Determine the necessary mass, volume, or concentration for preparing a solution.
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Protected from light,Store at -20°C,Argon charged Ships Ice chest + Ice pads 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 21 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
5-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway.5-HIAA is present in body fluids like cerebrospinal fluid (CSF), blood and urine. The expression levels of 5-HIAA is different among the normal and cancer patients.Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF.5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD).
5-Hydroxyindole-3-acetic acid is a major serotonin metabolite.
5-Hydroxyindole-3-acetic acid has been used as standard for the measurement of 5-HIAA in the brain tissue of mice using high performance liquid chromatography (HPLC).
A major serotonin metabolite.
| Pubchem Sid | 504750509 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504750509 |
| Sonrisas canónicas | C1=CC2=C(C=C1O)C(=CN2)CC(=O)O |
| IUPAC Name | 2-(5-hydroxy-1H-indol-3-yl)acetic acid |
| InChIKey | DUUGKQCEGZLZNO-UHFFFAOYSA-N |
| INCHI | 1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14) |
| Isómeros SMILES | C1=CC2=C(C=C1O)C(=CN2)CC(=O)O |
| WGK Alemania | 3 |
| RTECS | NL3650000 |
| CAS alternativo | 54-16-0 |
| PubChem CID | 1826 |
| Número NSC | 90432 |
| Términos de entrada MeSH | 5 Hydroxy 3 Indoleacetic Acid;5 Hydroxyindolamine Acetic Acid;5-HIAA;5-Hydroxy-3-Indoleacetic Acid;5-Hydroxyindolamine Acetic Acid;Acetic Acid, 5-Hydroxyindolamine;Acid, 5-Hydroxy-3-Indoleacetic;Acid, 5-Hydroxyindolamine Acetic;Acid, Hydroxyindoleacetic;H |
| Peso molecular | 191.19 |
| Beilstein | 168797 |
| Reaxy-Rn | 168797 |
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 |
| Clase | Indoles and derivatives |
| Subclass | Indolyl carboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Indole-3-acetic acid derivatives |
| Alternative Parents | Hydroxyindoles 3-alkylindoles 1-hydroxy-2-unsubstituted benzenoids Substituted pyrroles Heteroaromatic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Indole-3-acetic acid derivative - 3-alkylindole - Hydroxyindole - Indole - 1-hydroxy-2-unsubstituted benzenoid - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxide - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. |
| External Descriptors | indole-3-acetic acids |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| 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 | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | May 20, 2026 | H615671 | |
| Certificate of Analysis | Apr 01, 2026 | H615671 | |
| Certificate of Analysis | Apr 01, 2026 | H615671 | |
| Certificate of Analysis | Apr 01, 2026 | H615671 | |
| Certificate of Analysis | Apr 01, 2026 | H615671 | |
| Certificate of Analysis | Oct 22, 2025 | H615671 | |
| Certificate of Analysis | Oct 22, 2025 | H615671 | |
| Certificate of Analysis | Oct 22, 2025 | H615671 | |
| Certificate of Analysis | Oct 22, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Apr 19, 2025 | H615671 | |
| Certificate of Analysis | Jun 29, 2024 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 | |
| Certificate of Analysis | Sep 08, 2023 | H615671 |
| Solubilidad | Soluble in 50 mg/ml ethanol. |
