the population[HSDB] May cause eye and respiratory tract irritationProlonged skin contact may cause irritation and contact dermatitis[CAMEO] An eye and mild skin irritantMay cause skin sensitization[eChemPortal: ERMA] Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin. [Kanerva, p. 1822-3] May cause irritation[MSDSonline] |
| FDA-Anforderungen | Propylparaben is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.Substances classified as antimycotics, when migrating from food-packaging material shall include: propylparaben.Substance added directly to human food affirmed as generally recognized as safe (GRAS). ... The ingredient is used in food at levels not to exceed good manufacturing practices. Current good manufacturing practice results in a maximum level of 0.1 percent in food.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: propylparaben is included in topical antifungal drug products.This substance is generally recognized as safe for use at a level not exceeding 0.1 percent in accordance with good manufacturing or feeding practice. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate EstersPhenols and Cresols |
| Special Reports | Cosmetic Ingredient ReviewFinal Amended Report on the Safety Assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in Cosmetic Products Int J Toxicol 27 Suppl 4: 1-82 (2008)[Available from, as of November 21, 2016: http://online.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/PR427.pdf] |
| FIFRA-Anforderungen | Residues of propyl p-hydroxybenzoate are exempted from the requirement of a tolerance when used as a preservative for formulations in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.Residues of propyl p-hydroxybenzoate are exempted from the requirement of a tolerance when used as a preservative (Limit: meets specifications of Food Chemical Codexnot to exceed 0.1% in formulations) in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Propyl paraben is found on List D. Case No: 4071Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.Active ingredient (AI): Propyl parabenAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled." |
| Reactivity Profile | Maximum stability of PROPYL-4-HYDROXYBENZOATE occurs at a pH of 4 to 5. Incompatible with alkalis and iron salts. Also incompatible with strong oxidizing agents and strong acids (NTP, 1992). |
| Air and Water Reactions | Water soluble [Hawley]. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| Erste Hilfe | 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 areatake 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 usedif 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) |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place.Containers should be stored in a dry place & kept tightly sealed when not in use. /Parabens/ |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. 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. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992) |
| Entsorgungsverfahren | SRP: 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal companyContaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.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.For more Preventive Measures (Complete) data for PROPYLPARABEN (8 total), please visit the HSDB record page. |
| Allowable Tolerances | Residues of propyl p-hydroxybenzoate are exempted from the requirement of a tolerance when used as a preservative for formulations in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.Residues of propyl p-hydroxybenzoate are exempted from the requirement of a tolerance when used as a preservative (Limit: meets specifications of Food Chemical Codexnot to exceed 0.1% in formulations) in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. |
| Personal Protective Equipment (PPE) | 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: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). |
| Körperbelastung | Propylparaben had a frequency of detection of 96% in urine samples from a group of US male and female adults sampled from 2003 to 2005(1).Concentration of urinary p-hydroxybenzoic acid and propylparaben in children and adults from the United States and China(1).[Table#788] |
| Wechselwirkungen | Butylated hydroxyanisole and propylparaben are phenolic preservatives commonly used in food, pharmaceutical and personal care products. Both chemicals have been subjected to extensive toxicological studies, due to the growing concern regarding their possible impacts on environmental and human health. However, the cytotoxicity and underlying mechanisms of co-exposure to these compounds have not been explored. In this study, a set of relevant cytotoxicity endpoints including cell viability and proliferation, oxidative stress, DNA damage and gene expression changes were analyzed to assess whether the antioxidant butylated hydroxyanisole could prevent the pro-oxidant effects caused by propylparaben in Vero cells. We demonstrated that binary mixtures of both chemicals induce greater cytotoxic effects than those reported after single exposureto each compound. Simultaneous