56552-80-8

Basic information

• Product Name: 1-O-BENZYL-RAC-GLYCEROL
• Synonyms: 1-O-BENZYL-RAC-GLYCEROL;L-A-O-BENZYLGLYCEROL;1-Benzyloxy-2,3-propanediol;(R)-Glycerol 1-benzyl ether, 3-O-Benzyl-sn-glycerol, 3-Benzyl-sn-glycerol;(R)-Glycerol 1-benzyl ether, 3-Benzyl-sn-glycerol;(R)-(+)-1-Benzylglycerol,97%;(R)-(+)-3-Benzyloxy-1,2-propanediol,(R)-Glycerol 1-benzyl ether, 3-Benzyl-sn-glycerol;1,2-Propanediol, 3-(phenylMethoxy)-, (2R)-
• CAS NO: 56552-80-8
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• EINECS: 225-358-7
• Product Categories: Heterocyclic Compounds;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 56552-80-8.mol
• Article Data: 187

Chemical Properties

• Melting Point: 25-29 °C(lit.)
• Boiling Point: 140-145
• Flash Point: >230 °F
• Appearance: /
• Density: 1.140 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: n20/D 1.533
• Storage Temp.: 2-8°C
• PKA: 13.65±0.20(Predicted)
• Stability: Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
• BRN: 2048922
• CAS DataBase Reference: 1-O-BENZYL-RAC-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-BENZYL-RAC-GLYCEROL(56552-80-8)
• EPA Substance Registry System: 1-O-BENZYL-RAC-GLYCEROL(56552-80-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: TY3180000
• F: 3-9
• Hazardous Substances Data: 56552-80-8(Hazardous Substances Data)

Usage

Chemical Properties

colourless crystalline solid

Uses

Employed in the synthesis of a cyclopropyl chiron used in the preparation of 2,3-methanoamino acids. Chiral building block in the synthesis of petrosynes and biologically important phospholipid analogs.

InChI:InChI=1/C10H14O3/c11-6-10(12)8-13-7-9-4-2-1-3-5-9/h1-5,10-12H,6-8H2/t10-/m1/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 1708-40-3 2-phenyl-[1,3]dioxan-5-ol 
• 109-65-9 1-bromo-butane 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 108-86-1 bromobenzene 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 507-20-0 tertiary butyl chloride 
• 112-29-8 1-bromo dodecane 
• 75-26-3 isopropyl bromide 
• 56-81-5 glycerol 
• 108826-60-4 2-Phenyl-[1,3]dioxolane-4-carbaldehyde 
• 103-50-4 dibenzyl ether 

Downstream Products

• 108609-67-2 benzyl (2S)-2,3-bis(hexanoyloxy)-1-propyl ether 
• 688021-88-7 1,2-di-O-octanoyl-3-O-benzyl-sn-glycerol 
• 56586-08-4 3-O-benzyl-1,2-dioctadecanoyl-sn-glycerol 
• 6236-22-2 1-benzyloxy-3-stearoyloxy-propan-2-ol 
• 76189-95-2 3-O-benzyl-1,2-di-O-stearoyl-rac-glycerol 
• 28959-03-7 (+)(R)-2.3-dimethoxy-1-benzyloxy-propane 
• 949-97-3 4-phenylmethoxymethyl-1,3-dioxolan-2-one 
• 4152-39-0 1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 17325-87-0 (2R)-1,2-diacetoxy-3-(benzyloxy)propane 
• 17325-86-9 (+)-(S)-1,2-di-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 151212-86-1 (+)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 121787-44-8 (-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 94650-69-8 1,14-Bis-7-benzyloxymethyl-3,6,9,12-tetraoxatetradecane 
• 75427-80-4 3-Benzyloxypropylenbis(3,6,9-trioxadecanoat) 

Relevant articles and documents

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The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol

Daptomycin (dap) is an important antibiotic that interacts with the bacterial membrane lipid phosphatidylglycerol (PG) in a calcium-dependent manner. The enantiomer of dap (ent-dap) was synthesized and was found to be 85-fold less active than dap against

Dendritic Oligoglycerol Regioisomer Mixtures and Their Utility for Membrane Protein Research

Dendrons are an important class of macromolecules that can be used for a broad range of applications. Recent studies have indicated that mixtures of oligoglycerol detergent (OGD) regioisomers are superior to individual regioisomers for protein extraction. The origin of this phenomenon remains puzzling. Here we discuss the synthesis and characterization of dendritic oligoglycerol regioisomer mixtures and their implementation into detergents. We provide experimental benchmarks to support quality control after synthesis and investigate the unusual utility of OGD regioisomer mixtures for extracting large protein quantities from biological membranes. We anticipate that our findings will enable the development of mixed detergent platforms in the future.

Preparation, supramolecular aggregation and immunological activity of the bona fide vaccine adjuvant sulfavant S

In aqueous conditions, amphiphilic bioactive molecules are able to form self-assembled colloidal structures modifying their biological activity. This behavior is generally neglected in preclinical studies, despite its impact on pharmacological development. In this regard, a significative example is represented by a new class of amphiphilic marine-inspired vaccine adjuvants, collectively named Sulfavants, based on the β-sulfoquinovosyl-diacylglyceride skeleton. The family includes the lead product Sulfavant A (1) and two epimers, Sulfavant R (2) and Sulfavant S (3), differing only for the stereochemistry at C-2 of glycerol. The three compounds showed a significant difference in immunological potency, presumably correlated with change of the aggregates in water. Here, a new synthesis of diastereopure 3 was achieved, and the study of the immunomodulatory behavior of mixtures of 2/3 proved that the bizarre in vitro response to 1–3 effectively depends on the supramolecular aggregation states, likely affecting the bioavailability of agonists that can effectively interact with the cellular targets. The evidence obtained with the mixture of pure Sulfavant R (2) and Sulfavant S (3) proves, for the first time, that supramolecular organization of a mixture of active epimers in aqueous solution can bias evaluation of their biological and pharmacological potential.