|---|---|
| Sensibilidad | Heat,Light,Air sensitive. |
| Punto de fusión (°C) | 162 °C(dec.) |
| Peso molecular | 191.180 g/mol |
| XLogP3 | 1.100 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Exact Mass | 191.058 Da |
| Monoisotopic Mass | 191.058 Da |
| Topological Polar Surface Area | 73.300 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 231.000 |
| 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. Huimin Zhou, Anni Zhu, Caiyin Wang, Xiaoyu Guo, Ye Ying, Yiping Wu, Xinling Liu, Feng Wang, Ying Wen, Haifeng Yang. (2023) Preparation of gold nanoparticles loaded MOF-199 for SERS detection of 5-hydroxyindole-3-acetic acid in serum. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:37619474] [10.1016/j.saa.2023.123280] |
| 2. Wenting Lin, Kan Li, Yingjun Qin, Xing Han, Xiaohui Chen, Yuan Ren. (2023) Flunitrazepam induces neurotoxicity in zebrafish through microbiota-gut-brain axis. SCIENCE OF THE TOTAL ENVIRONMENT, [PMID:37532048] [10.1016/j.scitotenv.2023.165974] |
| 3. Pan Hu, Xin Yan, Yijia Zeng, Zherui Jiang, Juan Liu, Wu-wen Feng. (2023) An UPLC-MS/MS method for targeted analysis of microbial and host tryptophan metabolism after administration of polysaccharides from Atractylodes macrocephala Koidz. in ulcerative colitis mice. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:37523866] [10.1016/j.jpba.2023.115585] |
| 4. Qixing Nie, Yonggan Sun, Mingzhi Li, Sheng Zuo, Chunhua Chen, Qiongni Lin, Shaoping Nie. (2023) Targeted modification of gut microbiota and related metabolites via dietary fiber. CARBOHYDRATE POLYMERS, [PMID:37321707] [10.1016/j.carbpol.2023.120986] |
| 5. Xin Huang, Rui Wang, Yikai Wang, Changbao Chen, Shuying Liu. (2022) Investigation on property differences of ginseng and American ginseng by spatial metabolomics of neurochemicals with desorption electrospray ionization mass spectrometry imaging. JOURNAL OF ETHNOPHARMACOLOGY, [PMID:36516905] [10.1016/j.jep.2022.116006] |
| 6. Rong Li, Xiaoxia Li, Liu Su, Hetong Qi, Xuanfeng Yue, Honglan Qi. (2021) Label-free Electrochemical Aptasensor for the Determination of Serotonin. ELECTROANALYSIS, 34 (6): (1048-1053). [PMID:] [10.1002/elan.202100373] |
| 7. Yuanyuan Xia, Yuan Wang, Meng Zhang, Faqiong Zhao, Baizhao Zeng. (2020) A highly selective electrochemical sensor based on surface molecularly imprinted copolymer for the detection of 5-hydroxytryptamine. MICROCHEMICAL JOURNAL, [PMID:] [10.1016/j.microc.2020.105748] |
| 8. Di Wang, Erjun Sun. (2020) Loading carboxyfluorescein into porous SiO2 spheres and UCNPs-cored porous SiO2 spheres: Emission turn-on sensing with a warning signal for tumor-biomarker 5-HIAA urine test. MICROPOROUS AND MESOPOROUS MATERIALS, [PMID:] [10.1016/j.micromeso.2020.110131] |
| 9. Lu Shi, Feifei Cao, Limin Zhang, Yang Tian. (2020) I-motif Formed at Physiological pH Triggered by Spatial Confinement of Nanochannels: An Electrochemical Platform for pH Monitoring in Brain Microdialysates. ANALYTICAL CHEMISTRY, [PMID:32052626] [10.1021/acs.analchem.9b05732] |
| 10. Yuanyuan Xia, Faqiong Zhao, Baizhao Zeng. (2019) A molecularly imprinted copolymer based electrochemical sensor for the highly sensitive detection of L-Tryptophan. TALANTA, [PMID:31514823] [10.1016/j.talanta.2019.120245] |
