5-Hydroxyindole-3-acetic Acid(5-HIAA) - ≥97% , CAS No.54-16-0

CAS: 54-16-0 Cat. No.: H615671 Molecular Weight: 191.19 Beilstein Registry Number: 168797 EC Number: 200-195-4 PubChem CID: 1826
AVAILABLE TO ORDER
GRADE & PURITY ≥97%
Synonyms
NCGC00015522-08 | UNII-YHC763JY1P | 5-Hydroxy-3-indolylacetate | 5-Oxyindoleacetate | (1-AMINO-1-METHYLPROPYL)PHOSPHONICACIDHYDRATE | (5-Hydroxy-1H-indol-3-yl)aceticacid | 5-hydroxyindole-3-acetic-2,2-d2 acid | J-006135 | NSC90432 | NSC-90432 | (5-Hydroxy
Storage
Protected from light,Store at -20°C,Argon charged
Shipped In
Ice chest + Ice pads
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Size
Status
Price
Qty
50mg
H615671-50mg
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$9.90
100mg
H615671-100mg
2
$22.90
250mg
H615671-250mg
2
$29.90
1g
H615671-1g
3
$79.90
5g
H615671-5g
1
$362.90
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Why this grade

≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Protected from light,Store at -20°C,Argon charged Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 21 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

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.

Specifications

Synonyms
NCGC00015522-08 | UNII-YHC763JY1P | 5-Hydroxy-3-indolylacetate | 5-Oxyindoleacetate | (1-AMINO-1-METHYLPROPYL)PHOSPHONICACIDHYDRATE | (5-Hydroxy-1H-indol-3-yl)aceticacid | 5-hydroxyindole-3-acetic-2, 2-d2 acid | J-006135 | NSC90432 | NSC-90432 | (5-Hydroxy
Specifications & Purity
≥97%
Biochemical and Physiological Mechanisms
Major serotonin metabolite.
Storage
Protected from light, Store at -20°C, Argon charged
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Purity
≥97%
Names and Identifiers
Pubchem Sid504750509
Pubchem Sid Urlhttps://pubchem.ncbi.nlm.nih.gov/substance/504750509
Canonical SmilesC1=CC2=C(C=C1O)C(=CN2)CC(=O)O
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
InChIKeyDUUGKQCEGZLZNO-UHFFFAOYSA-N
INCHI1S/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)
Isomeric SMILES C1=CC2=C(C=C1O)C(=CN2)CC(=O)O
WGK Germany 3
RTECS NL3650000
Alternate CAS 54-16-0
PubChem CID 1826
NSC Number 90432
MeSH Entry Terms 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
Molecular Weight 191.19
Beilstein 168797
Reaxy-Rn 168797

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives
SubclassIndolyl carboxylic acids and derivatives
Intermediate Tree Nodes Not available
Direct ParentIndole-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 FrameworkAromatic 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
DescriptionThis 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
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLA Tclin Alpha-galactosidase A (5444 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Tchem Serum albumin (2651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR17 Tchem Uracil nucleotide/cysteinyl leukotriene receptor (291 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PMP22 Tbio Peripheral myelin protein 22 (699 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A8 Tclin Solute carrier family 22 member 8 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Npsr1 Neuropeptide S receptor (260 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NS3 NS3 (1121 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nfo Endonuclease 4 (425 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

24 results found

Lot NumberCertificate TypeDateItem
H2405105Certificate of AnalysisMay 20, 2026 H615671
D2616311Certificate of AnalysisApr 01, 2026 H615671
D2616312Certificate of AnalysisApr 01, 2026 H615671
D2616319Certificate of AnalysisApr 01, 2026 H615671
D2616320Certificate of AnalysisApr 01, 2026 H615671
K2520034Certificate of AnalysisOct 22, 2025 H615671
K2504473Certificate of AnalysisOct 22, 2025 H615671
K2504472Certificate of AnalysisOct 22, 2025 H615671
K2504471Certificate of AnalysisOct 22, 2025 H615671
G2509098Certificate of AnalysisApr 19, 2025 H615671
E2512501Certificate of AnalysisApr 19, 2025 H615671
D2527247Certificate of AnalysisApr 19, 2025 H615671
D2527246Certificate of AnalysisApr 19, 2025 H615671
D2527218Certificate of AnalysisApr 19, 2025 H615671
D2527217Certificate of AnalysisApr 19, 2025 H615671
D2527195Certificate of AnalysisApr 19, 2025 H615671
I2509362Certificate of AnalysisJun 29, 2024 H615671
G2405105Certificate of AnalysisSep 08, 2023 H615671
B2513034Certificate of AnalysisSep 08, 2023 H615671
H2405064Certificate of AnalysisSep 08, 2023 H615671
I2306304Certificate of AnalysisSep 08, 2023 H615671
I2306315Certificate of AnalysisSep 08, 2023 H615671
I2306331Certificate of AnalysisSep 08, 2023 H615671
I2306332Certificate of AnalysisSep 08, 2023 H615671

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Chemical and Physical Properties
SolubilitySoluble in 50 mg/ml ethanol.
SensitivityHeat,Light,Air sensitive.
Melt Point(°C)162 °C(dec.)
Molecular Weight191.180 g/mol
XLogP31.100
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass191.058 Da
Monoisotopic Mass191.058 Da
Topological Polar Surface Area73.300 Ų
Heavy Atom Count14
Formal Charge0
Complexity231.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Citations of This Product
References
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]
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