Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥99% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Argon charged,Room temperature Ships Normal 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 33 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Trans-4-Hydroxy-L-proline is a versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes. trans-4-Hydroxy-L-proline is a natural constituent of animal structural proteins such as collagen and elastin.
| Pubchem Sid | 488179943 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488179943 |
| Sonrisas canónicas | C1C(CNC1C(=O)O)O |
| IUPAC Name | (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid |
| InChIKey | PMMYEEVYMWASQN-DMTCNVIQSA-N |
| INCHI | 1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 |
| Isómeros SMILES | C1[C@H](CN[C@@H]1C(=O)O)O |
| WGK Alemania | 3 |
| Peso molecular | 131.13 |
| Beilstein | 81441 |
| Reaxy-Rn | 81437 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=81437&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 | Organic acids and derivatives |
| Clase | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Proline and derivatives |
| Alternative Parents | L-alpha-amino acids Pyrrolidine carboxylic acids Secondary alcohols Amino acids 1,2-aminoalcohols Monocarboxylic acids and derivatives Dialkylamines Carboxylic acids Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Proline or derivatives - Alpha-amino acid - L-alpha-amino acid - Pyrrolidine carboxylic acid - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine - 1,2-aminoalcohol - Amino acid - Secondary alcohol - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Azacycle - Secondary amine - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Alcohol - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Amine - Carbonyl group - Aliphatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
| External Descriptors | Other amino acids |
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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 | Jun 15, 2026 | H111005 | |
| Certificate of Analysis | Jun 15, 2026 | H111005 | |
| Certificate of Analysis | Jun 15, 2026 | H111005 | |
| Certificate of Analysis | Apr 07, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 25, 2026 | H111005 | |
| Certificate of Analysis | Mar 04, 2026 | H111005 | |
| Certificate of Analysis | Mar 04, 2026 | H111005 | |
| Certificate of Analysis | Mar 04, 2026 | H111005 | |
| Certificate of Analysis | Dec 10, 2025 | H111005 | |
| Certificate of Analysis | Sep 09, 2025 | H111005 | |
| Certificate of Analysis | Sep 09, 2025 | H111005 | |
| Certificate of Analysis | Jul 15, 2025 | H111005 | |
| Certificate of Analysis | Jul 15, 2025 | H111005 | |
| Certificate of Analysis | May 19, 2025 | H111005 | |
| Certificate of Analysis | May 09, 2025 | H111005 | |
| Certificate of Analysis | Apr 03, 2025 | H111005 | |
| Certificate of Analysis | Apr 03, 2025 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Sep 07, 2024 | H111005 | |
| Certificate of Analysis | Jul 01, 2024 | H111005 | |
| Certificate of Analysis | Jul 01, 2024 | H111005 | |
| Certificate of Analysis | Jul 01, 2024 | H111005 | |
| Certificate of Analysis | Jul 01, 2024 | H111005 | |
| Certificate of Analysis | Jul 08, 2022 | H111005 | |
| Certificate of Analysis | Jul 08, 2022 | H111005 | |
| Certificate of Analysis | Jul 08, 2022 | H111005 | |
| Certificate of Analysis | Jul 08, 2022 | H111005 | |
| Certificate of Analysis | Jul 08, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jul 04, 2022 | H111005 | |
| Certificate of Analysis | Jun 30, 2022 | H111005 | |
| Certificate of Analysis | Jun 27, 2022 | H111005 | |
| Certificate of Analysis | Jun 27, 2022 | H111005 | |
