15818-46-9

Basic information

• Product Name: 1,3-DILINOLEIN
• Synonyms: DELTA 9 CIS, 12 CIS DILINOLEIN 1-3 ISOMER;1,3-DI-[(CIS,CIS)-9,12-OCTADECADIENOYL]-RAC-GLYCEROL;1,3-DILINOLEIN;1,3-DILINOLEOYLGLYCEROL;glyceryl 1,3-dilinoleate;1,3-Di-([cis,cis]-9,12-octadecadienoyl)-rac-glycerol, 1,3-Dilinolein;1,3-Dilinoleoyl-rac-glycerol;1,2,3-Propanetriol 1,3-dilinolate
• CAS NO: 15818-46-9
• Molecular Formula: C₃₉H₆₈O₅
• Molecular Weight: 616.95
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 15818-46-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 677.1±50.0 °C(Predicted)
• Appearance: /
• Density: 0.946±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.63±0.20(Predicted)
• Stability: Light Sensitive, Temperature Sensitive, Unstable Even At -20°C
• CAS DataBase Reference: 1,3-DILINOLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DILINOLEIN(15818-46-9)
• EPA Substance Registry System: 1,3-DILINOLEIN(15818-46-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 15818-46-9(Hazardous Substances Data)

Usage

Description

1,3-DILINOLEIN, also known as a 1,3-diglyceride with both acyl groups specified as linoleoyl, is a naturally occurring lipid compound derived from wheat germ. It is characterized by its yellow oil appearance and is known for its potential health benefits and applications in various industries.

Uses

Used in Pharmaceutical Industry:
1,3-DILINOLEIN is used as a derivative of α-glucosidase inhibitory phosphatidic acids for its potential therapeutic effects. It may play a role in the development of treatments for conditions related to glucose metabolism, such as diabetes.
Used in Food Industry:
1,3-DILINOLEIN is used as a natural additive in the food industry due to its beneficial properties. It can be incorporated into various products to enhance their nutritional value and provide health-promoting effects.
Used in Cosmetic Industry:
Due to its lipid nature and potential health benefits, 1,3-DILINOLEIN can be used as an ingredient in the cosmetic industry. It may be included in skincare products for its moisturizing and nourishing properties, as well as for its potential to improve skin health.
Used in Research:
1,3-DILINOLEIN is also used in scientific research as a model compound to study the properties and functions of diglycerides and their role in various biological processes. This can contribute to a better understanding of lipid metabolism and the development of new therapeutic strategies.

Upstream product

• 60-33-3 linoleic acid 
• 56-81-5 glycerol 
• 537-40-6 1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane 
• 1078-61-1 dihydrocaffeic acid 

Downstream Products

• 59925-33-6 1,3-dilinoleoyl-2-<1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl>glyceride 
• 175656-66-3 1-(β-apo-8'-carotenoyl)glycerol 
• 504-40-5 1,3-distearoylglycerol 

Relevant articles and documents

Distinct roles of adipose triglyceride lipase and hormone-sensitive lipase in the catabolism of triacylglycerol estolides

Branched esters of palmitic acid and hydroxy stearic acid are antiinflammatory and antidiabetic lipokines that belong to a family of fatty acid (FA) esters of hydroxy fatty acids (HFAs) called FAHFAs. FAHFAs themselves belong to oligomeric FA esters, known as estolides. Glycerol-bound FAHFAs in triacylglycerols (TAGs), named TAG estolides, serve as metabolite reservoir of FAHFAs mobilized by lipases upon demand. Here, we characterized the involvement of two major metabolic lipases, adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL), in TAG estolide and FAHFA degradation. We synthesized a library of 20 TAG estolide isomers with FAHFAs varying in branching position, chain length, saturation grade, and position on the glycerol backbone and developed an in silico mass spectra library of all predicted catabolic intermediates. We found that ATGL alone or coactivated by comparative gene identification-58 efficiently liberated FAHFAs from TAG estolides with a preference for more compact substrates where the estolide branching point is located near the glycerol ester bond. ATGL was further involved in transesterification and remodeling reactions leading to the formation of TAG estolides with alternative acyl compositions. HSL represented a much more potent estolide bond hydrolase for both TAG estolides and free FAHFAs. FAHFA and TAG estolide accumulation in white adipose tissue of mice lacking HSL argued for a functional role of HSL in estolide catabolism in vivo. Our data show that ATGL and HSL participate in the metabolism of estolides and TAG estolides in distinct manners and are likely to affect the lipokine function of FAHFAs.

Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids

The enzymatic transesterification of selected phenolic acids with TAG, including trilinolein (TLA) and trilinolenin (TLNA), was investigated in an organic solvent medium. Maximal bioconversion of 66% was obtained with a dihydrocaffeic acid (DHCA) to TLA ratio of 1:2 after 5 d of reaction. Similarly, the highest bioconversion of 62% was obtained with a DHCA to TLNA ratio of 1:2, but after 12 d of reaction. However, a ratio of 1:4 DHCA/TLA decreased the bioconversion to 53%. Transesterification reactions of ferulic acid with both TAG, using a ratio of 1:2, resulted in low bioconversion of 16 and 14% with TLA and TLNA, respectively. The overall results indicated that bioconversion of phenolic MAG was higher than that of phenolic DAG. The structures of mono- and dilinoleyl dihydrocaffeate as well as those of mono- and dilinolenyl dihydrocaffeate were confirmed by LC-MS analyses. The phenolic lipids demonstrated moderate radical-scavenging activity. Copyright