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Valeriansure
PENTANOIC ACID · N-VALERIC ACID · valeric · N-PENTANOIC ACID · FEMA 3101 · VALERIANIC ACID · Valproic Acid Impurity A · NA 1760
Identifikatoren & physikalische Daten
| CAS No. | 109-52-4 |
|---|---|
| Summenformel | C5H10O2 |
| Durchschnittliche Molmasse | 102,13 g/mol |
| Monoisotopische Masse | 102,06807956 g/mol |
| SMILES | CCCCC(=O)O |
| InChIKey | NQPDZGIKBAWPEJ-UHFFFAOYSA-N |
| PubChem CID | 7991 |
| ChEMBL | CHEMBL268736 |
| ChEBI | CHEBI:17418 |
| EC No. | 203-677-2 |
| DTXSID | DTXSID7021655 |
| Lokaler Name | Valeriansure |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 59 |
| LogP (Verteilungskoeffizient) | 1.39log Kow = 1.39 |
| Geruch | UNPLEASANT ODOR, SIMILAR TO BUTYRIC ACIDPenetrating odor |
| Geschmack | Unpleasant flavor, similar to butyric acidFRUITY TASTEPenetrating taste |
| Dichte | 0.939 (USCG, 1999) - Less dense than waterwill float0.939 at 20 °C/4 °CRelative density (water = 1): 0.940.935-0.9400.940 @ 20°C0.939 g/mL at 25 °C(lit.) |
| Viscosity | 2.30 cP at 20 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | 10 to 50 mg/mL at 72 °F (NTP, 1992)24000Freely soluble in alcohol, etherSoluble in oxygenated solvents.Slightly soluble in carbon tetrachlorideIn water, 2.4X10+4 mg/L at 25 °C40g/l40 g/L (20 ºC) |
| Flammpunkt | 192 °F (NTP, 1992)96 °C205 °F (96 °C) (Open cup)86 °C c.c. |
| Siedepunkt | 365 °F at 760 mmHg (NTP, 1992)186.1186-187 °C186 °C186.4 °C @760 [mm Hg]110-111 °C10 mm Hg(lit.) |
| Decomposition | Thermal decomposition products include carbon dioxide and carbon monoxide. /Organic acids and related compounds/When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -30.1 °F (NTP, 1992)-34-34.5 °C-34 °C−20-−18 °C(lit.) |
| Dampfdichte | 3.52 (NTP, 1992) - Heavier than airwill sink (Relative to Air)3.5 (Air = 1)Relative vapor density (air = 1): 3.523.5 (vs air) |
| Dampfdruck | 0.15 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.408(lit.) |
| FEMA | 3101 | VALERIC ACID |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 4.84(at 25℃) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to pale yellow |
| pH | 3.95(1 mM solution)3.43(10 mM solution)2.92(100 mM solution) |
| Geruch | at 1.00 % in propylene glycol. sickening putrid acidic sweaty rancid |
| Geruchsart | cheesy |
| Biologische Quelle | synthetic |
| Geruchsschwelle | 0.000037ppm |
| Explosionsgrenze | 1.8-7.3%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 2.06 J/(g·K), at 25℃ |
| JECFA Number | 90 |
| Merck | 14,9904 |
| BRN | 969454 |
| Henry-Konstante | 2.3×101 mol/(m3Pa) at 25℃, Staudinger and Roberts (2001) |
| Dielektrizitätskonstante | 2.7(20℃) |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7) |
| InChIKey | NQPDZGIKBAWPEJ-UHFFFAOYSA-N |
| SMILES | CCCCC(O)=O |
| LogP (Verteilungskoeffizient) | 1.8 at 25℃ |
| Oberflächenspannung | 27.23mN/m at 293.15K |
| CAS Datenbank | 109-52-4(CAS DataBase Reference) |
| NIST chemische Informationen | Pentanoic acid(109-52-4) |
| EPA chemische Informationen | Valeric acid (109-52-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Pentanoic acidPentanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanoic acid 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: 21-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14438Pentanoic acid: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. (USCG, 1999)Combustible. Above 86 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Combustible liquid. |
| Gesundheitsgefahren | Corrosive. Very destructive to tissues of the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, nausea and vomiting. Extremely destructive to skin. May be absorbed through the skin. (USCG, 1999) |
| Gefahrenübersicht | A corrosive substance that can cause injury to the skin, eyes, and respiratory tract[ICSC] Emergency treatment: Acids[HSDB] Causes altered sleep time and seizures in intravenous, lethal-dose studies of mice[RTECS] Safe when used as a flavoring agent in food[JECFA] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] |
| FDA-Anforderungen | Pentanoic acid 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. |
| Reaktive Gruppe | Acids, Carboxylic |
| EG-Einstufung | Symbol: CR: 34-52/53S: (1/2)-26-36-45-61 |
| UN-Einstufung | UN Hazard Class: 8 |
| Special Reports | Leung HW, Paustenbach DJOrganic Acids and Bases: Review of Toxicological StudiesAm J Ind Med 18 (6): 717-35 (1990). |
