1,2-dimyristoyl-sn-glycero-3-phosphocholine(DMPC) - ≥99% , CAS No.18194-24-6

CAS: 18194-24-6 Cat. No.: D130420 Peso molecular: 677.93 Beilstein Registry Number: 3921768 Número EC: 242-085-9

GRADE & PURITY ≥99%

Synonyms

CHEBI:45240 | 1,2-Dimyristoyl-3-lecithin | DIMYRISTOYL LECITHIN [ORANGE BOOK] | Dmpc, l- | I8F3948441 | 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride | HY-10

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

228,229

Descripción general

A synthetic phospholipid utilized in liposomes and lipid bilayers for the study of biological membranes.

Specifications

Sinónimos

CHEBI:45240 | 1, 2-Dimyristoyl-3-lecithin | DIMYRISTOYL LECITHIN [ORANGE BOOK] | Dmpc, l- | I8F3948441 | 16, 17-dimethoxy-5, 7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2, 10}.0^{4, 8}.0^{15, 20}]henicosa-1(13), 2, 4(8), 9, 14, 16, 18, 20-octaen-13-ylium chloride | HY-10

Especificaciones y pureza

≥99%

Mecanismos bioquímicos y fisiológicos

Phosphatidylcholine containing myristoyl groups. For use in lipid bilayer studies and in biological systems. See similar compounds

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥99%

Nombres e identificadores

• Sonrisas canónicas: [O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCC)=O)=O
• IUPAC Name: [(2R)-2,3-di(tetradecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: CITHEXJVPOWHKC-UUWRZZSWSA-N
• INCHI: 1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1
• Isómeros SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC
• WGK Alemania: 3
• Peso molecular: 677.93
• Beilstein: 3921768
• Reaxy-Rn: 3921768
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3921768&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Glycerophospholipids
      • Subclass Glycerophosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphatidylcholines
• Alternative Parents: Phosphocholines Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Tetraalkylammonium salts Carboxylic acid esters Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Diacylglycero-3-phosphocholine - Phosphocholine - Fatty acid ester - Dialkyl phosphate - Dicarboxylic acid or derivatives - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Quaternary ammonium salt - Tetraalkylammonium salt - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Amine - Organic salt - Hydrocarbon derivative - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
• External Descriptors: Diacylglycerophosphocholines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (no humanos)

Human immunodeficiency virus 1 (70413 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Heat sensitive,Hygroscopic
• Rotación específica [α]: +7.0 to +10.0 deg(C=2, CHCl3)
• Punto de fusión (°C): 220°C
• Peso molecular: 677.900 g/mol
• XLogP3: 11.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 36
• Exact Mass: 677.5 Da
• Monoisotopic Mass: 677.5 Da
• Topological Polar Surface Area: 111.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 765.000
• 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

Referencias

1. Zhenjiang Zheng, Dingchuan Peng, Mengfei Li, Xuehan Lu, Songlin Gong, Yuan Yuan, Epiphane K. Silli, Jiali Tang, Qiaoyun Zhao, HaoYun Xu, Yufei Lan, Chunlu Tan, Ying Wang.  (2023)  Gemcitabine and Pin1 siRNA co-delivery with fucoidan-coated nano-liposomes for therapy of pancreatic cancer.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2023.104872]

2. He Li, Yue Yan, Jing Chen, Ke Shi, Chuwen Song, Yanglimin Ji, Liyan Jia, Jianming Li, Yan Qiao, Yiyang Lin.  (2023)  Artificial receptor-mediated phototransduction toward protocellular subcompartmentalization and signaling-encoded logic gates.  Science Advances,  9  (9):   [PMID:36857444] [10.1126/sciadv.ade5853]

3. Mengfei Li, Hongyu Chen, Dingchuan Peng, Xuehan Lu, Jianping Kong, Shujun Luo, Shiqi Li, Chunlu Tan, Ying Wang.  (2022)  FU-coating pH-sensitive liposomes for improving the release of gemcitabine by endosome escape in pancreatic cancer cells.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2022.104135]

