Your Location:Home >Products >Intermediates >367-93-1

367-93-1

  • Product NameIsopropyl-beta-D-thiogalactopyranoside
  • Molecular FormulaC9H18O5S
  • Molecular Weight238.305
  • Purity99%
  • Appearancewhite crystalline powder
Inquiry

Product Details

Quick Details

  • CasNo: 367-93-1
  • Molecular Formula: C9H18O5S
  • Appearance: white crystalline powder
  • Purity: 99%

Factory Supply High Purity Wholesale Isopropyl-beta-D-thiogalactopyranoside 367-93-1 with Competitive Price

  • Molecular Formula:C9H18O5S
  • Molecular Weight:238.305
  • 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 

Isopropyl-beta-D-thiogalactopyranoside(Cas 367-93-1) Usage

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.

Chemical Properties

White crystalline powder

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.

Definition

ChEBI: Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.

Application

IPTG (Isopropyl-β-D-thiogalactopyranoside) is a galactose analogue not recognized by β-galactosidase. IPTG is a non-metabolizable galactose analog that induces expression of the lac operon in Escherichia coli. It is a commonly used reagent in cloning procedures that require induction of b-galactosidase activity and is used in conjunction with X-Gal. It is commonly used in cloning procedures that require induction of β-galactosidase activity. It is also used in conjunction with X-Gal or Bluo-Gal in blue-white selection of recombinant bacterial colonies that induce expression of the lac operon in Escherichia coli. IPTG functions by binding to the lacI repressor and altering its conformation, which prevents the repression of the β-galactosidase coding gene lacZ.

Preparation

a synthetic method of isopropyl-β-D-thiogalactoside. The steps are as follows:Step 1: Dissolve β-D-galactose pentaacetate in any organic solvent of methylene chloride, chloroform or 1,2-dichloroethane, and add Lewis acid (boron trifluoride ether, (Aluminum trichloride, zinc chloride) catalyst and potassium ethylxanthate or sodium ethylxanthate are reacted to obtain tetraacetylgalactose ethylxanthate after treatment.Step 2: Dissolve tetraacetyl galactose ethyl xanthate, 2-bromopropane and sodium carbonate in methanol or ethanol at a temperature of 20°C to 80°C and react for 4-6 hours to obtain isopropyl group after treatment Isopropyl-β-D-thiogalactoside.

General Description

Inducer for β-galactosidase, an enzyme that promotes lactose utilization. Use in conjunction with X-Gal. Molecular Biology grade.Stock solutions:X-Gal: 20 mg/ml in DMFIPTG: 20 mg/ml in waterUse 4:1 (X-Gal:IPTG)Assay: ≥99%Dioxane: None detectedMelting point: 110-114°CSpecific rotation [a]25/D (1%, water): -34.0 to -29.0° Intended for laboratory and manufacturing use only. Not for drug, food, or household use.

storage

Store powder at -20°C away from direct sunlight. Once opened and recapped, place container in a low humidity environment at the same storage temperature. Protect from moisture and light by keeping container tightly closed.

InChI:InChI=1/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9?/m1/s1

367-93-1 Relevant articles

Effect of Photocaged Isopropyl β-d-1-thiogalactopyranoside Solubility on the Light Responsiveness of LacI-controlled Expression Systems in Different Bacteria

Hogenkamp, Fabian,Hilgers, Fabienne,Knapp, Andreas,Klaus, Oliver,Bier, Claus,Binder, Dennis,Jaeger, Karl-Erich,Drepper, Thomas,Pietruszka, J?rg

, p. 539 - 547 (2021)

Photolabile protecting groups play a sig...

One-Pot Relay Glycosylation

Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing

supporting information, p. 5498 - 5503 (2020/04/09)

A novel one-pot relay glycosylation has ...

Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells

Wang, Haoyan,Li, Wei-Guang,Zeng, Kaixing,Wu, Yan-Jiao,Zhang, Yixin,Xu, Tian-Le,Chen, Yiyun

supporting information, p. 561 - 565 (2019/01/04)

The photo-manipulation of bioactive mole...

Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)

-

Paragraph 0013; 0031; 0038-0039, (2018/03/26)

The present invention provides a kind of...

367-93-1 Process route

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
55692-87-0

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

isopropyl β-D-thiogalactopyranoside
367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
Conditions Yield
With sodium methylate; In methanol; at 20 ℃; pH=10;
98%
With sodium methylate; In methanol; for 0.5h;
90%
With sodium methylate; In methanol; at 20 ℃; for 5h; pH=10;
81%
With sodium methylate; In methanol;
75.6%
With sodium methylate; acetic acid; In methanol;
74.3%
With sodium methylate; In methanol; for 1h; Ambient temperature;
72%
With sodium methylate; In methanol; Concentration;
71.5%
With sodium methylate; In methanol; at 20 ℃; for 1h;
 
D-Galactose
10257-28-0

D-Galactose

2-propanethiol
75-33-2

2-propanethiol

isopropyl β-D-thiogalactopyranoside
367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
Conditions Yield
D-Galactose; 2-propanethiol; With aluminum (III) chloride; acetic anhydride; at 5 - 10 ℃;
With sodium methylate; In methanol; Reagent/catalyst;
74.3%

367-93-1 Upstream products

  • 75-33-2
    75-33-2

    2-propanethiol

  • 3068-32-4
    3068-32-4

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

  • 55692-87-0
    55692-87-0

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

  • 4163-60-4
    4163-60-4

    β-D-galactose peracetate

367-93-1 Downstream products

  • 669695-14-1
    669695-14-1

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

  • 440652-81-3
    440652-81-3

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

  • 615570-19-9
    615570-19-9

    3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside

  • 847225-62-1
    847225-62-1

    isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside

;