イソプロピル 1-チオ-β-D-ガラクトピラノシド

isopropyl beta-D-thiogalactopyranoside

HCID 656894

基本情報

CAS
367-93-1
標準SMILES
CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChIKey
BPHPUYQFMNQIOC-NXRLNHOXSA-N
分子式
C9H18O5S
平均分子量
238.3 g/mol
単同位体質量
238.08749468

概要

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

名称と識別子

優先名称
isopropyl beta-D-thiogalactopyranoside
IUPAC
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
現地名
イソプロピル 1-チオ-β-D-ガラクトピラノシド
英語名
IPTG
分子式
C9H18O5S
分子量
238.3

名称と別名

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
名称をさらに表示
イソプロピル 1-チオ-β-D-ガラクトピラノシドイソプロピルβ-D-チオガラクトピラノシドイソプロピル-β-D-チオガラクトピラノシドイソプロピル-β-D-チオ-ガラクトピラノシド1-(イソプロピルチオ)-1-デオキシ-β-D-ガラクトピラノースイソプロピルチオガラクトシドイソプロピルβ-チオガラクトピラノシドイソプロピルβ-チオガラクトシドイソプロピルチオβ-D-ガラクトピラノシドイソプロピルチオ-β-D-ガラクトピラノシドイソプロピル-β-D(-)-チオガラクトピラノシドイソプロピルβ-D-チオガラクトシドイソプロピル1-チオ-β-D-ガラクトピラノシドイソプロピルチオ-β-D-チオガラクトシドイソプロピル-D-チオガラクトピラノシド1-メチルエチル1-チオ-β-D-ガラクトピラノシド1-S-(1-メチルエチル)-1-チオ-β-D-ガラクトピラノースイソプロピルチオ-β-D-ガラクトシドイソプロピル-チオ-β-D-ガラクトシドイソプロピル-1-チオ-ガラクトピラノシド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

データベース識別子

CAS
367-93-1
PubChem CID
656894
DTXSID
DTXSID6041052
ChEMBL
CHEMBL1233651
ChEBI
CHEBI:61448
UNII
X73VV2246B
EC Number
206-703-0
Nikkaji
J193.883E

物性

構造計算による物性

XLogP
-0.5
極性表面積
115 Ų
水素結合供与体数
4
水素結合受容体数
6
回転可能結合数
3
重原子数
15

実験および物理化学的性質

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

物理化学的性質

融点
105 °C · 105 °C
比旋光度
-31 · -31 º (c=1, water)
沸点
350.9 °C · 350.9°C (rough estimate)
比重(密度)
1.3329 · 1.3329 (rough estimate)
屈折率
1.506 · 1.5060 (estimate)
貯蔵温度
2 · 2-8°C

化学的性質

化学的特性White crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 2 件

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%)

安全データ

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

化学と産業

用途と製造

UsesUsed to induce protein synthesis and to detect lac gene activity; [Merck Index]
General Manufacturing Information.beta.-D-Galactopyranoside, 1-methylethyl 1-thio-: ACTIVE
応用分野 · 5 件

用途イソプロピル-β-チオガラクトピラノシド(Isopropyl β-D-1-thiogalactopyranoside)は、分子生物学で使用される試薬の一つである。通常は略してIPTGと呼ばれる。 この化合物はアロラクトースの類似体として用いられ、ラクトースオペロンの転写を誘導する。アロラクトースとは異なり、生体内では硫黄原子の部分で分解されないため、ラクトースオペロンは常に誘導された状態となる。 IPTGはラクトースリプレッサーに結合してその働きを阻害し、ラクトースを分解するβ-ガラクトシダーゼの発現を誘導する。クローニングにおいては、lacZ遺伝子の部分に目的の遺伝子が導入され、IPTGはその遺伝子の発現を誘導することになる。

用途β-ガラクトシダーゼの誘導物質(inducer)。

説明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.

使用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.

一般的な説明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.

調製方法 · 1 件

製造方法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.

サプライヤー100 社

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]

補足説明

定義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.

関連反応

66 件

化合物ノート

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