Isopropyl-beta-D-thiogalaktopyranosid

isopropyl beta-D-thiogalactopyranoside

HCID 656894CAS 367-93-1

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

IPTG367-93-1Isopropyl-beta-D-thiogalactopyranosideIsopropyl beta-D-thiogalactopyranosideISOPROPYL THIOGALACTOSIDEIsopropyl-beta-D-thiogalactosideIsopropyl beta-D-1-thiogalactopyranosideIsopropyl beta-D-thiogalactosideIsopropyl 1-Thio-beta-D-galactopyranosideDTXSID6041052X73VV2246B(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
Weitere Namen anzeigen
isopropyl β-d-1-thiogalactopyranosideISOPROPYL-B-D-THIOGALACTOPYRANOSIDEIsopropyl-B-D-thiogalactosideIsopropyl-β-D-thiogalatopyranosideIsopropyl β-D-Thiogalactopyranoside (IPTG)
CHEBI:61448beta-D-Galactopyranoside, 1-methylethyl 1-thio-(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyl-oxane-3,4,5-triolThiogalactoside, Isopropylisopropyl beta-thiogalactosideIsopropyl 1 Thio beta D galactopyranoside1-Thio-beta-D-galactopyranoside, IsopropylRefChem:389084

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Uses -> Biochemical Research
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionWhite solid with an odor of sulfur; [Promega MSDS]

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.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 2 Einträge

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

Hazards SummaryAn eye irritant; Harmful by ingestion; May cause liver and kidney injury; [Promega MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (12%)

Sicherheitsdaten

F
10
wgk
3
tsca
TSCA listed
hs_code
29389090
risk_code
19-40-66-36/37/38
hazard_code
Xn,Xi

Chemie und Industrie

Verwendung und Herstellung

UsesUsed to induce protein synthesis and to detect lac gene activity; [Merck Index]
General Manufacturing Information.beta.-D-Galactopyranoside, 1-methylethyl 1-thio-: ACTIVE
Anwendungen · 2 Einträge

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 · 1 Eintrag

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.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
清宁生物(江苏博泉生物科技有限公司)19352250998 · [email protected]

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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