1487-50-9

Basic information

• Product Name: [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol
• Synonyms: [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol;Hexadecanoic acid (2S)-2-hydroxy-3-(benzyloxy)propyl ester
• CAS NO: 1487-50-9
• Molecular Formula: C₂₆H₄₄O₄
• Molecular Weight: 0
• Mol File: 1487-50-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol(1487-50-9)
• EPA Substance Registry System: [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol(1487-50-9)

Safety Data

• Hazardous Substances Data: 1487-50-9(Hazardous Substances Data)

Usage

Description

[S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol is a complex lipid chemical compound consisting of a benzyl group, palmitoyl group, and glycerol moiety. It is known for its potential biological activities and is widely used in research for studying various physiological processes, such as lipid metabolism and inflammation.

Uses

Used in Research Applications:
[S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol is used as a research compound for investigating its role in physiological processes like lipid metabolism and inflammation. Its unique structure and properties make it a valuable molecule for scientific exploration and potential practical applications.
Used in Drug Delivery Systems:
In the pharmaceutical industry, [S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol is used as a component in drug delivery systems. Its lipid nature and potential biological activities contribute to the development of novel drug formulations that can enhance the efficacy and bioavailability of therapeutic agents.
Used in Cosmetic Formulations:
[S,(+)]-3-O-Benzyl-1-O-palmitoyl-L-glycerol is also used as an ingredient in the cosmetic industry. Its potential applications in cosmetic formulations are being explored due to its unique structure and properties, which may offer benefits in skincare and other personal care products.

Upstream product

• 100-39-0 benzyl bromide 
• 693-38-9 vinyl palmitate 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 14618-80-5 (R)-benzyl glycidol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 2930-05-4 Benzyloxymethyl-oxiran 

Downstream Products

• 935852-33-8 3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol 
• 542-44-9 (S)-2,3-dihydroxypropyl hexadecanoic acid ester 
• 134907-95-2 1-hexadecanoyl-2-[(9Z)-octadeca-9-enoyl]-3-tetradecanoyl-sn-glycerol 
• 73649-99-7 1-O-palmitoyl-2-[(9z,12z)-octadenoyl]-glycerol 
• 35418-58-7 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphorylcholine 
• 6931-84-6 lecithin 
• 29541-66-0 1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 30334-71-5 1,2-dipalmitoyl-sn-glycerol 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 30403-51-1 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol 
• 256494-15-2 1-O-palmitoyl-2-arachidonoyl-3-benzylglycerol 
• 256494-16-3 1-O-palmitoyl-2-[(9z,12z)-octadenoyl]-3-benzylglycerol 
• 1487-52-1 1-O-palmitoyl-2-[(9z)-octadenoyl]-3-benzylglycerol 

Relevant articles and documents

Synthesis of enantiopure ABC-type triacylglycerols

The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils.

Total synthesis and mass spectrometric analysis of a: Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The approach features a two-step synthesis of (R)-tuberculostearic acid, involving an (S)-citronellyl bromide linchpin, and the pho

Synthesis and structure of phosphatidylinositol dimannoside

(Chemical Equation Presented) (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (5)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl) phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.