Galactosylglycerol

Base Information

• Chemical Name: Galactosylglycerol
• CAS No.: 16232-91-0
• Molecular Formula: C9H18 O8
• Molecular Weight: 254.237
• Hs Code.: 2938909090
• ChEMBL ID: CHEMBL446492
• DSSTox Substance ID: DTXSID90936687
• Metabolomics Workbench ID: 39034,50246
• Nikkaji Number: J362.297E
• Wikidata: Q27098216
• Mol file: 16232-91-0.mol

Synonyms:16232-91-0;3-beta-D-Galactosyl-sn-glycerol;CCRIS 8734;Galactosylglycerol;3-O-beta-D-Galactopyranosyl-sn-glycerol;(2R)-2,3-Dihydroxypropyl-b-D-galactopyranoside;3-O-beta-D-galactosyl-sn-glycerol;CHEBI:15754;(2R)-2,3-dihydroxypropyl beta-D-galactopyranoside;(2R)-Glycerol-O-|A-D-galactopyranoside;CHEMBL446492;beta-D-Galactopyranoside, (2R)-2,3-dihydroxypropyl;3ga5;SCHEMBL1901456;DTXSID90936687;BDBM50478441;AKOS030531243;(2R)-Glycerol-O-?-D-galactopyranoside;(2R)-Glycerol-O-??-D-galactopyranoside;PD017884;RGG;HY-116055;CS-0063692;C05401;W-201475;Q27098216;WURCS=2.0/2,2,1/[h2h][a2112h-1b_1-5]/1-2/a1-b1;2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)tetrahydropyran-3,4,5- triol;(2R,3R,4S,5R,6R)-2-((R)-2,3-Dihydroxypropoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of Galactosylglycerol

Chemical Property:

• Melting Point: 140.5-141.5°C
• PSA: 139.84000
• LogP: -3.84390
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 254.10016753
• Heavy Atom Count: 17
• Complexity: 225

Purity/Quality:

98%Min ^*data from raw suppliers

(2R)-Glycerol-O-β-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OCC(CO)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H](CO)O)O)O)O)O
• Description: (2R)-Glycerol-O-β-D-galactopyranoside is a substrate for β-galactosidase, the lactose repressor, the galactose-binding protein, and the β-methylgalactoside transport system. It also serves as a substrate for the third lac operon encoded enzyme, thiogalactoside transacetylase.
• Uses: An excellent substrate for β-galactosidase and the lactose transport system as well as the lac repressor in E. coli. RGG serves as a substrate for the third lac operon encoded enzyme, thiogalactoside transacetylase.

Technology Process of Galactosylglycerol

There total 20 articles about Galactosylglycerol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(2R)-1-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol (42869-31-8) → (2R)-1-O-β-D-galactopyranosylglycerol (16232-91-0)

Guidance literature:

With potassium hydroxide; In methanol; at 50 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201608827

Reference yield: 92.0%

arabidopside A → (2R)-1-O-β-D-galactopyranosylglycerol (16232-91-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(03)01148-1

Reference yield: 32.0%

(2'S)-2'-O-(tetradecanoyl)-3'-O-(9Z,12Z,15Z-octadecatrienoyl)-glyceryl-β-D-galactopyranoside (133174-17-1) → (2R)-1-O-β-D-galactopyranosylglycerol (16232-91-0)

Guidance literature:

With phosphate buffer; Candida cylinracea lipase; Triton X-100; In water; at 38 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)85063-8

upstream raw materials:

bis-((S)-β-benzoyloxy-β'-hydroxy-isopropoxy)-methane

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

(2R,3R,4S,5R,6R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

3-O-(β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Downstream raw materials:

(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

Refernces

• 1、 Murakami, Akira,Nakamura, Yoshimasa,Koshimizu, Koichi,Ohigashi, Hajime. "Glyceroglycolipids from Citrus hystrix, a Traditional Herb in Thailand, Potently Inhibit the Tumor-Promoting Activity of 12-O-Tetradecanoylphorbol 13-Acetate in Mouse Skin". . p. 2779 - 2783. Retrieved 1995.
• 2、 Murakami,Morimoto,Imamura,Ueda,Nagai,Sakakibara,Yamada. "Studies on glycolipids. III. Glyceroglycolipids from an axenically cultured cyanobacterium, Phormidium tenue". . p. 2277 - 2281. Retrieved 1991.
• 3、 Liu, Xiaohui,Dong, Ting,Zhou, Yu,Huang, Niu,Lei, Xiaoguang. "Exploring the Binding Proteins of Glycolipids with Bifunctional Chemical Probes". supporting information. p. 14330 - 14334. Retrieved 2016/11/11.