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 |
|---|
10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -80°C Ships Dry ice packs + Cold packs 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 30 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Lactobionic acid is an inhibitor of MMP.
An inhibitor of matrix metalloproteinases
| Canonical Smiles | C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)O |
|---|---|
| IUPAC Name | (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid |
| InChIKey | JYTUSYBCFIZPBE-AMTLMPIISA-N |
| INCHI | 1S/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5+,6+,7-,8-,9-,10-,12+/m1/s1 |
| Isomeric SMILES | C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C(=O)O)O)O)O)O)O)O |
| WGK Germany | 1 |
| UN Number | 3265 |
| Molecular Weight | 358.3 |
| Beilstein | 95054 |
| Reaxy-Rn | 25712943 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25712943&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 | Fatty Acyls |
| Subclass | Fatty acyl glycosides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Fatty acyl glycosides of mono- and disaccharides |
| Alternative Parents | Disaccharides O-glycosyl compounds Medium-chain hydroxy acids and derivatives Medium-chain fatty acids Beta hydroxy acids and derivatives Sugar acids and derivatives Heterocyclic fatty acids Hydroxy fatty acids Alpha hydroxy acids and derivatives Oxanes Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Oxacyclic compounds Polyols Acetals Hydrocarbon derivatives Primary alcohols Organic oxides Carbonyl compounds |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Fatty acyl glycoside of mono- or disaccharide - Gluconic_acid - Disaccharide - Glycosyl compound - O-glycosyl compound - Medium-chain hydroxy acid - Medium-chain fatty acid - Beta-hydroxy acid - Heterocyclic fatty acid - Hydroxy fatty acid - Alpha-hydroxy acid - Fatty acid - Hydroxy acid - Oxane - Secondary alcohol - Acetal - Carboxylic acid derivative - Carboxylic acid - Oxacycle - Organoheterocyclic compound - Polyol - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Primary alcohol - Carbonyl group - Organooxygen compound - Alcohol - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. |
| External Descriptors | disaccharide |
| 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 |
|---|
| Specific Rotation[α] | 26 ° (C=8.8, H2O) |
|---|---|
| Melt Point(°C) | 113-118°C |
| Molecular Weight | 358.300 g/mol |
| XLogP3 | -5.000 |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 8 |
| Exact Mass | 358.111 Da |
| Monoisotopic Mass | 358.111 Da |
| Topological Polar Surface Area | 218.000 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 405.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| 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. Yang Fu, Chaohui Ji, Zhiheng Ma, Defeng Xu, Hang Hu. (2023) Targeted Delivery of Doxorubicin to Hepatoma Cells by Lactobionic Acid-Decorated Dual Redox-Responsive Polyethylene Glycol-Doxorubicin Nanoparticles. International Journal of Nanoscience, [PMID:] [10.1142/S0219581X23500199] |
| 2. Zi Chao Wu, Xin Yu Liu, Jia Yan Liu, Jing Shu Piao, Ming Guan Piao. (2022) Preparation of Betulinic Acid Galactosylated Chitosan Nanoparticles and Their Effect on Liver Fibrosis. International Journal of Nanomedicine, [PMID:36134203] [10.2147/IJN.S373430] |
| 3. Xiaohui Xiao, Yupeng Wang, Jieyao Chen, Peng Qin, Peiyao Chen, Dongfang Zhou, Yue Pan. (2022) Self-targeting platinum(IV) amphiphilic prodrug nano-assembly as radiosensitizer for synergistic and safe chemoradiotherapy of hepatocellular carcinoma. BIOMATERIALS, [PMID:36126545] [10.1016/j.biomaterials.2022.121793] |
| 4. Hang Hu, Defeng Xu. (2022) pH-Sensitive nanoparticles co-loaded with dimethylcurcumin and regorafenib for targeted combinational therapy of hepatocellular carcinoma. EUROPEAN POLYMER JOURNAL, [PMID:] [10.1016/j.eurpolymj.2022.111434] |
