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3-甲基吲哚
糞素 · 烘臭类 · 糞臭素 · 粪臭素 · 3-甲基吲 · 3-甲吲哚 · 3-甲基吲哚 · β-甲基吲哚
标识与物理属性
| CAS No. | 83-34-1 |
|---|---|
| 分子式 | C9H9N |
| 平均分子量 | 131.17 g/mol |
| 单同位素质量 | 131.07349929 g/mol |
| SMILES | Cc1c[nH]c2ccccc12 |
| InChIKey | ZFRKQXVRDFCRJG-UHFFFAOYSA-N |
| PubChem CID | 6736 |
| ChEMBL | CHEMBL1329793 |
| ChEBI | CHEBI:9171 |
| EC No. | 201-471-7 |
| DTXSID | DTXSID8021775 |
| 中文名 | 3-甲基吲哚 |
化学与物理性质
| XLogP | 2.6 |
|---|---|
| 极性表面积 | 15.8 |
| 氢键供体 | 1 |
| 氢键受体 | 0 |
| 可旋转键 | 0 |
| 重原子 | 10 |
| 形式电荷 | 0 |
| 复杂度 | 122 |
| 物质类别 | Nitrogen Compounds -> IndolesWaste-water effluent contaminant |
| SpringerMaterials Properties | Angular frequency |
| 香料 | Fragrance Ingredient (Skatole) -> IFRA transparency List |
| LogP（油水分配系数） | LogP= 2.60 |
| 气味 | CHARACTERISTIC FECAL ODOR AT HIGH LEVELS, BECOMING PLEASANT, SWEET, AND WARM AT VERY LOW LEVELSindole-like odor |
| 味道 | WARM, OVER-RIPE, FRUITY FLAVOR BELOW 0.1 PPM |
| 食品添加剂 | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 食用香料 | EU Flavoring substances |
| Color/Form | LEAVES FROM PETROLEUM ETHERWHITE-BROWN SCALESWhite crystalline substance, browning upon aging. |
| 溶解性 | SOL IN HOT WATER, ALC, BENZENE, CHLOROFORM, ETHERSOL IN ACETONE, WATER, ETHANOL, ETHER0.498 mg/mLSoluble in boiling waterSoluble (in ethanol)6.8 [ug/mL] (The mean of the results at pH 7.4)Chloroform (Slightly), Methanol (Slightly)Soluble in water, Ether, Alcohols, Benzene, Acetone, Chloroform. |
| 沸点 | 265-266 °C @ 755 MM HG265.00 to 266.00 °C. @ 755.00 mm Hg265-266 °C (lit.) |
| 熔点 | 95 °C97.5 °C92-97 °C (lit.) |
| 密度 | 1.0111 (estimate) |
| FEMA | 3019 | SKATOLE |
| 折射率 | 1.6070 (estimate) |
| 闪点 | 132 °C |
| 储存条件 | Store below +30°C. |
| pKa（酸度系数） | 17.30±0.30(Predicted) |
| 形态 | Crystalline Powder or Flakes |
| 颜色 | Almost white to pale brown |
| 嗅觉阈值 | 0.0000056ppm |
| 香型 | animal |
| 生物来源 | synthetic |
| 敏感性 | Light Sensitive |
| Merck | 14,8560 |
| JECFA Number | 1304 |
| BRN | 111296 |
| 亨利常数 | 2.9×10-5 mol/(m3Pa) at 25℃, Wetlaufer et al. (1964) |
| 稳定性 | Stable, but light-sensistive. Stench! Incompatible with strong oxidizing agents, strong acids, acid ahydrides, acid chlorides. Combustible. |
| 主要应用 | flavors and fragrances |
| 化妆品成分功效 | PERFUMING |
| InChI | 1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 |
| InChIKey | ZFRKQXVRDFCRJG-UHFFFAOYSA-N |
| SMILES | Cc1c[nH]c2ccccc12 |
| LogP（油水分配系数） | 2.60 |
| CAS 数据库 | 83-34-1(CAS DataBase Reference) |
| NIST化学物质信息 | 1H-Indole, 3-methyl-(83-34-1) |
| EPA化学物质信息 | 3-Methylindole (83-34-1) |
化学性质
白色结晶。沸点265-266℃，熔点93-96℃，溶于3体积95%乙醇及油质香料。有带咸臭而强的吲哚样动物香，气势非常有力，扩散力强，很持久。浓度高时的气息令人作呕，仅在极低浓度下才有大灵猫香样动物香，味觉是温暖过熟熟果样口味。
安全与法规
| GHS 分类 | This chemical does not meet GHS hazard criteria for 76% (304 of 400) of all reports.WarningH315 (19.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 400 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 法规信息 | Chemical: 1H-Indole, 3-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Cease Manufacture Update: 21-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/235051H-Indole, 3-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 其他安全信息 | IMAP assessments - 1H-Indole, 3-methyl-: Human health tier I assessment |
