96960-92-8

Basic information

• Product Name: 1-O-HEXADECYL-2-O-METHYL-SN-GLYCEROL
• Synonyms: 1-O-HEXADECYL-2-O-METHYL-SN-GLYCEROL;HEXADECYL METHYL GLYCEROL;1-O-hexadecyl-2-O-Methyl-sn-glycerol (PMG);1-O-hexadecyl-2-O-methyl-sn-glycerol (PMG);1-C16-2-C1 DG;1-O-Hexadecyl-2-O-methyl-sn-glycerol≥ 98% (HPLC)
• CAS NO: 96960-92-8
• Molecular Formula: C₂₀H₄₂O₃
• Molecular Weight: 330.55
• Mol File: 96960-92-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 35-36 °C
• Boiling Point: 430.6±25.0 °C(Predicted)
• Appearance: /
• Density: 0.895±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: ≤8.3mg/ml in DMSO;8.3mg/ml in dimethyl formamide
• PKA: 14.20±0.10(Predicted)
• CAS DataBase Reference: 1-O-HEXADECYL-2-O-METHYL-SN-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-HEXADECYL-2-O-METHYL-SN-GLYCEROL(96960-92-8)
• EPA Substance Registry System: 1-O-HEXADECYL-2-O-METHYL-SN-GLYCEROL(96960-92-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 96960-92-8(Hazardous Substances Data)

Usage

Description

1-O-Hexadecyl-2-O-methyl-sn-glycerol is a synthetic diacylglycerol with a hexadecyl chain at the sn-1 position and a methyl group at the sn-2 position. It is known for its ability to inhibit protein kinase C activity in human neutrophils, which results in the prevention of the respiratory burst induced by both phorbol 12,13-dibutyrate and fMLP.

Uses

Used in Pharmaceutical Industry:
1-O-Hexadecyl-2-O-methyl-sn-glycerol is used as a pharmaceutical agent for its potential anti-inflammatory properties. It inhibits protein kinase C activity in human neutrophils, which can help in reducing inflammation and preventing the respiratory burst induced by certain stimuli.
Used in Research Applications:
1-O-Hexadecyl-2-O-methyl-sn-glycerol is used as a research tool to study the role of diacylglycerols and protein kinase C in cellular processes, particularly in the context of inflammation and immune response. Its ability to inhibit protein kinase C activity makes it a valuable compound for investigating the underlying mechanisms of these processes.

Biological Activity

hexadecyl methyl glycerol, also known as amg-c16 with a hexadecyl chain at the sn-1 position, is a novel inhibitor of protein kinase c with ic50 value of about 80 μm [1].protein kinase c is a phospholipid-dependent kinase and the intracellular receptor for phorbol 12-myristate-13-acetate (pma), a substance that activates both the respiratory burst and protein kinase c. pkc enzymes are activated by signals such as increases in the concentration of diacylglycerol (dag) or calcium ions (ca2+) [1].hexadecyl methyl glycerol is a structural analog of diacylglycerol with a hexadecyl chain at the sn-1 position and a methyl group at the sn-2 position. hexadecyl methyl glycerol inhibited the activation of purified protein kinase c by diacylglycerol in the presence of phosphatidylserine. in neutrophilic granulocytes, hexadecyl methyl glycerol inhibited the respiratory burst induced by pdbu in a dose-dependent way. in neutrophils, hexadecyl methyl glycerol inhibited the phosphorylation of purified 47-kda protein, an important substrate of protein kinase c [1].

references

[1]. kramer im1, van der bend rl, tool at, et al. 1-o-hexadecyl-2-q-methylglycerol, a novel inhibitor of protein kinase c, inhibits the respiratory burst in human neutrophils. j biol chem. 1989 apr 5;264(10):5876-84.

Upstream product

• 111247-99-5 1-hexadecyl-2-methyl-3-(triphenylmethyl)-sn-glycerol 
• 122822-32-6 1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol 
• 122822-34-8 1-O-hexadecyl-2-O-methyl-3-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 96960-91-7 1-O-hexadecyl-2-O-methyl-D-threitol 
• 156737-66-5 1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol 
• 112-82-3 hexadecanyl bromide 
• 156737-65-4 1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 84379-55-5 1-O-hexadecyl-2-O-benzyl-3,4-O-isopropylidene-D-threitol 
• 96960-89-3 1-O-hexadecyl-3,4-O-isopropylidene-D-threitol 
• 96960-90-6 1-O-hexadecyl-3,4-O-isopropylidene-2-O-methyl-D-threitol 
• 36653-82-4 1-Hexadecanol 
• 120019-37-6 3-hexadecyloxy-2R-hydroxypropyl 1-para-toluenesulphonate 
• 119879-76-4 3-O-Hexadecyl-sn-glycerol 1-(tert-butyldiphenylsilyl ether) 

Downstream Products

• 78858-44-3 1-O-hexadecyl-2-O-methyl-sn-glycero(3)phosphocholine 
• 180714-35-6 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-yl ester 
• 180714-34-5 1-O-hexadecyl-2-O-methyl-3-O-(2'-O-acetyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)-sn-glycerol 
• 342883-88-9 Phosphoric acid 2-chloro-phenyl ester (R)-3-hexadecyloxy-2-methoxy-propyl ester 
• 342883-90-3 2-chlorophenyl 5'-(3'-azido-3'-deoxythymidinyl)-1-hexadecyl-2-methoxy-sn-glyceryl phosphate 
• 180714-42-5 (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran 
• 180714-43-6 (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran 
• 180714-37-8 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol 
• 180714-36-7 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol 
• 180714-39-0 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-5-methoxy-tetrahydro-pyran 
• 180714-38-9 (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-5-methoxy-tetrahydro-pyran 
• 180714-41-4 Dithiocarbonic acid O-[(2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-yl] ester S-methyl ester 
• 180714-40-3 Dithiocarbonic acid O-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-yl] ester S-methyl ester 

Relevant articles and documents

Ether phospholipid-AZT conjugates possessing anti-HIV and antitumor cell activity. Synthesis, conformational analysis, and study of their thermal effects on membrane bilayers

The 1-O-hexadecyl-2-O-methyl-sn-glyceryl phosphodiester AZT 4 and hexadecyl-phosphodiester AZT 5 derivatives were synthesized and found to be active against HIV-1, HIV-2, and tumor cell proliferation. Compared to AZT, compound 4 possessed ca. 10-fold lowe

Synthesis and growth inhibitory properties of glycosides of 1-O- hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET- 18-OCH3 (edelfosine)

Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl- 2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O- methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and - mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 °C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: β- and α-2- deoxy-D-arabino-hexopyranosyl, α-D-mannopyranosyl, 2-O-methyl-β-D- glucopyranosyl, and 2-O-methyl-α-D-mannopyranosyl. 1-O-Hexadecyl-2-O- methyl-3-O-(2'-deoxy-β-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer cells. 2-Deoxy-β-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.

Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids

A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.