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Valeraldehyd
PENTANAL · N-PENTANAL · 1-pentanal · N-VALERALDEHYDE · FEMA 3098 · AMYLALDEHYDE · Pentanal 95% · Valeraldehyd
Identifikatoren & physikalische Daten
| CAS No. | 110-62-3 |
|---|---|
| Summenformel | C5H10O |
| Durchschnittliche Molmasse | 86,13 g/mol |
| Monoisotopische Masse | 86,07316494 g/mol |
| SMILES | CCCCC=O |
| InChIKey | HGBOYTHUEUWSSQ-UHFFFAOYSA-N |
| PubChem CID | 8063 |
| ChEMBL | CHEMBL18602 |
| ChEBI | CHEBI:84069 |
| EC No. | 203-784-4 |
| DTXSID | DTXSID7021653 |
| Lokaler Name | Valeraldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 32,9 |
| Stoffklassen | Other Classes -> AldehydesFlammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Fatty Acyls [FA] -> Fatty aldehydes [FA06] |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (Valeraldehyde) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 1.31 |
| Geruch | POWERFUL, ACRID, PUNGENT ODORStrong, acrid, pungent odor |
| Geschmack | WARM, SLIGHTLY FRUITY, & NUT-LIKE AT LOW LEVELSPLEASANT, CHOCOLATE AROMA & TASTE... IT HAS SHARP, PENETRATING FLAVOR |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.811 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8095 g/cu cm at 20 °CRelative density (water = 1): 0.80.805-0.8090.81 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 0.54 mPa-s at 20 °C |
| Schmelzpunkt | -92 °C |
| Siedepunkt | 103 °C |
| Dampfdruck | 36 hPa (20 °C) |
| Brechungsindex | n20/D 1.394(lit.) |
| FEMA | 3098 | VALERALDEHYDE |
| Flammpunkt | 54 °F |
| Lagerbedingungen | Store at +2°C to +8°C. |
| Löslichkeit | soluble in ethyl alcohol, ethyl ether, and other common organic solvents.14 g/L (20 ºC) |
| Aggregatzustand | liquid |
| Farbe | Colorless to Light yellow |
| Geruch | at 1.00 % in dipropylene glycol. fermented bready fruity nutty berry |
| Geruchsart | fermented |
| Geruchsschwelle | 0.00041ppm |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 1.7-6.8%(V) |
| Merck | 14,9902 |
| JECFA Number | 89 |
| BRN | 1616304 |
| Henry-Konstante | 6.6×10-2 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 13.9(Ambient) |
| Stabilität | Stable. Highly flammable. Incompatible with strong oxidizing agents, acids, strong alkalies, strong reducing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 |
| InChIKey | HGBOYTHUEUWSSQ-UHFFFAOYSA-N |
| SMILES | [H]C(=O)CCCC |
| LogP (Verteilungskoeffizient) | 1.5 at 25℃ and pH7 |
| CAS Datenbank | 110-62-3(CAS DataBase Reference) |
| NIST chemische Informationen | Pentanal(110-62-3) |
| EPA chemische Informationen | Pentanal (110-62-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1939 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: PentanalPentanal is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanal 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: 20-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14541Pentanal: HSNO Approval: HSR001234 Approved with controlsThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Pentanal: Human health tier II assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. |
| Brandpotenzial | A very dangerous fire hazard when exposed to heat or flame. |
| Gesundheitsgefahren | Vapor may irritate eyes. Liquid irritates eyes and skin. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | If left on clothing, can cause reddening of skin[CHRIS] A skin, eye, and respiratory tract irritant[ICSC] See ALDEHYDES. |
| DOT-Nummer und Handbuch | 2058 129 |
| FDA-Anforderungen | Pentanal 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 | Aldehydes |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: II |
| Special Reports | Organization for Economic Cooperation and DevelopmentScreening Information Data Set for n-Valeraldehyde, 110-62-3 (October 2005).[Available from the Database Query page at, as of January 15, 2009: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html] |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 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.General First Aid:(General first aid procedures) |
