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

Description

1-O-Benzyl-rac-glycerol is a synthetic compound derived from glycerol, a naturally occurring organic compound and a triol with three hydroxyl groups. The benzyl group attached to the primary hydroxyl group of glycerol provides unique properties and reactivity, making it a versatile intermediate in organic synthesis.

Uses

Used in Pharmaceutical Industry:
1-O-Benzyl-rac-glycerol is used as a chiral building block for the synthesis of various biologically active compounds and pharmaceuticals. Its unique structure allows for the creation of enantiomerically pure compounds, which are essential in the development of drugs with fewer side effects and improved efficacy.
Used in Organic Synthesis:
1-O-Benzyl-rac-glycerol is used as an intermediate in the synthesis of complex organic molecules, such as petrosynes and other natural products. Its benzyl-protected hydroxyl group can be selectively removed under mild conditions, facilitating the synthesis of target molecules with high yields and selectivity.
Used in the Synthesis of Chiral Building Blocks:
1-O-Benzyl-rac-glycerol is used as a chiral building block in the preparation of cyclopropyl chirons, which are key intermediates in the synthesis of 2,3-methanoamino acids. These chirons are valuable for the development of novel pharmaceuticals and agrochemicals, as they can be used to create enantiomerically pure compounds with potential biological activity.
Used in the Synthesis of Phospholipid Analogs:
1-O-Benzyl-rac-glycerol is used as a starting material for the synthesis of biologically important phospholipid analogs. These analogs can be used to study the structure and function of cellular membranes, as well as to develop new drugs targeting membrane-associated processes.

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

• 556-52-5 oxiranyl-methanol 
• 100-51-6 benzyl alcohol 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 20194-18-7 sodium phenyl-methanolate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 4704-76-1 4-(benzyloxymethyl)-1,3-dioxo-2-thiolane 2-oxide 
• 100-46-9 benzylamine 
• 1708-40-3 2-phenyl-[1,3]dioxan-5-ol 
• 132531-98-7 (+/-)-3-O-benzylglyceraldehyde 
• 7664-93-9 sulfuric acid 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-44-7 benzyl chloride 
• 56-81-5 glycerol 

Downstream Products

• 60276-38-2 1-[(2,3-dibromopropoxy)methyl]benzene 
• 85254-39-3 (S)-1-benzyloxy-2,3-bis-methanesulfonyloxy-propane 
• 209802-30-2 (+/-)-1-benzyloxy-2,3-bis-methanesulfonyloxy-propane 
• 108609-67-2 benzyl (2S)-2,3-bis(hexanoyloxy)-1-propyl ether 
• 103160-49-2 1,2-di-O-decanoyl-3-O-benzyl-sn-glycerol 
• 73083-33-7 1-(tetradecanoyl)-3-O-benzyl-sn-glycerol 
• 73083-33-7 3-(benzyloxy)propane-1,2-diyl ditetradecanoate 
• 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 
• 30403-51-1 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol 
• 1487-51-0 1-O-benzyl-3-O-palmitoyl-rac-glycerol 
• 69176-47-2 1,2-di-O-palmitoyl-3-O-benzyl-rac-glycerol 
• 142924-85-4 α-Oleonyl-α'-benzyl-glycerin 

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.