Indole
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120-72-9c1ccc2[nH]ccc2c1SIKJAQJRHWYJAI-UHFFFAOYSA-N1H-indole is an indole and a polycyclic heteroarene. It has a role as an Escherichia coli metabolite. It is a tautomer of a 3H-indole.
120-72-9DTXSID0020737CHEMBL15844CHEBI:16881Nitrogen Compounds -> Indoles
Waste-water effluent contaminant
Log P= 2.14
2.14
2.27
ALMOST FLORAL ODOR WHEN HIGHLY PURIFIED, OTHERWISE EXHIBITS CHARACTERISTIC ODOR OF FECES
Unpleasant odor in high concentration but pleasant in dilute solution.
Light jasmine odor
LEAFLETS (WATER, PETROLEUM), CRYSTALS (ETHER)
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
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.
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
Chemical: 1H-Indole
Commission Regulation (EC) No 1565/2000 (Repealed by Com.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)
REACH registered substance: Indole (EC: 204-420-7)
1H-Indole: Does not have an individual approval but may be used under an appropriate group standard
Acute Tox. 4 (100%)
Acute toxicity (Oral) - Category 4
The effects of heterocyclic cmpd on hepatic xenobiotic metabolizing enzymes were studied in mice. Female CD-1 mice were admin 5 u mol/kg coumarin, trimethylene oxide (TMO), or trimethylene sulfide (TMS) for 6 days by gavage, or benzofuran, indole, or indole-3-carbinol (IC) daily for 10 days. Animals were /sacrificed/ 1 or 2 days after the last dose; livers were removed and assayed for epoxide hydrolase, glutathione-S-transferase (GST), reduced NADH-quinone-reductase (NADH/QR), glucose-6-phosphate-dehydrogenase (G6PDH), glutathione-reductase (GSSG-red), uridine-diphosphate-glucose-dehydrogenase (UDPGDH), aniline-hydroxylase, 7-ethoxycoumarin-deethylase (ECOD), and cytochrome-c-reductase (cyt-c-red) activities, and cytochrome p450. All cmpd except indole, significantly enhanced epoxide hydrolase activity. GST activities were elevated by all cmpd except TMO and TMS. NADH/QR activity was incr only by coumarin and benzofuran. Indole incr only GST, UDPGDH and cyt-c-red activities. IC enhanced GST, UDPGDH, cyt-c-red, epoxide hydrolase and cytochrome p450 and related monooxygenase activities. Benzofuran and coumarin showed more varied responses. Both cmpd incr epoxide hydrolase, GST and NADH/QR activities. Benzofuran decr cytochrome p450 content and elevated ECOD activity.
INDOLE UNDERGOES SCISSION OF PYRROLE RING TO YIELD N-FORMYLANTHRANILIC ACID, AN UNSTABLE COMPD WHICH DECOMP INTO ANTHRANILIC ACID & FORMIC ACID. INDOLE IS FIRST HYDROXYLATED TO GIVE INDOXYL & THEN ISATIN, & IT IS PROBABLY LATTER WHICH UNDERGOES HYDROLYTIC RING OPENING.
...INDOLE IS METABOLIZED BY RAT TO INDOXYL, OXINDOLE, 5-HYDROXYOXINDOLE & ISATIN...
YIELDS 2,2-BIS(3-INDOLYL)INDOXYL IN HORSERADISH. DEOXYVIOLACEIN IN CHROMOBACTERIUM. CIS-6,7-DIHYDRO-6,7-DIHYDROXYINDOLE PROBABLY IN PSEUDOMONAS. /FROM TABLE/
YIELDS 3,3'-DIINDOLYLACETIC ACID IN PEA. O-FORMAMIDOBENZALDEHYDE IN TECOMA. 3-HYDROXYOXINDOLE IN COCCUS. /FROM TABLE/
For more Metabolism/Metabolites (Complete) data for INDOLE (10 total), please visit the HSDB record page.
Indole has known human metabolites that include Oxindole, 6-Hydroxyindole, and Indoxyl.
불러오는 중…
Colorless to yellowish scales, turning red on exposure to light and air.
WHITE CRYSTALLINE SOLID
Colorless, shiny flakes
SOL IN HOT WATER, HOT ALC, ETHER, BENZENE
1 G IN 2 ML OF 70% ALC
SOL IN TOLUENE
Soluble in fixed oils; insoluble in mineral oil and glycerol.
