Isopropyl β-D-1-thiogalactopyranoside

Isopropyl β-d-1-thiogalactopyranoside
Names
IUPAC name
Propan-2-yl 1-thio-β-D-galactopyranoside
Systematic IUPAC name
(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-[(propan-2-yl)sulfanyl]oxane-3,4,5-triol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.094
MeSH Isopropyl+Thiogalactoside
UNII
  • 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
    Key: BPHPUYQFMNQIOC-NXRLNHOXSA-N
  • InChI=1/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
    Key: BPHPUYQFMNQIOC-NXRLNHOXBD
  • CC(C)S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
Properties
C9H18O5S
Molar mass 238.30 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isopropyl β-d-1-thiogalactopyranoside (IPTG) is a molecular biology reagent. This compound 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.

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