Basic information Chemical properties Uses The standard of allowable maximum amount and residue Production methods Safety Supplier Related
ChemicalBook >  Product Catalog >  Flavors and fragrances >  Synthetic fragrances >  Halogen, sulfur, nitrogen compounds >  Nitrogen-containing compounds >  3-Methylindole

3-Methylindole

Basic information Chemical properties Uses The standard of allowable maximum amount and residue Production methods Safety Supplier Related

3-Methylindole Basic information

Product Name:
3-Methylindole
Synonyms:
  • FEMA 3019
  • BETA-METHYLINDOLE
  • 3-MI
  • 3-METHYL-1H-INDOLE
  • 3-METHYLINDOLE
  • SCATOLE
  • SKATOL
  • SKATOLE
CAS:
83-34-1
MF:
C9H9N
MW:
131.17
EINECS:
201-471-7
Product Categories:
  • Simple Indoles
  • Pyrroles & Indoles
  • IndoleDerivative
  • Pyrroles & Indoles
  • Indoles
  • Aromatics
  • Indole Derivatives
  • Heterocycle-Indole series
  • Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines
  • VX:15689727968
Mol File:
83-34-1.mol
More
Less

3-Methylindole Chemical Properties

Melting point:
92-97 °C (lit.)
Boiling point:
265-266 °C (lit.)
Density 
1.0111 (estimate)
FEMA 
3019 | SKATOLE
refractive index 
1.6070 (estimate)
Flash point:
132 °C
storage temp. 
Store below +30°C.
pka
17.30±0.30(Predicted)
form 
Crystalline Powder or Flakes
color 
Almost white to pale brown
Odor
indole-like odor
Odor Threshold
0.0000056ppm
Water Solubility 
Soluble in water, Ether, Alcohols, Benzene, Acetone, Chloroform.
Sensitive 
Light Sensitive
JECFA Number
1304
Merck 
14,8560
BRN 
111296
Stability:
Stable, but light-sensistive. Stench! Incompatible with strong oxidizing agents, strong acids, acid ahydrides, acid chlorides. Combustible.
InChIKey
ZFRKQXVRDFCRJG-UHFFFAOYSA-N
CAS DataBase Reference
83-34-1(CAS DataBase Reference)
NIST Chemistry Reference
1H-Indole, 3-methyl-(83-34-1)
EPA Substance Registry System
3-Methylindole (83-34-1)
More
Less

Safety Information

Hazard Codes 
Xi,N
Risk Statements 
36/37/38-51/53
Safety Statements 
26-36-61
RIDADR 
UN3077 - class 9 - PG 3 - DOT/IATA UN3335 - Environmentally hazardous substances, solid, n.o.s., HI: all (not BR)
WGK Germany 
2
RTECS 
NM0350000
8-13
TSCA 
Yes
HS Code 
29339920
Hazardous Substances Data
83-34-1(Hazardous Substances Data)
Toxicity
MLD in frogs (mg/kg): 1000 s.c. (Bin-Ichi)

MSDS

More
Less

3-Methylindole Usage And Synthesis

Chemical properties

It is a kind of white crystal. The boiling point is 265-266 ° C; melting point is 93-96 ° C; soluble in 95% ethanol and oil spices three times of its volume. It has the indole-like incense of animals with a salty and strong flavor. The flavor is very strong, with a solid proliferating ability and a long lasting long time. High concentration of it makes people disgusting; only a very low concentration bears a large civet-like and animals-like incense. Moreover, It has a warm ripe fruit-like taste.

