(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(propan-2-ylsulfanyl)oxane-3,4,5-triol

• ChemBase ID: 102548
• Molecular Formular: C9H18O5S
• Molecular Mass: 238.30122
• Monoisotopic Mass: 238.08749468
• SMILES: S(C(C)C)[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](SC(C)C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(propan-2-ylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: IPTG
• Synonyms: Isopropyl-β-D-Thiogalactoside; IPTG; ISOPROPYL-β-D-THIOGALACTOPYRANOSIDE; Isopropyl β-D-thiogalactoside; IPTG solution; Isopropyl β-D-thiogalactopyranoside solution; Isopropyl β-D-thiogalactopyranoside; Isopropyl β-D-1-thiogalactopyranoside; Isopropyl-beta-D-thiogalactoside, dioxane-free; Isopropyl 1-thio-b-D-galactopyranoside; IPTG 溶液; 异丙基 β-D-硫代半乳糖吡喃糖苷 溶液; 异丙基 β-D-硫代半乳糖吡喃糖苷; 异丙基 β-D-硫代半乳糖苷; 异丙基 β-D-1-硫代半乳糖吡喃糖苷; 异丙基-β-D-硫代半乳糖苷, 不含二氧六环

Database IDs

• CAS Number: 367-93-1
• EC Number: 206-703-0
• MDL Number: MFCD00063273
• Beilstein Number: 4631
• PubChem SID: 24896069; 24896093; 24881691; 24895928; 162089923
• PubChem CID: 656894

CALCULATED PROPERTIES

• Acid pKa: 12.480839
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.0125945
• LogD (pH = 7.4): -1.012598
• Log P: -1.0125945
• Molar Refractivity: 56.0606 cm^3
• Polarizability: 22.944511 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 105 °C(lit.); 109-115°C; 122°C
• Optical Rotation: [α]20/D -29°, c = 1 in H2O; [α]20/D -32.0±1.0°, c = 1% in H2O (dry matter); -32 (c=1 in water)

Safety Information

• Storage Condition: 0°C, Desiccate
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 19-40
• Safety Statements: 36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H351
• GHS Precautionary statements: P281-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US); Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: >99%; ≥99% (TLC); ≥99.0%; ≥99.0% (TLC); 97%; 99%
• Ignition Residue: ≤0.2%
• Description: non-ionic
• Impurities: <5% water; ≤0.1% Dioxane; 10.0-22.0% Dioxane
• Loss on Drying: ≤6% loss on drying
• Quality Level: PREMIUM
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C9H18O5S

DETAILS

MP Biomedicals - 05222029

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194029

Molecular Biology Reagent
Purity: >99%
Cell culture media component for use in molecular genetics.
β-Galactoside inducer.

MP Biomedicals - 02102101

Crystalline
Dioxane-free
β-Galactosidase inducer.

Sigma Aldrich - I1284

Application
Isopropyl thiogalactose (IPTG) is a sugar derivative widely used for the induction of the expression of recombinant proteins in E. coli. This expression system requires that the gene of interest is cloned in plasmids containing the Lac promoter. IPTG Ready Made is a 0.2 μm filter sterilized solution of 200 mM IPTG. This reagent remains liquid at its storage temperature (-20 °C), thus avoiding freeze-thaw cycles and providing a user-friendly solution.
Biochem/physiol Actions
Isopropyl β-D-thiogalactopyranoside binds to the lac repressor and releases the tetrameric repressor from the lac operator in an allosteric manner. This binding allows the transcription of genes in the lac operon, such as the gene coding for β--galactosidase. The β-galactosidase gene is transcribed and monosaccharides are the product.. Since Isopropyl β-D-thiogalactopyranoside cannot be metabolized by E. coli its concentration remains constant. Therefore, it is not a variable in the experiment.1

Sigma Aldrich - 59740

Application
IPTG is commonly used in cloning procedures that require induction of β-galactosidase activity. It is 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.
Other Notes
Non-metabolizable galactose analog.
IPTG is an inducer of β-galactosidase activity in bacteria and is used to detect lac gene activity during cloning experiments1

Sigma Aldrich - I6758

Application
IPTG 常用于需要诱导 β-半乳糖苷酶活性的克隆实验。它常与 X-Gal 或 Bluo-Gal 结合使用，用于重组细菌菌落的蓝白筛选，这些菌落可以诱导 lac 操纵子在大肠杆菌中的表达。IPTG 与 lacI 阻遏蛋白结合并改变其构象而发挥作用，防止 β-半乳糖苷酶编码基因 lacZ 的抑制。
Other Notes
非代谢性半乳糖类似物。
包装
1, 5, 10 g in glass bottle
Reconstitution
将 IPTG 溶于水，然后经无菌过滤，配制成储存液 (0.1M)。指示板中 IPTG 最终浓度应为 0.2mM。

Sigma Aldrich - I5502

Application
IPTG 常用于需要诱导 β-半乳糖苷酶活性的克隆实验。它常与 X-Gal 或 Bluo-Gal 结合使用，用于重组细菌菌落的蓝白筛选，这些菌落可以诱导 lac 操纵子在大肠杆菌中的表达。IPTG 与 lacI 阻遏蛋白结合并改变其构象而发挥作用，防止 β-半乳糖苷酶编码基因 lacZ 的抑制。
Other Notes
非代谢性半乳糖类似物。
Reconstitution
将 IPTG 溶于水，然后经无菌过滤，配制成储存液 (0.1M)。指示板中 IPTG 最终浓度应为 0.2mM。

Sigma Aldrich - 15-2461

Application
IPTG is commonly used in cloning procedures that require induction of β-galactosidase activity. It is 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.
Other Notes
Non-metabolizable galactose analog.
Suitability
for biological purposes