4. Fen Xiao, Jianxin Tang, Xing Huang, Wenji Kang, Guiyin Zhou.  (2022)  A robust, low swelling, and lipid-lubricated hydrogel for bionic articular cartilage substitute.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:36088692] [10.1016/j.jcis.2022.08.146]

5. Yu-gang Shi, Shan Lin, Wen-xuan Chen, Lai Jiang, Qing Gu, Dong-hui Li, Yue-wen Chen.  (2022)  Dual-Stage Blue-Light-Guided Membrane and DNA-Targeted Photodynamic Inactivation Using Octyl Gallate for Ultraefficient Eradication of Planktonic Bacteria and Sessile Biofilms.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:35687111] [10.1021/acs.jafc.2c01667]

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7. Ru Song, Qingqing Shi, Peiyu Yang, Rongbian Wei.  (2017)  Identification of antibacterial peptides from Maillard reaction products of half-fin anchovy hydrolysates/glucose via LC-ESI-QTOF-MS analysis.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2017.07.026]

8. Tao Chunxu, Wang Junyan, Zhu Ying, Ding Chao, Shen Zhuoyue, Sun Danni, Cao Shanshan, Jiang Xinrong, Li Yaqi, Liu Chang, Zhang Qi, Li Shijie, Zhang Xinyan, Shi Qiaoqiao, Kong Dezhao.  (2024)  A highly sensitive fluorescence biosensor for aflatoxins B1 detection based on polydiacetylene liposomes combined with exonuclease III-assisted recycling amplification.  MICROCHIMICA ACTA,  191  (7): (1-12).  [PMID:38877314] [10.1007/s00604-024-06482-2]

9. Silli Epiphane K., Zheng Zhenjiang, Zhou Xintao, Li Mengfei, Tang Jiali, Guo Ruizhe, Tan Chunlu, Wang Ying.  (2024)  Design optimization of Fucoidan-coating Cationic Liposomes for enhance Gemcitabine delivery.  INVESTIGATIONAL NEW DRUGS,      [PMID:39154300] [10.1007/s10637-024-01455-x]

10. Yibo Yan, Ruilin Yang, Yanan Wang, Yinan Wu, Xiaofei Gu, Xiaoqiang Qiao.  (2024)  Esterified styrene-maleic acid copolymer modified silica as mixed-mode polymer-brush stationary phases for chromatographic separation.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:39116685] [10.1016/j.chroma.2024.465227]

11. Zhongnan Wang, Meiqi Zhang, Xu Zhang, Yao Hu, Haihui Lan, Beiji Gao, Wanxing Xu, Hongjiang He, Xiaolei Li, Zhaoyu Wang, E. Peisan (Sharel), Bo Gao, Bin Wang, Qiuying Chang, Haihui Lan, Tianyi Han, Chenhui Zhang.  (2025)  Electrotunable interfacial friction of polyacrylamide composite hydrogels.  COMPOSITES COMMUNICATIONS,      [PMID:] [10.1016/j.coco.2025.102562]

12. Yang Ruilin, Wang Ping, Guan Xinhui, Gu Xiaofei, Qiao Xiaoqiang.  (2025)  Exploiting metal-free atom transfer radical polymerization for fabrication of styrene-maleic acid polymer-brush grafting chromatographic stationary phase and its separation performances for phospholipids.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:40781368] [10.1007/s00216-025-06053-1]

13. Xin Huang, Lei Tang, Fen Xiao, Sihua Liu, Libo Nie, Guiyin Zhou, Kehui Sun.  (2025)  Bionic Hydrogels Inspired by Articular Cartilage with Lipid-Based Boundary Lubrication Properties.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.5c03268]

14. Ping Wang, Meijuan Xue, Xinhui Guan, Xiaofei Gu, Xiaoqiang Qiao.  (2026)  Preparation of styrene-maleic anhydride copolymer nanobrush chromatographic stationary phase and its application in phospholipid analysis of exosomes.  ANALYTICA CHIMICA ACTA,      [PMID:41796493] [10.1016/j.aca.2026.345260]