| Sichere Lagerung | Fireproof. Well closed. Cool. |
| Firefighting Hazards | Burning Rate: 1.9 mm/minFlashback along vapor trail may occur. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | Foam, dry chemical, or carbon dioxide. Water may be ineffective. |
| Lagerbedingungen | ...Store in tightly closed containers in a cool, well-ventilated area. Sources of ignition such as smoking and open flames are prohibited where Valeraldehyde is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of Valeraldehyde should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of Valeraldehyde. |
| Reinigungsverfahren | Absorb the spills with rags or other available absorbing materials. Evaporate in a hood and dispose by burning the rag or the absorbing materials. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| 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.Dissolve in a combustible solvent, thence spray the solvent into the furnace with afterburner. |
| Körperbelastung | In EPA's National Human Adipose Tissue Survey (NHATS) for 1982, all 46 composite samples analyzed contained pentanal: in all 12 samples for 0-14, in all 17 samples for 15-44, and in all 17 samples for 45 and over years of age(1). Pentanal was detected, but not quantified, in 7 of 8 samples of mother's milk analyzed from 4 U.S. urban areas(2). |
| Zielorgane | Eyes, skin, respiratory system |
| Ökotoxizitätswerte | LC50Species: Pimephales promelas (Fathead minnow, age 31 days, mean length 19.8 mm, mean weight 0.119 g)Conditions: flow-through bioassay with measured concentrations, 24.5 °C, dissolved oxygen 6.1 mg/L, hardness 37.5 mg/L calcium carbonate, alkalinity 44.1 mg/L calcium carbonate, and pH 7.52Concentration: 12.4 mg/L for 96 hr (95% confidence limit 11.3-13.6 mg/L) /99% purity/Species: Pimephales promelas (Fathead minnow, age 28 days, mean length 18.8 mm, mean weight 0.101 g)Conditions: flow-through bioassay with measured concentrations, 24.1 °C, dissolved oxygen 6.9 mg/L, hardness 45.3 mg/L calcium carbonate, alkalinity 49.6 mg/L calcium carbonate, and pH 7.48Concentration: 13.4 mg/L for 96 hr (95% confidence limit 12.8-14.0 mg/L) /99% purity/Species: Oncorhynchus mykiss (Rainbow trout, juvenile, average length 4.2 + or -0.3 cm, weight 0.623 + or -0.125 g)Conditions: freshwater, flow through, 13.0 + or -1 °C, hardness 68-76 mg/L CaCO3, alkalinity 28-40 mg/L CaCO3, conductivity 155-162 umhos/cm, residual chlorine <10 ppbConcentration: 46.5 mg/L for 24 hr /99.6% purity/Concentration: 29.4 mg/L for 48 hr (95% confidence interval: 26.6-32.3 mg/L) /99.6% purity/For more Ecotoxicity Values (Complete) data for PENTANAL (19 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a water solubility of 1.17X10+4 mg/L(2) and a regression-derived equation(3), indicates that pentanal is expected to have very high mobility in soil(SRC). Volatilization of pentanal from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.47X10-4 atm-cu m/mole(4). Pentanal is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 26 mm Hg(5). In activated sludge from waste treatment plants in operation, pentanal had a theoretical oxygen demand of 17.8% after 24 hrs(6), suggesting that biodegradation may be an important fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a water solubility of 1.17X10+4 mg/L(2) and a regression-derived equation(3), indicates that pentanal is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.47X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In activated sludge from waste treatment plants in operation, pentanal had a theoretical oxygen demand of 17.8% after 24 hrs(6), suggesting biodegradation is an important environmental fate process in water(SRC). Pentanal is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentanal, which has a vapor pressure of 26 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase pentanal is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-lives for this reaction in air are estimated to be 14.6 and 13.5 hours(SRC), calculated from rate constants of 2.63X10-11(3) and 2.85X10-11(4) cu cm/molecule-sec at 25 °C, respectively. Vapor-phase pentanal is also degraded in the atmosphere by reaction with photochemically-produced nitrate radicalsthe half-life for this reaction in air is estimated to be 49 hours(SRC), calculated from rate constant of 1.65X10-14 cu cm/sec(3). Pentanal contains chromophores that absorb at wavelengths >290 nm(5) and will undergo photodegradation to form propene, vinyl alcohol and ethanal(6). |
