2465-32-9

Basic information

• Product Name: 1,3-DIOLEIN
• Synonyms: GLYCEROL-1,2- AND -1,3-DIOLEATE;GLYCERYL DIOLEATE;GLYCEROL DIOLEATE;DIOLEIN;DIOLEOYL GLYCEROL;DELTA 9 CIS DIOLEIN;DELTA 9 CIS DIOLEIN 1-3 ISOMER;1,3-DI-[(CIS)-9-OCTADECENOYL]GLYCEROL
• CAS NO: 2465-32-9
• Molecular Formula: C₃₉H₇₂O₅
• Molecular Weight: 620.99
• EINECS: 219-569-3
• Mol File: 2465-32-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 21.5°C
• Boiling Point: 581.86°C (rough estimate)
• Flash Point: 17℃
• Appearance: /
• Density: 0.9170
• Vapor Pressure: 2.58E-21mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: −20°C
• PKA: 12.63±0.20(Predicted)
• CAS DataBase Reference: 1,3-DIOLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIOLEIN(2465-32-9)
• EPA Substance Registry System: 1,3-DIOLEIN(2465-32-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN1282 - class 3 - PG 2 - Pyridine, solution
• WGK Germany: 1
• Hazardous Substances Data: 2465-32-9(Hazardous Substances Data)

Usage

Uses

1,3-Dioleoylglycerol is used in the synthesis of amphiphilic gadolinium complexes as MRI contrast agents.

Definition

ChEBI: A 1,3-diglyceride with both acyl groups specified as oleoyl.

InChI:InChI=1/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18+

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 143-19-1 sodium Oleate 
• 112-79-8 Elaidic Acid 
• 56-81-5 glycerol 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 111-03-5 1-monooleoyl glycerol 
• 2442-61-7 1,2-dioleoylglycerol 
• 112-62-9 Methyl oleate 
• 112-80-1 cis-Octadecenoic acid 
• 3896-58-0 vinyl oleate 
• 24472-44-4 2-oxopropane-1,3-diyl dioleate 
• 122-32-7 trioleoylglycerol 
• 143997-01-7 (S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate 
• 111-62-6 oleic acid ethyl ester 

Downstream Products

• 1716-07-0 1,3-dioleoyl-2-palmitoylglycerol 
• 19229-69-7 Dioleo-β-lecithin 
• 148691-24-1 (Z,Z,Z,Z,Z)-icosa-5,8,11,14,17-pentaenoic acid 2-((Z)-octadec-9-enoyloxy)-1-((Z)-octadec-9-enoyloxymethyl)ethyl ester 
• 112-62-9 Methyl oleate 
• 628-13-7 pyridine hydrochloride 

Relevant articles and documents

SOME PROPERTIES OF DIACYLGLYCEROL ACYLTRANSFERASE IN A PARTCULATE FRACTION FROM MATURING SAFFLOWER SEEDS

The activity of diacylglycerol acyltransferase of a subcellular particulate fraction from maturing safflower seeds was remarkably stimulated by the addition of 1,2-diacylglycerols which were previously emulsified in a gelatin solution by sonication.Metal ions were inhibitory to the reaction.Deoxycholate and diisopropyl fluorophosphate were the most effective inhibitors.Sulfhydryl groups seemed to be of limited significance in the enzyme.Both 1,2-dioleoyl-sn-glycerol and 2,3-dioleoyl-sn-glycerol were good substrates of diacylglycerol acyltransferase, but the 1,3-isomer did not serve as an acyl acceptor.The enzyme showed broad specificity for synthetic rac-1,2-diacylglycerols containing various fatty acids.However, rac-1,2-diecetylglycerol and rac-1,2-dibutylglycerol, which are soluble in water, were ineffective.The enzyme exhibited no significant specificity for saturated and unsaturated fatty acyl-CoA thioesters as acyl donors.This suggests that the fatty acid composition at the 3-position of the glycerol molecule of safflower triacylglycerols may depend on the composition of the endogenous acyl-CoA pool.Key Word Index - Carthamus tinctorius; Compositae; safflower; seeds; triacylglycerol synthesis; diacylglycerol acyltransferase.

Triglyceride-mimetic structure-gated prodrug nanoparticles for smart cancer therapy

Off-target drug release and insufficient drug delivery are the main obstacles for effective anticancer chemotherapy. Prodrug-based self-assembled nanoparticles bioactivated under tumor-specific conditions are one of the effective strategies to achieve on-demand drug release and effective tumor accumulation. Herein, stimuli-activable prodrugs are designed yielding smart tumor delivery by combination of the triglyceride-mimic (TG-mimetic) prodrug structure and disulfide bond. Surprisingly, these prodrugs can self-assemble into uniform nanoparticles (NPs) with a high drug loading (over 40%) and accumulate in tumor sites specifically. The super hydrophobic TG structure can act as a gate that senses lipase to selectively control over NP dissociation and affect the glutathione-triggered prodrug activation. In addition, the impacts of the double bonds in the prodrug NPs on parent drug release and the following cytotoxicity, pharmacokinetics, and antitumor efficiency are further demonstrated. Our findings highlight the promising potential of TG-mimetic structure-gated prodrug nanoparticles for tumor-specific drug delivery.

LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

LIPID PRODRUGS OF GLUCOCORTICOIDS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.