| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:09:56 UTC |
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| Update date | 2019-11-26 03:05:57 UTC |
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| Primary ID | FDB012008 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Indole |
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| Description | Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs
Indole is a major constituent of coal-tar, and the 220-260 °C distillation fraction is the main industrial source of the material. Indole and its derivatives can also be synthesized by a variety of methods. The main industrial routes start from aniline.; Indole is a solid at room temperature. Indole can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an indole ring are called indoles. The most famous derivative is the amino acid tryptophan.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.; The Leimgruber-Batcho indole synthesis is an efficient method of sythesizing indole and substituted indoles. Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. This method is especially popular in the pharmaceutical industry, where many pharmaceutical drugs are made up of specifically substituted indoles.; The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. Indole is found in many foods, some of which are flaxseed, agar, american pokeweed, and pear. |
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| CAS Number | 120-72-9 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C16H14N2 |
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| IUPAC name | 1H-indole; 3H-indole |
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| InChI Identifier | InChI=1S/2C8H7N/c2*1-2-4-8-7(3-1)5-6-9-8/h1-4,6H,5H2;1-6,9H |
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| InChI Key | AYVVZVSBYJTFGL-UHFFFAOYSA-N |
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| Isomeric SMILES | C1C=NC2=C1C=CC=C2.N1C=CC2=C1C=CC=C2 |
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| Average Molecular Weight | 234.2958 |
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| Monoisotopic Molecular Weight | 234.115698458 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indoles |
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| Direct Parent | Indoles |
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| Alternative Parents | |
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| Substituents | - Indole
- Benzenoid
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Imine
- Aromatic heteropolycyclic compound
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| Molecular Framework | Not Available |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 776 |
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| ChEMBL ID | CHEMBL15844 |
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| KEGG Compound ID | C00463 |
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| Pubchem Compound ID | 798 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 16881 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB04532 |
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| HMDB ID | HMDB00738 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HCM26-E:HCM26-E |
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| EAFUS ID | 1794 |
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| Dr. Duke ID | INDOLE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00001418 |
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| HET ID | IND |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | 120-72-9 |
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| GoodScent ID | rw1006511 |
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| SuperScent ID | 798 |
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| Wikipedia ID | Indole |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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