| Lebensmitteluntersuchungswerte | Pentanal has been identified as a volatile in the following foods: Korean chamchwi(1), baked potatoes(2), cassava(3), French mountain cheese(4), raw beef(5-6), roasted filberts(7), boiled short-necked clams and clams(8), scrambled eggs(9), delicious apples(10), frankfurters(11), Italian-type dry-cured ham(12), and fried chicken(13). Pentanal was found in popcorn using dry extraction method at 36 ug/kg and not detected using wet extraction method(14). Commercial rice cakes were found to contain 130-440 ppb of pentanal(15). Fermented soybean (Glycine max) curds were found to contain 24.6-151.3 ug/kg of pentanal(16). Pentanal was detected in the emissions from heated rapeseed oil(17) and in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(18). |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour.inhalation, ingestion, skin and/or eye contact |
| Milk Concentrations | ENVIRONMENTAL: Pentanal was detected, but not quantified, in 7 of 8 samples of mother's milk analyzed from 4 US urban areas(1). Pentanal was detected, not quantified, in cold storage, store bought milk in Australia(2). |
| Average Daily Intake | AIR INTAKE: Assuming a mean concn of 0.05-1.07 ppb(1,2) of pentanal in the atmosphere an avg daily intake of 0.0036-0.765 ug is expected(SRC). |
| Plant Concentrations | Pentanal is a plant volatile(1). The concn of pentanal is relatively high in undeveloped apples but then decreases to undetectable levels as the harvest approaches(2). Pentanal was emitted from rape during the blooming period at a rate of 0.12 and 0.47 ppbv during May 8 and 9, 1998(3). |
| Signs and Symptoms | Cough. Sore throat.Redness.Redness. Pain.Nausea. Diarrhoea. Vomiting.irritation eyes, skin, nose, throat |
| Effluent Concentrations | Pentanal was emitted from samples of particle board with glued-on carpet and plywood coated with polyurethane at rates of 0.031 and 0.014 mg/sq m-hr, respectively(1). Pentanal was measured in the emissions of three paints at 0.26-0.48 mg/g of paint(2). Laboratory scale composting emissions contained pentanal after two days(3). The emission rate of pentanal during the operation of dry-process photocopiers was <10 ug/hr in idle mode and 540 ug/hr in print mode(4). Pentanal was released as fireplace emissions at 6.81 and 6.26 mg/kg of fuel burnt for soft and hard wood, respectively(5). Pentanal was found in emissions from a wood stove using hardwood at 13.05 mg/kg and using synthetic fuel at 6.74 mg/kg(5). Green aspen drying in a kiln at 160 °C for 2 hrs contained 70 ug/g of pentanal in a laboratory experiment(6). Wood drying in a mill for 10, 30, and 55 days at 160 °C emitted pentanal at concns of 42, 19, and 11 ug/g, respectively(6). Pentanal was emitted from wood dried in a kiln at 130 °C for 10 and 30 days was 2 and 5 ug/g(6). Pentanal was emitted from three day old floor coverings at rates of 3, 10, 8, 16, and 73 ug/sq m-hr for oak, pine, birch, oiled parquet, and waxed parquet, respectively(7). The emission rates at 28 days old were 1, 2, 6, 6, and 13 ug/sq m-hr for the same floor coverings(7). Pentanal was detected in 17 of 44 furniture emission samples(8). Pentanal was measured in the emissions of burnt wood at 32, 88, and 28 mg/kg of pine, oak, and eucalyptus, respectively, in the gas phase(9). Pentanal was detected but not quantified in the emissions of building materials with microbial growth(10). Pentanal was detected in the emissions of cookstoves in China using wheat crop residue, wood, coal, kerosene, liquid propane gas, and coal gas at concns of 13.1, 9.9, 2.2, 27.3, 4.7, and 2.2 mg/kg, respectively(11).Pentanal