1867-91-0

Basic information

• Product Name: rac 1-Oleoyl-2,3-dipalmitoyl Glycerol
• Synonyms: rac 1-Oleoyl-2,3-dipalmitoyl Glycerol
• CAS NO: 1867-91-0
• Molecular Formula: C₅₃H₁₀₀O₆
• Molecular Weight: 833.3575
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 1867-91-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 33-35°C
• Appearance: /
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Hexanes (Slightly)
• CAS DataBase Reference: rac 1-Oleoyl-2,3-dipalmitoyl Glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: rac 1-Oleoyl-2,3-dipalmitoyl Glycerol(1867-91-0)
• EPA Substance Registry System: rac 1-Oleoyl-2,3-dipalmitoyl Glycerol(1867-91-0)

Safety Data

• Hazardous Substances Data: 1867-91-0(Hazardous Substances Data)

Usage

Description

rac 1-Oleoyl-2,3-dipalmitoyl Glycerol, also known as 1,2-Dipalmitoyl-3-oleoyl-rac-glycerol, is a triacylglycerol that consists of palmitic acid at the sn-1 and sn-2 positions and oleic acid at the sn-3 position. It is a white waxy solid and has been identified in various sources such as Apiaceae seed oils, lard, tallow, palm oil, olein, and stearin. rac 1-Oleoyl-2,3-dipalmitoyl Glycerol has been utilized as a substrate to assess the regioselectivity and substrate specificity of lipases from Geotrichum species.

Uses

Used in the Food Industry:
rac 1-Oleoyl-2,3-dipalmitoyl Glycerol is used as an ingredient in the food industry for its emulsifying and stabilizing properties, which help improve the texture and shelf life of various products.
Used in the Cosmetics Industry:
In the cosmetics industry, rac 1-Oleoyl-2,3-dipalmitoyl Glycerol is used as an emollient and skin conditioning agent, providing moisturization and improving the skin's appearance.
Used in the Pharmaceutical Industry:
rac 1-Oleoyl-2,3-dipalmitoyl Glycerol is used as a substrate in the pharmaceutical industry to determine the regioselectivity and substrate specificity of lipases from Geotrichum species, which can be crucial for the development of targeted drug delivery systems and enzyme-based therapies.
Used in the Research and Development of Lipases:
In the field of research and development, rac 1-Oleoyl-2,3-dipalmitoyl Glycerol serves as a valuable tool for studying the properties and behavior of lipases, which are essential enzymes in the breakdown of fats and have numerous applications in biotechnology and medicine.

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 555-44-2 glyceroltripalmitate 
• 122-32-7 trioleoylglycerol 
• 14465-68-0 trilinolenin 
• 33001-45-5 (+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 111-03-5 1-monooleoyl glycerol 
• 112-67-4 n-hexadecanoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 

Downstream Products

• 53023-11-3 sn-1,2-dipalmitoyl-3-oleoylglycerol 
• 53023-10-2 1-oleoyl-2,3-dipalmitoyl-sn-glycerol 

Relevant articles and documents

Synthesis and physical properties of symmetrical and non-symmetrical triacylglycerols containing two palmitic fatty acids

A series of symmetrical (ABA) and non-symmetrical (AAB) triacylglycerol (TAG) isomers containing "A," palmitic (P; 16:0) acid, and "B," either oleic (O; 9c-18:1), elaidic (E; 9t-18:1), linoleic (L; 9c,12c-18:2) or linolenic (Ln; 9c,12c,15c-18:3) fatty acids were synthesized by esterification of the thermodynamically more-stable 1,3-di- or 1(3)-monoacylglycerols [1,3-DAG or 1(3)-MAG], respectively. 1,3- dipalmitoylglycerol (1,3P-DAG) was esterified with O, L or Ln acid to prepare the symmetrical TAG isomers POP, PLP and PLnP, while the O- E-, L- and Ln-1(3)MAG precursors, synthesized or obtained commercially, were esterified with P acid to prepare the non-symmetrical TAG isomers OPP, EPP, LPP and LnPP, respectively. The drop point(s), solid fat content and melting point values of the synthesized TAG were determined. The 1,3-dipalmitoylglycerol (1,3P-DAG) and 1(3)P-MAG precursors were prepared, in multi-gram quantities, by partial glycerolysis (glycerol/p-toluenesulfonic acid) of tripalmitin. After fractionation by silica gel chromatography, the 1(3)P-MAG and 1,3P-DAG isomers (ca. 80% of total MAG or DAG) were purified (>98%) by crystallization from acetone [silver ion-HPLC was utilized to determine the structural purities of the DAG (or MAG) precursors, and the synthesized TAG]. Esterification of the appropriate, thermodynamically more-stable MAG or DAG precursors was found to be a very versatile method for synthesis (in 80-90% yields) of multi-gram (3-5 g) quantities of symmetrical and non-symmetrical TAG isomers, in chemical and structural purities of >96 and 97-99%, respectively.

Synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol from palm oil

Human milk fat contains 20-25% palmitic acid (16:0) and 30-35% oleic acid (18:1). More than 60% of the palmitic acid occurs at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleoyl-2-palmitoylglycerol (OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl palmitate. In the second step, esterificalion of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum (40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content in the product acylglycerol mixture was 97%, and 66.1 % oleic acid was incorporated into TAG. Analysis of the FA composition at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil.