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インドール
インドール · 2,3-ベンゾピロール · ベンゾピロール · 1H-インドール · インドル · インドール類 · インド-ル · インドール標準品
識別子と物理属性
| CAS No. | 120-72-9 |
|---|---|
| 分子式 | C8H7N |
| 平均分子量 | 117.15 g/mol |
| 単同位体質量 | 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 |
| 現地名 | インドール |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 15.8 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 101 |
| LogP（分配係数） | 2.14Log P= 2.14 |
| LogS | -1.52 |
| 臭い | ALMOST FLORAL ODOR WHEN HIGHLY PURIFIED, OTHERWISE EXHIBITS CHARACTERISTIC ODOR OF FECESUnpleasant odor in high concentration but pleasant in dilute solution.Light jasmine odor糞便臭、フローラリン高希釈 |
| 密度 | 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 |
| 溶解度 | 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.メタノール: 0.1 g/mL、透明2.80g/L（25℃） |
| 沸点 | 254253 °C @ 762 mm Hg128-133 °C @ 28 mm Hg253.00 to 254.00 °C. @ 760.00 mm Hg253-254 °C (lit.) |
| 融点 | 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.) |
| 蒸気圧 | 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 |
| 屈折率 | 1.6300 |
| 引火点 | >230 °F |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 3.17 (quoted, Sangster, 1989) |
| 色 | 白～ほんのりピンク |
| pH | 5.9 (1000g/l, H2O, 20℃) |
| 臭気閾値 | 0.0003ppm |
| 由来生物 | synthetic |
| においのタイプ | 動物 |
| Merck | 14,4963 |
| JECFA Number | 1301 |
| BRN | 107693 |
| ヘンリー定数 | 1.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定していますが、光や空気に敏感な場合があります。強力な酸化剤、鉄および鉄塩とは相容れない。 |
| 化粧品成分の機能 | 香料 |
| 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（分配係数） | 2.14-2.24 |
| CAS データベース | 120-72-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Indole(120-72-9) |
| EPAの化学物質情報 | Indole (120-72-9) |
化学的特性
Indole has an unpleasant odor at high concentration, odor becomes floral at higher dilutions
化学性质
板状結晶，融点52℃，沸点254℃
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 有害性の概要 | 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 |
| 処分方法 | 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. |
| 体内負荷 | 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). |
| 相互作用 | POSITIVE INOTROPIC EFFECTS OF INDOLE ON ISOLATED GUINEA PIG ATRIA WAS ANTAGONIZED BY PROPRANOLOL & PRETREATMENT WITH RESERPINE. |
| 環境中動態 | 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). |
| 食品調査値 | 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 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | NL2450000 |
| 輸送番号（UN） | UN 2811 6.1/PG 3 |
| 毒性 | LD50 orally in rats: 1 g/kg (Smyth) |
| 税関コード | 2933 99 20 |
| 危険文句（R） | 21/22-37/38-41-50/53-36-39/23/24/25-23/24/25-52/53 |
| 化審法 | (5)-130 |
| 危険表示 | Xn,N,T |
| 安全措置（S） | 26-36/37/39-60-61-45-36/37 |
| 危険等級 | 9Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Eye Irrit. 2 |
| 包装等級 | III |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 120-72-9(Hazardous Substances Data) |
用途
解説
インドール，複素環式芳香族化合物の一つで，2,3‐ベンゾピロール，1‐アザインデン，1‐ベンズアゾールなどと呼ばれる。1866年J.F.W.A.vonバイヤーがインジゴの構造研究の際はじめて見いだし，インジゴにちなみ命名された。コールタール，ジャスミン油中に含まれ，またはトリプトファンの代謝生成物として動物の排泄物中に含まれる．工業的には，コールタールの220～270 ℃ 留分から分離するか，アニリンとアセチレンから合成する．また，o-ニトロトルエンとシュウ酸ジエチルを原料としてインドール-2-カルボン酸をつくり，これを脱炭酸して合成される．無色の結晶．融点53 ℃，沸点254 ℃．普通の有機溶媒に可溶．弱酸性化合物でNHのHはpKa 16.97，プロトン化したものはpKa －3.5．λmax 226，282，290 nm(ε 27800，6200，5500)．強酸により樹脂化する．特有の悪臭をもつが，希薄溶液にすると特有の芳香になり，香料調合上に不可欠な成分の一つとして利用される．
用途
亜硝酸イオンの検出、有機合成原料(染料、アルカロイド）、花精油調合原料。
用途
香水、合成香料
説明
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.
天然物の起源
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
使用
In highly dil solutions the odor is pleasant, hence indole has been used in perfumery.
一般的な説明
Indole 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.
使用用途
インドールの臭いは、便臭に似た臭いと形容されますが、非常に低濃度の場合は花のような香りを呈する物質です。そのため、香水や香料の成分、花精油調合原料としての用途があります。天然のジャスミン油は、およそ2.5%のインドールを含有しているとされますが、天然オイルはコストが高いため、インドールは合成ジャスミン油の製造にも用いられています。 また、インドールの構造 (インドール環) はいろいろな有機化合物、特に生体物質に含まれています。多くの重要なアルカロイドにインドール母核構造が存在しており、インドール誘導体から作られた医薬品は多いです。 インドール誘導体の一部は19世紀末まで重要な染料の成分として用いられていました。インドールという名前は、植物由来の染料物質である「インディゴ」に由来しています。化学的には、亜硝酸イオンの検出や、有機合成原料 (染料、アルカロイドなど) などの用途で用いられます。
製法・合成法
製造方法
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.
純化方法
It can be further purified by sublimation in a vacuum or by zone melting. The picrate forms orange crystals from EtOH and has m 175o. [Beilstein 20 II 196, 20 III/IV 3176, 20/7 V 5.]