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MedKoo Cat#: 591743 | Name: Indole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Indole is an aromatic heterocyclic organic compound with formula C₈H₇N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring.

Chemical Structure

Indole
Indole
CAS#120-72-9

Theoretical Analysis

MedKoo Cat#: 591743

Name: Indole

CAS#: 120-72-9

Chemical Formula: C8H7N

Exact Mass: 117.0578

Molecular Weight: 117.15

Elemental Analysis: C, 82.02; H, 6.02; N, 11.96

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
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Synonym
Indole; AI3-01540; AI3 01540; AI301540; Ketole; 1-Benzo(b)pyrrole; 1H-Indole
IUPAC/Chemical Name
1H-Indole
InChi Key
SIKJAQJRHWYJAI-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
SMILES Code
C12=C(NC=C2)C=CC=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Indole is an endogenous metabolite.
In vitro activity:
The RT-qPCR analysis and the promoter-lacZ fusion reporter assay results showed that mutation of abiS caused a decrease in the expression level of abaI (Fig. 7a and b). This study also found that the production of 3-OH-C12-HSL was reduced in the abiS mutant strain by 54.52% (Fig. 7c). These results demonstrated that indole positively regulated the AHL QS system in A. baumannii. Reference: Microbiol Spectr. 2022 Aug 31;10(4):e0102722. https://pubmed.ncbi.nlm.nih.gov/35862954/
In vivo activity:
Overall, production of indole was higher in the distal colon and rectum than in the cecum and proximal colon. Thus, oral administration of nicotine appeared to promote indole production in the distal colon and rectum. The indole level in the rectum and feces was associated with the severity of DSS-induced colitis. Reference: Front Med (Lausanne). 2021 Dec 13;8:789037. https://pubmed.ncbi.nlm.nih.gov/34966763/
Solvent mg/mL mM
Solubility
DMSO 66.5 567.64
Water 3.6 30.47
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 117.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Cui B, Chen X, Guo Q, Song S, Wang M, Liu J, Deng Y. The Cell-Cell Communication Signal Indole Controls the Physiology and Interspecies Communication of Acinetobacter baumannii. Microbiol Spectr. 2022 Aug 31;10(4):e0102722. doi: 10.1128/spectrum.01027-22. Epub 2022 Jul 6. PMID: 35862954; PMCID: PMC9431217. 2. Gupta R, Rhee KY, Beagle SD, Chawla R, Perdomo N, Lockless SW, Lele PP. Indole modulates cooperative protein-protein interactions in the flagellar motor. PNAS Nexus. 2022 May;1(2):pgac035. doi: 10.1093/pnasnexus/pgac035. Epub 2022 May 13. PMID: 35719892; PMCID: PMC9205328. 3. Nakajima A, Shibuya T, Sasaki T, Lu YJ, Ishikawa D, Haga K, Takahashi M, Kaga N, Osada T, Sato N, Nagahara A. Nicotine Oral Administration Attenuates DSS-Induced Colitis Through Upregulation of Indole in the Distal Colon and Rectum in Mice. Front Med (Lausanne). 2021 Dec 13;8:789037. doi: 10.3389/fmed.2021.789037. PMID: 34966763; PMCID: PMC8710606. 4. Knudsen C, Neyrinck AM, Leyrolle Q, Baldin P, Leclercq S, Rodriguez J, Beaumont M, Cani PD, Bindels LB, Lanthier N, Delzenne NM. Hepatoprotective Effects of Indole, a Gut Microbial Metabolite, in Leptin-Deficient Obese Mice. J Nutr. 2021 Jun 1;151(6):1507-1516. doi: 10.1093/jn/nxab032. PMID: 33693866; PMCID: PMC8169809.
In vitro protocol:
