Skatole

131.17

131.17

111296

201-471-7

9W945B5H7R

122024

DTXSID8021775

LEAVES FROM PETROLEUM ETHER; WHITE-BROWN SCALES|White crystalline substance, browning upon aging.

29339920

15.8

2.6

Almost white to pale brown Crystalline Powder or Flakes

1.1±0.1 g/cm3

95 °C

265-266 °C @ Press: 755 Torr

132 °C

1.655

soluble in water, Ether, Alcohols, Benzene, Acetone, Chloroform.

Store below +30°C.

0.0055 mm Hg

MLD in frogs (mg/kg): 1000 s.c. (Bin-Ichi)

CHARACTERISTIC FECAL ODOR AT HIGH LEVELS, BECOMING PLEASANT, SWEET, AND WARM AT VERY LOW LEVELS

WARM, OVER-RIPE, FRUITY FLAVOR BELOW 0.1 PPM

WITH POTASSIUM FERROCYANIDE AND SULFURIC ACID IT GIVES A VIOLET COLOR

UN3077 - class 9 - PG 3 - DOT/IATA UN3335 - Environmentally hazardous substances, solid, n.o.s., HI: all (not BR)

2

36/37/38-51/53

26-36-61

NM0350000

Xi,N

Stable, but light-sensistive. Stench! Incompatible with strong oxidizing agents, strong acids, acid ahydrides, acid chlorides. Combustible.

P261-P273-P305 + P351 + P338

H315-H319-H335-H411

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.

|Warning|H315 (89.61%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 457 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

Unspecified concentrations of 3-methylindole were detected in the secondary effluents of a municipal wastewater treatment facility in Addison Illinois(1).

...AFRICAN CIVET CAT; CELTIS RETICULOSA, A JAVANESE TREE.|Common naturally occurring sources of 3-methylindole are feces, beetroot, and nectrandra wood(1,2).

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).

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).

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).

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).

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).

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).

Unspecified concentrations of 3-methylindole were reported in groundwater samples obtained near the Hipps road landfill, Jacksonville Florida(1). Unspecified concentrations of 3-methylindole were detected in groundwater near a Barcelona, Spain landfill(2).

Cheese products obtained from dairy cattle in the French Alps were found to contain 3-methylindole(1). No concentration data are currently available.

No occupational exposure data for 3-methylindole are currently available. Limited monitoring data indicate that there may be instances of contaminated groundwater resulting in the general population possibly being exposed to 3-methylindole primarily through ingestion of contaminated groundwater(1-3) and contaminated food(4).

EXPTL USE: MEDICATION (VET): INJECTED IM FOR 15 CONSECUTIVE DAYS TO INFECTED GUINEA-PIGS WEIGHING 200-300 G, 5 MG SKATOLE/DAY EXHIBITED TUBERCULOSTATIC ACTIVITY AGAINST MYCOBACTERIUM TUBERCULOSIS HOMINIS.

AFTER ADMIN OF SKATOLE TO CATTLE IN A DOSE OF 0.1-0.2 G SKATOLE/KG INTRARUMINALLY OR 0.06 G/KG BY JUGULAR INFUSION, THE MEAN PLASMA CONCN OF SKATOLE BECAME MAXIMAL AT 3 AND 9 HR, RESPECTIVELY.|GOATS WERE GIVEN A 2 HR JUGULAR INFUSION OF 3-METHYLINDOLE (3MI) CONTAINING (14)C-3MI USING PROPYLENE GLYCOL AS THE VEHICLE. 3MI WAS RAPIDLY CLEARED FROM BLOOD PLASMA AND TISSUES AFTER INFUSION, AND 81% OF THE RADIOACTIVITY WAS EXCRETED IN THE URINE BY 24 HR. MAX CONCN OF UNMETABOLIZED 3MI IN THE TISSUES RANGED FROM 2.6 TO 15 UG 3MI/G, INCL 7.5 UG 3MI/G IN THE LUNG. THE LUNG CONTAINED THE HIGHEST PROPORTION OF METABOLITES. THE DATA DEMONSTRATE THAT 3MI DOES NOT SELECTIVELY CONCENTRATE IN THE LUNG AND THAT THE CONCN ARE LOWER THAN THOSE USUALLY ASSOC WITH DIRECT MEMBRANE DAMAGE.

