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0.5M for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C 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 43 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Canonical Smiles | C(C(CO)OP(=O)([O-])[O-])O.O.O.O.O.O.[Na+].[Na+] |
|---|---|
| IUPAC Name | disodium;1,3-dihydroxypropan-2-yl phosphate;pentahydrate |
| InChIKey | PEMUISUYOHQFQH-UHFFFAOYSA-L |
| INCHI | 1S/C3H9O6P.2Na.5H2O/c4-1-3(2-5)9-10(6,7)8;;;;;;;/h3-5H,1-2H2,(H2,6,7,8);;;5*1H2/q;2*+1;;;;;/p-2 |
| Isomeric SMILES | C(C(CO)OP(=O)([O-])[O-])O.O.O.O.O.O.[Na+].[Na+] |
| WGK Germany | 3 |
| RTECS | UA0600000 |
| Alternate CAS | 819-83-0 |
| Molecular Weight | 306.11 |
| Beilstein | 1(2)594 |
| Reaxy-Rn | 3922496 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3922496&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 | Lipids and lipid-like molecules |
| Class | Glycerophospholipids |
| Subclass | Glycerophosphates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Glycerophosphates |
| Alternative Parents | Alkyl phosphates Primary alcohols Organic sodium salts Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Sn-glycerol-2-phosphate - Alkyl phosphate - Phosphoric acid ester - Organic phosphoric acid derivative - Organic alkali metal salt - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organic sodium salt - Organic salt - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as glycerophosphates. These are compounds containing a glycerol linked to a phosphate group. |
| External Descriptors | Not available |
| Melt Point(°C) | 102-104°C |
|---|---|
| Molecular Weight | 306.110 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 3 |
| Exact Mass | 306.03 Da |
| Monoisotopic Mass | 306.03 Da |
| Topological Polar Surface Area | 118.000 Ų |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Complexity | 113.000 |
| 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 | 8 |
| 1. Haibin Li, Chunyan Zhang, Qiang Liu. (2023) Lumican silencing ameliorates β-glycerophosphate-mediated vascular smooth muscle cell calcification by attenuating the inhibition of APOB on KIF2C activity. Open Medicine, 18 (1): [PMID:37711155] [10.1515/med-2023-0790] |
| 2. Hanqi Wu, Weizheng Zhang, Xuhui Huang, Peng Gu, Qi Li, Xingzhang Luo, Zheng Zheng. (2023) Phosphorus conditions change the cellular responses of Microcystis aeruginosa to perfluorooctanoic acid. SCIENCE OF THE TOTAL ENVIRONMENT, [PMID:37660808] [10.1016/j.scitotenv.2023.166707] |
| 3. Yang Liu, Chuang Lang, Yaping Ding, Siyu Sun, Guangwei Sun. (2023) Chitosan with enhanced deprotonation for accelerated thermosensitive gelation with β-glycerophosphate. EUROPEAN POLYMER JOURNAL, [PMID:] [10.1016/j.eurpolymj.2023.112229] |
| 4. Cunguo Chen, Murong Hu, Yunyun Cao, Binbin Zhu, Jiashe Chen, Yashi Li, Junyi Shao, Sen Zhou, Pengfei Shan, Chen Zheng, Zhongyu Li, Zhiming Li. (2023) Combination of a STING Agonist and Photothermal Therapy Using Chitosan Hydrogels for Cancer Immunotherapy. BIOMACROMOLECULES, [PMID:37125731] [10.1021/acs.biomac.3c00196] |