| Reactivity Profile | PENTANOIC ACID is a carboxylic acid. Exothermically neutralizes bases, both organic and inorganic, producing water and a salt. Can react with active metals to form gaseous hydrogen and a metal salt. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts with sulfites, nitrites, thiosulfates and dithionites to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May catalyze (increase the rate of) chemical reactions. |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:SMALL FIRE: Dry chemical, CO2 or water spray.LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention . |
| 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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.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. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992) |
| Sichere Lagerung | Separated from strong bases. |
| Lagerbedingungen | Separated from strong bases. |
| Reinigungsverfahren | Collect leaking liquid in covered containers. Wash away spilled liquid with plenty of water. Do NOT let this chemical enter the environment. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024) |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Wash away remainder with plenty of water. |
| Preventive Measures | Strict precautions are necessary in handling ... any skin or eye splashes irrigated with copious amounts of water. /Saturated monocarboxylic acids/ |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Eye Prevention | Wear face shield. |
| Ökotoxizitätswerte | LC50 Daphnia magna (Water flea) 45 mg/L/48 hrstatic /formulated product/LC50 Lepomis macrochirus (Bluegill) 5,000 mg/L/24 hr /Conditions of bioassay not specified in source examined/ /Na salt/LC50 Pimephales promelas (Fathead minnow) >100 mg/L/1 hr, staticLC50 Pimephales promelas (Fathead minnow) >100 mg/L/24 hr, staticFor more Ecotoxicity Values (Complete) data for n-PENTANOIC ACID (8 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that n-pentanoic acid is expected to have high mobility in soil(SRC). The pKa of n-pentanoic acid is 4.84(4), indicating that this compound will partially exist 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 of n-pentanoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.72X10-7 atm-cu m/mole(6). n-Pentanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.96X10-1 mm Hg(7). n-Pentanoic acid is expected to be readily biodegradable in most environmental conditions based on several biodegradation tests where n-pentanoic acid reached 43%(8) to 68%(9) of its theoretical BODs in sewage inoculum after 5 days.AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that n-pentanoic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.72X10-7 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). n-Pentanoic acid is expected to be readily biodegradable in most environmental conditions based on several biodegradation tests where n-pentanoic acid reached 43%(7) to 68%(8) of its theoretical BODs in sewage inoculum after 5 days.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-pentanoic acid, which has an estimated vapor pressure of 1.96X10-1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-pentanoic 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 3.9 days(SRC), calculated from its rate constant of 4.11X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| Lebensmitteluntersuchungswerte | n-Pentanoic acid has been identified as a volatile component of roasted filberts(1), Parma ham(2), fried chicken flavor(3), bacon flavor(4), baked potato flavor(5), and raw beef(6). n-Pentanoic acid was identified as a volatile fatty acid occurring in dalieb fruit pulp at a concn of 5 mg/kg pulp(7). Pentanoic acid has been identified as a volatile flavor component of mutton, chicken, beef, and pork(8). n-Pentanoic acid was identified as a volatile component of microwave popcorn at a concn of 130 ug/kg(9). n-Pentanoic acid was identified as a volatile component of two commercial rice cakes at concns of 210 ppb and 270 ppb(10). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Expositionspfade | The substance can be absorbed into the body by inhalation and by ingestion. |
| Signs and Symptoms | Burning sensation. Cough. Sore throat.Redness. Pain. Skin burns.Redness. Pain. Severe burns.Burning sensation. Abdominal pain. Shock or collapse. |