Uses

1. 3-Methylindole has perfect fragrant value, often used as a fixative, but only used for the trace analysis of floral fragrance in comparison to large civet. It is also used to prepare large civet incense. A combination use with phenylacetic acid, cynomolone or giant ring ketone can get a fine natural animal fragrance. The ultimate trace analysis is used for grape, cheese, fruit, nuts and other fragrant flavor.
2. 3-methylindole has an unpleasant odor, while there is a pleasant fragrance after an enough dilution, especially the smell of civet-based incense. It will be effective in the cheese, nuts, grapes and other products by adding only a small amount. It can acquire a fish flavor when adding to seafood essence.
3. Used for organic synthesis reagents.
4. Used as a biochemical reagent with an inhibiting effect on trypsin. There is a floral fragrance after macrodilution. It is used in cigarettes, perfume in the fragrance, fragrance agent and food spices.
5. pharmaceutical intermediates; perfume fixative.

The standard of allowable maximum amount and residue

Name of additives: β-methyl indole
Name of food allowable for the additive: food
Function of the additive:Spices used in food
Maximum allowable amount (g/kg):The amount of spices to compound essence should be lower than the allowable maximum amount and residue listed in GB 2760.
Maximum allowable residue (g/kg):

Production methods

3-Methylindole present in civet, human, cheese, milk and tea. Propionaldehyde and phenylhydrazine can be heated to remove water molecules to obtain propanal phenylhydrazone in industrial production, and then the intermediates heated with zinc chloride or sulfuric acid, through the removal of ammonia molecules can obtain 3-Methylindole.

Chemical Properties

slightly brown platelets

Chemical Properties

Skatole has a characteristic putrid, fecal odor at high concentrations, becoming pleasant, jasmine-like, fruity sweet, warm at very low concentrations. It has a warm overripe fruity flavor below 1 ppm.

Occurrence

Reported found in beetroot, feces, coal tar, Swiss cheese, Gruyere cheese, mozarella cheese, butter, milk, goat and sheep milk, boiled egg, fatty fish, coffee, tea, trassi, rice bran, dried bonito and squid.

Uses

A highly fluorescent guanosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3?5?phosphodiester linkage using an automated DNA synthesizer

Uses

insect attractant

Uses

A naturally abundant pneumotoxin, found primarily in mammalian feces providing its strong fecal odor. In lower concentrations however, the compound has a pleasent aroma, giving orange blossoms and ja smine their pleasing scent. It is often a component of commercial fragrances and perfumes.

Definition

ChEBI: A methylindole carrying a methyl substituent at position 3. It is produced during the anoxic metabolism of L-tryptophan in the mammalian digestive tract.

Preparation

Prepared synthetically from the phenylhydrazone of propionaldehyde or by cyclization of o-toluidides (Bedoukian, 1967).

Aroma threshold values

Detection: 0.2 ppb

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 3532, 1977 DOI: 10.1021/ja00452a073
The Journal of Organic Chemistry, 45, p. 2709, 1980 DOI: 10.1021/jo01301a032
Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

Pharmacology

Skatole (l00mg dissolved in 2 ml sesame oil administered by gastric intubation) failed to prevent apoplexy in the adrenals of rats when administered 24 hr before injection of 5 mg of 7,12-dimethylbenz[a]anthracene (Huggins & Fukunishi, 1964).
In rat costal cartilage, skatole inhibited 35SO42-incorporation into chondroitin sulphate and 14C-labelled proline incorporation into protein (Liberti & Rogers, 1970). In concentrations of 5-10 mM, it inhibited oxygen uptake in slices of rat liver and rat-brain cortex (Lascelles & Taylor, 1968; Walshe et al. 1958). Skatole has also shown depressant (catatonic-like) activity on the swimming behaviour of guppies and the exploratory behaviour of rats (Sprince, 1969). When injected ip, 1 mmol/kg did not have any radioprotective effect in mice, the survival effect (ratio of mean survival time in a treated group to that of the control in 30 days after irradiation) being 0.97 or 0.70 when skatole was administered 30 or 5 min, respectively, before X-irradiation with 800 R (Shinoda et al 1974).
Skatole (1.0mM) caused >50% inhibition of the anaphylactic release of histamine from chopped, sensitized guinea-pig lung by chymotrypsin substrates and inhibitors (Austen & Brocklehurst, 1961). It had a non-specific excitatory action on the heart of the marine mollusc Venus mercenaria (Greenberg, 1960) and in a 194 μM concentration produced half-maximal positive inotropic activity in isolated left guinea-pig atria (Zetler, 1974).