| 5. Shihuai Li, Yunan Qing, Yan Lou, Ruiyan Li, Hao Wang, Xingyue Wang, Boda Ying, Xiongfeng Tang, Yanguo Qin. (2023) Injectable thermosensitive black phosphorus nanosheet- and doxorubicin-loaded hydrogel for synergistic bone tumor photothermal-chemotherapy and osteogenesis enhancement. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:36972826] [10.1016/j.ijbiomac.2023.124209] |
| 6. Yutong Wu, Hongbo Ai, Yuchi Zou, Qiankun Yang, Ce Dou, Jianzhong Xu. (2022) Osteoclast-derived extracellular miR-106a-5p promotes osteogenic differentiation and facilitates bone defect healing. CELLULAR SIGNALLING, [PMID:36464103] [10.1016/j.cellsig.2022.110549] |
| 7. Tingting Wu, Binglin Li, Wanshun Wang, Lingling Chen, Zhan Li, Ming Wang, Zhengang Zha, Zefeng Lin, Hong Xia, Tao Zhang. (2020) Strontium-substituted hydroxyapatite grown on graphene oxide nanosheet-reinforced chitosan scaffold to promote bone regeneration. Biomaterials Science, 8 (16): (4603-4615). [PMID:32627770] [10.1039/D0BM00523A] |
| 8. Peng Mengke, Hu Fenyan, Du Minting, Mai Bingjie, Zheng Shurong, Liu Peng, Wang Changhao, Chen Yashao. (2019) Hydrothermal growth of hydroxyapatite and ZnO bilayered nanoarrays on magnesium alloy surface with antibacterial activities. Frontiers of Materials Science, 14 (1): (14-23). [PMID:] [10.1007/s11706-020-0489-5] |
| 9. Ye He, Caiyun Mu, Xinkun Shen, Zhang Yuan, Ju Liu, Weizhen Chen, Chuanchuan Lin, Bailong Tao, Bin Liu, Kaiyong Cai. (2018) Peptide LL-37 coating on micro-structured titanium implants to facilitate bone formation in vivo via mesenchymal stem cell recruitment. Acta Biomaterialia, [PMID:30266635] [10.1016/j.actbio.2018.09.036] |
| 10. Lyu Zhengtian, Yuan Gaoxiang, Zhang Yuying, Zhang Fengwenhui, Liu Yan, Li Yifan, Li Guang, Wang Ying, Zhang Ming, Hu Yongfei, Guo Yuming, Liu Dan. (2024) Anaerostipes caccae CML199 enhances bone development and counteracts aging-induced bone loss through the butyrate-driven gut–bone axis: the chicken model. Microbiome, 12 (1): (1-24). [PMID:39438898] [10.1186/s40168-024-01920-y] |
| 11. Maojiao Li, Qi Tang, Chengcheng Liao, Zhuo Wang, Siyuan Zhang, Qingqing Liang, Cheng Liang, Xiaodong Liu, Jingyi Zhang, Weidong Tian, Li Liao. (2024) Extracellular vesicles from apoptotic BMSCs ameliorate osteoporosis via transporting regenerative signals. Theranostics, [PMID:38948067] [10.7150/thno.96174] |
| 12. Pan Liu, Jiezhong Deng, Yusheng Yang, Wenxi Bai, Shengtao Dong, Zehua Zhang. (2025) Mycobacterium tuberculosis specific protein Rv1509 modulates osteoblast and osteoclast differentiation via TLR2 signaling. iScience, [PMID:40129707] [10.1016/j.isci.2025.112107] |
| 13. Dingkun Liu, Jinbing Chen, Linjuan Gao, Xing Chen, Liujun Lin, Yuan Liu, Xia Wei, Yu Pan, Yinghui Wang, Hui Cheng. (2025) Nano Sim@ZIF8@PDA modified injectable temperature sensitive nanocomposite hydrogel for photothermal/drug therapy for peri-implantitis. CARBOHYDRATE POLYMERS, [PMID:39978909] [10.1016/j.carbpol.2025.123327] |
| 14. Yijie Li, Shuni Duan, Yinhao Zhang, Runping Liu, Rong Sun, Jianzhi Wu, Zhi Ma, Xiaojiaoyang Li. (2025) Precise subcellular organelle-targeted analyses of hepatotoxicity of Polygonum multiflorum. Chinese Herbal Medicines, [PMID:41584695] [10.1016/j.chmed.2025.03.001] |
