HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Indol
1H-INDOLE · Indol · FEMA 2593 · Benzazole · 2,3-BENZOPYRROLE · 1H-Indol · Indole-15N · 1-BENZAZOLE
Identifikatoren & physikalische Daten
| CAS No. | 120-72-9 |
|---|---|
| Summenformel | C8H7N |
| Durchschnittliche Molmasse | 117,15 g/mol |
| Monoisotopische Masse | 117,05784923 g/mol |
| SMILES | c1ccc2[nH]ccc2c1 |
| InChIKey | SIKJAQJRHWYJAI-UHFFFAOYSA-N |
| PubChem CID | 798 |
| ChEMBL | CHEMBL15844 |
| ChEBI | CHEBI:16881 |
| EC No. | 204-420-7 |
| DTXSID | DTXSID0020737 |
| Lokaler Name | Indol |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 15,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 101 |
| LogP (Verteilungskoeffizient) | 2.14Log P= 2.14 |
| LogS | -1.52 |
| Geruch | ALMOST FLORAL ODOR WHEN HIGHLY PURIFIED, OTHERWISE EXHIBITS CHARACTERISTIC ODOR OF FECESUnpleasant odor in high concentration but pleasant in dilute solution.Light jasmine odor |
| Dichte | 1.22 g/cu cm at 25 °C |
| Color/Form | LEAFLETS (WATER, PETROLEUM), CRYSTALS (ETHER)Colorless to yellowish scales, turning red on exposure to light and air.WHITE CRYSTALLINE SOLIDColorless, shiny flakes |
| Löslichkeit | 3560SOL IN HOT WATER, HOT ALC, ETHER, BENZENE1 G IN 2 ML OF 70% ALCSOL IN TOLUENESoluble in fixed oilsinsoluble in mineral oil and glycerol.For more Solubility (Complete) data for INDOLE (6 total), please visit the HSDB record page.methanol: 0.1 g/mL, clear2.80 g/L (25 ºC) |
| Siedepunkt | 254253 °C @ 762 mm Hg128-133 °C @ 28 mm Hg253.00 to 254.00 °C. @ 760.00 mm Hg253-254 °C (lit.) |
| Schmelzpunkt | 52.552 °CHeat of Formation= 1.5660X10+8 J/kmolHeat of Fusion at the Melting Point= 9.0000X10+6 J/kmol52.5 °C51-54 °C (lit.) |
| Dampfdruck | 0.01 [mmHg]0.0122 mm Hg at 25 °C0.016 hPa (25 °C) |
| Heat of Combustion | 3.650 kJ/kg at 25 °C |
| Physical Description | Dry PowderLiquidWhite to yellowish solid with an unpleasant odorPleasant odor in dilute solutionsTurns red when exposed to light or air[Hawley] White or yellow crystalline powder[MSDSonline]White lustrous, flakey crystalline solidUnpleasant odour at high concentration, odour becomes floral at higher dilutions |
| Stability/Shelf Life | NOT VERY STABLE ON EXPOSURE TO LIGHT (TURNS RED) |
| FEMA | 2593 | INDOLE |
| Brechungsindex | 1.6300 |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 3.17 (quoted, Sangster, 1989) |
| Farbe | White to slightly pink |
| pH | 5.9 (1000g/l, H2O, 20℃) |
| Geruch | fecal odor, floral in high dilution |
| Geruchsschwelle | 0.0003ppm |
| Biologische Quelle | synthetic |
| Geruchsart | animal |
| Merck | 14,4963 |
| JECFA Number | 1301 |
| BRN | 107693 |
| Henry-Konstante | 1.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable, but may be light or air sensitive. Incompatible with strong oxidizing agents, iron and iron salts. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H |
| InChIKey | SIKJAQJRHWYJAI-UHFFFAOYSA-N |
| SMILES | c1ccc2[nH]ccc2c1 |
| LogP (Verteilungskoeffizient) | 2.14-2.24 |
| CAS Datenbank | 120-72-9(CAS DataBase Reference) |
| NIST chemische Informationen | Indole(120-72-9) |
| EPA chemische Informationen | Indole (120-72-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H311 (99%): Toxic in contact with skin [Danger Acute toxicity, dermal]H318 (11.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P262, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P316, P317, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1996 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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: 1H-IndoleCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)1H-Indole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Indole 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: 25-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/210201H-Indole: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | External application to rabbit eyes scored 8 on a scale of 1-10 (10 being most severe) for degree of injury after 24 hours[HSDB] Safe when used as a flavoring agent in food[JECFA] A severe eye irritant[RTECS] |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute Tox. 3 (99%)Eye Dam. 1 (11.6%)Acute toxicity (Oral) - Category 4Acute toxicity (Dermal) - Category 3Serious eye damage/eye irritation - Category 2AHazardous to the aquatic environment (Acute) - Category 1 |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Körperbelastung | 4 of 46 human adipose tissue samples, collected in 1982, contained indole (3 in age category 45+, 1 in age category 15-44 years)(1).PERSONAL AIR: Expired air from control (n= 20), but not prediabetic (n= 14) or diabetic (n= 28) human study populations contained indole at unreported concns(1). |