treatment with butylated hydroxyanisole and propylparaben caused G0/G1 cell cycle arrest as a result of enhanced generation of oxidative stress and DNA double strand breaks. DNA microarray analysis revealed that a cross-talk between transforming growth factor beta (TGFbeta) and ataxia-telangiectasia mutated kinase (ATM) pathways regulates the response of Vero cells to the tested compounds in binary mixture. Our findings indicate that butylated hydroxyanisole potentiates the pro-oxidant effects of propylparaben in cultured mammalian cells and provide useful information for their safety assessment.Endocrine-disrupting compounds can interfere with the endocrine organs or hormone system and cause tumors, birth defects and developmental disorders in humans. The estrogen-like activity of compounds has been widely studied but little is known concerning their possible modulation of the glucocorticoid receptor. Steroidal (synthetic and natural) and non-steroidal endocrine-active compounds commonly occur as complex mixtures in human environments. Identification of such molecular species, which are responsible for modulating the glucocorticoid receptor are necessary to fully assess their risk. We have used the MDA-kb2 cell line, which expresses endogenous glucocorticoid receptor and a stably transfected luciferase reporter gene construct, to quantify the glucocorticoid-like activity of four compounds present in products in everyday use -propylparaben (PP), butylparaben (BP), diethylhexyl phthalate (DEHP) and tetramethrin (TM). We tested all possible combinations of these compounds at two concentrations (1 uM and 10 nM) and compared their glucocorticoid-like activity. At the concentration of 1 uM seven mixtures were identified to have glucocorticoid-like activity except: DEHP+TM, BP+TM, DEHP+PP+TM, BP+PP+TM. At the concentration of 10 nM only three mixtures have glucocorticoid modulatory activity: DEHP+PP, BP+PP, DEHP+BP+PP+TM. Identified glucocorticoid-like activities were between 1.25 and 1.51 fold at the concentration of 1 uM and between 1.23 and 1.44 fold at the concentration of 10 nM in comparison with the solvent control. Individually BP, PP, and DEHP had glucocorticoid-like activity of 1.60, 1.57 and 1.50 fold over the solvent control at the concentration of 1 uM. On the other hand PP and DEHP, at the concentration of 10nM, showed no glucocorticoid-like activity, while BP showed 1.44 fold. The assertion that individual glucocorticoid-like compounds do not produce harm because they are present at low, ineffective levels in humans may be irrelevant when we include... Evidence that the antimicrobial effects of the parabens and sodium benzoate are additive. /Parabens/ |
| Ökotoxizitätswerte | EC50Species: Daphnia magna (Water flea)Conditions: freshwater, static, pH 7.6-7.7, dissolved oxygen 100% saturatedConcentration: 27500 ug/L for 24 hr (95% confidence interval: 20300-45800 ug/L)Effect: intoxication, immobilization /formulation/Concentration: 15400 ug/L for 48 hr (95% confidence interval: 7970-32300 ug/L)LC50Species: Dugesia japonica (Flatworm) body length 0.7 cmConditions: freshwater, static, 25 °CConcentration: 14700 ug/L for 24 hr (95% confidence interval: 13100-15100 ug/L) />99% purity/Concentration: 12300 ug/L for 96 hr (95% confidence interval: 13100-15100 ug/L) />99% purity/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a structure estimation method(2), indicates that propylparaben is expected to have moderate mobility in soil(SRC). The estimated pKa of propylparaben is 8.5(3), indicating that this compound will exist partially 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(4). Volatilization of propylparaben from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Propylparaben is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Using the Zahn-Wellens test, 100% biodegradation was attained in 6 days using analogous methyparaben(6), suggesting that biodegradation in soil may be an important environmental fate process for propylparaben(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a structure estimation method(2), indicates that propylparaben is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.3X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 50(SRC), from its log Kow of 3.04(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). A direct photolysis half-life of 2.5 days was reported in water(7). Using the Zahn-Wellens test, 100% biodegradation was attained in 6 days using analogous methyparaben(8), suggesting that biodegradation in water may be an important environmental fate process for propylparaben(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propylparaben, which has an estimated vapor pressure of 3.1X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase propylparaben 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 1 day(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase propylparaben may be removed from the air by wet and dry deposition(SRC). Propylparaben contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Occurrence of propylparaben in food samples collected from several grocery stores in Albany, NY in 2008, 2011 and 2012(1).