16232-91-0

Basic information

• Product Name: (2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside
• Synonyms: (2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside;(2R)-2,3-Dihydroxypropyl β-D-Galactopyranoside;(R)-Glyceryl β-D-Galactopyranoside;D-Glycerol-β-D-galactopyranoside
• CAS NO: 16232-91-0
• Molecular Formula: C₉H₁₈O₈
• Molecular Weight: 254.23
• Product Categories: Carbohydrates & Derivatives;Fatty Acid Derivatives & Lipids;Glycerols;Carbohydrates & Derivatives, Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 16232-91-0.mol

Chemical Properties

• Melting Point: 140.5-141.5°C
• Appearance: /
• Refractive Index: 1.592
• CAS DataBase Reference: (2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside(16232-91-0)
• EPA Substance Registry System: (2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside(16232-91-0)

Safety Data

• Hazardous Substances Data: 16232-91-0(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology and Genetics:
(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside is used as a research tool for studying the function and regulation of the lac operon in E. coli. It serves as a substrate for the third lac operon encoded enzyme, thiogalactoside transacetylase, which aids in understanding the genetic control of lactose metabolism and the regulation of gene expression in bacteria.
Used in Enzyme Assays and Screening:
(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside is used as a substrate in enzyme assays to study the activity and specificity of β-galactosidase, an enzyme that plays a crucial role in the breakdown of lactose. This application is essential for the development of new drugs targeting β-galactosidase-related diseases and for screening potential inhibitors or activators of the enzyme.
Used in Drug Delivery Systems:
(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside can be used as a component in the development of targeted drug delivery systems, particularly for cancer therapy. Its ability to serve as a substrate for various enzymes and systems in E. coli makes it a promising candidate for the design of novel drug carriers that can specifically target cancer cells while minimizing side effects on healthy cells.
Used in Analytical Chemistry:
(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside can be employed as a reference compound in the development and validation of analytical methods for the detection and quantification of related compounds in various samples, such as food, pharmaceuticals, and biological fluids. This application is crucial for ensuring the quality, safety, and efficacy of products containing these compounds.
Used in the Food Industry:
(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside can be used as a component in the development of novel food products with enhanced nutritional properties, such as prebiotics or functional foods. Its ability to serve as a substrate for various enzymes and systems in E. coli may contribute to the development of products that promote gut health and overall well-being.

InChI:InChI=1/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4-,5?,6+,7+,8?,9-/m1/s1

Upstream product

• 74628-97-0 bis-((S)-β-benzoyloxy-β'-hydroxy-isopropoxy)-methane 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 130930-94-8 (2R,3R,4S,5R,6R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 55955-32-3 3-O-(β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol 
• 133174-17-1 (2'S)-2'-O-(tetradecanoyl)-3'-O-(9Z,12Z,15Z-octadecatrienoyl)-glyceryl-β-D-galactopyranoside 
• 171520-42-6 3-O-β-D-galactopyranosyl-1-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol 
• 124-41-4 sodium methylate 
• 171743-44-5 (7Z,10Z)-Hexadeca-7,10-dienoic acid (R)-1-hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 
• 57731-81-4 3-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol 
• 67-56-1 methanol 
• 1038401-98-7 (2S)-1-O-5,8,11,14,17-eicosapentaenoyl-2-O-6,9,12-hexadecatrienoyl-3-O-[β-D-galactopyranosyl]glycerol 
• 42869-31-8 (2R)-1-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol 
• 63180-02-9 (2S)-3-O-β-D-galactopyranosyl-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol 
• 55955-33-4 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol 

Downstream Products

• 145014-07-9 (Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 

Relevant articles and documents

Cerebrosides and a monoacylmonogalactosylglycerol from Clinacanthus nutans

A mixture of nine cerebrosides and a monoacylmonogalactosylglycerol were seperated from the leaves of Clinacanthus nutans. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8Z)-2-amino-8(Z)- octadecene-1,3,4-triol with nine 2-hydroxy fatty acids of varying chain lengths (C16, C18, C20-26) linked to the amino group. The glycosylglyceride was characterized as (2S)-1-O-linolenoyl-3-O-β-D- galactopyranosylglycerol. The structures were established on the basis of the spectroscopic data and chemical reactions.