| Wechselwirkungen | POSITIVE INOTROPIC EFFECTS OF INDOLE ON ISOLATED GUINEA PIG ATRIA WAS ANTAGONIZED BY PROPRANOLOL & PRETREATMENT WITH RESERPINE. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), and a measured Koc of 187 from a synthetic soil with 0-2% added humic acid(4), indicate that indole will have moderate mobility in soil(SRC). Volatilization of indole should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.3X10-7 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(5) and water solubility(6). Indole is expected to readily biodegrade under both aerobic and anaerobic conditions in soil(SRC). Indole, added to Chernozem soil at 1 and 10 g/kg soil, was completely biodegraded in 19 and 135 days, respectively(7). Indole was completely biodegraded by suspensions of an organic soil (Carlisle muck) under methanogenic and denitrifying conditions within 67 and 144 days, respectivelyoxindole was reported as a metabolite of this process(8).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), and a measured Koc value of 187(3) indicate that indole may adsorb to suspended solids and sediment in water(SRC). Indole is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 5.3X10-7 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5). According to a classification scheme(6), an estimated BCF value of 25(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Indole is expected to readily biodegrade under both aerobic and anaerobic conditions in water(SRC). At 10 °C, aerobic groundwater containing a mixture of aromatic compounds completely biodegraded indole in 310 hours, including an acclimation period of 130 hours(7). Complete metabolism of indole by methanogenic sediments from the shore, edge, and bottom of Buffalo Run stream, PA, occurred within 33 daysoxindole was formed during this process(8). Indole was completely biodegraded under denitrifying conditions in 7 days using a sewage inoculum(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), indole, which has a measured vapor pressure of 0.0122 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase indole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, nitrate radicals, and ozone(SRC)the half-lives for these reactions in air are estimated to be about 2 to 3 hours, < 1 minute, and 6 hours, respectively(3,SRC). |
| Lebensmitteluntersuchungswerte | Different samples of Beaufort cheese from the French Alps contained indole at unreported concns(1). Indole, at unreported concns, was reported as a volatile flavor compound in fried bacon(2), roasted filbert nuts(3), short-necked clams and corbicula(4), and pork(5). Water-boiled duck meat and duck fat contained indole at 1.72 and 2.28 ppb, wet basis, respectively(6). |
| Plant Concentrations | Volatile compounds identified in Lonicera japonica flowers (Japanese honeysuckle) contained indole at concns of 52, <20, and 87 ug/kg for fresh flowers, flowers after 12 hours, and flowers after 24 hours, respectively(1). |
| Effluent Concentrations | Indole was detected in industrial wastewaters from the following industries: timber products, leather tanning, iron and steel manufacturing, inorganics and plastics, synfuels, and publicly owned treatment works(1). Process water derived from the Fischer Assay retorting of oil shale from Rundle, Australia contained indole at 3 mg/l(2). A grab sample of final effluent from the Addison, IL publicly-owned treatment works in April 1980 contained indole at unreported concns(3). Wastewater obtained during the gasification of Indian Head lignite contained indole at an estimated concn of 1 mg/l(4). Wastewater and sludge from the Iona Island Sewage Treatment plant, Vancouver, British Columbia contained indole at unreported concns(5).Untreated coke plant wastewater contained indole from 23 to 26,000 ug/l(1). Volatile components in poultry manure contained indole at concns of 5.08 and 10.4 mg/kg(2). Indole was identified in creosote oil extracts at 7700 ug/g(3). Basin floodwater, taken from Fort Devens, MA, following primary treatment, contained indole at 11 ug/l(4,5). Chlorinated still bottom extract contained indole at unreported concns(6). |
| Soil Adsorption/Mobility | A Koc of 187 was measured for indole on a synthetic soil consisting of 88-90% sand, 10% clay and 0-2% humic acid(1). The Koc of indole is estimated as approximately 350(SRC), using a measured log Kow of 2.14(2) and a regression-derived equation(3,SRC). According to a recommended classification scheme(4), these Koc values suggest that indole has moderate mobility in soil(SRC). |
| Natural Pollution Sources | Indole is found as a component of jasmine oil and orange-blossom oil(1). |
| Atmospheric Concentrations | INDOOR AIR: Indoor air from 11% of the sampled private homes in the Chicago, IL area contained indole at unreported concns (n= 36)(1).URBAN AIR: Both vapor phase and aerosol fractions of urban air contained indole at unreported concns(1). Indole was identified on aerosols collected from the Southern North Atlantic Ocean at a mean concn of 0.18 ng/cu m(2). |
| Fish/Seafood Concentrations | Three samples of commercial Mytilus edulis (blue mussel), collected near Holbaek, Denmark, contained indole(1). |
| Artificial Pollution Sources | Indole's production and use as a chemical intermediate(1,2), a perfume fixative(2), a synthetic flavor(3) and its possible use as a kairomone (a volatile chemical released by a plant to attract phytophagus insects - used for insect control of adult rootworms)(4) may result in its release to the environment through various waste streams(SRC). Indole is released directly to the environment as a component of tobacco smoke(5). High-temperature coal tar contains on average just under 0.2% indole(6). |