| 危害概述 | Caused no irritation in humans following 24 hour closed patch test (2% in petrolatum)[HSDB] Lethal doses by intravenous and oral routes produced pulmonary lesions in cattle[RTECS] Safe when used as a flavoring agent in food[JECFA] See Indole. |
| Hazard Classes and Categories | Skin Irrit. 2 (19.5%) |
| 清理方法 | CHEM SCRUBBING SYSTEMS ARE ATTRACTIVE FOR CONTINUOUSLY HANDLING LARGE VOL OF GAS CONTAINING VERY LOW CONCN OF POTENT ODORANTS. THESE SYSTEMS USUALLY FUNCTION BY OXIDN OF THE ODORANT. THE ODOR CONTROL OF SKATOLE IS DISCUSSED FOR EACH OF THE OXIDIZERS: NAOCL, CL2, KMNO4, AND O3.TWO TYPES OF AIR WASHERS, CROSS-CURRENT AND COUNTERCURRENT, WERE INSTALLED IN THE VENTILATION OF THE EXHAUST SYSTEM IN LIVESTOCK AND POULTRY FARMS, TO DEODORIZE THE AIR. ACTIVATED SLUDGE FROM A SEWAGE PLANT WAS ADDED TO THE CIRCULATING WATER. WASH WATER SAMPLES CONTAINED SKATOLE. |
| 处置方法 | 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. |
| 环境归趋 | TERRESTRIAL FATE: A methanogenic consortium, enriched from wetland soil completely mineralized 13 mg of 3-methylindole within 35 days(1). Based on a recommended classification scheme(2), an estimated Koc value of 600(SRC), indicates that 3-Methylindole will have low mobility in soil(SRC). Volatilization of 3-methylindole may occur slowly from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.1X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 600(SRC), determined from a structure estimation method(2), indicates that 3-methylindole is expected to adsorb to suspended solids and sediment in water(SRC). 3-Methylindole will volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 2.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 20 and 148 days, respectively(1,SRC). According to a classification scheme(5), an estimated BCF value of 56(1,SRC), from an experimental log Kow(4), suggests that bioconcentration in aquatic organisms is moderate, not high(SRC). When exposed to natural sunlight 3-methylindole may undergo photo-oxidative degradation. The aqueous rate constant for the photolysis of 3-methylindole was measured as 0.18 hr-1 with a half life of 3.8 hours(6). The major product of the aqueous photo-oxidative degradation of 3-methylindole is thought to be o-(N-formyl)aminoacetophenone(6).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-Methylindole, which has an extrapolated vapor pressure of 0.005 mm Hg at 25 °C(4,SRC), will exist primarily as a vapor in the ambient atmosphere. Vapor-phase 3-methylindole 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 about 0.64 hours(3,SRC). |
| 食品调查数值 | Cheese products obtained from dairy cattle in the French Alps were found to contain 3-methylindole(1). No concentration data are currently available. |
| Effluent Concentrations | Unspecified concentrations of 3-methylindole were detected in the secondary effluents of a municipal wastewater treatment facility in Addison Illinois(1). |
| Soil Adsorption/Mobility | The Koc of 3-methylindole is estimated as approximately 600(SRC), using an experimental log Kow of 2.60(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 3-methylindole has low mobility in soil(SRC). The value of Koc may be influenced by the pH of the soil for this compound due to the basic nature of the amine group(SRC). |