| Effluent Concentrations | n-Pentanoic acid was identified in trench leachate from low-level radioactive waste disposal sites in Maxey Flats, KY and West Valley, NY at an average concn of 3.8 and 47 mg/L, respectively(1). n-Pentanoic acid was detected in raw and processed wastewater from the Lurgi-Process Plant in Sasolburg, South Africa at concns of 12 and 7 mg/L, respectively(2). n-Pentanoic acid was identified as a volatile component of kitchen waste exudate(3). n-Pentanoic acid was identified in the final effluent from the Los Angeles County wastewater treatment plant between Nov 1980 and August 1981 at a concn of 50 ug/L(4). Groundwater samples collected near an area known to be contaminated by wood-preserving chemicals in Pensacola, FL contained n-pentanoic acid at concns of 6.55, 1.53, and 0.51 mg/L 6.1, 3.3, and 5.8 m below the surface, respectively(5). n-Pentanoic acid was detected in groundwater from a landfill well near Norman, OK at an estimated concn of 1.1 ug/L(6). n-Pentanoic acid was detected in the acidic fraction of oil shale retort water at a concn of 210 mg/L(7). Groundwater samples collected 15.5 feet below the land surface near an area contaminated with gasoline contained n-pentanoic acid at a concn of 2 ug/L(8).n-Pentanoic acid was detected in the leachate of a sanitary landfill located in Barcelona, Spain at an unreported concn(1). n-Pentanoic acid was identified in the effluent of a publicly owned treatment works facility located in an industrial area of NJ at an estimated concn of 8 ppb(2). n-Pentanoic acid was detected in: product water samples from an in situ coal gasification site in Hanna, WY at a concn of 1060 ppmretort water from in situ oil shale processing in Rock Springs, WY at a concn of 5 ppmand boiler blowdown water from in situ shale oil processing in DeBeque, CO at a concn of 4 ppm(3). Pentanoic acid was detected in condensate retort water and process retort water from the Occidental Oil Shale, Inc facility in Logan Wash, CO at concns of 0.3 and 110 mg/L, respectively(4). n-Pentanoic acid was identified as a byproduct of chlorine dioxide disinfection of drinking water at a pilot plant in Evansville, IN(5). n-Pentanoic acid was detected in primary and secondary effluents from four sewage treatment plants at concns ranging from 3.7 to 379 ug/L and 0.6 to 40 ug/L, respectively(6).ONE OF VOLATILE ACIDS IDENTIFIED IN THE RAW SEWAGE IN HAIFA, ISRAEL WAS VALERIC ACID.n-Pentanoic acid was detected in groundwater down-gradient from a crude oil spill in Bemidiji, MN from 1986-1990 at concentrations ranging from 0.009 to 0.326 uM(1). Samples were taken from distances ranging from 0-90 m downgradient from the spill(1). n-Pentanoic acid was extracted from oil-field wastewater samples from an oil processing facility located in California in concentrations ranging from 0.0009 mg/L to 1.37 mg/L(2). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | The Koc of n-pentanoic acid is estimated as 140(SRC), using a log Kow of 1.39(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that n-pentanoic acid is expected to have high mobility in soil. In aqueous solution, n-pentanoic acid adsorbed 15.4 and 37.9% onto the clay minerals kaolinite and montmorillonite, respectively, after 144 hours at 22 °C(4). The pKa of n-pentanoic acid is 4.84(5), indicating that this compound will partially exist 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(6). |
| TSCA Test Submissions | Pentanoic acid (CAS # 109-52-4) was evaluated for subchronic dermal toxicity in New Zealand White rabbits exposed to 0 or 500 mg/kg (in mineral oil solution) non-occluded applications upon abraded skin (3/5 males, 2/5 females) or shaved intact skin (3/5 females, 2/5 males) on 5 consecutive days/week for 2 weeks (10 total applications). One female died on the 7th day of treatment, exhibiting hypopnea, hypoactivity, diminished food consumption, and red anal discharge prior to death. Pharmacotoxic signs noted among survivors included diminished food consumption, nasal discharge, and vocalization upon handling. Without exception, the animals showed transient weight loss in the second week of treatment and worsening signs of dermal irritation including severe erythema, moderate to severe edema, necrosis with eschar, atonia, desquamation, and dermal fissuring. Eschar tissue exfoliated during the second week of treatment and all animals were free of any signs of toxicity by end of study. Upon necropsy, no increased incidence of gross pathological changes relative to controls were identified. Micropathological evaluation of the collective irritative eschar found epidermal hyperplasia, and hyperkeratosis, as well as diffuse and perifollicular dermal inflammation. Rabbits surviving 2-week post-treatment recovery demonstrated some persisting epidermal hyperplasia and hyperkeratosis, but were otherwise free of irritative signs. No significant difference was noted in irritative responses on abraded or intact