1,2-Dioleoyl-sn-glycerol

Base Information

• Chemical Name: 1,2-Dioleoyl-sn-glycerol
• CAS No.: 24529-88-2
• Molecular Formula: C39H72 O5
• Molecular Weight: 620.998
• Hs Code.: 2916190090
• UNII: 0B6KAM5VNK
• DSSTox Substance ID: DTXSID001312870
• Wikidata: Q27123383
• Metabolomics Workbench ID: 5835
• ChEMBL ID: CHEMBL590047
• Mol file: 24529-88-2.mol

Synonyms:1,2-Dioleoyl-sn-glycerol;24529-88-2;Sn-1,2-Diolein;sn-1,2-Dioleoylglycerol;DG(18:1(9Z)/18:1(9Z)/0:0);Glyceryl 1,2-dioleate, (S)-;1,2-dioleoyl-glycerol;(Z)-(S)-3-Hydroxypropane-1,2-diyl dioleate;UNII-0B6KAM5VNK;0B6KAM5VNK;1,2-di-(9Z-octadecenoyl)-sn-glycerol;DG(18:1/18:1/0:0);CHEMBL590047;CHEBI:52333;BRN 1730457;Olein, 1,2-di-, (S)-(-)-;[(2S)-3-hydroxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate;9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester, (S)-;4-02-00-01662 (Beilstein Handbook Reference);DG 36:2;1,2-DIOLEOYL-GLYCEROL (18:1);1,2-dioleoyl-sn-glyc-erol;(S)-glyceryl 1,2-dioleate;SCHEMBL160985;"1,2-Dioleoyl-rac-glycerol";9-octadecenoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester, (9Z,9'Z)-;AFSHUZFNMVJNKX-LLWMBOQKSA-N;DTXSID001312870;HMS3649C17;Diacylglycerol(18:1n9/18:1n9);Diacylglycerol(18:1w9/18:1w9);BDBM50307105;LMGL02010049;1,2-Dioleoyl-sn-glycerol, >=97%;1,2-DI-O-OLEOYL-SN-GLYCEROL;DAG(18:1n9/18:1n9);DAG(18:1w9/18:1w9);DG(18:1n9/18:1n9);DG(18:1w9/18:1w9);1,2-Bis(O-9Z-octadecenoyl)-sn-glycerol;PD020891;HY-141572;CS-0181664;(Z)-(S)-3-Hydroxypropane-1,2-diyldioleate;DG(18:1_18:1);SR-01000947053;J-015554;SR-01000947053-1;Q27123383;(2S)-3-hydroxypropane-1,2-diyl (9Z)bis-octadec-9-enoate;9-OCTADECENOIC ACID (9Z)-, (1S)-1-(HYDROXYMETHYL)-1,2-ETHANEDIYL ESTER;9-OCTADECENOIC ACID (9Z)-, 1,1'-((1S)-1-(HYDROXYMETHYL)-1,2-ETHANEDIYL) ESTER;9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester, (S)- (9CI)

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 670.8°Cat760mmHg
• PKA: 13.69±0.10(Predicted)
• Flash Point: 186.3°C
• PSA: 72.83000
• Density: 0.934g/cm³
• LogP: 11.50870
• Storage Temp.: −20°C
• XLogP3: 14.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 36
• Exact Mass: 620.53797539
• Heavy Atom Count: 44
• Complexity: 671

Purity/Quality:

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

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

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Ambiguous Lipids; Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC/C=C\CCCCCCCC
• Description: 1,2-Dioleoyl-sn-glycerol is an analog of the protein kinase C-activating second messenger DAG. 1,2-Dioleoyl-sn-glycerol and 1,2-dioctanoyl-sn-glycerol are nearly equipotent in induction of the acrosome reaction in human sperm.
• Uses: 1,2-Dioleoyl-sn-glycerol is an analog of 1,3-Dioleoylglycerol (D4842100 which is used in the synthesis of amphiphilic gadolinium complexes as MRI contrast agents. 18:1 DG may be used: in the lipid-protein overlay screen assay with Arabidopsis Rho-like GTPases recombinant protein and Arabidopsis plasma membrane H+-ATPasein the preparation of the Golgi-like liposomesin giant unilamellar vesicles (GUVs) preparation

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

There total 19 articles about 1,2-Dioleoyl-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: 51.0%

trioleoylglycerol (122-32-7) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4) + 1,3-diolein (2465-32-9,98168-52-6) + 1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6)

Guidance literature:

at 200 ℃; for 48h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Inert atmosphere;

DOI:10.1039/c3gc36907b

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4) + 1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6)

Guidance literature:

With 1.05HO₃P*0.95C₆H₅O₃P^(2-)*0.1H₂O*Zr⁽²⁺⁾; at 180 ℃; for 1h; Reagent/catalyst;

DOI:10.1016/j.apcata.2013.04.043

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → trioleoylglycerol (122-32-7) + 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4) + 1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6)

Guidance literature:

With 1.05HO₃P*0.95C₆H₅O₃P^(2-)*0.1H₂O*Zr⁽²⁺⁾; at 180 ℃; for 1h; Reagent/catalyst;

DOI:10.1016/j.apcata.2013.04.043

upstream raw materials:

Elaidic Acid

glycerol

cis-Octadecenoic acid

(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate

Downstream raw materials:

phosphoric acid-((R)-2,3-bis-oleoyloxy-propyl ester)-((R)-2,3-dihydroxy-propyl ester)

1,3-diolein

(Z)-Octadec-9-enoic acid 2-[(2,4-dichloro-phenoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester; compound with triethyl-amine

(Z)-Octadec-9-enoic acid (R)-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester

Refernces

• 1、 Bi, Yan-Hong,Wang, Zhao-Yu,Duan, Zhang-Qun,Zhao, Xiang-Jie,Chen, Xiao-Ming,Nie, Ling-Hong. "An insight into the solvent effect on the positional selectivity of the immobilized lipase from Burkholderia cepacia in 1,3-diolein synthesis". . p. 23122 - 23124. Retrieved 2015/06/02.
• 2、 Meng, Xiao,Xu, Gang,Zhou, Qin-Li,Wu, Jian-Ping,Yang, Li-Rong. "Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles". . p. 319 - 324. Retrieved 2013/10/08.