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3-Methylindole, also known as skatole, is an organic compound. The appearance is white or slightly brown crystals, which may gradually turn brown after prolonged storage. It is soluble in organic solvents such as hot water, alcohols, benzene, chloroform, and ethers, and appears purple when reacting with potassium ferrocyanide and sulfuric acid, and blue purple when reacting with potassium ferrocyanide and hydrochloric acid. It is sensitive to light and will gradually turn brown after prolonged storage.
Naturally present in mammalian feces, catnip, cheese, milk, and tea, it is an important component of fecal odor. It can also be prepared by Fischer indole synthesis method, or by reacting phenylhydrazine with acetaldehyde to obtain hydrazone, which is then heated and deaminated under the catalysis of zinc chloride. It can be used as a biochemical reagent for scientific research. Although it has a foul odor at high concentrations, it exhibits a pleasant aroma when diluted to extremely low levels. Therefore, it can be used as an important raw material for the preparation of jasmine flavor flavor, and can also be combined with indole, quinoline and other derivatives to prepare artificial civet ointment, or used as the essence of beverages, candy, chewing gum and other foods.
Additional information of chemical compound:
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Chemical Formula |
C9H9N |
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Exact Mass |
131.07 |
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Molecular Weight |
131.18 |
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m/z |
131.07 (100.0%), 132.08 (9.7%) |
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Elemental Analysis |
C, 82.41; H, 6.92; N, 10.68 |
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Melting point |
92-97℃(lit.) |
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Boiling point |
265-266℃(lit.) |
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Density |
1.0111 (estimate) |
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Storage conditions |
Store below +30℃ |
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3-Methylindole has multiple uses, and the following is a detailed summary of its uses:
This compound can be used as an organic synthesis reagent in chemical research, for synthesizing other organic compounds or conducting specific chemical reactions. Its unique chemical properties and structure make it an important raw material or intermediate in certain chemical reactions; It can be used as a reagent for biochemical research to explore its metabolic pathways, biological activities, and interactions with other biomolecules in organisms.
This substance also has an inhibitory effect on trypsin activity. Trypsin is an important digestive enzyme that can break down proteins. By studying the inhibitory effect of this compound on trypsin, we can further understand its regulatory mechanism in the digestive process and potential drug development applications; It may also have other potential biochemical applications, such as serving as a substrate or product in certain biochemical reactions, participating in specific biosynthesis or degradation processes, etc.
Although the compound itself has a strong fecal odor, when its concentration is diluted to an extremely low level, it exhibits a pleasant jasmine fragrance. Especially similar to the fragrance of Lingmao Xiangji. This unique aroma characteristic makes it occupy an important position in the spice industry. Therefore, in the spice industry, it is used as one of the raw materials for blending spices, especially for preparing jasmine type spices. In food processing, adding small amounts of this compound to products such as cheese, nuts, and grapes can add a special flavor to them.
This flavor is not only unique, but also enhances the overall taste and quality of the food; At the same time, in seafood essence, the compound can simulate the aroma of fish and enhance the overall flavor level. This makes it play an important role in the seasoning and essence preparation of seafood. It can also be combined with derivatives such as indole and quinoline to prepare artificial spirit cat fragrance. This artificial ointment has a fragrance similar to that of natural civet, and can be used in perfume, cosmetics and other products.
Because of its unique aroma characteristics, the compound has also been used as essence of food and beverage. For example, it can be added to candies, chewing gum, beverages, and other foods to enhance their aroma and taste. However, it should be noted that due to its strong odor, the dosage and dilution ratio must be strictly controlled during use to avoid adverse effects on food.
other purposes
This compound may also have other potential application values. In the field of medicine, it may serve as a synthetic raw material or intermediate for certain drugs; In the field of environmental science, it may be used to monitor or analyze certain pollutants in the environment. However, further research and exploration are needed to confirm these potential application values. It can also be used as a raw material for organic synthesis to synthesize other organic compounds. In the chemical industry, it can be transformed into other compounds with specific functions through a series of chemical reactions, providing support for the development of the chemical industry.
The chemical keys leading to the eukaryotic world in cross-disciplinary dialogues
3-Methylindole (also known as Skatole), this name not only reveals its unique chemical properties but also implies its extensive and subtle role in nature. As an important member of the indole family, skatole, with its unique bicyclic structure - a pyrrole ring connected to a benzene ring through a conjugated system, forming a planar molecule with aromaticity, serves as a chemical bridge connecting inorganic and organic, simple and complex, non-living and living worlds.
The "contradictory messenger" of nature
Skatole is widely present in the feces of vertebrates, the urine of civets, certain plants (such as sweet roots, nectariferous cypresswood), and coal tar. The term "fecal odor" in its name stems from the strong putrid smell at high concentrations, but when diluted to extremely low concentrations, it can emit a fragrance similar to jasmine, even with the sweet aroma of ripe fruits.
This "contradictory" characteristic makes it a unique chemical messenger in nature: on the one hand, as a product of the metabolic process of tryptophan by intestinal bacteria, it participates in regulating the interaction between the host and microorganisms; on the other hand, it affects the proliferation, differentiation and immune function of intestinal epithelial cells by activating the aromatic hydrocarbon receptor (AhR) and the p38 signaling pathway, becoming a key molecule connecting the intestinal microbiota and the physiological homeostasis of the host.