| Certificate of Analysis | Jun 27, 2022 | H111005 | |
| Certificate of Analysis | Jun 27, 2022 | H111005 | |
| Certificate of Analysis | Jun 27, 2022 | H111005 | |
| Certificate of Analysis | Dec 18, 2021 | H111005 | |
| Certificate of Analysis | Dec 18, 2021 | H111005 | |
| Certificate of Analysis | Dec 18, 2021 | H111005 | |
| Certificate of Analysis | Dec 18, 2021 | H111005 | |
| Certificate of Analysis | Sep 16, 2021 | H111005 |
| Solubilidad | Soluble in water. |
|---|---|
| Sensibilidad | Air Sensitive |
| Rotación específica [α] | -74.0 to -77.0 deg(C=4, H2O) |
| Punto de fusión (°C) | 273°C |
| Peso molecular | 131.130 g/mol |
| XLogP3 | -3.300 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 131.058 Da |
| Monoisotopic Mass | 131.058 Da |
| Topological Polar Surface Area | 69.600 Ų |
| Heavy Atom Count | 9 |
| Formal Charge | 0 |
| Complexity | 125.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| 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. Hongxian Luo, Gang Li, Longxin Ju, Qiang Lv. (2023) Liquid phase aldol condensation of formaldehyde and propionaldehyde catalyzed by L-proline functional polymers. APPLIED CATALYSIS A-GENERAL, [PMID:] [10.1016/j.apcata.2023.119545] |
| 2. Xuexia Xu, Qin Yang, Lanteng Wang, Jie Zheng, Yang Gu, Xiwen Xing, Jiahai Zhou. (2023) Enzymatic hydrolysis of L-azetidine-2-carboxylate ring opening. Catalysis Science & Technology, 13 (13): (3953-3962). [PMID:] [10.1039/D3CY00366C] |
| 3. Chen Qin, Fu Xiaomin, Cai Huawei, Fu Shengxiang, Cai Zhongyuan, Li Mufeng, Wu Xiaoai, Tian Rong, Ai Hua. (2023) 68Ga-labeled amphiphilic polymer nanoparticles for PET imaging of sentinel lymph node metastasis. Regenerative Biomaterials, [PMID:37081862] [10.1093/rb/rbad029] |
| 4. Yu Zhang, Dekun Cheng, Zhangtie Wang, Yiwen Guo, Ming Chang, Ruijie Liu. (2022) Protective Effect of Orbitides from Linseed (Linum usitatissimum L.) against Ultraviolet B-induced Photoaging in Zebrafish. PHOTOCHEMISTRY AND PHOTOBIOLOGY, [PMID:36484266] [10.1111/php.13758] |
| 5. Mingyue Liu, Xiangsheng Wang, Jie Cui, Hongsheng Wang, Binbin Sun, Jufang Zhang, Bernd Rolauffs, Muhammad Shafiq, Xiumei Mo, Zhanyong Zhu, Jinglei Wu. (2022) Electrospun flexible magnesium-doped silica bioactive glass nanofiber membranes with anti-inflammatory and pro-angiogenic effects for infected wounds. Journal of Materials Chemistry B, 11 (2): (359-376). [PMID:36507933] [10.1039/D2TB02002E] |
| 6. Mingyue Liu, Weixing Zhang, Zhe Chen, Yangfan Ding, Binbin Sun, Hongsheng Wang, Xiumei Mo, Jinglei Wu. (2022) Mechanisms of magnesium oxide-incorporated electrospun membrane modulating inflammation and accelerating wound healing. JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, 111 (1): (132-151). [PMID:36205298] [10.1002/jbm.a.37453] |
| 7. Yangfan Ding, Weixing Zhang, Binbin Sun, Xiumei Mo, Jinglei Wu. (2022) Cyclic freeze–thaw grinding to decellularize meniscus for fabricating porous, elastic scaffolds. JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, 110 (11): (1824-1839). [PMID:36082975] [10.1002/jbm.a.37435] |
| 8. Yan Bao, Lu Gao, Feitong Wang, Jianzhong Ma. (2021) Heterocyclic cationic Gemini surfactants for efficient antibacterial, dispersion and fixation. PROCESS SAFETY AND ENVIRONMENTAL PROTECTION, [PMID:] [10.1016/j.psep.2021.12.058] |
| 9. Zhongqiu Liu, Yuanyuan Yu, Shengnan Li, Yaqi Liu, Guoqiang Zhang, Long Han, Yujing Liu, Jinmao You, Anguo Ying. (2021) Collaborative fabrication of poly(L-proline)s with well-defined mesopores and hydrophobicity: Synergistic effect of mesoporous confinement and hydrophobic micro-environment on organic transformations. JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, [PMID:] [10.1016/j.jiec.2021.09.006] |
