1-arachidoyl-2-hydroxy-sn-glycero-3-phosphocholine - ≥99% , CAS No.108341-80-6

CAS: 108341-80-6 Cat. No.: A130497 Molecular Weight: 551.736

GRADE & PURITY ≥99%

Synonyms

PC(20:0/0:0) | CHEBI:74968 | Methyl-(2-pyridin-2-yl-ethyl)-amine | Sulfuric acid compound with N''-benzyl-N,N'-dimethylguanidine (1:1) | b-Propiolactone | DTXSID401109429 | LysoPC(20:0/0:0) | Lysophosphatidylcholine(20:0/0:0) | 3,5,9-Trioxa-4-phosphanonac

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Purity :>99% LPC; may contain up to 10% of the 2-LPC isomer

20:0 Lyso PC has been used as an internal standard for the quantification of serum cholesterol and triacylglycerol using liquid chromatography-mass spectrometry (LC-MS) preceded by single-step liquid-liquid extraction method

Specifications

Synonyms

PC(20:0/0:0) | CHEBI:74968 | Methyl-(2-pyridin-2-yl-ethyl)-amine | Sulfuric acid compound with N''-benzyl-N, N'-dimethylguanidine (1:1) | b-Propiolactone | DTXSID401109429 | LysoPC(20:0/0:0) | Lysophosphatidylcholine(20:0/0:0) | 3, 5, 9-Trioxa-4-phosphanonac

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• IUPAC Name: [(2R)-2-hydroxy-3-icosanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: UATOAILWGVYRQS-HHHXNRCGSA-N
• INCHI: 1S/C28H58NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h27,30H,5-26H2,1-4H3/t27-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Molecular Weight: 551.736
• Reaxy-Rn: 24414148
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24414148&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphocholines
        • Level5 Lysophosphatidylcholines
          • Level6 1-acyl-sn-glycero-3-phosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: Lysophosphatidylcholines
• Direct Parent: 1-acyl-sn-glycero-3-phosphocholines
• Alternative Parents: Phosphocholines Fatty acid esters Dialkyl phosphates Tetraalkylammonium salts Secondary alcohols Carboxylic acid esters Monocarboxylic acids and derivatives Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-acyl-sn-glycero-3-phosphocholine - Phosphocholine - Fatty acid ester - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Tetraalkylammonium salt - Quaternary ammonium salt - Secondary alcohol - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organic oxide - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Alcohol - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic salt - Amine - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
• External Descriptors: Monoacylglycerophosphocholines

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

Chemical and Physical Properties

• Molecular Weight: 551.700 g/mol
• XLogP3: 7.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 28
• Exact Mass: 551.395 Da
• Monoisotopic Mass: 551.395 Da
• Topological Polar Surface Area: 105.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 575.000
• 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

References

1. Lili Song, Jiayi Wang, Jiaxuan Nie, Yue Zhang, Rui Han, Huimin Liu, Ningning Ma, Zhen Yang, Yubo Li.  (2023)  Study on toxicity/efficacy related substances and metabolic mechanism of Tripterygium wilfordii Hook. f based on O2LPS correlation analysis.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:37506782] [10.1016/j.jep.2023.116949]

2. Jie Zhang, Xiaoling Zang, Peng Jiao, Jiangyu Wu, Wei Meng, Lizhen Zhao, Zhihua Lv.  (2024)  Alterations of Ceramides, Acylcarnitines, GlyceroLPLs, and Amines in NSCLC Tissues.  JOURNAL OF PROTEOME RESEARCH,      [PMID:39317643] [10.1021/acs.jproteome.4c00344]

3. Tong Jin, Si-Yuan Li, Hong-Li Zheng, Xiao-Dan Liu, Yue Huang, Gan Ma, Ya-Xuan Zhao, Xiao-Tian Zhao, Li Yang, Qi-Hui Wang, Hong-Jun Wang, Chengyong Gu, Zhiqiang Pan, Fuqing Lin.  (2025)  Gut microbes–spinal connection is required for itch sensation.  Gut Microbes,      [PMID:40289281] [10.1080/19490976.2025.2495859]