Glyceroglycolipids from Citrus hystrix, a Traditional Herb in Thailand, Potently Inhibit the Tumor-Promoting Activity of 12-O-Tetradecanoylphorbol 13-Acetate in Mouse Skin

Two glyceroglycolipids were isolated from the leaves of Citrus hystrix (bitter orange), a traditional herb in Thailand.They were identified as 1,2-di-O-α-linolenoyl-3-O-β-galactopyranosyl-sn-glycerol (DLGG, 1) and a mixture of two compounds, 1-O-α-linolenoyl-2-O-palmitoyl-3-O-β-galactopyranosyl-sn-glycerol (2a) and its counterpart (2b) (LPGG, 2).Both lipids were potent inhibitors of tumor promoter-induced Epstein-Barr virus (EBV) activation.The IC50 values of 1 and 2 were strikingly lower than those of representative cancer preventive agents such as α-linolenic acid, β-carotene, or (-)-epigallocatechin gallate.In a two-stage carcinogenesis experiment on ICR mouse skin with dimethylbenzanthracene (DMBA) and 12-O-tetradecanoylphorbol 13-acetate (TPA), compound 1 exhibited anti-tumor-promoting activity even at a dose 10 times lower than that of α-linolenic acid.As some synthetic detergents or saponins were entirely inactive in the EBV activation inhibition test, detergency was suggested not to play a major role in the mode of inhibitory action in vivo.The inhibition of the arachidonic acid cascade may be involved in anti-tumor promotion since 1 inhibited TPA-induced edema formation in the anti-inflammation test using ICR mouse ears.Keywords: Cancer chemoprevention; anti-tumor promoter; EB virus; Raji cells; glyceroglycolipid; Citrus hystrix; herb; spice

Secondary metabolites from the leaves of Feijoa sellowiana Berg.

The investigation of the lipid extract of leaves of Feijoa sellowiana cultivated along the east coast of Sicily has yielded in addition to the widespread secondary metabolites: α-tocopherol, flavone, stigmasterol and β-carotene, an inseparable mixture of tyrosol esters of lignoceric (1a), cerotic (1b) and montanic (1c) acids, and a novel galactolipid identified as (2S)-1,2,6′-tri-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl] -3-O-β-d-galactopyranosyl glycerol (2).

Studies on glycolipids. III. Glyceroglycolipids from an axenically cultured cyanobacterium, Phormidium tenue

Seven new monogalactosyl diacylglycerols (1-7) and six new digalactosyl diacylglycerols (11-16) were isolated from an axenically cultured cyanobacterium, P. tenue. Their structures were elucidated on the basis of physicochemical evidence and the results of enzymatic hydrolysis using a lipase (from Rhizopus arrhizus). Comparison of antialgal activity for P. tenue between monogalactosyl diacylglycerols (1-8) and digalactosyl diacylglycerols (11-19) revealed that the former showed more potent activity than the latter.

Arabidopsides A and B, two new oxylipins from Arabidopsis thaliana

Two new oxylipins, arabidopsides A (1) and B (2), were isolated from the aerial parts of Arabidopsis thaliana, and their structures and absolute stereochemistries were elucidated by spectroscopic data and chemical means. Arabidopsides A (1) and B (2) were rare monogalactosyl diacylglycerides containing 12-oxophytodienoic acid and/or dinor-oxophytodienoic acid.

Exploring the Binding Proteins of Glycolipids with Bifunctional Chemical Probes

Glycolipids are important structural components of biological membranes and perform crucial functions in living systems, including signaling transduction and interaction with extracellular environment. However, the mechanistic exploration of glycolipids in vivo is challenging because they are not genetically encoded. Herein, we designed and synthesized a series of bifunctional monogalactosyldiacylglycerol (MGDG) probes as a model by introducing diazirine and terminal alkyne moieties on an aliphatic chain. In combination with proteome profiling and molecular modeling, we have demonstrated that MGDG alleviates inflammation by antagonizing TLR4.

Apoptosis-inducing galactolipids from a cultured marine diatom, Phaeodactylum tricornutum

Two monogalactosyl diacylglycerols, 1 and 2, were isolated from the marine diatom Phaeodactylum tricornutum, using the patented ApopScreen cell-based screen for apoptosis-inducing, potential anticancer compounds. The molecular structures of the galactolipids were determined using a combination of NMR, mass spectrometry, and chemical degradation. The bioactivities were confirmed using a specific apoptosis induction assay based on genetically engineered mammalian cell lines with differential, defined capacities for apoptosis. The galactolipids induce apoptosis in micromolar concentrations. This is the first report of apoptosis induction by galactolipids.

CHEMOENZYMATIC SYNTHESIS OF 1-O-ACYL-3-O-(6'-O-ACYL-β-D-GALACTOPYRANOSYL)-SN-GLYCEROL

Convenient synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl)sn-glycerol was studied.The lipase from Achromobacter sp. catalyzed acylation of 3-O-β-D-galactopyranosyl-sn-glycerol, which contains two primary hydroxyl functions, proceeded regioselectively to furnish 1-O-acyl-3-O-β-D-galactopyranosyl-sn-glycerol.

Enzymatic transformation of glyceroglycolipids into sn-1 and sn-2 lysoglyceroglycolipids by use of Rhizopus arrhizus lipase

Lipase from Rhizopus arrhizus catalyzed deacylation of two classes of glyceroglycolipids, monogalactosyl diacylglycerol(MGDG), and digalactosyl diacylglycerol(DGDG), proceeded regiospecifically to furnish sn-1 lysoglyceroglycolipids quantitatively. The lipase also catalyzed complete acyl migration of sn-1 lysoglycerogalactolipids leading to sn-2 lysoglycerogalactolipids.