| 15. Jian Wang, Dongyang Zhou, Ruiyang Li, Shihao Sheng, Guangfeng Li, Yue Sun, Peng Wang, Yulin Mo, Han Liu, Xiao Chen, Zhen Geng, Qin Zhang, Yingying Jing, Long Bai, Ke Xu, Jiacan Su. (2024) Protocol for engineering bone organoids from mesenchymal stem cells. Bioactive Materials, [PMID:39687559] [10.1016/j.bioactmat.2024.11.017] |
| 16. Shurong Zheng, Guangyao Dai, Qimei Xue, Ruiqi Liang, Wancheng Zhu, Changhao Wang, Yashao Chen. (2024) Rational design of pH-responsive hydrogel micropatterns on magnesium alloy with enhanced biological activity. SURFACE & COATINGS TECHNOLOGY, [PMID:] [10.1016/j.surfcoat.2024.130528] |
| 17. Dong Wei, Wang Guihu, Chai Yichao, Li Wenjuan, Liu Shichang, Liu Huasheng, Guo Wenlei, Li Senyang, He Xinrui, Wan Mingxi, Li Zongfang, Zong Yujin. (2025) Two-step ultrasonic cavitation controlled delivery of brain exogenous nucleic acids for ischemic stroke using acoustic-cationic-polymeric-nanodroplets. Drug Delivery and Translational Research, [PMID:40048146] [10.1007/s13346-025-01828-6] |
| 18. Zi Fu, Ling Huang, Xinyu Zhang, Zhichao Zheng, Lihong Wu, Huade Zheng. (2025) Enhanced photothermal therapy for oral cancer using benzothiadiazole-based nanoparticle-loaded hydrogels. Artificial Cells Nanomedicine and Biotechnology, [PMID:40739986] [10.1080/21691401.2025.2540648] |
| 19. Yawen Sun, Guangxiao Zhang, Bowen Zhao, Chenxue Fu, Bin Li, Fang Wang, Ming Tian, Minghui Wang, Hai Lin, Haifang Li. (2025) In ovo Vitamin D3 Injection Leads to a Long-term Improvement of Bone Development in Laying Chicks. POULTRY SCIENCE, [PMID:40803225] [10.1016/j.psj.2025.105617] |
| 20. Danhong Zhou, Xueting Wang, Hui Zhang, Qifeng Jiang, Qinmeng Zhang, Xiaoyan Miao, Ying Wang, Guoli Yang, Zhiwei Jiang. (2025) Lrp5 A241T High-Bone-Mass Mutation Enhances Implant Osseointegration: An Experimental Murine Study. ORAL DISEASES, [PMID:41025443] [10.1111/odi.70102] |
| 21. Zehao Chen, Binghao Wang, Chengliang Yang, Zhendong Lv, Yu Wei, Tianming Pan, Fuqing Xuan, Xingdie Zhou, Hao Chen, Hongxing Shen, Liqiang Wang, Yuhui Zhang. (2024) 3D Printed Pedicle Screws with Microarc Oxidation Ceramic Interfaces Enhance Osteointegration and Orthopedic Fixation Feasibility. ACS Applied Materials & Interfaces, [PMID:38865688] [10.1021/acsami.4c03628] |
| 22. Shang Wang, Huan Lei, Yu Mi, Pei Ma, Daidi Fan. (2024) Chitosan and hyaluronic acid based injectable dual network hydrogels - Mediating antimicrobial and inflammatory modulation to promote healing of infected bone defects. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:38897505] [10.1016/j.ijbiomac.2024.133124] |
| 23. Ruonan Liu, Yanpeng Wang, Haoxiang Chu, Yiqi Li, Yehan Li, Yunjun Zhao, Ye Tian, Zhixiu Xia. (2024) High-performance gelatin-based hydrogel flexible sensor for respiratory monitoring and human–machine interaction. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2024.157975] |
