IPTG CAS 367-93-1
Introduction：Basic information about IPTG CAS 367-93-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
IPTG Basic information
| Product Name: | IPTG |
| Synonyms: | POLYETYLENE GLYCOL 6000 MOL. BIOLOGY GRA;SULPHURIC ACID 0,01 MOL/L 0,02 N;YPD BROTH E;Isopropyl 2,3-O-isopropylidene-4-O-benzoyl-β-L-thiorhamnopyranoside;IPTG (Isopropyl-β-D-thiogalatopyranoside);1-ISOPROPYL-BETA-D-THIOGALACTOPYRANOSIDE;isopropyl-thiogalactopyranoside;1-methylethyl1-thio-.beta.-D-Galactopyranoside |
| CAS: | 367-93-1 |
| MF: | C9H18O5S |
| MW: | 238.3 |
| EINECS: | 206-703-0 |
| Product Categories: | substrate;Biochemistry;Galactose;Glycosides;Sugars;Thioglycosides;Substrates;13C & 2H Sugars;Enzyme substrates;Carbohydrates & Derivatives;Carbohydrates;Imidazolines/Imidazolidines ,Imidazoles ,Heterocyclic Acids;Glycon Biochem |
| Mol File: | 367-93-1.mol |
IPTG Chemical Properties
| Melting point | 105 °C |
| alpha | -31 º (c=1, water) |
| Boiling point | 350.9°C (rough estimate) |
| density | 1.3329 (rough estimate) |
| refractive index | 1.5060 (estimate) |
| storage temp. | 2-8°C |
| solubility | Soluble in Water or Methanol. |
| form | Crystalline Powder |
| pka | 13.00±0.70(Predicted) |
| color | White |
| PH | 5-7 (50g/L) |
| biological source | synthetic |
| Water Solubility | soluble |
| Merck | 14,5082 |
| BRN | 4631 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/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 |
| InChIKey | BPHPUYQFMNQIOC-NXRLNHOXSA-N |
| SMILES | S([C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)CO)C(C)C |
| CAS DataBase Reference | 367-93-1(CAS DataBase Reference) |
| EPA Substance Registry System | Isopropyl .beta.- thiogalactoside (367-93-1) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 19-40-66-36/37/38 |
| Safety Statements | 23-24/25-36/37-22-36/37/39-27-26 |
| WGK Germany | 3 |
| F | 10 |
| TSCA | TSCA listed |
| HS Code | 29389090 |
| Storage Class | 11 - Combustible Solids |
| 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 DMF IPTG: 20 mg/ml in water Use 4:1 (X-Gal:IPTG) Assay: ≥99% Dioxane: None detected Melting point: 110-114°C Specific 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. |
| Synthesis | 55692-87-0 367-93-1 GENERAL STEPS: To a 250 mL round bottom flask was added (2R,3S,4S,5R,6S)-2-(acetyloxymethyl)-6-(isopropylsulfanyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (52 mmol, 21.4 g), followed by the addition of 50 mL of sodium methanol solution (pH = 10). The reaction mixture was stirred at room temperature for 12 to 24 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated under reduced pressure. The product was purified by recrystallization from methanol and acetone to give 12.1 g of isopropyl-β-D-thiogalactopyranoside in 98% yield. |
| Solubility in organics | IPTG is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF). The solubility of IPTG in ethanol and DMSO is approximately 20 mg/ml and approximately 30 mg/ml in DMF. |
| 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. |
| References | [1] Patent: CN103087121, 2018, B. Location in patent: Paragraph 0013; 0031; 0038-0039 [2] Liebigs Annalen der Chemie, 1983, # 7, p. 1249 - 1256 [3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 3, p. 839 - 853 [4] Patent: CN103665063, 2016, B. Location in patent: Paragraph 0032; 0034; 0036 [5] Patent: CN103709209, 2016, B. Location in patent: Paragraph 0021; 0023 |
IPTG Preparation Products And Raw materials
| Raw materials | D-Galactopyranose pentaacetate-->D-(+)-GALACTOSE-->.beta.-D-Galactopyranose-->(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate-->2-Propanethiol-->beta-D-Galactose pentaacetate-->Methanol-->Sodium Methoxide |
| Preparation Products | Sarsasapogenin 3-O-β-D-galactopyranosid |