| Environmental Biodegradation | Groundwater containing a mixture of aromatic hydrocarbons and aromatic nitrogen-, sulfur-, and oxygen-containing heterocyclics, including indole initially present at 0.2 to 1 mg/l, gave an aerobic degradation time (defined as the total time from the start of the experiment until a concn less than 1 ug/l is reached) for indole of 310 hours including an acclimation time of 130 hours at 10 °C(1). Indole, in a 5 day BOD test, reached 49.5% of the theoretical BOD using a mixed microbial inoculum obtained from an enrichment culture(2). A 5 day BOD test gave a BOD of 2.07 g/g for indole using a sewage inoculum(3). First order biodegradation rate constants of 4.3X10-2 BOD/hr and 7.7X10-2 spec/hr were measured for indole at 1.6, 2.5, and 3.2 mg/l for a BOD and a UV spectrophotometry detection method, respectivelythe inoculum used was a mixed culture obtained from an enrichment culture technique(3). A reaction pathway for the aerobic biodegradation of indole was proposed: indole to indoxyl to dihydroxyindole to isatin to formylanthranilic acid to anthranilic acid to catechol(5). Indole, added to Chernozem soil at 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 g/kg soil, was completely biodegraded in 19, 37, 62, 72, 84, 92, 102, 131, and 135 days, respectively(6).Indole was completely biodegraded in 10 days under methanogenic conditions using a 9% anaerobic sewage sludge inoculum forming oxindole as an intermediate metabolitethe concn of indole in the sterile control over this time remained unchanged(1). Throughout the incubation period, net methane production increased, indicating that indole was mineralized(1). Complete metabolism of indole by methanogenic sediments from the shore, edge, and bottom of Buffalo Run stream, PA, occurred within 33 days. As indole disappeared, stoichiometric amounts of oxindole appeared in the sediment suspensions and persisted for over 4 weeks and was completely eliminated over 110 days(2). Complete biodegradation of indole was reported in 24 days using a 9% digested sludge inoculum at 22 °C under methanogenic conditions(2). Indole was completely biodegraded by suspensions of an organic soil (Carlisle muck) under methanogenic conditions within 67 daysconcurrently, oxindole appeared, and persisted in near stoichiometric amounts for about 3 weeks(2). No oxindole accumulated under denitrifying conditions, using a soil inoculum, during the 144 days which were required for indole to disappear(2). This pattern was again seen using a 9% sewage sludge inoculum under methanogenic and denitrifying conditionsboth conditions required 7 days for complete disappearance of indolehowever, oxindole accumulated temporarily in the methanogenic culture but was not seen in the denitrifying culture probably due to rapid metabolism of this compound(2). |
| F | 8-13 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 2933 99 20 |
| RTECS-Nr. | NL2450000 |
| R-Sätze (R) | 21/22-37/38-41-50/53-36-39/23/24/25-23/24/25-52/53 |
| Toxizität | LD50 orally in rats: 1 g/kg (Smyth) |
| Gefahrensymbole | Xn,N,T |
| Sicherheitshinweise (S) | 26-36/37/39-60-61-45-36/37 |
| Gefahrenklasse | 9Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Eye Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 120-72-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Indole has an almost floral odor when highly purified. Otherwise, it exhibits the characteristic odor of feces. It is not very stable on exposure to light (turns red). Indole may be obtained from the 220 - 260°C boiling fraction of coal tar or by heating sodium phenylglycine-o-carboxylate with NaOH, saturating the aqueous solution of the melt with C 02, and finally reducing with sodium amalgam; can be prepared also by the reduction of indoxyl, indoxyl carboxylic acid, or indigo.
Occurrence
Reported occurring in several natural products as a complex compound that decomposes during enfleurage or steam distillation yielding free indole; reported found in the essential oil from flower of Jasminum grandiflorum, in neroli oil and in the oil extracted from flowers of bitter orange; also reported in the flowers of several plants: lemon, coffee, Hevea brasiliensis and Randia formosa in the oil extracted from flowers of Jasminum odoratissinium L. and in the oil of Narcissus jonquilla. Also reported found in apricot, mandarin orange peel oil, grapes, kohlrabi, French fried potato, crispbread, cheeses, butter, milk, milk powder, boiled egg, fish oil, chicken, beef, pork, beer, rum, Finnish whiskey, red and white wine, coffee, tea, soybean, mushrooms, cauliflower, figs, rice, licorice, buckwheat, malt, wort, elder flower, clary sage, shrimp, okra, crab, clam, squid and green maté
Verwenden
In highly dil solutions the odor is pleasant, hence indole has been used in perfumery.
Herstellung & Synthese
synthetische
Obtained from the 220 to 260°C boiling fraction of coal tar or by heating sodium phenyl-glycine-o-carboxylate with NaOH, saturating the aqueous solution of the melt with CO2 and finally reducing with sodium amalgam; can be prepared also by the reduction of indoxyl, indoxyl carboxylic acid or indigo.