| 5. Dao-Qiang Lu, Dahai Liu, Justin Liu, Wen-Xing Li, Yilong Ai, Jun Wang, Daogang Guan. (2022) Facile synthesis of chitosan-based nanogels through photo-crosslinking for doxorubicin delivery. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:35870629] [10.1016/j.ijbiomac.2022.07.112] |
| 6. Jiahong Guo, Xiaoyu Ma, Fernando Bouffard, Sophia Yi Zhang. (2022) A Novel multi-fruit acids formula design on molecular basis for skin brightening via a system biology approach. Journal of Cosmetic Dermatology, 21 (11): (6145-6155). [PMID:35713107] [10.1111/jocd.15163] |
| 7. Yingying Zhao, Xiaoli Ji, Lili Wu, Jiaying Tian, Chaocan Zhang. (2021) Preparation of demulsifying functional membrane and its application in separation of emulsified oil. SEPARATION AND PURIFICATION TECHNOLOGY, [PMID:] [10.1016/j.seppur.2021.119299] |
| 8. Panxianzhi Ni, Renpeng Li, Sheng Ye, Jing Shan, Tun Yuan, Jie Liang, Yujiang Fan, Xingdong Zhang. (2021) Lactobionic acid-modified chitosan thermosensitive hydrogels that lift lesions and promote repair in endoscopic submucosal dissection. CARBOHYDRATE POLYMERS, [PMID:33858584] [10.1016/j.carbpol.2021.118001] |
| 9. Jun Wang, Zongyong Zhang, Yilong Ai, Fang Liu, Min-Min Chen, Dahai Liu. (2021) Lactobionic acid-modified thymine-chitosan nanoparticles as potential carriers for methotrexate delivery. CARBOHYDRATE RESEARCH, [PMID:33657498] [10.1016/j.carres.2021.108275] |
| 10. Hui Xu, Zijie Feng, Yingxiang Du. (2019) Synthesis, application and molecular modeling study of ionic liquid functionalized lactobionic acid, 3-methyl-1-(3-sulfopropyl)-1H-imidazol-3-ium lactobionate, as a chiral selector in capillary electrophoresis. ANALYST, 145 (3): (1025-1032). [PMID:31832629] [10.1039/C9AN02009H] |
| 11. Aiyun Liu, Huaisong Wang, Xiaoshuang Hou, Yu Ma, Gongjun Yang, Yanglong Hou, Ya Ding. (2019) Combinatory antitumor therapy by cascade targeting of a single drug. Acta Pharmaceutica Sinica B, [PMID:32322469] [10.1016/j.apsb.2019.08.011] |
| 12. Yuzhe Huang, Jian Guo, Shuangying Gui. (2018) Orally targeted galactosylated chitosan poly(lactic-co-glycolic acid) nanoparticles loaded with TNF-ɑ siRNA provide a novel strategy for the experimental treatment of ulcerative colitis. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, [PMID:30315858] [10.1016/j.ejps.2018.10.009] |
| 13. Shasha He, Chan Li, Qingfei Zhang, Jianxun Ding, Xing-Jie Liang, Xuesi Chen, Haihua Xiao, Xiaoyuan Chen, Dongfang Zhou, Yubin Huang. (2018) Tailoring Platinum(IV) Amphiphiles for Self-Targeting All-in-One Assemblies as Precise Multimodal Theranostic Nanomedicine. ACS Nano, [PMID:29906087] [10.1021/acsnano.8b03476] |
| 14. Yuxia Pei, Menghuan Li, Yanhua Hou, Yan Hu, Guangyu Chu, Liangliang Dai, Ke Li, Yuxin Xing, Bailong Tao, Yonglin Yu, Chencheng Xue, Ye He, Zhong Luo, Kaiyong Cai. (2018) An autonomous tumor-targeted nanoprodrug for reactive oxygen species-activatable dual-cytochrome c/doxorubicin antitumor therapy. Nanoscale, 10 (24): (11418-11429). [PMID:29881865] [10.1039/C8NR02358A] |
| 15. Yuhua Chen, Feng Zhang, Qian Wang, Huiming Lin, Ruihan Tong, Na An, Fengyu Qu. (2018) The synthesis of LA-Fe3O4@PDA-PEG-DOX for photothermal therapy–chemotherapy. DALTON TRANSACTIONS, 47 (7): (2435-2443). [PMID:29379913] [10.1039/C7DT04080F] |
| 16. Aisha Roshan Mohamed Wali, Jie Zhou, Shengnan Ma, Yiyan He, Dong Yue, James Zhenggui Tang, Zhongwei Gu. (2017) Tailoring the supramolecular structure of amphiphilic glycopolypeptide analogue toward liver targeted drug delivery systems. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:28396247] [10.1016/j.ijpharm.2017.04.009] |
| 17. Jia Liu, Wim E. Hennink, Mies J. van Steenbergen, Renxi Zhuo, Xulin Jiang. (2016) A facile modular approach toward multifunctional supramolecular polyplexes for targeting gene delivery. Journal of Materials Chemistry B, 4 (43): (7022-7030). [PMID:32263569] [10.1039/C6TB01671E] |
| 18. Jinxia An, Xiaomei Dai, Yu Zhao, Qianqian Guo, Zhongming Wu, Xinge Zhang, Chaoxing Li. (2015) A biodegradable and fluorescent nanovehicle with enhanced selective uptake by tumor cells. Polymer Chemistry, 6 (36): (6529-6542). [PMID:] [10.1039/C5PY00795J] |