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Indoles (skatole) with various substituents in the 2 and 3 position can be synthesized via the Fisher indole synthesis, which involves two steps and utilizes a phenylhydrazine and an aliphatic or aromatic aldehyde or ketone as starting materials.

Metabolic pathway

Three major metabolites of 14C-skatole are found in the plasma/urine of pigs given skatole and are identified as 6-sulfatoxyskatole, 3-hydroxy-3- methyloxindole, and the mercapturate adduct of skatole, 3-[(N-acetylcysteine-S-yl)methyl]indole. For other pathways, see the references in the text.

Metabolism

3-Methylindole (skatole) has been reported by several authors to be excreted as an ethereal sulphate by dogs, rats and man; distillation of the urine results in the formation of indole, which might well be derived by decarboxylation of indolyl-3-carboxylic acid, an expected oxidation product of skatole (Williams, 1959). Oral administration of skatole to rats resulted in the urinary excretion of a mixture of sulphate esters of hydroxyskatoles (Dalgliesh, Kelly & Horning, 1958; Horning, Sweeley, Dalgliesh & Kelly, 1959). The faeces of rats fed a chow diet were found to contain typtophan metabolites, including up to 0.78 ?g skatole/g wet faeces (Anderson, 1975). Metabolites of skatole were detected in the urine of a human subject fed skatole (Sano & Miyanoki, 1955). In man, skatole has been shown to undergo hydroxylation mainly at position 6. In rats and man, 6-hydroxyskatole is excreted chiefly as the sulphate (Horning et al. 1959), but it may also be excreted as the glucuronide (Sohler, 1966). The metabolites of skatole excreted in the urine of man and 16 species of domestic and wild mammals were also studied by Decker & Gerdemann (1959). After administration of skatole to cattle in a dose of 0.1-0.2 g skatole/kg intraruminally or 0.06g/kg by jugular infusion, the mean plasma concentration of skatole became maximal at 3 and 9hr, respectively (Carlson et al. 1975).

Purification Methods

Crystallise skatole from *benzene or pet ether (m 96.5o). It has also been purified by zone melting. The picrate has m 182o (from Et2O or Et2O/MeOH). [Beilstein 20 III/IV 3206, 20/7 V 69.]

3-Methylindole Preparation Products And Raw materials

Raw materials

3-MethylindoleSupplier

Ningbo Taikang Chemical Co., Ltd. Gold
Tel
0574-87365517-
Email
sales@taikangchem.com
Products Intro
Product Name:3-MethylindoleFEMA 3019;BETA-METHYLINDOLE;3-MI;3-METHYL-1H-INDOLE;3-METHYLINDOLE;SCATOLE;SKATOL;SKATOLE
CAS:83-34-1
Purity:98% HPLC Package:1kg;5kg;10kg;25kg
Wuhan kemike Biomedical Technology Co., Ltd Gold
Tel
Email
yeqiu416@163.com
Products Intro
Product Name:3-Methylindole
CAS:83-34-1
Purity:99%
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Products Intro
Product Name:3-Methylindole, 96%
CAS:83-34-1
Purity:96% Package:100G;25G;5G
PharmaBlock Sciences (Nanjing),Inc.
Tel
400-025-5188
Email
sales@pharmablock.com
Products Intro
Product Name:3-methyl-1H-indole
CAS:83-34-1
Purity:97% HPLC Package:50 G
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Email
sh@meryer.com
Products Intro
Product Name:3-Methylindole
CAS:83-34-1
Purity:99% Package:1g Remarks:A23015