skin.n-Pentanoic acid (CAS # 109-52-4) was evaluated for carcinogenic potential in adermal study of C3H/HeJ mice (50/group) administered interscapular applications of 50 mg/kg undiluted test substance twice weekly for 80 weeks. Severe dermal and systemic toxicity noted upon a 4th application was in excess of that observed during an initial pilot study and necessitated amendment of treatment and dermal doses were reduced to 25 mg/kg for the remainder of the study. Despite this change in protocol, decreased survival (10%) among the treated animals relative to controls (no treatment) lowered a final effective number of mice living long enough to develop treatment-related tumors. Depressed bodyweight gains (17%), and epilation, ulceration, and crustiness of the skin at treatment sites were also exhibited among treated mice. The condition of the treated skin further complicated gross recognition of dermal neoplasms. Seven of 12 treated animals demonstrating benign and/or malignant tumors were identified upon microscopic examination of treated dermis, while 5/12 were identified at twice daily examinations during the in-life portion of study. Observed neoplasms in treated mice were characterized as squamous cell carcinomas of the skin (4/4 mice), fibrosarcomas (6/6 mice), fibromas (5/3 mice) and a solitary incidence of keratoacanthoma, relative to one malignant squamous cell carcinoma of the skin noted in a control animal. An average latent period for 5/12 neoplasms observed in living mice was 61.8 weeks. Due to the profound systemic toxicity, 19/50 treated mice also underwent histologic evaluation of all major visceral organs and the brain. No additional gross pathology or microscopic findings in excess of controls was documented.n-Valeric acid (CAS # 109-52-4) was evaluated for genotoxic effects in the Chinese Hamster Ovary (CHO)/HGPRT gene mutation test. Based on preliminary cytotoxicity tests, cultures of chinese hamster ovary cells incorporating metabolic activation with Aroclor 1254-induced S-9 rat liver homogenate were exposed for 5 hours to concentrations of 0.2 to 1.6 mg/ml, while non-activated cultures were exposed to concentrations of 0.6 to 1.4 mg/ml. In both activated and non-activated cultures, doses of 1.0 mg/ml and above were associated with excessive cytotoxicity, however throughout the range of exposure concentrations no dose-related mutagenicity was established relative to solvent control (ethanol). Investigators reported a steep cytotoxicity curve for the test substance and CHO cells at 1.0 - 1.3 mg/ml. A numerical increase in mutagenicity was seen in association with 0.6 mg/ml exposures in the non-activated cultures, and background mutagenicity in control cultures with metabolic activation were found excessively high relative to historical controls. These findings prompted a second investigation of test concentrations centered about 0.6 mg/ml in metabolically non-activated cultures. In the CHL/HGPRT gene mutation test with concentrations of 0.20 to 0.60 mg/ml (-S9) and 0.60 to 1.20 (+S9), no reproducible or dose-related mutagenic effects were noted in association with any concentration in either culture preparation.n-Valeric acid (CAS # 109-52-4) was evaluated for genotoxic effects in the Chinese Hamster Ovary (CHO)/HGPRT in vitro chromosome aberration test. Based on preliminary cytotoxicity tests and equivocal results in an initial genotoxicity test, ovary cell cultures incorporating metabolic activation with Aroclor 1254-induced S-9 rat liver homogenate were exposed for 8 or 12 hours to concentrations of 0.6 to 1.2 mg/ml, while non-activated cultures were exposed to concentrations of 0.07 to 0.2 mg/ml. Cytotoxicity testing established that, in activated and non-activated cultures, 1.2 and 0.3 mg/ml were associated with 66.7% and 55.6% reduction in the respective mitotic indices. In genotoxicity testing, incidence of chromosome aberrations were determined from 100-cell samples of those cultures exposed to the highest concentrations not producing excessive mitotic inhibition. S9-activated cultures exposed to 1.1 and 1.2 mg/ml sampled at both 8 hours and 12 hours demonstrated significant (p < 0.05 and 0.01, respectively) dose-related clastogenic effects relative to control (ethanol solvent), as did the 0.2 mg/ml exposed non-activated cultures (p < 0.05) sampled at 12 hours. Chromatid breaks characterized the majority of aberrations associated with the test substance.Valeric acid (C-180109-52-4) was evaluated for developmental effects in 22 female Crl:COBS, CD(SD)BR rats administered 750 mg/kg of the test substance by gavage on days 6 through 15 of gestation. A control group received corn oil. Maternal animals showed an increased incidence of clinical observations (specific signs not reported). Offspring showed an increased incidence of delayed ossification of several bone structures. |
