56586-08-4

Basic information

• Product Name: [S,(+)]-3-O-Benzyl-1-O,2-O-distearoyl-L-glycerol
• Synonyms: [S,(+)]-3-O-Benzyl-1-O,2-O-distearoyl-L-glycerol
• CAS NO: 56586-08-4
• Molecular Formula: C₄₆H₈₂O₅
• Molecular Weight: 715.14
• Mol File: 56586-08-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [S,(+)]-3-O-Benzyl-1-O,2-O-distearoyl-L-glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(+)]-3-O-Benzyl-1-O,2-O-distearoyl-L-glycerol(56586-08-4)
• EPA Substance Registry System: [S,(+)]-3-O-Benzyl-1-O,2-O-distearoyl-L-glycerol(56586-08-4)

Safety Data

• Hazardous Substances Data: 56586-08-4(Hazardous Substances Data)

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 112-76-5 Stearoyl chloride 
• 111-63-7 vinyl stearate 
• 4145-51-1 3-O-Benzyl-1-O-octadecanoyl-sn-glycerin 
• 57-11-4 stearic acid 
• 638-08-4 stearic anhydride 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 1429-59-0 1,2-distearoyl-sn-glycerol 
• 195970-40-2 Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester 

Relevant articles and documents

Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids

The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position. These compounds formed six enantiomer pairs, which were separated with recycling high-performance liquid chromatography using chiral columns and UV detection. The chromatographic retention behavior of the enantiomers and the stereospecific elution order were studied. The enantiomer with an n-3 PUFA in the sn-1 position eluted faster than the enantiomer with the n-3 PUFA in the sn-3 position, regardless of the carbon chain length and number of double bonds of the PUFA. TAG enantiomers containing DHA exhibited highly different retention on the chiral column and were separated after the first column, whereas recycling was needed to separate the enantiomer pairs containing ALA or EPA. The system using two identical columns and one mobile phase, without sample derivatization, proved to be very effective also for peak purity assessment, confirming the enantiopurity of the synthesized structured TAGs being higher than 98 percent (96 percent ee).

PHOSPHATIDYLINOSITOL

The invention relates to a new pharmaceutical compound, diacyl phosphatdylinositol in which both the sn-1 and the sn-2 place are taken by stearic acid (18:0) (diacyl [18:0; 18:0] phosphatidylinositol), more preferably, wherein said diacyl phosphatidylinositol is compound 1 as depicted in Fig. 10 or a racemate of compounds 1 and 2 as depicted in Fig. 10. Said pharmaceutical compound and pharmaceutical compositions comprising this compound are specifically useful for the treatment of a disease or a condition wherein suppression of T-cell activation is desirable, such as asthma, diabetes Type 1, rheumatoid arthritis, inflammatory bowel disease or psoriasis. Also part of the invention are food items containing the compound(s) of the invention and use thereof in a diet to treat or prevent the disease or condition mentioned above

Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses

Chiral sulfoquinovosyldiacylglycerols (SQDGs) have been synthesized to determine the absolute stereochemistry and the biological activities. The 1 H NMR spectrum of a natural SQDG is comparable to that of synthetic (2S)-SQDG rather than that of the (2R) analogue. The biological activity of the respective isomers for DNA polymerase α and β inhibition was not distinguishable in the enzymatic assay.