1,2-Dipalmitoyl-sn-glycerol

Base Information

• Chemical Name: 1,2-Dipalmitoyl-sn-glycerol
• CAS No.: 30334-71-5
• Molecular Formula: C35H68O5
• Molecular Weight: 568.922
• Hs Code.: 2915900090
• European Community (EC) Number: 250-131-4
• DSSTox Substance ID: DTXSID001036210
• Nikkaji Number: J347.938B
• Wikidata: Q27156468
• Metabolomics Workbench ID: 5795
• ChEMBL ID: CHEMBL87852
• Mol file: 30334-71-5.mol

Synonyms:1,2-Dipalmitoyl-sn-glycerol;30334-71-5;1,2-Dihexadecanoyl-sn-glycerol;(S)-1,2-Dipalmitin;DG(16:0/16:0/0:0);(S)-3-Hydroxypropane-1,2-diyl dipalmitate;[(2S)-2-hexadecanoyloxy-3-hydroxypropyl] hexadecanoate;Diacylglycerol(16:0/16:0);CHEBI:82929;(2S)-3-hydroxypropane-1,2-diyl dihexadecanoate;(S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitate;DAG(16:0/16:0);Hexadecanoic acid, (1S)-1-(hydroxymethyl)-1,2-ethanediyl ester;DG(16:0/16:0);C35H68O5;Hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester, (S)-;(S)-Glycerol 1,2-dipalmitate;C35-H68-O5;D-,-Dipalmitin;761-35-3;CMC_6810;L-1,2-Dipalmitin;sn-1,2-Dipalmitin;(?)-1,2-Dipalmitin;1,2-Dipalmitin-sn-glycerol;CHEMBL87852;SCHEMBL594854;(S)-(-)-1,2-Dipalmitin;1,2-Di-O-palmitoyl-sn-glycerol;DTXSID001036210;Palmitin, L-1,2-di- (6CI);CMC_7218;CMC_8101;CMC_10485;CMC_11730;CMC_12683;LMGL02010009;MFCD00067471;Palmitin, 1,2-di-, L- (8CI);CS-W011452;HY-W010736;1,2-Dipalmitoyl-sn-glycerol, >=99%;AS-75956;BP-29827;(S)-3-Hydroxypropane-1,2-diyldipalmitate;D97630;Q27156468;Hexadecanoic acid, (1S)-1-(hydroxymethyl)-1,2-ethanediyl ester (9CI);Hexadecanoic acid,1,1'-[(1S)-1-(hydroxymethyl)-1,2-ethanediyl]ester;hexadecanoic acid, (1S)-2-hydroxy-1-[[(1-oxohexadecyl)oxy]methyl]ethyl ester;8ND

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

Chemical Property:

• Vapor Pressure: 5.19E-18mmHg at 25°C
• Melting Point: 66-69 °C
• Refractive Index: 1.465
• Boiling Point: 620.8°Cat760mmHg
• PKA: 13.69±0.10(Predicted)
• Flash Point: 174.7°C
• PSA: 72.83000
• Density: 0.93g/cm³
• LogP: 10.39630
• Storage Temp.: −20°C
• XLogP3: 14
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 34
• Exact Mass: 568.50667527
• Heavy Atom Count: 40
• Complexity: 536

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Dipalmitoyl-sn-glycerol 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCCCC
• Uses: 1,2-Dipalmitoyl-sn-glycerol (1,2-DPG) is an analog of the protein kinase C (PKC)-activating second messenger diacylglycerol. 1,2-Dipalmitoyl-sn-glycerol is a weak activator of PKC. 16:0 DG has been used to spike brain samples for mass spectrometric analysis. It may be used as diacyl-glycerol source in diacylglycerol O-acyltransferase 1 (DGAT1) enzyme assay in human leukemic?K562 cells and in Golgi-like liposomes reconstitution.

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

There total 19 articles about 1,2-Dipalmitoyl-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%

1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol (30403-51-1) → 1,2-dipalmitoyl-sn-glycerol (30334-71-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In ethanol; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.0c00487

Reference yield: 98.0%

(+)-3-O-(4-methoxybenzyl)-1,2-di-O-hexadecanoyl-sn-glycerol (183430-01-5) → 1,2-dipalmitoyl-sn-glycerol (30334-71-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; acetic acid; for 3h;

DOI:10.1021/jo961226g

Reference yield: 96.0%

Hexadecanoic acid (S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-hexadecanoyloxymethyl-ethyl ester → 1,2-dipalmitoyl-sn-glycerol (30334-71-5)

Guidance literature:

In methanol; tetrachloromethane; at 25 - 40 ℃; for 1h; ultrasonic;

DOI:10.1080/00397919708005904

upstream raw materials:

1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol

Hexadecanoic acid (S)-2-(3,4-dimethoxy-benzyloxy)-1-hexadecanoyloxymethyl-ethyl ester

(+)-3-O-(4-methoxybenzyl)-1,2-di-O-hexadecanoyl-sn-glycerol

Hexadecanoic acid (R)-2-(9H-fluoren-9-ylmethoxycarbonyloxy)-1-hexadecanoyloxymethyl-ethyl ester

Downstream raw materials:

1,2-dipalmitoyl-sn-glycerol-3-O-succinic acid monoester

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyloxy)-phosphanyloxy]-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-2-{methoxy-[(1R,2S,3S,4R,5R,6S)-3,4,5-tris-(bis-benzyloxy-thiophosphoryloxy)-2,6-bis-methoxymethoxy-cyclohexyloxy]-thiophosphoryloxy}-ethyl ester

Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-2-{methoxy-[(1R,2S,3S,4R,5R,6S)-3,4,5-tris-(bis-benzyloxy-thiophosphoryloxy)-2,6-bis-methoxymethoxy-cyclohexyloxy]-phosphoryloxy}-ethyl ester

Refernces

• 1、 Nishida, Yoshihiro,Mengfei, Yuan,Fujisawa, Kaito,Kitagawa, Sakura,Dohi, Hirofumi,Uzawa, Hirotaka. "Verification study for an empirical rule in diverse helical conformational behaviors of asymmetric 1,2-diacyl-sn-glycerols in the solution state". . p. 1435 - 1443. Retrieved 2017.
• 2、 Gan, Chin Heng,Hua, Kuo-Feng,Lam, Yulin,Li, Lan-Hui,Peng, Yi-Jen,Wei, Chih-Feng,Wijaya, Hadhi,Wu, Shih-Hsiung. "H-Phosphonate Synthesis and Biological Evaluation of an Immunomodulatory Phosphoglycolipid from Thermophilic Bacteria". supporting information. . Retrieved 2020/04/02.
• 3、 Ghotekar, Balasaheb K.,Kulkarni, Suvarn S.,Podilapu, Ananda Rao. "Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of Streptococcus pneumoniae and Streptococcus oralis Uo5". supporting information. . Retrieved 2020/02/04.