| 10. Xiaofeng He, Liling Xie, Xiaoshan Zhang, Fan Lin, Xiaobo Wen, Bo Teng. (2021) The Structural Characteristics of Collagen in Swim Bladders with 25-Year Sequence Aging: The Impact of Age. Applied Sciences-Basel, 11 (10): (4578). [PMID:] [10.3390/app11104578] |
| 11. Jiayuan Yu, Anker Degn Jensen, Lei Wang, Chunshan Li, Suojiang Zhang. (2020) Catalytic synthesis of methacrolein via the condensation of formaldehyde and propionaldehyde with L-proline. GREEN CHEMISTRY, 22 (13): (4222-4230). [PMID:] [10.1039/D0GC00726A] |
| 12. Mingjie Deng, Feiyan Lin, Caiping Zhou, Yuyan Chen, Leijie Xuan, Hongzhe Wang, Tiantian Feng, Lufeng Hu. (2020) Determination of 27 amino acids’ levels in seminal plasma of asthenospermia and oligospermia patients and diagnostic value analysis. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:32126460] [10.1016/j.jpba.2020.113211] |
| 13. Liubing Kong, Ying Gan, Tao Liang, Longjie Zhong, Yuxiang Pan, Dmitry Kirsanov, Andrey Legin, Hao Wan, Ping Wang. (2019) A novel smartphone-based CD-spectrometer for high sensitive and cost-effective colorimetric detection of ascorbic acid. ANALYTICA CHIMICA ACTA, [PMID:31735208] [10.1016/j.aca.2019.09.071] |
| 14. Ting Yin, Sheng Zhang, Mengxuan Li, Carl Redshaw, Xin-Long Ni. (2018) Macrocycle encapsulation triggered supramolecular pKa shift: A fluorescence indicator for detecting octreotide in aqueous solution. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2018.10.136] |
| 15. Yan Bao, Yuanxia Zhang, Jiajia Guo, Jianzhong Ma, Yuyao Lu. (2018) Application of green cationic silicon-based gemini surfactants to improve antifungal properties, fiber dispersion and dye absorption of sheepskin. Journal of Cleaner Production, [PMID:] [10.1016/j.jclepro.2018.09.186] |
| 16. Fangmiao Yu, Chuhong Zong, Shujie Jin, Jiawen Zheng, Nan Chen, Ju Huang, Yan Chen, Fangfang Huang, Zuisu Yang, Yunping Tang, Guofang Ding. (2018) Optimization of Extraction Conditions and Characterization of Pepsin-Solubilised Collagen from Skin of Giant Croaker (Nibea japonica). Marine Drugs, 16 (1): (29). [PMID:29342895] [10.3390/md16010029] |
| 17. Sai-Sai Chen, Zhong-Zhi Yang, Ai-Jun Wang, Ke-Ming Fang, Jiu-Ju Feng. (2017) Facile synthesis of bimetallic gold-palladium nanocrystals as effective and durable advanced catalysts for improved electrocatalytic performances of ethylene glycol and glycerol oxidation. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:28881200] [10.1016/j.jcis.2017.08.063] |
| 18. Yan Ren, Juanjuan Zhao, Yanan Shi, Caiyun Chen, Xiangming Chen, Changjun Lv. (2017) Simple determination of L-hydroxyproline in idiopathic pulmonary fibrosis lung tissues of rats using non-extractive high-performance liquid chromatography coupled with fluorescence detection after pre-column derivatization with novel synthetic 9-acetylimidazol-carbazole. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:28477449] [10.1016/j.jpba.2017.04.033] |
| 19. Shuang Gao, Weimin Guo, Mingxue Chen, Zhiguo Yuan, Mingjie Wang, Yu Zhang, Shuyun Liu, Tingfei Xi, Quanyi Guo. (2017) Fabrication and characterization of electrospun nanofibers composed of decellularized meniscus extracellular matrix and polycaprolactone for meniscus tissue engineering. Journal of Materials Chemistry B, 5 (12): (2273-2285). [PMID:32263618] [10.1039/C6TB03299K] |
| 20. Shuang Gao, Zhiguo Yuan, Weimin Guo, Mingxue Chen, Shuyun Liu, Tingfei Xi, Quanyi Guo. (2016) Comparison of glutaraldehyde and carbodiimides to crosslink tissue engineering scaffolds fabricated by decellularized porcine menisci. Materials Science & Engineering C-Materials for Biological Applications, [PMID:27987786] [10.1016/j.msec.2016.10.074] |
