Isopropyl-beta-D-thiogalactopyranoside

Base Information

• Chemical Name: Isopropyl-beta-D-thiogalactopyranoside
• CAS No.: 367-93-1
• Deprecated CAS: 30323-26-3,1044658-74-3
• Molecular Formula: C9H18O5S
• Molecular Weight: 238.305
• Hs Code.: 29389090
• European Community (EC) Number: 206-703-0
• UNII: X73VV2246B
• DSSTox Substance ID: DTXSID6041052
• Nikkaji Number: J193.883E
• Wikipedia: Isopropyl_%CE%B2-D-1-thiogalactopyranoside
• Wikidata: Q419229
• Metabolomics Workbench ID: 49933
• Mol file: 367-93-1.mol

Synonyms:1-Thio-beta-D-galactopyranoside, Isopropyl;IPTG;Isopropyl 1 Thio beta D galactopyranoside;Isopropyl 1-Thio-beta-D-galactopyranoside;Isopropyl Thiogalactoside;Thiogalactoside, Isopropyl

Chemical Property of Isopropyl-beta-D-thiogalactopyranoside

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.58E-09mmHg at 25°C
• Melting Point: 105 ºC
• Refractive Index: 1.577
• Boiling Point: 438.4 ºC at 760 mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 219 ºC
• PSA: 115.45000
• Density: 1.37 g/cm³
• LogP: -1.07210
• Storage Temp.: −20°C
• Solubility.: Soluble in Water or Methanol.
• Water Solubility.: soluble
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 238.08749484
• Heavy Atom Count: 15
• Complexity: 201

Purity/Quality:

99.0%min ^*data from raw suppliers

IPTG, Dioxane Free ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 19-40-66-36/37/38
• Safety Statements: 23-24/25-36/37-22-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CC(C)SC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CC(C)S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Description: IPTG (also known as Isopropyl-β-D-Thiogalactopyranoside) is a molecular biology reagent that functions as an inducer of galactosidase activity by binding to and inhibiting the repressor. It is a molecular mimic of allolactose, a lactose metabolite that triggers transcription of the lac operon, and it is therefore used to induce protein expression where the gene is under the control of the lac operator. IPTG cannot be hydrolyzed or broken down by the E. coli therefore the concentration remains constant during cell replication. IPTG is often used at a final concentration ranging from 0.5-1.0 mM. X-Gal is often used with IPTG since it provides an easy visual method to monitor whether protein expression has occurred. X-Gal as the name implies contains a galactose group that once metabolized causes a bright blue color change.
• Uses: Isopropyl-β-D-thiogalactoside is used as a reagent in molecular biology. It is used as an effective β-galactosidase inducer of protein expression where the gene is under the control of the lac operator. It is used with 5-bromo-4-chloro-3-indolyl-beta-D-galactopyranoside to identify the non-recombinant plasmid in cloning experiments by blue-white screen methodology.

Technology Process of Isopropyl-beta-D-thiogalactopyranoside

There total 16 articles about Isopropyl-beta-D-thiogalactopyranoside 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: 98.0%

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55692-87-0) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; pH=10;

Reference yield: 92.0%

2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat (29587-08-4) + isopropyl bromide (75-26-3) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Guidance literature:

With methanol; potassium carbonate; at 60 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 75.0%

isopropylthio-6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbonate)-β-D-galactopyranoside → isopropyl β-D-thiogalactopyranoside (367-93-1)

Guidance literature:

With sodium L-ascorbate; fluorescein free acid; In aq. phosphate buffer; for 0.5h; pH=7.4; Irradiation;

DOI:10.1002/anie.201811261

upstream raw materials:

2-propanethiol

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

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

(2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

isopropylthio 6-O-(tert-butyldimethylsilyloxy)-3-O-benzoyl-β-D-galactopyranoside

Refernces

• 1、 Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing. "One-Pot Relay Glycosylation". supporting information. p. 5498 - 5503. Retrieved 2020/04/09.
• 2、 -. "Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)". Paragraph 0013; 0031; 0038-0039. . Retrieved 2018/03/26.