[Table#789] |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Toxizitätsübersicht | The CIR Expert Panel concluded that the following 20 parabens are safe in cosmetics in the present practices of use and concentration described in the safety assessment when the sum of the combined concentration of parabens in any given formulation does not exceed 0.8 %...Propylparaben...Safe for use in cosmetics, with qualificationsIDENTIFICATION AND USE: Propylparaben is a stable, non-volatile compound used as an antimicrobial preservative in foods, drugs and cosmetics. HUMAN EXPOSURE AND TOXICITY: Sensitization has occurred when medications containing parabens have been applied to damaged or broken skin. Parabens have been implicated in numerous cases of contact sensitivity associated with cutaneous exposure, but high concentrations of 5-15% in patch testing are needed to elicit reaction in susceptible individuals. ANIMAL STUDIES: Acute toxicity studies in animals indicate that propylparaben is relatively non-toxic by both oral and parenteral routes, although it is mildly irritating to the skin. Following chronic administration, no-observed-effect levels (NOEL) as high as 1200-4000 mg/kg have been reported and a no-observed-adverse-effect level (NOAEL) of 5500 mg/kg was reported in the rat. Propylparaben is not carcinogenic, mutagenic or clastogenic. It is not cytogenic in vitro in the absence of carboxyesterase inhibitors. Propylparaben in the diet produced cell proliferation in the forestomach of rats. Propylparaben was noncarcinogenic in a study of transplacental carcinogenesis. In one in vitro study, sperm were not viable at concentrations as low as 3 mg/mL Propylparaben. Propylparaben did affect sperm counts in vivo at all levels from 0.01% to 1.0%. ECOTOXICITY STUDIES: In a rainbow trout Oncorhynchus mykiss test system, increases in average plasma vitellogenin levels were seen at oral exposure to 33 mg propylparaben/kg/2 daysthe most sensitive fish responded to 7 mg/kg. Zebrafish exposure to propylparaben at the concentrations of 0.10.4 and 0.9 mg/L elicited statistically significant decline of vitellogenin production. |
| Average Daily Intake | Estimated daily intakes of propylparaben from indoor dust (13 cities, 4 countries) from the United States, China, Korea and Japan (all ng/kg bw/day)(1).[Table#787] |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ The estrogenic effect of propylparaben was investigated in a rainbow trout Oncorhynchus mykiss test system. Propylparaben was administered orally to sexually immature rainbow trout every second day for up to 10 days in doses between 7 and 1830 mg/kg/2 days and in the water at 50 and 225 ug/L for 12 days. Plasma vitellogenin was measured before and during the exposures and the concentrations of propylparaben in liver and muscle were determined at the end of experiments. Increases in average plasma vitellogenin levels were seen at oral exposure to 33 mg propylparaben/kg/2 daysthe most sensitive fish responded to 7 mg/kg. The ED(50) values for increase in vitellogenin synthesis were 35, 31 and 22 mg/kg/2 days at day 3, 6 and 11, respectively. Exposure to 225 ug propylparaben/L increased vitellogenin synthesis, but exposure to 50 ug/L did not. Propylparaben showed little tendency to bioaccumulation in rainbow trout<1 per thousand of the total amount of propylparaben administered orally at 1830 mg/kg/2 days over the 10 day experimental period was retained in muscle and liver 24 hr after the end of the experiment. Exposure to 225 ug propylparaben/L for 12 days led to concentrations of 6700 and 870 ug propylparaben/kg liver and muscle, respectively. Half lives for propylparaben were 8.6 hr in liver and 1.5 hr in muscle./AQUATIC SPECIES/ Xenoestrogenic potential of propylparaben (PP), one of the most commonly used preservatives in drugs, cosmetics and food, was investigated in vivo using zebrafish (Danio rerio). Juvenile zebrafish (20 days post hatching) were exposed to three different concentrations of propylparaben (PP) dissolved in ethanol and added into the water. After 20 days of exposure the fish were euthanized and vitellogenin concentrations in their whole body homogenates were measured by the method of direct sandwich ELISA. Simultaneously, vitellogenin concentrations in either fish from the control group (exposed to solvent without the substance tested) and in fish from the positive control group (exposed to natural estrogen 17beta-estradiol) were measured. Vitellogenin concentration in whole body homogenates of control fish was 400 (396-540) ng/mL (geometric mean (95% CI)). Zebrafish exposure to propylparaben at the concentrations of 0.1, 0.4 and 0.9 mg/L elicited statistically significant decline (P<0.001) of vitellogenin production, i.e. geometric means of vitellogenin concentrations in whole body homogenates were 240 (186-311)218 (175-270) and 270 (234-311) ng/mL, respectively. Conversely, the geometric mean of vitellogenin concentration in whole body homogenates of zebrafish