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1-Hexanol
HEXANOL · N-HEXANOL · HEXYL ALCOHOL · HEXAN-1-OL · 1-Hexenol · 1-Hexyl alcohol · N-HEXYL ALCOHOL · FEMA 2567
Identifikatoren & physikalische Daten
| CAS No. | 111-27-3 |
|---|---|
| Summenformel | C6H14O |
| Durchschnittliche Molmasse | 102,17 g/mol |
| Monoisotopische Masse | 102,10446507 g/mol |
| SMILES | CCCCCCO |
| InChIKey | ZSIAUFGUXNUGDI-UHFFFAOYSA-N |
| PubChem CID | 8103 |
| ChEMBL | CHEMBL14085 |
| ChEBI | CHEBI:87393 |
| EC No. | 203-852-3 |
| DTXSID | DTXSID8021931 |
| Lokaler Name | 1-Hexanol |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 27,4 |
| Stoffklassen | Flammable agents - 2nd degree |
| Lipide | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Solvents | Solvents -> Alcohols (<C12) |
| Kosmetika | SurfactantHydrotropeSolventAntifoaming |
| SpringerMaterials Properties | Activity |
| Duftstoffe | Fragrance Ingredient (Hexyl alcohol) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 2.03 |
| Geruch | Characteristicsweet alcoholpleasant |
| Geschmack | FATTY, FRUITYAROMATIC FLAVOR |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.85 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8153 at 25 °C/4 °C0.8082 at 35 °C/4 °CBulk density = 6.8 lb/galRelative density (water = 1): 0.820.816-0.8210.8204 @ 20°C0.814 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Schmelzpunkt | -52 °C (lit.) |
| Siedepunkt | 156-157 °C (lit.) |
| Dampfdichte | 4.5 (vs air) |
| Dampfdruck | 1 mm Hg ( 25.6 °C) |
| Brechungsindex | n20/D 1.418(lit.) |
| FEMA | 2567 | HEXYL ALCOHOL |
| Flammpunkt | 140 °F |
| Lagerbedingungen | no restrictions. |
| Löslichkeit | ethanol: soluble(lit.)6 g/L (25 ºC) |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 15.38±0.10(Predicted) |
| Farbe | Clear colorless |
| Geruch | Sweetmild. |
| Geruchsart | herbal |
| Geruchsschwelle | 0.006ppm |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 1.2-7.7%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 2.35 J/(g·K), at 25℃ |
| JECFA Number | 91 |
| Merck | 14,4697 |
| BRN | 969167 |
| Henry-Konstante | 7.6×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 13.3(24℃) |
| Stabilität | Stable. Substances to be avoided include strong acids, strong oxidizing agents. Combustible. |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIFOAMINGSOLVENTPERFUMINGSURFACTANT - CLEANSINGSURFACTANT - HYDROTROPE |
| InChI | 1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 |
| InChIKey | ZSIAUFGUXNUGDI-UHFFFAOYSA-N |
| SMILES | CCCCCCO |
| LogP (Verteilungskoeffizient) | 1.8 |
| Oberflächenspannung | 24.511mN/m at 298.15K |
| CAS Datenbank | 111-27-3(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Hexanol(111-27-3) |
| EPA chemische Informationen | 1-Hexanol (111-27-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)H226 (34.3%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P264+P265, P270, P280, P301+P317, P302+P352, P303+P361+P353, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: 1-HexanolChemical: Hexanol1-Hexanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Hexanol 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: 22-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/132651-Hexanol: HSNO Approval: HSR001167 Approved with controlsHexanol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | IMAP assessments - 1-Hexanol: Environment tier I 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.Combustible. Above 63 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable liquid when exposed to heat, sparks or flame. |
| Gesundheitsgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Liquid causes eye burns and skin irritation. Breathing vapors is not expected to cause systemic illness. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | May cause first degree burns after short exposure and second degree burns after longer contact[CHRIS] Undiluted 1-Hexanol is a mild irritant. Application of 0.2 ml to 27-28 volunteers caused no noticeable skin effects. 1-Hexanol caused corneal burns from which patients recovered within 48 hours. Ingestion can lead to symptoms of alcohol intoxication. [CHEMINFO] |
| DOT-Nummer und Handbuch | 2282 129 |
| FDA-Anforderungen | Hexyl alcohol 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 | Alcohols and Polyols |
| EG-Einstufung | Symbol: XnR: 22S: (2)-24/25 |
| FIFRA-Anforderungen | 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 future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Hexanol is found on List D. Case No: 4004Pesticide type: Insecticide, HerbicideCase Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): HexanolAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."Residues of n-hexyl alcohol are exempted from the requirement of a tolerance when used as a solvent, cosolvent 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 n-hexyl alcohol are exempted from the requirement of a tolerance when used as a solvent, cosolvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.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. Do NOT induce vomiting. Give one or two glasses of water to drink. |
