1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) - ≥98% , CAS No.26853-31-6

CAS: 26853-31-6 Cat. No.: P278649 Peso molecular: 760.08 Beilstein Registry Number: 4173237 Número EC: 248-056-7

GRADE & PURITY ≥98%

Synonyms

POPC | PC(16:0/18:1(9Z)) | LMGP01010005 | (R,Z)-2-(Oleoyloxy)-3-(palmitoyloxy)propyl(2-(trimethylammonio)ethyl)phosphate | phosphatidylcholine (1-16:0-2-18:1) | EINECS 218-619-1 | cis-1,2-Dimethylcyclohexane, 99% | Brain PC, L-alpha-phosphatidylcholine (B

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

POPC is typically considered one of the model lipids for biophysical experiments. The fatty acid composition, i.e., saturated chain in the sn-1 position and unsaturated chain in the sn-2 position, mimics mammalian phospholipid composition. Since the major constituent in Egg PC is 1-palmitoyl-2-oleoyl PC, POPC is an excellent synthetic substitute for EPC.
The effect of non-ionic detergent on liposomes was studied with giant POPC liposomes. Increasing concentrations of detergent cause tubular protrusions, then indentations, to develop on spherical liposomes. At higher detergent concentrations, the liposomes burst.

Specifications

Sinónimos

POPC | PC(16:0/18:1(9Z)) | LMGP01010005 | (R, Z)-2-(Oleoyloxy)-3-(palmitoyloxy)propyl(2-(trimethylammonio)ethyl)phosphate | phosphatidylcholine (1-16:0-2-18:1) | EINECS 218-619-1 | cis-1, 2-Dimethylcyclohexane, 99% | Brain PC, L-alpha-phosphatidylcholine (B

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

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

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488195587
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195587
• Sonrisas canónicas: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
• IUPAC Name: [(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: WTJKGGKOPKCXLL-VYOBOKEXSA-N
• INCHI: 1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1
• Isómeros SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
• WGK Alemania: 3
• CAS alternativo: 59491-62-2
• Peso molecular: 760.08
• Beilstein: 4173237
• Reaxy-Rn: 4173236
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4173236&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

Propiedades químicas y físicas

• Sensibilidad: moisture & light tsensitive
• Peso molecular: 760.100 g/mol
• XLogP3: 13.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 41
• Exact Mass: 759.578 Da
• Monoisotopic Mass: 759.578 Da
• Topological Polar Surface Area: 111.000 Ų
• Heavy Atom Count: 52
• Formal Charge: 0
• Complexity: 899.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. 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]

2. Fenghua Wang, Zehui Guo, Zixuan Yang, Xueying Li, Xue Zhang, Xiangyang Ma, Zhuoxuan Han, Fuping Lu, Yihan Liu.  (2022)  Utilization of Soybean Oil Waste for a High-Level Production of Ceramide by a Novel Phospholipase C as an Environmentally Friendly Process.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:35229592] [10.1021/acs.jafc.1c08362]

3. Minglei Chen, Kambere Amerigos Daddy J.C., Zhigui Su, Nida El Islem Guissi, Yanyu Xiao, Li Zong, Qineng Ping.  (2019)  Folate Receptor-Targeting and Reactive Oxygen Species-Responsive Liposomal Formulation of Methotrexate for Treatment of Rheumatoid Arthritis.  Pharmaceutics,  11  (11): (582).  [PMID:31698794] [10.3390/pharmaceutics11110582]

4. Chuanye Tang, Lei Feng, Pinghua Ling, Qiuting Wang, Wenwen Xu, Danjie Song, Yalong Qiao, Feng Gao.  (2025)  DNA Logic Gate-Triggered Membrane Fusion for Accurately Detecting and Killing Cancer Cells.  ACS Applied Materials & Interfaces,      [PMID:39907089] [10.1021/acsami.4c20737]

5. Jinlei Yang, Jing Wang, Runsong Cheng, Tianyi Liao, Siyuan Pan, Murong Du, Weiliang Liu, Liying Yan, Sichun Zhang, Xinrong Zhang.  (2025)  Microseparation of Lipophilic and Hydrophilic Metabolites for Single Oocyte Mass Spectrometry Analysis.  ANALYTICAL CHEMISTRY,      [PMID:39800910] [10.1021/acs.analchem.4c04900]

6. Zhirong Li, Lulu Zhang, Zhanzhong Wang, Xiongli Kang, Huiying Jin, Wenjie Zhao, Jun Zhang, Haiquan Su.  (2024)  Quantification of Phosphatidylserine Molecules on the Surface of Individual Cells Using Single-Molecule Force Spectroscopy.  ANALYTICAL CHEMISTRY,      [PMID:38173079] [10.1021/acs.analchem.3c03517]

7. Yalong Qiao, Linyu Wang, Wenwen Xu, Pei Yang, Chuanye Tang, Danjie Song, Pinghua Ling, Feng Gao.  (2024)  Reversible Modulation of Cell–Cell Interactions Using Electrochemistry.  ACS Applied Materials & Interfaces,      [PMID:39103300] [10.1021/acsami.4c08619]

8. Dawei Yu, Haifeng Zhang, Pei Gao, Fang Yang, Dongxing Yu, Wenshui Xia, Qixing Jiang.  (2025)  Decoding flavor precursors in channel catfish (Ictalurus punctatus): Lipidomics-guided discovery of phosphatidylcholine oxidation pathways under thermal processing.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107647]