1. Cui B, Chen X, Guo Q, Song S, Wang M, Liu J, Deng Y. The Cell-Cell Communication Signal Indole Controls the Physiology and Interspecies Communication of Acinetobacter baumannii. Microbiol Spectr. 2022 Aug 31;10(4):e0102722. doi: 10.1128/spectrum.01027-22. Epub 2022 Jul 6. PMID: 35862954; PMCID: PMC9431217. 2. Gupta R, Rhee KY, Beagle SD, Chawla R, Perdomo N, Lockless SW, Lele PP. Indole modulates cooperative protein-protein interactions in the flagellar motor. PNAS Nexus. 2022 May;1(2):pgac035. doi: 10.1093/pnasnexus/pgac035. Epub 2022 May 13. PMID: 35719892; PMCID: PMC9205328.
In vivo protocol:
1. Nakajima A, Shibuya T, Sasaki T, Lu YJ, Ishikawa D, Haga K, Takahashi M, Kaga N, Osada T, Sato N, Nagahara A. Nicotine Oral Administration Attenuates DSS-Induced Colitis Through Upregulation of Indole in the Distal Colon and Rectum in Mice. Front Med (Lausanne). 2021 Dec 13;8:789037. doi: 10.3389/fmed.2021.789037. PMID: 34966763; PMCID: PMC8710606. 2. Knudsen C, Neyrinck AM, Leyrolle Q, Baldin P, Leclercq S, Rodriguez J, Beaumont M, Cani PD, Bindels LB, Lanthier N, Delzenne NM. Hepatoprotective Effects of Indole, a Gut Microbial Metabolite, in Leptin-Deficient Obese Mice. J Nutr. 2021 Jun 1;151(6):1507-1516. doi: 10.1093/jn/nxab032. PMID: 33693866; PMCID: PMC8169809.
1: Li Z, Lu S, Jin J, Wang T. Preparation of a new cellulose magnetic molecularly imprinted polymer micro-spheres to extract and analyze the indole-3-acetic acid in plant tissues. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jun 21;1092:343-349. doi: 10.1016/j.jchromb.2018.06.023. [Epub ahead of print] PubMed PMID: 29936370. 2: Mishra S, Kaur M, Chander S, Murugesan S, Nim L, Arora DS, Singh P. Rational modification of a lead molecule: Improving the antifungal activity of indole - triazole - amino acid conjugates. Eur J Med Chem. 2018 Jun 18;155:658-669. doi: 10.1016/j.ejmech.2018.06.039. [Epub ahead of print] PubMed PMID: 29936353. 3: Chen CM, Chen WL, Hung CT, Lin TH, Chao CY, Lin CH, Wu YR, Chang KH, Yao CF, Lee-Chen GJ, Su MT, Hsieh-Li HM. The indole compound NC009-1 inhibits aggregation and promotes neurite outgrowth through enhancement of HSPB1 in SCA17 cells and ameliorates the behavioral deficits in SCA17 mice. Neurotoxicology. 2018 Jun 21. pii: S0161-813X(18)30215-8. doi: 10.1016/j.neuro.2018.06.009. [Epub ahead of print] PubMed PMID: 29936316. 4: Long SY, Song Y, Zhao QJ, Chen D. Indole alkaloids from the aerial parts of Kopsia fruticosa and their cytotoxic, antimicrobial and antifungal activities. Fitoterapia. 2018 Jun 20. pii: S0367-326X(18)30886-4. doi: 10.1016/j.fitote.2018.06.017. [Epub ahead of print] PubMed PMID: 29935259. 5: Liu Y, Chen X, Wang X, Fang Y, Huang M, Guo L, Zhang Y, Zhao H. Improving biomass and starch accumulation of bioenergy crop duckweed (Landoltia punctata) by abscisic acid application. Sci Rep. 2018 Jun 22;8(1):9544. doi: 10.1038/s41598-018-27944-7. PubMed PMID: 29934519. 6: Carqueijeiro IT, Brown S, Chung K, Dang TT, Walia M, Besseau S, Dugé de Bernonville T, Oudin A, Lanoue A, Billet K, Munsch T, Koudounas K, Melin C, Godon C, Razafimandimby B, de Craene JO, Glévarec G, Marc J, Giglioli-Guivarc'h N, Clastre M, St-Pierre B, Papon N, Andrade RB, O'Connor S, Courdavault V. Two tabersonine 6,7-epoxidases start synthesis of lochnericine-type alkaloids in Catharanthus roseus. Plant Physiol. 2018 Jun 22. pii: pp.00549.2018. doi: 10.1104/pp.18.00549. [Epub ahead of print] PubMed PMID: 29934299. 7: Gong Y, Bai JL, Yang HT, Zhang WD, Xiong YW, Ding P, Qin S. Phylogenetic diversity and investigation of plant growth-promoting traits of actinobacteria in coastal salt marsh plant rhizospheres from Jiangsu, China. Syst Appl Microbiol. 2018 Jun 12. pii: S0723-2020(18)30167-X. doi: 10.1016/j.syapm.2018.06.003. [Epub ahead of print] PubMed PMID: 29934111. 