Grundinformationen
- Standard-SMILES
CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O- InChIKey
BPHPUYQFMNQIOC-NXRLNHOXSA-N- Summenformel
- C9H18O5S
- Durchschnittliche Molmasse
- 238,3 g/mol
- Monoisotopische Masse
- 238,08749468
Überblick
Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.
Namen und Bezeichner
- Bevorzugter Name
- isopropyl beta-D-thiogalactopyranoside
- IUPAC
- (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
- Lokaler Name
- Isopropyl-beta-D-thiogalaktopyranosid
- Englischer Name
- IPTG
- Summenformel
- C9H18O5S
- Molmasse
- 238.3
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
367-93-1- PubChem CID
- 656894
- DTXSID
DTXSID6041052- ChEMBL
CHEMBL1233651- ChEBI
CHEBI:61448- UNII
- X73VV2246B
- EC Number
- 206-703-0
- Nikkaji
- J193.883E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 115 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 201
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 105 °C · 105 °C
- Siedepunkt
- 350.9 °C · 350.9°C (rough estimate)
- Dichte
- 1.3329 · 1.3329 (rough estimate)
- Brechungsindex
- 1.506 · 1.5060 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Soluble in Water or Methanol.
- Aggregatzustand
- Crystalline Powder
- pka
- 13 · 13.00±0.70(Predicted)
- Farbe
- White
- PH
- 5 · 5-7 (50g/L)
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- soluble
- Merck
- 14 · 14,5082
- BRN
- 4631 · 4631
- Stabilität
- 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 Datenbank
- 367 · 367-93-1(CAS DataBase Reference)
- EPA chemische Informationen
- Isopropyl .beta.- thiogalactoside (367-93-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 81% (115 of 142) of all reports.
Warning
H302 (12%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 142 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Isopropyl thiogalactoside: Does not have an individual approval but may be used under an appropriate group standard
Sicherheitsdaten
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29389090
- risk_code
- 19-40-66-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 23-24/25-36/37-22-36/37/39-27-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
Anwendungen
BeschreibungIPTG (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.
VerwendenIsopropyl-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.
Darstellung
synthetischea 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.
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Ergänzende Hinweise
DefinitionChEBI: Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.
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