| Natural Pollution Sources | ...AFRICAN CIVET CATCELTIS RETICULOSA, A JAVANESE TREE.Common naturally occurring sources of 3-methylindole are feces, beetroot, and nectrandra wood(1,2). |
| Human Toxicity Excerpts | TESTED AT 2% IN PETROLATUM IT PRODUCED NO IRRITATION AFTER A 48-HR CLOSED-PATCH TEST ON HUMAN SUBJECTS.SKATOLE AND ITS METABOLIC INTERMEDIATES MAY BE RELATED TO HUMAN PATHOLOGICAL CONDITIONS, INCL MALABSORPTION SYNDROMES AND CERTAIN ANEMIAS AND HEPATIC COMA. 6-HYDROXYSKATOLE, THE MAJOR METABOLITE OF SKATOLE IN MAN, MAY BE A PSYCHOTROPIC SUBSTANCEIT IS EXCRETED AS THE SULFATE IN ELEVATED AMOUNTS IN THE URINE OF SOME SCHIZOPHRENIC PT. |
| Artificial Pollution Sources | 3-Methylindole's production and use in the fragrance industry and as a food additive(1,2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | A methanogenic consortium, enriched from wetland soil completely mineralized 13 mg of 3-methylindole within 35 days(1). |
| Environmental Bioconcentration | An estimated BCF value of 56 was calculated for 3-methylindole(SRC), using an experimental log Kow of 2.60(4) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate, not high(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 3-methylindole is estimated as 2.1X10-6 atm-cu m/mole(SRC) from its extrapolated value for vapor pressure, 0.005 mm Hg(1), and experimental water solubility, 498 mg/l(2). This value indicates that 3-methylindole will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 20 days(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 148 days(3,SRC). 3-Methylindole's Henry's Law constant(1,2,SRC) indicates that volatilization from moist soil surfaces will not be important(SRC). |
| Non-Human Toxicity Excerpts | IN FROGS, THE MINIMUM LETHAL DOSE OF SKATOLE ADMIN SC OR INTO THE ABDOMINAL LYMPH SAC WAS 1 G/KGA PARALYTIC ACTION ON THE CENTRAL NERVOUS SYSTEM RESULTED IN A COMPLETE ABOLITION OF SPONTANEOUS REFLEX AND RESP MOVEMENTS. AN ORAL DOSE OF 0.3 G SKATOLE/KG GIVEN TO GOATS PRODUCED DIFFUSE PULMONARY EDEMA WHICH RESULTED IN DEATH, AND ORAL OR IV ADMIN TO COWS CAUSED PULMONARY LESIONS. DEATH FROM PULMONARY EDEMA & EMPHYSEMA RESULTED IN 3/3, 0/2 AND 1/3 COWS GIVEN 0.2 (ORAL), 0.1 (ORAL) AND 0.06 G/KG (IV IN PROPYLENE GLYCOL), RESPECTIVELY.MICE TREATED ORALLY WITH 100 MG SKATOLE/KG SHOWED NO SIGNS OF PULMONARY DISEASE. ORAL INGESTION OF 200 MG/KG BY MICE ALSO FAILED TO INDUCE PULMONARY EMPHYSEMA, BUT PULMONARY CONGESTION DID OCCUR, AS SHOWN BY A REDUCTION IN THE PHOSPHOLIPID CONTENT OF THE LUNG AND INCREASES IN HEMOGLOBIN CONTENT. ...WHEN MICE WERE GIVEN SKATOLE (10 MG/KG BODY WT) IP FOR 15 CONSECUTIVE DAYS...LESIONS OF THE LIVER, SPLEEN, KIDNEY AND LUNGS WERE PRESENT BUT SHOWED MARKED REGENERATION AFTER THE DOSE WAS STOPPED.RABBITS INJECTED IN THE KNEE JOINT WITH A SINGLE DOSE OF SKATOLE (0.26 MMOL IN 1 ML AQUEOUS 50% PROPYLENE GLYCOL) DEVELOPED ACUTE ARTHRITIS AND AN ACUTE INFLAMMATION ORIGINATING IN THE SYNOVIAL TISSUE, WHILE RABBITS INJECTED IN THE KNEE JOINT WITH 0.04-0.26 MMOL SKATOLE ONCE WEEKLY FOR 6 WK DEVELOPED CHRONIC ARTHRITIS, THE SEVERITY INCREASING WITH INCREASING DOSAGES. ...SKATOLE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS NOT