1,2-Dimyristoyl-sn-glycerol

Base Information

• Chemical Name: 1,2-Dimyristoyl-sn-glycerol
• CAS No.: 60562-16-5
• Molecular Formula: C31H60 O5
• Molecular Weight: 512.814
• Hs Code.: 2915900090
• UNII: B8KC2URW86
• DSSTox Substance ID: DTXSID201182801
• Nikkaji Number: J152.204C
• Wikidata: Q27149699
• Metabolomics Workbench ID: 6107
• Mol file: 60562-16-5.mol

Synonyms:1,2-dimyristoyl-sn-glycerol;60562-16-5;SN-1,2-dimyristin;SN-1,2-dimyristoylglycerol;1,2-Dimyristin, (S)-;1,2-Ditetradecanoyl-sn-glycerol;1,2-dimyristoyl-glycerol;1,2-Di-o-dimyristoyl-sn-glycerol;(S)-1,2-dimyristin;[(2S)-3-hydroxy-2-tetradecanoyloxypropyl] tetradecanoate;UNII-B8KC2URW86;B8KC2URW86;(2S)-3-hydroxypropane-1,2-diyl ditetradecanoate;Tetradecanoic acid, 1,1'-((1S)-1-(hydroxymethyl)-1,2-ethanediyl) ester;(S)-3-Hydroxypropane-1,2-diyl ditetradecanoate;DG(14:0/14:0/0:0);D-,-Dimyristin;C31H60O5;(?)-L-1,2-Dimyristin;1,2-Dimyristin-sn-glycerol;1,2-Dimyristyl-sn-glycerol;SCHEMBL593870;(S)-glycerol 1,2-dimyristate;Diacylglycerol(14:0/14:0);CHEBI:80651;DTXSID201182801;LMGL02010321;MFCD00048454;Tetradecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester, (S)-;AKOS027321143;14:0 DG;1,2-Dimyristoyl-sn-glycerol, >=95%;PD018799;DAG(14:0/14:0);HY-128468;CS-0099174;(S)-3-Hydroxypropane-1,2-diylditetradecanoate;Q27149699;1,1'-[(1S)-1-(Hydroxymethyl)-1,2-ethanediyl] ditetradecanoate;Tetradecanoic acid,1,1'-[(1S)-1-(hydroxymethyl)-1,2-ethanediyl]ester;FAW

Chemical Property of 1,2-Dimyristoyl-sn-glycerol

Chemical Property:

• Appearance/Colour: White powder with lumps
• Melting Point: 57-61 °C
• Boiling Point: 577.2 °C at 760 mmHg
• PKA: 13.69±0.10(Predicted)
• Flash Point: 166.8 °C
• PSA: 72.83000
• Density: 0.94 g/cm³
• LogP: 8.83590
• Storage Temp.: -15°C
• XLogP3: 11.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 30
• Exact Mass: 512.44407501
• Heavy Atom Count: 36
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dimyristoyl-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCC
• Description: 1,2-Dimyristoyl-sn-glycerol (1,2-DMG) is a saturated diacylglycerol (DAG) with myristic acid (14:0) side-chains attached at both the sn-1 and sn-2 positions. Most saturated DAGs, including 1,2-DMG, are weak second messengers for the activation of the PKC.
• Uses: 1,2-Dimyristoyl-sn-glycerol is a saturated diacylglycerol (DAG). It is a possible weak second messenger for the activation of the PKC. 1,2-Dimyristoyl-sn-glycerol (1,2-DMG) is a saturated diacylglycerol (DAG) with myristic acid (14:0) side-chains attached at both the sn-1 and sn-2 positions. Most saturated DAGs, including 1,2-DMG, are weak second messengers for the activation of the PKC.[Cayman Chemical]

Technology Process of 1,2-Dimyristoyl-sn-glycerol

There total 5 articles about 1,2-Dimyristoyl-sn-glycerol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(tetradecanoyl)-3-O-benzyl-sn-glycerol (73083-33-7) → 1,2-dimyristoyl-sn-glycerol (60562-16-5,56270-93-0)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; dichloromethane; at 20 ℃; for 2.5h; under 760.051 Torr;

DOI:10.1002/anie.201406529

Reference yield:

tetradecanoyl chloride (112-64-1) → 1,2-dimyristoyl-sn-glycerol (60562-16-5,56270-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / pyridine

2: 80 percent / H₂ / 10 percent Pd/C / ethyl acetate

With pyridine; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3423::AID-ANIE3423>3.0.CO;2-I

Reference yield:

→ 1,2-dimyristoyl-sn-glycerol (60562-16-5,56270-93-0)

Guidance literature:

With cyclohexane; palladium; Hydrogenation;

DOI:10.1021/ja01158a078

upstream raw materials:

1-(tetradecanoyl)-3-O-benzyl-sn-glycerol

tetradecanoyl chloride

n-tetradecanoic acid

Downstream raw materials:

Tetradecanoic acid 2-((2-chloro-phenoxy)-{2-[6-oxo-2-(9-phenyl-9H-xanthen-9-ylamino)-1,6-dihydro-purin-9-ylmethoxy]-ethoxy}-phosphoryloxy)-1-tetradecanoyloxymethyl-ethyl ester

(2R)-3-(((benzyloxy)(diisopropylamino)phosphanyl)oxy)propane-1,2-diyl ditetradecanoate

Tetradecanoic acid (R)-2-[{2-benzyloxy-3-[((R)-2,3-bis-tetradecanoyloxy-propoxy)-(2-chloro-phenoxy)-phosphoryloxy]-propoxy}-(2-chloro-phenoxy)-phosphoryloxy]-1-tetradecanoyloxymethyl-ethyl ester

2-O-benzyl-1,3-bis-(1,2-O-dimyristoyl-sn-glycero-3-phosphoryl)glycerol dimethyl ether

Refernces

• 1、 Nguyen, Huy Q.,Davis, Ryan A.,Gervay-Hague, Jacquelyn. "Synthesis and structural characterization of three unique helicobacter pylori a-cholesteryl phosphatidyl glucosides". supporting information. p. 13400 - 13403. Retrieved 2015/01/09.