SKATOLE IS PRODUCED IN THE GI TRACT (SMALL INTESTINE AND RUMEN) BY THE BACTERIAL DEGRADATION OF DIETARY TRYPTOPHAN RESIDUES...|MATURE BEEF COWS GRAZING ON DRY SUMMER RANGE WERE MOVED TO LUSH GREEN PASTURE TO INDUCE ACUTE BOVINE PULMONARY EDEMA AND EMPHYSEMA (ABPE) AND TO DETERMINE WHETHER PLASMA AND RUMINAL FLUID 3-METHYLINDOLE (3MI) CONCN ARE RELATED TO THE DEVELOPMENT OF ABPE. IN VITRO PRODN OF 3MI WAS OBSERVED IN CULTURE MEDIA INOCULATED WITH RUMINAL FLUID, DEMONSTRATING THAT MICROORGANISMS CAPABLE OF PRODUCING 3MI WERE IN THE RUMEN. APPARENTLY RUMINAL MICROORGANISMS OF CATTLE CONVERT TRYPTOPHAN (CONTAINED IN LUSH FORAGE) TO 3MI, WHICH UPON ABSORPTION BY THE ANIMAL MAY RESULT IN THE ONSET OF ABPE.|FORMED FROM INDOLE-3-ACETIC ACID. YIELDS O-FORMAMIDOACETOPHENONE IN RAT, WHEAT; FRYDMAN RB ET AL; FEBS LETTERS 17: 273 (1971). YIELDS 5-HYDROXYSKATOLE, 7-HYDROXYSKATOLE IN RAT; DALGLIESH CE ET AL; BIOCHEM J 70: 13P (1958). YIELDS 6-HYDROXYSKATOLE IN RABBIT; JEPSON JB ET AL; BIOCHIM BIOPHYS ACTA 62: 91 (1962). YIELDS SALICYLIC ACID IN PSEUDOMONAS; PROCTOR MM; NATURE (LONDON) 181: 1345 (1958). /FROM TABLE/|GOATS WERE GIVEN JUGULAR INFUSIONS OF (14)C-3-METHYLINDOLE (3MI). A MAJOR ROUTE OF METABOLISM INVOLVED FORMATION OF 3-METHYLOXINDOLE AND SUGGESTS THAT A MIXED FUNCTION OXIDASE, PYRROLOOXYGENASE, MAY BE THE MAJOR METABOLIC SYSTEM INVOLVED. A MINOR ROUTE OF METABOLISM INVOLVED OXIDATION OF THE METHYL CARBON OF 3MI.|For more Metabolism/Metabolites (Complete) data for 3-METHYLINDOLE (6 total), please visit the HSDB record page.|3-methylindole has known human metabolites that include 3-methyleneindolenine and 3-methylindole-2,3-epoxide.

NUCLEOPHILIC THIOL AGENTS, GLUTATHIONE, L-CYSTEINE AND N-ACETYL-L-CYSTEINE, PROTECTED MICROSOMAL PROTEINS AGAINST ALKYLATION BY THE REACTIVE METABOLITE OF 3-METHYLINDOLE. THE CYTOSOL FRACTION FROM THE LUNGS OF CATTLE INCR THE PROTECTIVE EFFECT OF THESE THIOL AGENTS. PRETREATMENT OF SHEEP WITH DIETHYLMALEATE, WHICH DEPLETES GLUTATHIONE, INCR THE SEVERITY OF THE PNEUMOTOXIC EFFECT OF 3-METHYLINDOLE, WHEREAS PRETREATMENT WITH L-CYSTEINE DECR THE SEVERITY OF THIS EFFECT. THESE FINDINGS ARE CONSISTENT WITH A HYPOTHESIS THAT AN ELECTROPHILIC REACTIVE METABOLITE OF 3-METHYLINDOLE IS RESPONSIBLE FOR ITS PNEUMOTOXIC EFFECT AND IMPLIES THAT GLUTATHIONE AND GLUTATHIONE S-TRANSFERASES ARE INVOLVED IN THE DETOXIFICATION OF THIS REACTIVE METABOLITE.|INCUBATION OF VARIOUS INDOLIC COMPD WITH GOAT LUNG MICROSOMES SHOWED THAT ONLY 3-METHYLINDOLE WAS ABLE TO GENERATE A FREE RADICAL IN THE NADPH-DEPENDENT MICROSOMAL SYSTEM, AS TESTED BY SPIN-TRAPPING. ENZYMIC RADICAL FORMATION FROM 3-METHYLINDOLE SUGGESTS A MICROSOMAL-ACTIVATED FREE RADICAL MECHANISM FOR THE SPECIFICITY OF 3-METHYLINDOLE-INDUCED PULMONARY TOXICITY.|Bioactivation of 3-methylindole (3MI), a highly selective pneumotoxin in goats, was investigated in human lung and liver tissues in order to provide information about the susceptibility of humans to 3MI toxicity. Human lung microsomes were prepared from eight organ transplantation donors and liver microsomes from one of the donors were /selected/. The 3MI turnover rate with human lung microsomes was 0.23 +/- 0.06 nmol/mg/min, which was lower than the rate with the human liver microsomes (7.40 mnol/mg/min). The activities were NADPH dependent and inhibited by l-aminobenzotriazole, a potent cytochrome p450 suicide substrate inhibitor. Covalent binding of 3MI reactive intermediates to human tissues was determined by incubation of (14)C-3MI and NADPH with human lung and liver microsomal proteins. Although human lung microsomes displayed measurable covalent binding activity (2.74 +/- 2.57 pmol/mg/min), the magnitude of this reaction was only 4% as large as that seen with human liver microsomes and also was inhibited by l-aminobenzotriazole. Therefore, the bioactivation of 3MI to covalently binding intermediates is catalyzed by cytochrome p450 in human pulmonary tissues. These activities were compared to those activities measured with tissues from goats. Proteins from goat and human pulmonary and hepatic microsomal incubations were incubated with radioactive 3MI, and radioactive proteins were analyzed by SDS-PAGE and HPLC and visualized by autoradiography and radiochromatography, respectively. The results showed that a 57-kDa protein was clearly the most prominently alkylated target associated with 3MI reactive intermediates. These data suggest that humans may be susceptible to 3MI mediated toxicities and that the specificity of covalent binding and the extent of binding to target proteins may play important roles in organ and species selective susceptibilities to 3MI pneumotoxicity.

