≥95% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
5,6-Dihydroxyindole-2-carboxylic Acid is an intermediate in the process of melanin synthesis. It may be possible for 5,6-Dihydroxyindole-2-carboxylic Acid to tautomerize into Dopachrome. The oligomers of 5,6-Dihydroxyindole-2-carboxylic Acid can form atropisomers that are strongly dependent on the presence of inter-monomer hydrogen bonds. These isomers of 5,6-Dihydroxyindole-2-carboxylic Acid have almost equivalent stability, and are characterized by their charge transfer properties. Oligomers rich in 5,6-Dihydroxyindole-2-carboxylic Acid may form a suitable basis for materials with high conductivity.
| Canonical Smiles | C1=C2C=C(NC2=CC(=C1O)O)C(=O)O |
|---|---|
| IUPAC Name | 5,6-dihydroxy-1H-indole-2-carboxylic acid |
| InChIKey | YFTGOBNOJKXZJC-UHFFFAOYSA-N |
| INCHI | 1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14) |
| Isomeric SMILES | C1=C2C=C(NC2=CC(=C1O)O)C(=O)O |
| Molecular Weight | 193.16 |
| Reaxy-Rn | 168167 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=168167&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Indolecarboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Indolecarboxylic acids and derivatives |
| Alternative Parents | Hydroxyindoles Indoles Pyrrole 2-carboxylic acids 1-hydroxy-2-unsubstituted benzenoids Substituted pyrroles Heteroaromatic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Indolecarboxylic acid derivative - Hydroxyindole - Indole - Pyrrole-2-carboxylic acid - Pyrrole-2-carboxylic acid or derivatives - 1-hydroxy-2-unsubstituted benzenoid - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Azacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. |
| External Descriptors | dihydroxyindole |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 H2515030 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403293 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403294 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403295 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403296 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403297 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| I2403298 | Certificate of Analysis | Aug 23, 2024 | D330878 |
| G2415002 | Certificate of Analysis | Apr 02, 2024 | D330878 |
| Melt Point(°C) | >190° C (dec.) |
|---|---|
| Molecular Weight | 193.160 g/mol |
| XLogP3 | 1.200 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 193.038 Da |
| Monoisotopic Mass | 193.038 Da |
| Topological Polar Surface Area | 93.600 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 245.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Zihui Ma, Xiaoyan Liu, Yutong Liu, Wei Chen, Chengtao Wang. (2022) Studies on the biosynthetic pathways of melanin in Auricularia auricula. JOURNAL OF BASIC MICROBIOLOGY, 62 (7): (843-856). [PMID:35419841] [10.1002/jobm.202100670] |
