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Moligand™, ≥99% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Protected from light 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 16 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
5-Hydroxy-L-tryptophan has been used:
· to inject experimental mice for serotonin detection
· as a precursor of 5-hydroxytryptamine and injected in pregnant mice and neonatal rats for vital neutral red staining of lung slices
· as a standard in citrate-acetate buffer for its use in high performance liquid chromatography (HPLC) analysis
| Pubchem Sid | 488189742 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488189742 |
| Canonical Smiles | C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N |
| IUPAC Name | (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid |
| InChIKey | LDCYZAJDBXYCGN-VIFPVBQESA-N |
| INCHI | 1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1 |
| Isomeric SMILES | C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)O)N |
| WGK Germany | 3 |
| RTECS | YN7110000 |
| Alternate CAS | 314062-44-7 |
| UN Number | 2811 |
| Packing Group | I |
| Molecular Weight | 220.22 |
| Beilstein | 88200 |
| Reaxy-Rn | 88199 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=88199&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 | Tryptamines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Serotonins |
| Alternative Parents | Indolyl carboxylic acids and derivatives 3-alkylindoles L-alpha-amino acids Hydroxyindoles 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Substituted pyrroles Heteroaromatic compounds Amino acids Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Serotonin - Indolyl carboxylic acid derivative - Alpha-amino acid - Alpha-amino acid or derivatives - 3-alkylindole - L-alpha-amino acid - Hydroxyindole - Indole - Aralkylamine - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Amino acid - Amino acid or derivatives - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organonitrogen compound - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Primary amine - Carbonyl group - Organopnictogen compound - Amine - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. |
| External Descriptors | non-proteinogenic L-alpha-amino acid - 5-hydroxytryptophan - hydroxy-L-tryptophan |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | May 09, 2026 | H111084 | |
| Certificate of Analysis | Feb 05, 2026 | H111084 | |
| Certificate of Analysis | Feb 05, 2026 | H111084 | |
| Certificate of Analysis | Feb 05, 2026 | H111084 | |
| Certificate of Analysis | Feb 05, 2026 | H111084 | |
| Certificate of Analysis | Aug 11, 2025 | H111084 | |
| Certificate of Analysis | Jan 09, 2025 | H111084 | |
| Certificate of Analysis | Jan 09, 2025 | H111084 | |
| Certificate of Analysis | Jan 09, 2025 | H111084 | |
| Certificate of Analysis | Mar 10, 2023 | H111084 | |
| Certificate of Analysis | Dec 09, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Dec 01, 2022 | H111084 | |
| Certificate of Analysis | Jul 26, 2022 | H111084 | |
| Certificate of Analysis | Sep 04, 2021 | H111084 | |
| Certificate of Analysis | Sep 04, 2021 | H111084 |
| Solubility | insoluble in EtOH; ≥10.42 mg/mL in H2O; ≥51.9 mg/mL in DMSO |
|---|---|
| Sensitivity | Light sensitive |
| Refractive Index | 1.4850 |
| Specific Rotation[α] | -33 ° (C=1, H2O) |
| Melt Point(°C) | 270°C |
| Molecular Weight | 220.220 g/mol |
| XLogP3 | -1.200 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Exact Mass | 220.085 Da |
| Monoisotopic Mass | 220.085 Da |
| Topological Polar Surface Area | 99.300 Ų |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Complexity | 272.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| 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. Jin Yuan Zhang, Ying Zhang, Yu Zou, Ze Li Bo Xu, Bo Zhang, Wang Ren. (2023) Physicochemically modulated fluorescence-scattering ratiometric sensor for selective and visual detection of levodopa. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:38091648] [10.1016/j.saa.2023.123746] |