was given off of six new vehicle interiors at an average of 29 ug/hr in new vehicles, 14 ug/hr in 20 day old vehicles and 16 ug/hr in 40 day old vehicles(1). Pentanal was detected, but not quantified, in gasoline and diesel fuel(2). Pentanal (as % of total non-methane organic compound emissions) was identified in regular gasoline (1.53%), high grade gasoline (1.49%), regular whole gas (2.97%), high grade whole gas (2.71%), roadway (1.91%), bus parking garage hot soak (0.70%), bus parking garage cold start (1.05%), motorcycle emissions (2.62%), petroleum refinery (0.83%), lead smelter (0.45%), cast iron factory emissions (0.58%), and natural gas (0.05%) in Cairo, Egypt(3). Pentanal sampling conducted in the Tuscarora Mountain Tunnel, PA gave the following results: light duty trucks emitted 0.05 mg/km traveled or 0.736 mg/L fuel used, heavy duty trucks emitted 0.617 mg/km traveled or 1.943 mg/L fuel used(4). Pentanal concns from automobile exhaust were 2.8-18 ppbv in models from 1971 and 1977(5). Pentanal was measured in the emissions of gasoline powered motor vehicles at a rate of 490 ug/km and 27,000 ug/km for catalyst equipped engines and non-catalyst equipped engines(6). Pentanal emissions from an automobile running on Swedish environmental classified diesel fuel were 3.6 mg/km and the same automobile running on European program emissions fuel were 2.8 mg/km(7). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| TSCA-Anforderungen | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91Reporting date: 11/27/91.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Pentanal is included on this list. Effective date 9/30/91Sunset date: 6/30/98. |
| F | 10-23 |
| Berufliche Expositionsstufe (OEB) | A |
| Arbeitsplatzgrenzwert (OEL) | TWA: 50 ppm (175 mg/m3) (Aldehydes) |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2058 |
| Zollcode | 29121900 |
| RTECS-Nr. | YV3600000 |
| R-Sätze (R) | 11-38-41-36/37/38 |
| Toxizität | LD50 orally in rats: 5.66 ml/kg (Smyth) |
| Gefahrensymbole | F,Xi |
| hazard_note | Irritant/Flammable/Air Sensitive |
| Sicherheitshinweise (S) | 16-26-33-39-37/39 |
| Gefahrenklasse | 3Acute Tox. 4 InhalationEye Irrit. 2Flam. Liq. 2Skin Sens. 1STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 110-62-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 428 °F |
Anwendungen & Verwendung
Beschreibung
Valeraldehyde is one of the key volatile flavor compounds identified in cooked rice, beef fish meat and uncured ham. Its smell is described as fermented, bready, fruity, nutty, berry.It is an alkyl aldehyde used in flavoring Compounds, resin chemistry, rubber accelerators.
Occurrence
Valeraldehyde is naturally occurring (e.g., plant volatile). Reported found among the constituents of several essential oils: Brazilian sassafras, Bulgarian rose, Bulgarian clary sage and others. Also in the distillates from leaves of various Eucalyptus species: E. cinereea, E. globulus, E. dives, E. maideni and E. hemilampra. Also reported found in fresh apple, banana, sweet cherry, black currant berries, fresh blackberry, Bantu beer, plum brandy, cardamom, coriander leaf, unprocessed rice, Bourbon vanilla, cooked shrimp, scallop, hog plum and clary sage.
Verwenden
Valeraldehyde is mainly used for hydrogenation to Isoamyl alcohol and oxidation to valeric acid. It can also be used as a raw material for fragrances, resin chemistry, and rubber accelerators.
Herstellung & Synthese
synthetische
Valeraldehyde can be prepared by oxidation of the corresponding alcohol, 1-pentanol or by reduction of n-valeric acid (Opdyke, 1979; Lewis, 1993). Valeraldehyde is one of a number of aliphatic aldehydes industrially prepared by the oxo process, which involves the reaction of olefins with carbon monoxide and hydrogen in the presence of a catalyst. Use of a cobalt carbonyl complex as catalyst required high pressure in an older process, which has been largely replaced by a low-pressure process based on rhodium complex catalysts, such as a tris (alkyldiarylphosphine) rhodium carbonyl hydride.