| 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 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:In case of contact, immediately flush skin and eyes with plenty of water. Wash eyes at least 15 min. and get medical care. (USCG, 1999)General First Aid: |
| Sichere Lagerung | Separated from strong oxidants. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).240.0 [ppm] |
| Brandbekämpfungsverfahren | Use carbon dioxide, dry chemical or "alcohol" foam extinguisher. Water is ineffective to fire fighting, but is effective to keep fire-exposed containers cool.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. Keep run off water out of sewers and water sources. |
| Lagerbedingungen | Protect containers against physical damage. Keep containers closed and store in well-ventilated, cool place. |
| Reinigungsverfahren | Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.AEROBIC: 5-Day theoretical BODs of 28%(1), 53% (initial concn of 100 ppm)(2) and 83.6% (initial concn of 2,000 ppm)(3) were observed for 1-hexanol in aerobic screening tests using a sewage inocula. An aerobic biodegradation rate constant of 7.99X10-2 1/hr(4), which corresponds to a half-life of 0.36 days(SRC), was determined in an aerobic screening test at pH 7 and 25 °C using an activated sludge inocula. In a similar screening test, the rate constant was measured to be 1.7X10-2 1/hr(5), which corresponds to a biodegradation half-life of 1.7 days(SRC).ANAEROBIC: Anaerobic biodegradation studies show 1-hexanol degradation rates of 75%(1) and 83%(2) in 7 days at 37 °C using a synthetic sewage inocula. |
| 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.Spray into the furnace. Incineration will become easier by mixing with a more flammable solvent. |
| Verschüttetes entsorgen | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Körperbelastung | 1-Hexanol was qualitatively identified in 1 of 46 adipose tissue samples collected during fiscal year 1982 according to the National Human Adipose Tissue Survey (NHATS)(1). |
| Ökotoxizitätswerte | LC50 Pimephales promelas (Fathead minnow, weight 0.12 g) 97.5 mg/L 96 hr flow-through bioassay, water hardness 45.5 mg/L CaCO3, temp: 25 +/- 1 °C, pH 7.5, dissolved oxygen >60% of saturation.LC50 Alburnus alburnus (Bleak) 120 mg/L/96 hr /Conditions of bioassay not specified in source examined/LC50 Nitocra spinipes (Harpacticoid copepod) 317 mg/L/96 hr /Conditions of bioassay not specified in source examined/LC50 Leuciscus idus (Golden orfe) 130 mg/L/48 hr /Conditions of bioassay not specified in source examined/For more Ecotoxicity Values (Complete) data for 1-HEXANOL (7 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value of 10.2(2), indicates that 1-hexanol is expected to have very high mobility in soil(SRC). Volatilization of 1-hexanol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.71X10-5 atm-cu m/mole(3). 1-Hexanol is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.928 mm Hg(4). Biodegradation studies show that 1-hexanol is expected to degrade rapidly in both aerobic and anaerobic conditions(5-11). 1-Hexanol has aerobic, measured biodegradation half-lives of 0.36(8) and 1.7 days(9). Anaerobic, seven day biodegradation rates of 75%(10) and 83%(11) were measured for 1-hexanol. These rates suggest that biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 10.2(2), indicates that 1-hexanol 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 1.71X10-5 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 2 days and 20 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 21(SRC), from its log Kow of 2.03(6) and regression-derived equations(7), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation studies show that 1-hexanol is expected to degrade rapidly in both aerobic and anaerobic conditions(8-14). 1-Hexanol has aerobic, measured biodegradation half-lives of 0.36(11) and 1.7 days(12). Anaerobic, seven day biodegradation rates of 75%(13) and 83%(14) were measured for 1-hexanol.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-hexanol, which has a vapor pressure of 0.928 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-hexanol 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 1.3 days(SRC), calculated from its rate constant of 1.71X10-5 cu cm/molecule-sec at 25 °C(3). |
| Lebensmitteluntersuchungswerte | 1-Hexanol was identified as 0.4 percent of all volatile components detected in mature kiwi fruit and 2 percent of all volatile components detected in ripe kiwi fruit(1). 1-Hexanol was identified as a volatile constituent of mature and overripe guava fruit at respective concns of 3,019.8 and 2,378.7 ug/kg(2). 1-Hexanol was found at a concn range of 50-180 ug/kg in volatile constituents of nectarines(3). 1-Hexanol was detected in the volatiles of dried legumes at a concn range of 2-69 ppb(4). 1-Hexanol was identified as a volatile component of garlic at a concn range of 0.08-0.23 ug/g garlic bulb(5). Fermented soybean (Glycine max) curds were found to contain 2886 to 3481 ug/kg of 1-hexanol(6).1-Hexanol was identified as a volatile component of fried bacon(1), roasted filberts(2), raw and roasted earth almonds (Cyperus esculentus L.)(3), mutton(4), chicken(4), pork(4), cured ham(5), raw beef(4,6), frankfurters(7), chickpeas(8), Kogyoku apple(9), Beaufort (Gruyere) cheese(10) and in food products processed from the Cassava root(11). 1-Hexanol was also identified as a volatile component of edible Korean chamchwi (Aster scaber Thunb)(12) and in heated peanut oil(13). 1-Hexanol was qualitatively identified as a volatile constituent of clams, including short-necked clams(14)./USED/ IN NON-ALCOHOLIC BEVERAGES AT 6.6 PPMICE CREAM, ICES, ETC 26 PPMCANDY 21 PPMBAKED GOOD 18 PPM& GELATINS & PUDDINGS 0.22-0.28 PPM. |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation and by ingestion. |