| 19. Meihao Liang, Xiaoliang Zheng, Linglan Tu, Zhen Ma, Zunyuan Wang, Dongmei Yan, Zhengrong Shen. (2014) The liver-targeting study of the N-galactosylated chitosan in vivo and in vitro. Artificial Cells Nanomedicine and Biotechnology, [PMID:24066968] [10.3109/21691401.2013.841173] |
| 20. Qiuxia Zheng, Jia Yao, Zongbin Sun, Rui Li, Yue Zhang, Pan Jiang, Ye Xie, Xiaojing Song, Hongfa Sun, Dan Zhu, Haixu Ni, Xun Li. (2025) Carboxymethyl chitosan/oxidized hyaluronic acid hydrogel-encapsulated hucMSC-derived exosomes for enhanced hepatic regeneration and post-hepatectomy applications. CARBOHYDRATE POLYMERS, [PMID:39914972] [10.1016/j.carbpol.2025.123248] |
| 21. Bowen Deng, Rui Huang, Rui Liang, Yang Fei, Qing Luo, Guanbin Song. (2024) Design and evaluation of collagenase-loaded nanoparticles for mechanical intervention of orthotopic hepatocellular carcinoma in rat model. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:39638179] [10.1016/j.ijbiomac.2024.138311] |
| 22. Xin Yu Liu, He Ying Mao, Shuai Hong, Cheng-Hua Jin, Hu-Lin Jiang, Ming Guan Piao. (2024) Dual-targeting galactose-functionalized hyaluronic acid modified lipid nanoparticles delivering silybin for alleviating alcoholic liver injury. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:39241932] [10.1016/j.ijpharm.2024.124662] |
| 23. Jiahui Chen, Liping Zhang, Ting Xie, Xiao Zhang, Congcong Pan, Fangli Sun, Wenfeng Li, Zhijie Sun, Deli Dong. (2025) Nitazoxanide protects against heart failure with preserved ejection and metabolic syndrome induced by high-fat diet (HFD) plus L-NAME “two-hit” in mice. Acta Pharmaceutica Sinica B, [PMID:40370562] [10.1016/j.apsb.2024.12.040] |
| 24. Wei Tian, Hanyao Sun, Ziqing Xu, Na Li, Xi Luo, Yang Li, Jiaqi Xu, Jiajia Tang, Yafei Luo, Jie Zhang, Chen Yuan, Shangyu Lu, Haibin Shi, Shouju Wang, Sheng Liu. (2025) Gold-embedded yolk-shell mesoporous organosilica nanocomposite for microwave-enhanced targeted chemotherapy and immune modulation in hepatocellular carcinoma. BIOMATERIALS, [PMID:40644790] [10.1016/j.biomaterials.2025.123533] |
| 25. Ranran Zhao, Hongxin Liu, Zhigang Xie, Min Zheng. (2025) Targeting chiral carbon dots to enhance melanoma immunotherapy. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:41016112] [10.1016/j.jcis.2025.139093] |
| 26. Kun Yan, Zongrun Zhang, Xianzhu Yang, Chenguang Yang, Zhentan Lu, Dong Wang. (2025) Glycosylation-Engineered Chitosan Bioelectronic Interfaces for P. aeruginosa Gradient Analysis. ANALYTICAL CHEMISTRY, [PMID:40570237] [10.1021/acs.analchem.5c01313] |
| 27. Mengmeng Xue, Yanyan Li, Shanshan Tie, Yunling Zhang, Xue Zhang, Shichang Li, Jianrui Sun, Dongyang Zhu, Yuwan Li, Shaobin Gu. (2025) Preparation and characterization of hyaluronic acid nanoparticles for procyanidins hepatocellular and mitochondrial targeting delivery. COLLOIDS AND SURFACES B-BIOINTERFACES, [PMID:41330273] [10.1016/j.colsurfb.2025.115334] |
| 28. Ting-Ting Hu, Ying Ding, Yi-Ren Yao, Xin Zhang, Xi-Wen Zhang, Yang Gu. (2026) Erythrocyte membrane-camouflaged doxorubicin nanoparticles for enhancing therapeutic efficacy in primary liver cancer. JOURNAL OF DRUG TARGETING, [PMID:] [10.1080/1061186X.2026.2647068] |
| 29. Qinglin Qu, Fan Liu, Huajing Gao, Xiangrui Kong, Xue Gao, Yukun Song, Mingqian Tan, Yannan Chen, Dapeng Li, Xintong Tan. (2026) Orally engineered liver-targeted garlic exosome-like nanovesicles for astaxanthin precise delivery against alcoholic liver disease in mice. FOOD RESEARCH INTERNATIONAL, [PMID:] [10.1016/j.foodres.2026.119022] |
| 30. Jiahong Xie, Shiyu Liu, Yang Xu, Boyu Song, Jingli Liu, Guangyi Du, Lianghua Xie, Wei Chen. (2026) Design and fabrication of multifunctional cyanidin-3-O-glucoside-loaded nanonutriosomes with enhanced physicochemical stability and hepatic targeting for mitigating alcoholic liver injury. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2026.174791] |