| 2. Shikai Zhang, Qing Xu, Changbo Ji, Xiaoyu Han, Yang Zhou, Chao Liang, Linran Ma, Weijian Sun, Yanling Li, Zhengyou Yang, Fengchun Zhao, Yuan Tian. (2023) Study on secondary metabolites of endophytic fungus Diaporthe sp. AC1 induced by tryptophan analogs. Frontiers in Microbiology, [PMID:37876783] [10.3389/fmicb.2023.1254609] |
| 3. Yan Wang, Bin Peng, Yuanyuan Gong, Yingrong Xie, Tingting Feng, Xiaolin Liu, Bowei Chen, Yong Zhang. (2023) Carboxyl and amino acid functionalized indole-based polymer for ultrafast uranium extraction in aqueous solution. JOURNAL OF MOLECULAR LIQUIDS, [PMID:] [10.1016/j.molliq.2023.122143] |
| 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. Ya-Qian Wang, Li Li, Jin Yin, Xu Yu, Xiaowei Wu, Li Xu. (2023) Turn on fluorescence detection of curcumin in food matrices by the novel fluorescence sensitizer. ANALYTICA CHIMICA ACTA, [PMID:37005020] [10.1016/j.aca.2023.341094] |
| 6. Feifei Song, Tao Gu, Lin Zhang, Jiaxing Zhang, Shengping You, Wei Qi, Rongxin Su. (2023) Rational design of tryptophan hydroxylation 1 for improving 5-Hydroxytryptophan production. ENZYME AND MICROBIAL TECHNOLOGY, [PMID:36736156] [10.1016/j.enzmictec.2023.110198] |
| 7. Qiuyang Huang, Xiaoling Zang, Zhiwei Zhang, Hang Yu, Baoyan Ding, Zhuangzhuang Li, Simin Cheng, Xin Zhang, Mustafa R.K. Ali, Xue Qiu, Zhihua Lv. (2023) Study on endogenous inhibitors against PD-L1: cAMP as a potential candidate. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:36646351] [10.1016/j.ijbiomac.2023.123266] |
| 8. Zhuangzhuang Li, Baoyan Ding, Mustafa R. K. Ali, Lizhen Zhao, Xiaoling Zang, Zhihua Lv. (2022) Dual Effect of Tryptamine on Prostate Cancer Cell Growth Regulation: A Pilot Study. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 23 (19): (11087). [PMID:36232383] [10.3390/ijms231911087] |
| 9. Qiao Chong, Chen Fei, Liu Zhan, Huang Tianfang, Li Wei, Zhang Guolin, Luo Yinggang. (2022) Functional characterization of a catalytically promiscuous tryptophan decarboxylase from camptothecin-producing Camptotheca acuminata. Frontiers in Plant Science, [PMID:36061783] [10.3389/fpls.2022.987348] |
| 10. Wu Lijuan, Ran Lisha, Wu Yazeng, Liang Manyu, Zeng Jing, Ke Famin, Wang Fang, Yang Jian, Lao Xiaoqing, Liu Li, Wang Qin, Gao Xiaowei. (2022) Oral Administration of 5-Hydroxytryptophan Restores Gut Microbiota Dysbiosis in a Mouse Model of Depression. Frontiers in Microbiology, [PMID:35572711] [10.3389/fmicb.2022.864571] |
| 11. Wang Yan, Liu Xiaolin, Xie Yingrong, Chen Bowei, Zhang Yong. (2022) Effective and rapid adsorption of uranium via synergy of complexation and cation-π interaction. JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, 331 (2): (1115-1126). [PMID:] [10.1007/s10967-021-08179-9] |
| 12. Zhang Yanfeng, He Yongzhi, Zhang Nan, Gan JiaJia, Zhang Shan, Dong Zhiyang. (2021) Combining protein and metabolic engineering strategies for biosynthesis of melatonin in Escherichia coli. Microbial Cell Factories, 20 (1): (1-13). [PMID:34454478] [10.1186/s12934-021-01662-8] |
| 13. Xu Da, Fang Mengjun, Wang Haijiao, Huang Lei, Xu Qinyang, Xu Zhinan. (2020) Enhanced production of 5-hydroxytryptophan through the regulation of L-tryptophan biosynthetic pathway. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 104 (6): (2481-2488). [PMID:32006050] [10.1007/s00253-020-10371-y] |
| 14. Qing Wang, Yao Long, Lin Yao, Li Xu, Zhi-Guo Shi, Lanying Xu. (2015) Preparation, characterization and application of a reversed phase liquid chromatography/hydrophilic interaction chromatography mixed-mode C18-DTT stationary phase. TALANTA, [PMID:26695288] [10.1016/j.talanta.2015.09.009] |
| 15. Ai Yulin, Huang Yusong, Zhao Hongru, Su Bingmei, Lin Juan. (2025) Engineered phenylalanine hydroxylase coupled with an effective cofactor synthesis and regeneration system for high-yield production of 5-hydroxytryptophan. Bioresources and Bioprocessing, 12 (1): (1-14). [PMID:40047997] [10.1186/s40643-025-00846-z] |
| 16. Chenjie Yang, Hailong Yu, Weihong Li, Hairu Lin, Hao Wu, Chunhui Deng. (2024) High-Throughput Metabolic Pattern Screening Strategy for Early Colorectal and Gastric Cancers Based on Covalent Organic Frameworks-Assisted Laser Desorption/Ionization Mass Spectrometry. ANALYTICAL CHEMISTRY, [PMID:38600676] [10.1021/acs.analchem.3c05527] |
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