| Milk Concentrations | 1-Hexanol was detected, not quantified in store bought milk in Australia(1). |
| Plant Concentrations | 1-Hexanol was identified as a volatile component of earth almonds (Cyperus esculentus L.)(1). 1-Hexanol has been identified as a volatile emission from dawn redwood trees and Rabbit bush(2). |
| Signs and Symptoms | Cough. Sore throat.Dry skin.Redness. Pain.Burning sensation. |
| Effluent Concentrations | 1-Hexanol was qualitatively identified in effluents from a refinery in Illinois(1) and leachate from a waste disposal site in the Netherlands(2). 1-Hexanol was found in wastewater being discharged into the Calcasieu River (Louisiana) from a petrochemical company(3). 1-Hexanol was qualitatively detected in the headspace of 3 household products, including wax paste for leather conservation and finish, liquid floor wax, and liquid wax for ceramic floors(4). Emissions of 1-hexanol with ethylbenzene, in percent of total carbon emission, were identified in gasoline headspace, regular (0.18) and high grade (0.18), whole gasoline, regular (2.55) and high grade(3.15), roadway emissions (1.94), bus parking garage, hot soak (0.88), bus parking garage, cold start (1.05), motorcycle emissions (1.81), petroleum refinery emissions (0.50), lead smelter (0.40), and cast iron factory emissions (0.68) in Cairo, Egypt(5). 1-Hexanol was detected but not quantified in the emissions of waste exudate(6), lab waste headspace(6) and kitchen waste exudate(7). |
| Soil Adsorption/Mobility | A Koc of 10.2 was determined for 1-hexanol on a Hagerstown silt loam soil(1). According to a suggested classification scheme(2), this Koc value suggests that 1-hexanol is expected to have very high mobility in soil. |
| Natural Pollution Sources | REPORTED FOUND AMONG CONSTITUENTS OF SEVERAL ESSENTIAL OILS & AROMAS: APPLE, STRAWBERRY, TEA, VIOLET (LEAVES & FLOWERS), JAVA CITRONELLA, BOURBON GERANIUM, LAVENDER, LAVANDIN, SPIKE, LITSEA ZEYLANICAALSO IDENTIFIED IN BITTER ORANGE.OCCURS AS ACETATE IN SEEDS & FRUITS OF HERACLEUM SPHONDYLIUM L & H GIGANTEUM FISCH, UMBELLIFERAE.1-Hexanol is a fatty alcohol and is derived from natural fats, oils, and waxes from a number of animal(1), vegetable(1-3), fruit(4) and marine sources(1,8). 1-Hexanol is released to the atmosphere in emissions from vegetation(5-6). For example, the emission rate of hexanol from apples harvested from two orchards in August-October of 1990 ranged from 3.8-117.6 pico-L/kg-hr(7). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2282 (HEXANOLS) |
| Zollcode | 29051900 |
| RTECS-Nr. | MQ4025000 |
| R-Sätze (R) | 22 |
| Toxizität | LD50 oral in rat: 720mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24/25 |
| Gefahrenklasse | 3Acute Tox. 4 DermalAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 111-27-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 559 °F |
Anwendungen & Verwendung
Beschreibung
Hexyl alcohol has a fruity odor and aromatic flavor. May be synthesized by reduction of n-caproic acid; the n-hexyl alcohol represents one of the 14 possible isomers of this alcohol.
Occurrence
Reported found among the constituents of several essential oils and aromas: apple, strawberry, tea, violet (leaves and flowers), Java citronella, Bourbon geranium, lavender, lavandin, spike, Litsea zeylanica; also identified in bitter orange. Also reported found in over 300 natural sources including apples, banana, sweet and sour cherry, citrus peel oils and juice, kumquat peel oil, berries, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, asparagus, kohlrabi, cabbage, celery, cucumber, lettuce, leek, garlic, raw and cooked potato, sauerkraut, tomato, bell pepper, ginger, mint oils, mustard, breads, cheeses, butter, milk, fatty fish, meats, cognac, whiskies, rum, cider, grape wines, coffee, tea, cocoa, peanut oil, pecans, soybeans, nuts, coconut meat and milk, avocado, olive, passion fruit, plum, beans, mushrooms, starfruit, mango, fenugreek, sesame seed oil, figs, kelp, cardamom, coriander, gin, rice, fruit brandies, prickly pear, licorice, lovage corn oil, endive, truffles and other sources
Verwenden
1-Hexanol was examined as a perturbing agent on actomyosin ATPase and and was found to modulate the function of actomyosin motor via intermediate-specific structural perturbation.
Herstellung & Synthese
synthetische
By reduction of n-caproic acid; the n-hexyl alcohol represents 1 of the 14 possible isomers of this alcohol