| 24. Mofei Han, Kaiqi Tang, Zhenhua Chen. (2024) Preparation of NIR responsive resveratrol@Au nanocages using for regulating oxidative stress microenvironment of periodontitis. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2024.158774] |
| 25. Xutao Wen, Qin Zhou, Sihan Lin, Huaming Mai, Ling Zhang. (2025) Selenium-modified hydroxyapatite titanium coating: enhancing osteogenesis and inhibiting cancer in bone invasion by head and neck squamous cell carcinoma. Frontiers in Bioengineering and Biotechnology, [PMID:40066360] [10.3389/fbioe.2025.1552661] |
| 26. Liuxin Yang, Guanhua Jiao, Dandan Wei, Tianzhu Zhang. (2025) Synthesis and characterization of photocrosslinked gelatin-silk fibroin composite microspheres for mesenchymal stem cell expansion and osteogenic differentiation. Materials Today Communications, [PMID:] [10.1016/j.mtcomm.2025.111912] |
| 27. Liu Lisha, Deng Dashi, Li Chenchen, Huang Guixiao, Zhang Wenjuan, Liang Ting, Liang Rui, Liang Mingkang, Su Yilin, Lin Chongyang, Li Guangzhi, Wu Song. (2024) The combination of modified acupuncture needle and melittin hydrogel as a novel therapeutic approach for rheumatoid arthritis treatment. JOURNAL OF NANOBIOTECHNOLOGY, 22 (1): (1-20). [PMID:39034393] [10.1186/s12951-024-02722-y] |
| 28. Yun Li, Meijuan Cheng, Jingjing Jin, Dongxue Zhang, Shenglei Zhang, Yaling Bai, Jinsheng Xu. (2024) Interaction of Sp1 and Setd8 promotes vascular smooth muscle cells apoptosis by activating Mark4 in vascular calcification. Aging-US, [PMID:38301049] [10.18632/aging.205492] |
| 29. San-yang Yu, Ting Wu, Kai-hao Xu, Ru-yue Liu, Tian-hao Yu, Zhen-hua Wang, Zhong-ti Zhang. (2025) 3D bioprinted biomimetic MOF-functionalized hydrogel scaffolds for bone regeneration: Synergistic osteogenesis and osteoimmunomodulation. Materials Today Bio, [PMID:40270888] [10.1016/j.mtbio.2025.101740] |
| 30. Perumal Ramesh Kannan, Supaporn Sangkert, Caiying Jiang, Yao Li, Ruibo Zhao, M. Zubair Iqbal, Xiangdong Kong. (2025) Ultrasmall zinc oxide nanoparticle-reinforced chitosan-fucoidan scaffolds for enhanced antibacterial activity and accelerated osteogenesis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:40268008] [10.1016/j.ijbiomac.2025.143390] |
| 31. Yang Liu, Yingkai Wang, Xiangzi Wang, Wanchen Zeng, Zehong Zhang, Zhengmian Zhang, Zhongquan Qi. (2025) Synergistic Antioxidant and Anti-Ferroptosis Therapy via BPNS-Encapsulated Thermoresponsive Chitosan Hydrogel for Spinal Cord Injury Regeneration. Pharmaceutics, 17 (5): (573). [PMID:40430865] [10.3390/pharmaceutics17050573] |
| 32. Songlun Jiang, Xu Zhang, Fanfan Chen, Zifan Zhao, Chenglong Zhang, Yuchun Sun. (2025) Ketone body 3-hydroxybutyrate mitigates apoptosis and enhances osteogenesis in bone organoid construction via the cAMP/PKA/CREB signaling pathway. FASEB JOURNAL, 39 (8): (e70510). [PMID:40277379] [10.1096/fj.202402974R] |
| 33. Yue Zhou, Yi-Ran Yao, Yan Xu, Xin Rong, Yue-Feng Qiu, Ting-Yue Qi. (2025) TiO2 NPs improve ultrasound response: CS/β‑GP/TiO2 NP hydrogel enabling on‑demand administration. Biomedical Reports, 23 (3): (1-10). [PMID:40599619] [10.3892/br.2025.2020] |
