1069-87-0

Basic information

• Product Name: 1,2-dioctanoylglycerol
• Synonyms: 1,2-dioctanoylglycerol;1,2-Dioctanoin;1-O,2-O-Dioctanoylglycerol;1-O,2-O-Dioctanoyl-sn-glycerol;2,3-Bis(octanoyloxy)-1-propanol;Dioctanoic acid 3-hydroxy-1,2-propanediyl ester;ZQBULZYTDGUSSK-UHFFFAOYSA-N
• CAS NO: 1069-87-0
• Molecular Formula: C₁₉H₃₆O₅
• Molecular Weight: 344.4861
• Mol File: 1069-87-0.mol

Chemical Properties

• Boiling Point: 429.1°Cat760mmHg
• Flash Point: 136.8°C
• Appearance: /
• Density: 0.992g/cm³
• Vapor Pressure: 3.65E-09mmHg at 25°C
• Refractive Index: 1.46
• PKA: 13.70±0.10(Predicted)
• CAS DataBase Reference: 1,2-dioctanoylglycerol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dioctanoylglycerol(1069-87-0)
• EPA Substance Registry System: 1,2-dioctanoylglycerol(1069-87-0)

Safety Data

• Hazardous Substances Data: 1069-87-0(Hazardous Substances Data)

Usage

Chemical structure

1,2-dioctanoylglycerol is a chemical compound consisting of a glycerol molecule with two octanoyl groups attached at the first and second positions.

Type of lipid

It is a type of diacylglycerol, which is a lipid that serves as a precursor for the synthesis of triacylglycerols and phospholipids.

Research applications

1,2-dioctanoylglycerol is often used in biochemical and pharmaceutical research as a model compound.

Activation of protein kinase C

It has the ability to activate protein kinase C, an enzyme involved in regulating cell growth and proliferation.

Therapeutic potential

It has been studied for its potential therapeutic applications in treating conditions such as cancer, diabetes, and cardiovascular diseases.

Study of lipid metabolism

Its structure and properties make it a valuable tool in studying lipid metabolism.

Study of cell signaling pathways

It is useful for investigating cell signaling pathways, as it can activate protein kinase C, which plays a role in these pathways.

Potential drug targets

1,2-dioctanoylglycerol can be used to identify and study potential drug targets for various diseases, given its ability to activate protein kinase C and its involvement in lipid metabolism and cell signaling.

InChI:InChI=1/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3

Upstream product

• 145827-12-9 1-O-benzyl-2,3-di-O-octanoyl-rac-glycerol 
• 115479-51-1 2-Iodo-benzoic acid 2,3-bis-octanoyloxy-propyl ester 
• 188187-50-0 Octanoic acid 2-[(2,4-dinitro-phenyl)-methoxycarbonyl-methoxy]-1-octanoyloxymethyl-ethyl ester 
• 124-07-2 Octanoic acid 
• 56-81-5 glycerol 
• 640721-06-8 3-O-[[(6-bromo-7-hydroxycoumarin-4-yl)methoxy]carbonyl]-1,2-di-O-octanoylglycerol 
• 538-23-8 tricaprilin 
• 111-64-8 n-octanoic acid chloride 

Related news

1,3-Dioctanoylglycerol (1,3-DiC8) Is as Effective as 1,2-dioctanoylglycerol (cas 1069-87-0) (1,2-DiC8) in Priming Phospholipase A2 Activation in Human Platelets and Neutrophils07/25/2019

In the present study, we investigated the effects of different diacylglycerols in comparison with phorbol 12-myristate 13-acetate (PMA) on eicosanoid-independent phospholipase A2 (PLA2) activation in human platelets and neutrophils. Eicosanoid-independent PLA2 activation was measured under condi...detailed

Relevant articles and documents

Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system

1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.

Regio- and stereoselectivity in preparation of 2-deoxysugar glycoglycerolipid derivatives evaluated by high resolution 1H NMR

New glycoglycerolipids, derivatives of 2-deoxysugars bearing one or two fatty acid chains have been synthesised. Various levels of regio- and stereoselectivity have been attained for the triphenylphosphine hydrobromide (TPHB) catalysed addition of the glycerol moiety to some representative glycals. The influence of the structure of glycal derivatives in glycosylation reactions is discussed.

Lipase-catalyzed alcoholysis of triglycerides for short-chain monoglyceride production

Lipase from Pseudomonas fluorescens efficiently catalyzed the alcoholysis of various TG in dry alcohols. For TG with short-chain FA, more MG were accumulated. The yields of MG were affected by the alcohols used. The maximum yields of MG were as follows: 8

Biobased catalyst in biorefinery processes: Sulphonated hydrothermal carbon for glycerol esterification

Sulphonated hydrothermal carbon (SHTC), obtained from d-glucose by mild hydrothermal carbonisation and subsequent sulphonation with sulphuric acid, is able to catalyse the esterification of glycerol with different carboxylic acids, namely, acetic, butyric and caprylic acids. Product selectivity can be tuned by simply controlling the reaction conditions. On the one hand, SHTC provides one of the best selectivity towards monoacetins described up to now without the need for an excess of glycerol. On the other hand, excellent selectivity towards triacylglycerides (TAG) can be obtained, beyond those described with other solid catalysts, including well-known sulphonic resins. Recovery of the catalyst showed partial deactivation of the solid. The formation of sulphonate esters on the surface, confirmed by solid state NMR, was the cause of this behaviour. Acid treatment of the used catalyst, with subsequent hydrolysis of the surface sulphonate esters, allows SHTC to recover its activity. The higher selectivity towards mono- and triesters and its renewable origin makes SHTC an attractive catalyst in biorefinery processes.

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Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols

(Equation Presented) Caged compounds can be used to regulate the spatial and temporal dynamics of signaling molecules in live cells. Photochemical properties of coumarin-4-ylmethoxy carbonates (1a-d) are investigated to construct caged compounds of hydroxy-containing molecules. All the compounds possess desired properties as phototriggers for alcohols and phenols. The 6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl (Bhcmoc) group has the highest photochemical efficiency and is applied to make caged compounds of 1,2-dioctanoylglycerol (diC8), Tyr-OMe, and adenosine.

Stereospecific protein kinase C activation by photolabile diglycerides

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