The "Chemical Key" of the Eukaryotic World
In eukaryotic organisms, the role of skatole goes far beyond odor regulation. Studies have shown that it can induce apoptosis of intestinal epithelial cells, activate intracellular signal transduction pathways through a time-dose-dependent manner, and thereby maintain the dynamic balance of intestinal mucosa. Moreover, skatole is also involved in regulating fat metabolism, inflammatory responses, and cell cycle progression. Its metabolite, 3-methylfuroylindole, can form adducts with proteins and affect cell functions. These characteristics make skatole an important tool for studying the symbiotic relationship between eukaryotic cells and microorganisms, and also provides potential targets for the development of new drugs.
"Cross-border Applications of Industry and Science"
The cross-border value of skatole is also reflected in its wide range of application fields. In the fragrance industry, it is used as a fixative to blend jasmine-type fragrances and artificial catnip ointments. Its extremely low-level usage can give fragrances a unique animal aroma. In the food industry, it is used as an edible fragrance to enhance the flavor of cheeses, nuts, grapes, etc. Although the dosage needs to be strictly controlled within a self-limiting range to avoid unpleasant odors, skatole is also used as a biochemical reagent for studying biological processes such as pancreatic protease activity inhibition and cell signal transduction, becoming a bridge connecting chemistry and biology.
Challenges and Future: From "Contradiction" to "Synergy"
Although skatole shows great potential in multiple fields, its application still faces challenges. Its toxicity at high concentrations, photosensitivity, and incompatibility with strong oxidants and strong acids limit its convenience in storage and use. In the future, through the development of nanocarrier technology, structural modification, and intelligent response systems, precise delivery and controlled release of skatole can be achieved, thereby maximizing its benefits and minimizing risks. Additionally, in-depth research on its interaction mechanisms with intestinal microorganisms and host cells will help reveal its role in disease occurrence and development, providing theoretical basis for the development of new therapeutic strategies.
The industrial production of 3-methylindole (skatole) is dominated by the Fischer indole synthesis, supplemented by the catalytic one-step process from aniline. These routes balance yield, cost, and scalability, with mature and stable overall technology.
I. Fischer Indole Synthesis (Traditional Classic Process)
It is prepared via a two-step cyclization using phenylhydrazine and propanal as core raw materials.In the first step, phenylhydrazine is dissolved in benzene, and a benzene solution of propanal is added dropwise, followed by 1 hour of reflux to form the intermediate propanal phenylhydrazone. The product is purified by vacuum distillation (112–117 °C / 133–266 Pa) with a yield of approximately 90%.In the second step, the phenylhydrazone undergoes deamination and cyclization at 180 °C using anhydrous zinc chloride as the catalyst. The indole ring is formed through [3,3]-sigmatropic rearrangement and aromatization, accompanied by ammonia release. After cooling, organic solvent extraction, and vacuum rectification, white crystals are obtained with a purity of 96–98% and an overall yield of 65–72%.This method features readily available raw materials and mature operation, making it the preferred choice for laboratory and small-to-medium scale production. However, it generates many by-products and has relatively high energy consumption.
II. Catalytic One-Step Process from Aniline (Mainstream Modern Industrial Route)
It adopts continuous fixed-bed production using aniline and 1,2-propanediol as raw materials.The reaction employs Ag/SiO₂ or Cu-ZnO-MnO/SiO₂ as the catalyst, carried out at 300–350 °C and 0.1–0.7 MPa, with a small amount of hydrogen and water vapor introduced to inhibit coking. The molar ratio of aniline to propanediol is 5:1, the space velocity is 0.4 h⁻¹, and the gas-phase residence time is 0.5 seconds, enabling one-step catalytic cyclization to skatole.After condensation, oil-water separation, and vacuum rectification, the product purity reaches ≥98% with a yield of 55–66%.This process has a short flow, low waste generation, and is suitable for large-scale production of ten-thousand-ton level, representing the current mainstream industrial route.
III. Extraction Method (Early Traditional Approach)
Skatole was isolated from coal tar and fecal extracts through alkali dissolution, acid precipitation, organic solvent extraction, and vacuum fractional distillation.Due to limitations in raw material supply, interference from impurities, and environmental constraints, this method was only used in early preparation and has now been completely replaced by chemical synthesis.
IV. Refining and Post-Treatment
The crude product is recrystallized from ethanol/water and rectified under reduced pressure to remove isomers and residual raw materials.The final product meets the standards of fragrance grade and biochemical reagent grade, with a melting point controlled at 93–96 °C, moisture ≤0.5%, and heavy metals ≤10 ppm.
FAQ
What is skatole used for?
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It is used as a fragrance and fixative in many perfumes and as an aroma compound. It is also used in low concentrations in some ice cream as a flavor enhancer. Its name derives from the Greek root skato-, meaning feces.
Why is skatole used in ice cream?
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Therefore, it is surprising that this unpleasant odor turns into a floral scent at lower concentrations (less than 1%; approx. 60 mM stock solution in ethanol). Thus, skatole is also present in essential oils and is widely used as a fragrance in perfumes [6,7] or even as a flavor enhancer in ice cream.
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