8: Chen Y, Fan CL, Wang Y, Zhang XQ, Huang XJ, Ye WC. [Chemical constituents from roots of Isatis indigotica]. Zhongguo Zhong Yao Za Zhi. 2018 May;43(10):2091-2096. doi: 10.19540/j.cnki.cjcmm.20180116.001. Chinese. PubMed PMID: 29933676. 9: Zhu H, Ma W, Han H, Xu C, Han Y, Ma W. Degradation characteristics of two typical N-heterocycles in ozone process: Efficacy, kinetics, pathways, toxicity and its application to real biologically pretreated coal gasification wastewater. Chemosphere. 2018 Jun 14;209:319-327. doi: 10.1016/j.chemosphere.2018.06.067. [Epub ahead of print] PubMed PMID: 29933168. 10: Campos KR, Woo JCS, Lee S, Tillyer RD. Correction to "A General Synthesis of Substituted Indoles from Cyclic Enol Ethers and Enol Lactones". Org Lett. 2018 Jun 22. doi: 10.1021/acs.orglett.8b01644. [Epub ahead of print] PubMed PMID: 29932663. 11: Liu S, He F, Lin N, Chen Y, Liang Z, Liao L, Lv M, Chen Y, Chen S, Zhou J, Zhang LH. Pseudomonas sp. ST4 produces variety of active compounds to interfere fungal sexual mating and hyphal growth. Microb Biotechnol. 2018 Jun 21. doi: 10.1111/1751-7915.13289. [Epub ahead of print] PubMed PMID: 29931737. 12: Nemoto T. Synthesis of 3,4-Fused Tricyclic Indoles Using 3-Alkylidene Indolines as Versatile Precursors. Chem Rec. 2018 Jun 21. doi: 10.1002/tcr.201800043. [Epub ahead of print] PubMed PMID: 29931736. 13: Sui X, Kumar Singh S, Patra B, Schluttenhofer C, Guo W, Pattanaik S, Yuan L. Cross-family Transcription Factor Interaction between MYC2 and GBFs Modulates Terpenoid indole Alkaloid Biosynthesis. J Exp Bot. 2018 Jun 20. doi: 10.1093/jxb/ery229. [Epub ahead of print] PubMed PMID: 29931167. 14: Castelan FP, Castro-Alves VC, Saraiva LA, Nascimento TP, Cálhau MFNS, Dias CTS, Cordenunsi-Lysenko BR. Natural Ecosystem Surrounding a Conventional Banana Crop Improves Plant Health and Fruit Quality. Front Plant Sci. 2018 Jun 7;9:759. doi: 10.3389/fpls.2018.00759. eCollection 2018. PubMed PMID: 29930565; PubMed Central PMCID: PMC6001115. 15: Devincenzi T, Prunier A, Meteau K, Prache S. How does barley supplementation in lambs grazing alfalfa affect meat sensory quality and authentication? Animal. 2018 Jun 22:1-8. doi: 10.1017/S1751731118001477. [Epub ahead of print] PubMed PMID: 29929567. 16: Yu HF, Qin XJ, Ding CF, Wei X, Yang J, Luo JR, Liu L, Khan A, Zhang LC, Xia CF, Luo XD. Nepenthe-Like Indole Alkaloids with Antimicrobial Activity from Ervatamia chinensis. Org Lett. 2018 Jun 21. doi: 10.1021/acs.orglett.8b01675. [Epub ahead of print] PubMed PMID: 29927253. 17: He LN, Qiao C, Liu XF, Fu HC, Yang HP, Zhang ZB. Directly Bridging Indoles to 3,3'-Bisindolylmethanes Using Carboxylic Acids and Hydrosilanes under Mild Conditions. Chem Asian J. 2018 Jun 21. doi: 10.1002/asia.201800766. [Epub ahead of print] PubMed PMID: 29926534. 18: Irgashev RA, Steparuk AS, Rusinov GL. A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization. Org Biomol Chem. 2018 Jun 20. doi: 10.1039/c8ob01110a. [Epub ahead of print] PubMed PMID: 29922780. 19: Zhang Y, Li M, Li X, Zhang T, Qin M, Ren L. Isoquinoline Alkaloids and Indole Alkaloids Attenuate Aortic Atherosclerosis in Apolipoprotein E Deficient Mice: A Systematic Review and Meta-Analysis. Front Pharmacol. 2018 Jun 5;9:602. doi: 10.3389/fphar.2018.00602. eCollection 2018. PubMed PMID: 29922166; PubMed Central PMCID: PMC5996168. 20: Thaxton-Weissenfluh A, Belal TS, DeRuiter J, Smith F, Abiedalla Y, Neel L, Abdel-Hay KM, Clark CR. GC-MS and GC-IR Analyses of the Methoxy-1-n-pentyl-3-(1-naphthoyl)-indoles: Regioisomeric Designer Cannabinoids. J Chromatogr Sci. 2018 Jun 16. doi: 10.1093/chromsci/bmy059. [Epub ahead of print] PubMed PMID: 29920587.