exposed to 100 ng/mL of 17beta-estradiol (positive control) was significantly higher (P<0.001) than values in all other groups, i.e. 35 553 (16 860-74 968) ng/mL. /The authors conclude that their/ results suggest an antiestrogenic potential of propylparaben tested in vivo in juvenile zebrafish (Danio rerio). The estrogenic effect of 17beta-estradiol was confirmed./AQUATIC SPECIES/ Ultra violet (UV) screens and preservatives are widely and increasingly used in cosmetics and pharmaceuticals. In the present study, ... the estrogenicity of 4-methyl-benzylidene camphor (4-MBC), octyl-methoxycinnamate (OMC), and propyl paraben (n-propyl-p-hydroxy-benzoatePP), among UV screens and preservatives, /were examined/ using male medaka (Oryzias latipes), in regard to production of vitellogenin (VTG) and choriogenin (CHG) which are known to be estrogen-responsive gene products. First, using a VTG enzyme-linked immunosorbent assay (ELISA) system, we determined the increase in VTG plasma concentration in medaka due to exposure to 4-MBC, OMC, and PP, and compared this concentration to the non-treated control. Next, we found increases in mRNA expression levels of VTG subtypes VTG-1 and VTG-2, and CHG subtypes CHG-L and CHG-H, in liver due to exposure to 4-MBC, OMC, and PP compared to the non-treated control. In addition, we also found increased mRNA expression levels of estrogen receptor (ER) alpha, among sex hormone receptors in the liver, due to exposure to 4-MBC, OMC, and PP compared to the non-treated control. In this study, we showed that 4-MBC, OMC, and PP have estrogenic activity in fish./AQUATIC SPECIES/ Here we proposed a battery of non-invasive biomarkers and a histological survey to examine physiological/anatomical features in embryos, eleutheroembryos (13 days post-fertilization, dpf), and larvae (28-42 dpf) of medaka to investigate the effects of embryonic exposure to propylparaben (PrP). Concentrations <1000 ug PrP/L didn't exert early or late toxic effects. However, survivorship was affected at 4000 ug/L in eleutheroembryos and at > or =1000 ug/L in larvae. Histological alterations were found in 37.5% of eleutheroembryos exposed to 4000 ug PrP/L. Morphometric analysis of the gallbladder revealed significant dilation at >or =400 ug/L throughout embryo development. Ethoxyresorufin-O-deethylase (EROD), as indicator of cytochrome P4501A activity, didn't reveal induction/inhibition although its combination with a P4501A agonist (i.e. beta-naphthoflavone) resulted in a synergic EROD response. Results suggest a low toxicity of PrP for fish and support the use of fish embryos and eleutheroembryos as alternatives of in vivo biomarkers indicative of exposure/toxicity.For more Ecotoxicity Excerpts (Complete) data for PROPYLPARABEN (7 total), please visit the HSDB record page. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of September 8, 2016: http://actor.epa.gov/dashboard/]The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=94-13-3] |
| Effluent Concentrations | The average concentration of propylparaben in 21 influent and effluent samples from wastewater treatment plants on the Turia River, Valencia, Spain were 163 ng/L (21 samples positive) and not detected, respectively. Sampling was conducted in October, 2012limit of quantitation = 0.5(1). Propylparaben was detected in raw sewage entering the Harbin municipal wastewater treatment plant, Harbin, China, monitored in May 2007(2). The compound was detected at a range of 598-3,090, 26-63 and 1-13 ng/L in influent, final effluent and surface waters, respectively, in the UK(3). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of propylparaben can be estimated to be 290(SRC). According to a classification scheme(2), this estimated Koc value suggests that propylparaben is expected to have moderate mobility in soil. The estimated pKa of propylparaben is 8.5(3), indicating that this compound will exist partially 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(4). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29182930 |
| RTECS-Nr. | DH2800000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: > 5000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-24/25-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 94-13-3(Hazardous Substances Data) |
| Gefahrenklasse | Aquatic Chronic 3 |
| Selbstentzündungstemperatur | >600 °C |
Anwendungen & Verwendung
Verwenden
propylparaben is one of the most frequently used preservatives against bacteria and mold. It has a low sensitizing and low toxicity factor, is reputed to be very safe, and considered to be a noncomedogenic raw material.
Herstellung & Synthese
synthetische
Produced by esterfying p-hydroxybenzoic acid with n-propanol, using an acid catalyst such as sulfuric acid and an excess of propanol. The materials are heated in a glass-lined reactor under reflux. The acid is then neutralized with caustic soda and the product is crystallized by cooling. The crystallized product is centrifuged, washed, dried under vacuum, milled and blended, all in corrosion-resistant equipment to avoid metallic contamination.