| 34. Yongbin Wang, Han Zhang, Zhili Xu, Weihang Zhu, Sheng Chang, Jiahao Wei, Shuqing Chen, Yong Liu, Weiqing Kong, Jianwei Guo. (2025) Icariin-loaded GelMa Hydrogel Encapsulated Potassium Sodium Niobate Biomimetic Piezoelectric Scaffold Regulates Macrophage Polarization to Accelerate Bone Defect Repair. Materials Today Bio, [PMID:41281663] [10.1016/j.mtbio.2025.102476] |
| 35. Muhammad Saqib, Wen-Xin Chen, Yun Lei, Ai-Lin Liu. (2025) Sericin as a New Coreactant for Lucigenin Chemiluminescence: A Novel System for the Ultrasensitive Detection of Sericin and Superoxide Dismutase. ANALYTICAL CHEMISTRY, [PMID:41147793] [10.1021/acs.analchem.5c04780] |
| 36. Tianyi Ma, Ming Huo, Ruinan Xing. (2025) Biomimic oleuropein-loaded mesoporous polydopamine nanocomposite in injectable hydrogels inhibits cell apoptosis and antioxidant for myocardial infarction. PARTICULATE SCIENCE AND TECHNOLOGY, [PMID:] [10.1080/02726351.2025.2578644] |
| 37. Feipeng Wu, Weiling Yin, Hui Shan, Jie Cang, Ruixing Shui, Xianwen Yan, Wenbo He, Junmeng Liu, Jia Gao, Dapeng Li, Guoqing Pan. (2025) A nano-bio-coordination dynamic hydrogel with photothermal effects and osteogenic activity for the treatment of osteosarcoma. MATERIALS & DESIGN, [PMID:] [10.1016/j.matdes.2025.115092] |
| 38. Yuanqing Niu, Hengrui Chang, Jiaxin Xu. (2025) Regenerative treatment of zinc-based nanoenzyme incorporated injectable hydrogel with mesenchymal stem cells alleviates spinal cord injury. JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION, [PMID:41167984] [10.1080/09205063.2025.2574942] |
| 39. Zhang Peng, Chen Dinghao, Fang Yu, Li Sangshuang, Zhou Ziao, Lu Huanfen, Cheng Jianjun, Wang Huaimin. (2025) Bone homeostasis regulation by in vivo generation of osteoclast-derived apoptotic bodies using targeted self-assembly. Nature Communications, 17 (1): (88). [PMID:41350258] [10.1038/s41467-025-66791-9] |
| 40. Fengmin CHEN, Yuqi ZHOU, Yao FENG, Hongguang ZHU. (2025) Study of micro-arc oxidation-polydopamine-nanoclay (MAO-PDA-NC) composite coating on osteogenesis in cranial defect areas of rats. DENTAL MATERIALS JOURNAL, [PMID:41443848] [10.4012/dmj.2025-145] |
| 41. Haifeng Hong, Cuiyun Zhou, Haibing Wang, Changhui Lin, Min Fang, Juntian Liu, Minhui Yang. (2026) PRMT1-rich exosomes derived from M2 macrophages as novel therapeutics for enhancing fracture healing. TISSUE & CELL, [PMID:41610641] [10.1016/j.tice.2026.103348] |
| 42. Chengsi Li, Jing Li, Chengyingjie Yang, Zhenghao Zhu, Yachen Zhang, Yin Xiang. (2026) Vericiguat improves CKD-related vascular calcification through the NO/cGMP/PKG pathway. INTERNATIONAL IMMUNOPHARMACOLOGY, [PMID:41723893] [10.1016/j.intimp.2026.116413] |
| 43. Jia Wang, Xuan Shi, Di Wang, Jie Gao, Kangmo Huang, Juanji Li, Weichen Dong, Yunzi Li, Hongquan Guo, Yi Wang, Zhenqian Huang, Zhihui Liu, Li Huang, Liangyuan Pan, Xinfeng Liu, Wusheng Zhu, Mengna Peng, Gelin Xu. (2026) Atherosclerotic plaque-derived extracellular vesicles mediate smooth muscle cell phenotypic switching and promote vascular remodeling: EVs promote VSMC phenotypic switching. CELLULAR AND MOLECULAR LIFE SCIENCES, 83 (1): (141). [PMID:41784666] [10.1007/s00018-026-06094-4] |