| 21. Yongkang Gai, Zhongping Hu, Zhao Rong, Xiang Ma, Guangya Xiang. (2015) A Practical Route for the Preparation of 1,4,7-Triazacyclononanyl Diacetates with a Hydroxypyridinonate Pendant Arm. MOLECULES, 20 (10): (19393-19405). [PMID:26512638] [10.3390/molecules201019393] |
| 22. Song Wang, Pingwei Liu, Wen-Jun Wang, Zhiguo Zhang, Bo-Geng Li. (2015) Hyperbranched polyethylene-supported L-proline: a highly selective and recyclable organocatalyst for asymmetric aldol reactions. Catalysis Science & Technology, 5 (7): (3798-3805). [PMID:] [10.1039/C5CY00250H] |
| 23. Hong Yang, Ming Xu, Ling-Xiang Guo, Hao-Fan Ji, Jun-Yu Wang, Bao-Ping Lin, Xue-Qin Zhang, Ying Sun. (2014) Organocatalysis in polysiloxane gels: a magnetic-stir-bar encapsulated catalyst system prepared by thiol–ene photo-click immobilization. RSC Advances, 5 (10): (7304-7310). [PMID:] [10.1039/C4RA16351F] |
| 24. Yi Yang, Bei Tian, Yi Xie, Peng Liu, Linyan Yao, Jianxi Xiao. (2024) Bioactive Triple-Helical Recombinant Collagen Gels for Improved Healing of Sunburned Skin. Cosmetics, 11 (4): (138). [PMID:] [10.3390/cosmetics11040138] |
| 25. Lu Wang, Limei Xiao, Shoujing Zheng, Jie Pang, Jiebo Chen. (2024) Characterization and assessment of free amino acids in different varieties of sugarcane. INDUSTRIAL CROPS AND PRODUCTS, [PMID:] [10.1016/j.indcrop.2024.118306] |
| 26. Shuangni Shi, Jingting Zhang, Yi Yang, Biyang Ling, Linyan Yao, Jianxi Xiao. (2025) Design and evaluation of transdermal nano collagen dressings for enhanced healing of UV-damaged skin. NEW JOURNAL OF CHEMISTRY, [PMID:] [10.1039/D4NJ04739G] |
| 27. Xiaolu Chen, Mingen Ding, Chuan Yang, Wei Zhang, Hao Deng, Dawei Yan, Haohao Ren, Yonggang Yan. (2024) Fabrication and biological evaluation of poly(amino acid)/bioactive glass/quartz fiber (PAA/BG/QF) composites with potential for bone defect repair. COMPOSITES PART A-APPLIED SCIENCE AND MANUFACTURING, [PMID:] [10.1016/j.compositesa.2024.108697] |
| 28. Yuxia Li, Min Li, Liuzhi Hu, Baozhu Zhang. (2024) Fluorescence Sensors for the Detection of L-Histidine Based on Silver Nanoclusters Modulated by Copper Ions. MOLECULES, 29 (10): (2167). [PMID:38792029] [10.3390/molecules29102167] |
| 29. Xiaoxiao Liang, Yanru Wu, Yuehua Deng, Xingye Zeng, Shufeng Shan, Yanbin Jiang, Huaiyu Yang. (2024) Supramolecular self-assembly strategy for the enhanced solubility/dissolution rate and anti-cancer efficacy of osimertinib: Insights from multi-component crystals to drug chemistry. CHEMICAL ENGINEERING SCIENCE, [PMID:] [10.1016/j.ces.2024.120520] |
| 30. Xin Xu, Qingwu Wang, Xiaodong Xu, Qiaoyi Han, Xiaojuan Nie, Xu Ding, Xia Liu, Junqing Li, Qiang Shi, Hongxing Dong. (2024) Unconventional luminescent CS–PEC-based composite hemostasis sponge with antibacterial activity and visual monitoring for wound healing. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:38281531] [10.1016/j.ijbiomac.2024.129735] |
| 31. Peng Ding, Yanfang Sun, Guohua Jiang, Lei Nie. (2025) Hydroxyproline-Modified Chitosan-Based Hydrogel Dressing Incorporated with Epigallocatechin-3-Gallate Promotes Wound Healing Through Immunomodulation. Gels, 11 (9): (732). [PMID:41002506] [10.3390/gels11090732] |
| 32. Yi Yang, Bei Tian, Xinyu Tian, Linyan Yao, Jianxi Xiao. (2025) Highly stable and bioactive yak type I collagen gels for accelerated healing of photoaging skin. NEW JOURNAL OF CHEMISTRY, [PMID:] [10.1039/D5NJ02557E] |
| 33. Chi Yan, Xingyu Chen, Wenqing Gao, Chunlan Tang, Liwen Du, Chengyi Xie, Feng Xu, Keqi Tang, Jiancheng Yu. (2025) Chiral Derivatization Enables High-Resolution Ion Mobility Spectrometry of 30 Amino Acid Enantiomers. ANALYTICAL CHEMISTRY, [PMID:41451537] [10.1021/acs.analchem.5c06382] |
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