| 11. Xue-Mei Han, Yan-Jie Qin, Ying Zhu, Xin-Lin Zhang, Nan-Xi Wang, Ying Rang, Xue-Jia Zhai, Yong-Ning Lu. (2019) Development of an underivatized LC-MS/MS method for quantitation of 14 neurotransmitters in rat hippocampus, plasma and urine: Application to CUMS induced depression rats. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:31288191] [10.1016/j.jpba.2019.06.043] |
| 12. Xi Zhou, Xuexia Gao, Fengyan Song, Chunpeng Wang, Fuxiang Chu, Shishan Wu. (2017) A sensing approach for dopamine determination by boronic acid-functionalized molecularly imprinted graphene quantum dots composite. APPLIED SURFACE SCIENCE, [PMID:] [10.1016/j.apsusc.2017.06.199] |
| 13. Dezhen Wang, Xinru Wang, Ping Zhang, Yao Wang, Renke Zhang, Jin Yan, Zhiqiang Zhou, Wentao Zhu. (2016) The fate of technical-grade chlordane in mice fed a high-fat diet and its roles as a candidate obesogen. ENVIRONMENTAL POLLUTION, [PMID:28041837] [10.1016/j.envpol.2016.11.028] |
| 14. Xue-jia Zhai, Fen Chen, Chao-ran Zhu, Yong-ning Lu. (2015) A simple LC-MS/MS method for quantitative analysis of underivatized neurotransmitters in rats urine: assay development, validation and application in the CUMS rat model. BIOMEDICAL CHROMATOGRAPHY, 29 (11): (1737-1743). [PMID:25944269] [10.1002/bmc.3487] |
| 15. Yuying Han, Xingyu Hou, Yali Li, Xiaopeng Yang, Xue Sun, Xinxin Bian, Na Sun, Yuguang Lv, Lixin Ding, Ze Li. (2025) A ratiometric fluorescent probe for a smartphone-based dual-emission carbon dot fluorescence sensor for the rapid detection of 5-HIAA. MICROCHEMICAL JOURNAL, [PMID:] [10.1016/j.microc.2025.113448] |
| 16. Qixing Nie, Yonggan Sun, Wenbing Hu, Chunhua Chen, Qiongni Lin, Shaoping Nie. (2024) Glucomannan promotes Bacteroides ovatus to improve intestinal barrier function and ameliorate insulin resistance. iMeta, [PMID:38868507] [10.1002/imt2.163] |
| 17. Jiankun Cao, Mingwei Wang, Yehong Han, Mingyu Wang, Hongyuan Yan. (2024) Hydrophilic molecularly imprinted resin-hexagonal boron nitride composite as a new adsorbent for selective extraction and determination of a carcinoid tumor biomarker in urine. ANALYTICA CHIMICA ACTA, [PMID:38336412] [10.1016/j.aca.2024.342289] |
| 18. Miaomiao Hu, Changchun Wen, Jian Liu, Minzhe Li, Nan Leng, Xiaohuan Guo, Qi Fang, Qinjie Kou, Rong Huang, Xiang-Cheng Lin. (2024) Ratiometric surface-enhanced Raman spectroscopy detection of 5-hydroxyindole-3-acetic acid based on Au@MIL-125@MIPs substrates. TALANTA, [PMID:39277938] [10.1016/j.talanta.2024.126880] |
| 19. Shi Zhong, Yu-Qing Sun, Jin-Xi Huo, Wen-Yi Xu, Ya-Nan Yang, Jun-Bo Yang, Wei-Jie Wu, Yong-Xin Liu, Chong-Ming Wu, You-Gui Li. (2024) The gut microbiota-aromatic hydrocarbon receptor (AhR) axis mediates the anticolitic effect of polyphenol-rich extracts from Sanghuangporus. iMeta, [PMID:38882491] [10.1002/imt2.180] |
| 20. Jie Fu, Jiawang Wang, Yihong Ding, Shouzhe Deng, Cherie S. Tan, Shuang Li. (2025) Wearable physicochemical-sensing system integrated with diaper for pheochromocytoma monitoring. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2025.137520] |
| 21. Chuzheng Pan, Feng Chen, Yan Yan, Haiwen Li, Chengfeng Qiu. (2025) Tryptophan metabolites as biomarkers to predict the severity and prognosis of acute ischemic stroke patients. Journal of Stroke & Cerebrovascular Diseases, [PMID:40553901] [10.1016/j.jstrokecerebrovasdis.2025.108382] |