IRRITATING.3-METHYLINDOLE (3MI) WAS ORALLY ADMIN AS A SINGLE DOSE OF 0.1-0.2 G/KG WHICH THEN PRODUCED ACUTE PULMONARY EDEMA IN CATTLE. LUNG TISSUE COLLECTED AFTER 72 HR REVEALED VESICULATION AND DESQUAMATION OF ALVEOLAR TYPE I CELLS AS WELL AS HYPERPLASIA OF THE ALVEOLAR TYPE II CELLS. HYALINE MEMBRANE FORMATION, ALONG WITH MASSIVE ACCUMULATION OF TUBULAR MYELIN IN THE ALVEOLAR SPACES, WAS OBSERVED. PULMONARY CAPILLARIES WERE OCCLUDED WITH MICROTHROMBI, AND LEUKOCYTES INFILTRATED THE INTERSTITIUM AS WELL AS THE ALVEOLI. ACCUMULATION OF LARGE AGGREGATES OF GLYCOGEN IN THE ALVEOLAR TYPE II CELLS WERE THE MOST UNUSUAL CHANGES SEEN IN EXPTL ANIMALS.THE PATHOLOGIC FEATURES OF BRONCHIOLITIS WERE STUDIED IN HORSES AND PONIES FROM 30 MIN TO 27 DAYS AFTER AN ORAL DOSE OF 3-METHYLINDOLE (3MI). FROM 30 MIN TO 3 HR, LESIONS WERE LIMITED TO NONCILIATED BRONCHIOLAR EPITHELIAL (CLARA) CELLS, WHICH LOST APICAL CAPS AND CYTOPLASMIC GRANULES AND HAD DILATED SMOOTH ENDOPLASMIC RETICULUM (SER). AT 12 HR, NECROTIC CLARA CELLS WERE EXFOLIATEDDEGENERATION AND NECROSIS WERE EVIDENT, IN BRONCHIOLAR CILIATED CELLS. RARE EPITHELIAL CELLS WITH HYPERPLASTIC SER APPEARED ON THE DENUDED BASAL LAMINA AT 24 HR. INFLAMMATORY CELLS, EPITHELIA, FIBROBLASTLIKE CELLS, COLLAGEN, AND DEBRIS OCCLUDED MANY BRONCHIOLAR LUMENS FROM 3 TO 6 DAYS. REORGANIZATION RESULTED IN A SIMPLE COLUMNAR BRONCHIOLAR EPITHELIUM WITH RELATIVELY NORMAL CILIATED CELLS AND FEWER FIBROBLASTLIKE CELLS. HOWEVER, MATURE CLARA CELLS WERE RARE AT 27 DAYS, AND COLLAGENOUS BANDS STILL DIVIDED BRONCHIOLAR LUMENS. |
| Environmental Abiotic Degradation | When exposed to natural sunlight the aqueous rate constant for the photolysis of 3-methylindole was measured as 0.18 hr-1 with a half life of 3.8 hours(1). The major product of the photo-oxidative degradation of 3-methylindole is thought to be o-(N-formyl)aminoacetophenone(1). The vapor-phase reaction of 3-methylindole with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(2,SRC). This corresponds to an atmospheric half-life of about 0.64 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(3,SRC). |
| F | 8-13 |
| 水危害等级（WGK） | 2 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | MLD in frogs (mg/kg): 1000 s.c. (Bin-Ichi) |
| RTECS 号 | NM0350000 |
| 储存类别 | 11 - Combustible Solids |
| 安全说明（S） | 26-36-61 |
| 海关编码 | 29339920 |
| 危险品标志 | Xi,N |
| 危险类别 | Aquatic Chronic 2 |
| 危险类别码（R） | 36/37/38-51/53 |
| 毒害物质数据 | 83-34-1(Hazardous Substances Data) |
| 运输编号（UN） | UN3077 - class 9 - PG 3 - DOT/IATA UN3335 - Environmentally hazardous substances, solid, n.o.s., HI: all (not BR) |
用途与应用
概述
粪臭素白色鳞片或粉末状结晶(由石油醚中)，暴露于空气中时逐渐变深色；带(fecal)而强的吲哚样动物香。气势非常有力，扩散力强，很持久。浓度高时的气息令人作呕，仅在极低的浓度下才有大灵猫香样动物香。味觉是温暖过熟熟果样口味。熔点96℃(93～96℃)；沸点265～266℃；溶于沸水，溶于乙醇及其他一般有机溶剂中。
用途
粪臭素有很好的定香价值，常做定香剂使用，但只能用痕量才能在花香型香精中赋于大灵猫香，给人以一种过熟的花香。常用来配制大灵猫香。在香精配方中，常与苯乙酸、灵猫酮或巨环酮类同用来取得好的天然动物香效果，与檀香香气香料同用效果较好。
用途
有很好的定香价值，常作定香剂使用，但只能痕量用于花香型香精中来比拟大灵猫香，也常用来配制大灵猫香。还常与苯乙酸、灵猫酮或巨环酮类共用来取得好的天然动物香效果。极限痕量用于葡萄、干酪果香、坚果香等食用香精中。
用途
3-甲基吲哚具有令人不愉快的粪臭味，但经大量稀释后有愉快的香味，特别具有灵猫香基的香韵，在干酪、坚果、葡萄等制品中加入少量就有效果，在海味香精中加入，可具鱼肉味。
用途
用作有机合成试剂
用途
可用于生化试剂，对胰蛋白酶活性具有抑制作用。大量稀释后具有花香味，被用于香烟、香水中的香精、定香剂以及食物香料等。
用途
医药中间体；定香剂
制备与合成方法
生产方法
3-甲基吲哚存在于灵猫香、人类、干酪、牛奶和茶中。工业生产可由丙醛与苯肼加热脱去水分子而获得丙醛苯腙，然后同氯化锌或硫酸加热，脱去氨分子而得到3-甲基吲哚。