69176-47-2

Basic information

• Product Name: 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL
• Synonyms: 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL;glyceryl 1,2-rac-dipalmitate-3-O-benzoate
• CAS NO: 69176-47-2
• Molecular Formula: C₄₂H₇₄O₅
• Molecular Weight: 659.03
• Mol File: 69176-47-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL(69176-47-2)
• EPA Substance Registry System: 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL(69176-47-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 69176-47-2(Hazardous Substances Data)

Usage

Description

1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL is a complex glycerol derivative with a unique structure that features two palmitoyl groups attached to the first and second carbon atoms, and a benzyl group attached to the third carbon atom. 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL is known for its potential applications in various industries due to its distinct properties.

Uses

Used in Pharmaceutical Industry:
1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL is used as a precursor for the synthesis of glycerophospholipid derivatives, which serve as antioxidants and lipid peroxide inhibitors. These derivatives play a crucial role in protecting cells from oxidative damage and maintaining cellular integrity, making them valuable in the development of pharmaceutical agents for various health conditions.
Used in Cosmetic Industry:
In the cosmetic industry, 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL and its derivatives are utilized for their antioxidant and lipid peroxide inhibitory properties. These properties help in maintaining the stability and effectiveness of cosmetic products, as well as providing skin protection against environmental stressors and promoting overall skin health.
Used in Food Industry:
1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL and its glycerophospholipid derivatives can be used in the food industry as natural antioxidants and preservatives. They help in extending the shelf life of food products by inhibiting the formation of lipid peroxides, which can lead to rancidity and spoilage. Additionally, these compounds can contribute to the overall quality and safety of food products.

Upstream product

• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 112-67-4 n-hexadecanoyl chloride 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 57-10-3 1-hexadecylcarboxylic acid 
• 100-44-7 benzyl chloride 
• 1487-51-0 1-O-benzyl-3-O-palmitoyl-rac-glycerol 

Downstream Products

• 19698-29-4 1,2-Dipalmitoylphosphatidic acid 
• 115290-76-1 C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾ 
• 3036-84-8 Hexadecanoic acid 2-[((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-phenoxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 176776-97-9 Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester 
• 148286-68-4 (2-Chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate 

Relevant articles and documents

Studies on the synthesis of dehydroepiandrosterone (DHEA) phosphatide

Synthetic dehydroepiandrosterone (DHEA) phosphatide 1c, (R = C15H31), was prepared by three methods. The most efficient of these involved the coupling of the commercially available DHEA 1a and commercially available phosphatidic acid

Synthetic method of alkynyl-modified phospholipid derivative for preparing functional phospholipid giant vesicle

The invention discloses a synthetic method of an alkynyl-modified phospholipid derivative for preparing a functional phospholipid giant vesicle. The method comprises the following steps: with solketalas a starting raw material, selectively introducing an alkyl chain through benzyl protection, deprotection and DCC-DMAP catalytic condensation, synthesizing 3-hydroxy-1,2- dipalmitin, using 2-chloro-2-oxo-1,3,2-dioxaphospholane as a phosphorylation reagent, carrying out ring opening reaction by using 1-dimethylamine-2-allylene, and preparing the alkynyl-modified phospholipid derivative. The method is simple in synthetic route, a highly toxic reagent does not need to be used, and the phospholipid giant vesicle with an adjustable surface reactivity group density can be prepared by mixing the obtained alkynyl-modified phospholipid derivative and common phospholipid available in the market according to a certain proportion. The possibility is provided for the further stabilization and functionalization of this type of the vesicle.

[F-18]labeiing of 1,2-diacylglycerols

We have developed two kinds of [18F]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(ω-[18F]fluoroacyl)-2-acylglycerols (1*,2-[18F]FDAGs) and 2-(ω[18F]fluoroacyl)-1-acylglycerols (1,2*-[18F]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[18F]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with ω-[18F]fluoroacyl chlorides (method A) and 1-(16-[18F]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C16,C16)) and 1-(8-[18F]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[18F]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(ω-[18F]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(ω-bromoacyl)-1-acylglycerol with [18F]F- (method B) and 2-(16-[18F]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C16)) and 2-(8-[18F]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[18F]FDAGs were obtained in radiochemical yields of 8-35% (based on [18F]F-) with radiochemical purities of > 97% and the purified 1,2*-[18F]FDAGs were in radiochemical yields of 5-15% with radiochemical purities of > 95%. The total synthesis time from the start of the reactive [18F]F- production, including HPLC purification, was 100-135 min (method A) and 115-175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[18F]FDAG(C16,C16), 1*,2-[18F]FDAG (C8,C16), and 1,2*-[18F]FDAG(C16,C16), 1,2*-[18F]FDAG(C16,C8) for animal studies.