| Natural Pollution Sources | THE ACID IS NOT COMMON IN NATURE. REPORTED (AS THE CORRESPONDING ESTER) FOUND IN ESSENTIAL OIL OF BORONIA ANEMONIFOLIA, IN PINEAPPLE FRUITS, & IN OTHER PLANTSALSO IDENTIFIED AS ACID OR THE CORRESPONDING ESTER IN THE ESSENTIAL OIL OF LEMON PETITGRAIN.n-Pentanoic acid was identified as a volatile fatty acid occurring in dalieb fruit pulp at a concentration of 5 mg/kg pulp(1). |
| Atmospheric Concentrations | URBAN/SUBURBAN: n-Pentanoic acid was detected in the daytime air of Fukaya, Takasaki, and Karuizawa, Japan at 0.01, 0.02, and 0.01 ppb, respectively, in 1986(1).SOURCE DOMINATED: n-Pentanoic acid has been reported as a component of diesel exhaust(1). On Sept 8-9, 1993 n-pentanoic acid was detected in the ambient air during a photochemical smog episode in Los Angeles, CA at an average concn of 0.26 ug/cu m for 6 samples with a high and low concn of 0.00 ug/cu m and 0.34 ug/cu m(2). |
| F | 13 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3265 8/PG 3 |
| Zollcode | 29156090 |
| RTECS-Nr. | YV6100000 |
| R-Sätze (R) | 34-52/53 |
| Toxizität | LD50 i.v. in mice: 1290 ±53 mg/kg (Or, Wretlind) |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36-45-61 |
| Gefahrenklasse | 8Aquatic Chronic 3Eye Dam. 1Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 109-52-4(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 707 °F |
Anwendungen & Verwendung
Beschreibung
Farblose, übelriechende Flüssigkeit; Siedepunkt: 184-187 ℃; Schmelzpunkt: -34 ℃; n20D: 1.4085; schlecht löslich in Wasser, gut in Ethanol und Ether. Valeriansäure kommt in der Natur vor allem in Baldrianen (Valeriana) zusammen mit der isomeren Isovaleriansäure (3-Methylbutansäure) vor. Weiterhin ist sie Bestandteil der Duftmarke verschiedener Säugetiere und kommt in geringen Spuren in einer Reihe von Lebensmitteln, wie Käse, sowie im Magen von Wiederkäuern vor. Die technische Synthese von Valeriansäure erfolgt aus But-1-en durch Hydroformylierung zu Pentanal und anschließende Oxidation zur Carbonsäure. Valeriansäure wird hauptsächlich zur Herstellung ihrer Salze und Ester eingesetzt. Die Natrium- und Calciumsalze dienen als Rotentizide und Fungizide. Die durch Veresterung mit aliphatischen Alkoholen gewonnenen Valerate werden als Duftstoffe und künstliche Aromen verwendet. Die durch Veresterung mit Glycolen und Polyolen gewonnenen Verbindungen dienen als Schmierstoffe.
Beschreibung
Valeric acid, or pentanoic acid, is a straight - chain alkyl carboxylic acid with the chemical formula C5H10O2. Like other lowmolecular- weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Its primary use is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors. Valeric acid appears similar in structure to GHB and the neurotransmitter GABA in that it is a short-chain carboxylic acid, although it lacks the alcohol and amine functional groups that contribute to the biological activities of GHB and GABA, respectively. It differs from valproic acid simply by lacking a 3- carbon side - chain.
Occurrence
The acid is not too common in nature; reported (as the corresponding ester) found in the essential oil of Boronia anemonifolia, in pineapple fruits and in other plants; also identified as acid or the corresponding ester in the essential oil of lemon petitgrain. Also reported found in apple, apple juice, banana, orange juice, bilberry, cranberry, strawberry, raspberry, papaya, grapes, celery, onion, baked potato, tomato, corn mint oil, breads, cheeses, milk, yogurt, butter, cheddar cheese, lean and fatty fish, fish oil, cooked meats, hop oil, beer, rum, whiskies, grape wines, cocoa, tea, roasted filberts, peanuts and pecans, honey, soybeans, coconut meat and milk, cloudberry, passion fruit, starfruit, trassi, mango, jackfruit, licorice, calamus, sake, buckwheat, watercress, laurel, peated malt, wort, kiwifruit, loquat, Bourbon vanilla, shrimps, oyster, scallop, cape gooseberry, sea buckthorn, Chinese quince and maté.
Verwenden
valeric acid is obtained from valerian extract, which is considered skin conditioning.
Herstellung & Synthese
synthetische
By oxidation of n-amyl alcohol or, together with other isomers, by distillation of valerian roots; also by reacting butyl bromide and sodium cyanide with subsequent saponification of the formed butyl nitrile.