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 SUBSTANCE; IT IS EXCRETED AS THE SULFATE IN ELEVATED AMOUNTS IN THE URINE OF SOME SCHIZOPHRENIC PT.

3 Methylindole

1H-Indole, 3-methyl-: ACTIVE|SKATOLE (0.001-0.1% IN THE DIET) ADVERSELY AFFECTED LARVAL GROWTH AND DEVELOPMENT AND THE SUBSEQUENT REPRODUCTIVE CAPACITY OF THE BOLLWORM, HELIOTHIS ZEA. IT IS AN ATTRACTANT FOR THE PALM WEEVIL RHYNCHOPHORUS PALMARUM AND FOR HIPPELATES EYE GNATS. ... SKATOLE HAS BEEN SHOWN TO...CAUSE, AT LEVELS OF 0.2-0.4 MG/ML, TOTAL INHIBITION OF LATERAL GROWTH BY SCLEROTINA TRIFOLIORUM, THE CLOVER ROT FUNGUS, TO EFFECT IN 100 PPM CONCN GREATER THAN 75% INHIBITION AGAINST THE RUBBER-TREE MOLDY-ROT FUNGUS MYCELIUM...|SKATOLE ACTS AS A PLANT HORMONE SHOWING AUXINIC EFFECTS IN LENS CULINARIS ROOTS AND AFFECTING SEED GERMINATION AND GROWTH OF STELLARIA MEDIA AND HYPTIS SUAVEOLENS AS WELL AS THE GROWTH OF PLANT TISSUES IN VITRO.|SYNTHETIC FLAVOR INGREDIENTS- SKATOLE: FLAVOR USEFUL IN CHEESE, GRAPE, BERRY, NUT, EGG.|REPORTED USES: NON-ALCOHOLIC BEVERAGES, 0.75 PPM; ICE CREAM, ICES, ETC, 1.0 PPM; CANDY, 0.78 PPM; BAKED GOODS, 0.80 PPM; GELATINS AND PUDDINGS, 0.01 PPM; CHEWING GUM, 0.10 PPM.|For more General Manufacturing Information (Complete) data for 3-METHYLINDOLE (7 total), please visit the HSDB record page.

PRODUCT ANALYSIS: GAS CHROMATOGRAM, RIFM NUMBER 74-150; INFRA-RED CURVE, RIFM NUMBER 74-150.|ANALYSIS OF POLYCYCLIC AROMATIC COMPOUNDS CONTAINING NITROGEN AND OXYGEN BY MATRIX ISOLATION FOURIER TRANSFORM IR SPECTROSCOPY.|TEXT

GAS CHROMATOGRAPHIC DETERMINATION OF INDOLES IN HUMAN MOUTH SALIVA USING A FLAMELESS ALKALI SENSITIZED DETECTOR (NITROGEN/PHOSPHORUS-SPECIFIC DETECTOR, NPD).

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