For more Solubility (Complete) data for INDOLE (6 total), please visit the HSDB record page.
253 °C @ 762 mm Hg; 128-133 °C @ 28 mm Hg
253.00 to 254.00 °C. @ 760.00 mm Hg
Indole has an unpleasant odor at high concentration, odor becomes floral at higher dilutions
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.
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).
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, respectively; oxindole 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 days; oxindole 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).
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).
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).
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).
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).
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).
Found in feces, neroli oil, jasmine oil, orange-blossom oil, certain flowers, tobacco smoke, and coal tar; Used in perfumery, flavoring, and as chemical reagent, intermediate, and feedstock; [HSDB]
USED IN PERFUMERY
SYNTHETIC FLAVOR
Chemical reagent
Used as a chemical intermediate for the synthesis of indol-3-ylacetic acid; 4-indol-3-ylbutyric acid; L-tryptophan.
For more Uses (Complete) data for INDOLE (6 total), please visit the HSDB record page.
2023: 21,192 lb
(1986) No Data
PREPN FROM O-FORMOTOLUIDE: TYSON, ORG SYN COLL VOL III, 479 (1955); BY DEHYDROCYCLIZING ORTHO ALKYL ANILINES: ERNER ET AL, US PATENT 2,953,575 (1960 TO HOUDRY PROCESS); FROM N-(2-TOLYL)-N'-METHYL-N'-PHENYLFORMAMIDINE: LORENZ ET AL, J ORG CHEM 30, 2531 (1965).
OBTAINED FROM 240-260 °C FRACTION FROM COAL TAR: WEISSGERBER, CHEMISCHE BERICHTE 43, 3520 (1910); FROM FECES: BERGEIM, J BIOL CHEM 32, 17 (1917).
CAN BE PREPARED ALSO BY REDN OF INDOXYL, INDOXYL CARBOXYLIC ACID, OR INDIGO.
INDOLE IS PRODUCED BY CONDENSING ANILINE WITH BENZOIN IN THE PRESENCE OF ZINC CHLORIDE
For more Methods of Manufacturing (Complete) data for INDOLE (6 total), please visit the HSDB record page.
FOUND IN NEROLI OIL IN TRACE QUANTITIES /approx 0.1%/
CONSTITUTES 2.5% OF JASMINE OIL
Technical, CP, FCC
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Miscellaneous Manufacturing
1H-Indole: ACTIVE
REPORTED USES: NON-ALCOHOLIC BEVERAGE 0.26 PPM, ICE CREAMS, ICES, ETC 0.28 PPM; CANDY 0.50 PPM, BAKED GOODS 0.58 PPM, GELATINS & PUDDINGS 0.02-0.40 PPM.
FEMA NUMBER 2593
Adult corn rootworms are attracted strongly to a variety of kairomones, including indole...
개요인돌. 방향족 두고리 헤테로고리 화합물이다. N이 있어서 염기성일 것 같지만 질소의 전자가 모조리 방향족 전자구조에 기여하기 때문에 전혀 염기성이 아니다. 다섯고리 헤테로고리 화합물인 피롤에 벤젠이 달라붙어서 10개의 π전자를 갖게 되어 분자가 방향족성을 띈다.
용도순수한 인돌은 꽃향기가 난다(애초에 인돌이 속한 방향족 탄화수소에서 방향(芳香)이 꽃향기를 뜻한다). 향수 산업의 필수적인 화합물로, 자스민 오일은 2.5%의 인돌을 포함하고 있다. 하지만 스카톨과 함께 방귀의 산캐한냄새의 한 축을 담당하기도 한다.
개요Indole 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.
출처Reported 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
용도In highly dil solutions the odor is pleasant, hence indole has been used in perfumery.
일반 설명Indole is classified under the volatile flavor compounds (VFCs). It is known to play significant role in various biological functions such as anti-inflammatory, anticonvulsant, cardiovascular and antibacterial activities.
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.
정의indole: A yellow solid, C8H7N, m.p.52°C. Its molecules consist of a benzenering fused to a nitrogen-containingfive-membered ring. It occurs insome plants and in coal tar, and isproduced in faeces by bacterial action.It is used in making perfumes.Indole has the nitrogen atom positionednext to the fused benzenering. An isomer with the nitrogentwo atoms away from the fused ringis called isoindole.