2-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6H,7H,8H,9H,10H-cyclohexa[c]chromen-6-one

• ChemBase ID: 155768
• Molecular Formular: C19H22O9
• Molecular Mass: 394.37258
• Monoisotopic Mass: 394.12638228
• SMILES: c1c2c(cc(c1O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)oc(=O)c1c2CCCC1
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3oc(=O)c4c(c3cc2O)CCCC4)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C19H22O9/c20-7-14-15(22)16(23)17(24)19(28-14)27-13-6-12-10(5-11(13)21)8-3-1-2-4-9(8)18(25)26-12/h5-6,14-17,19-24H,1-4,7H2/t14-,15+,16+,17-,19-/m1/s1
• InChIKey: HDJJDRXZHJRVGA-DIKXUDHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6H,7H,8H,9H,10H-cyclohexa[c]chromen-6-one
• IUPAC Traditional name: 2-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7H,8H,9H,10H-cyclohexa[c]chromen-6-one
• Synonyms: 3,4-Cyclohexenoesculetin β-D-galactopyranoside; S-Gal®

Database IDs

• CAS Number: 182805-65-8
• PubChem SID: 162249906
• PubChem CID: 71312219

CALCULATED PROPERTIES

• Acid pKa: 9.652799
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.028487062
• LogD (pH = 7.4): 0.026114205
• Log P: 0.0285174
• Molar Refractivity: 93.6937 cm^3
• Polarizability: 37.30479 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C19H22O9

DETAILS

Sigma Aldrich - S9811

Application
S-Gal is a patented autoclavable chromogenic substrate for β-galactosidase that is designed to replace X-Gal in blue-white selection of recombinant bacterial colonies with the lac+ phenotype.
Caution
For black color development to occur, ferric ion must be present. Although we recommend ferric ammonium citrate (500mg/L of media), other ferric compounds can be used to provide this requirement, depending upon your particular system.
Features and Benefits
When S-Gal is cleaved by β-galactosidase, the resulting product will chelate ferric ion to create a black, insoluble precipitate. Lac+ colonies grown in the presence of S-Gal and ferric ion turn an intense black color, allowing for easy differentiation between lac+ and lac- colonies. S-Gal is autoclavable and can be added to your medium of choice prior to autoclaving. S-Gal is not light sensitive and does not require any protection from light sources.
Other Notes
Autoclavable, microwavable growth medium complete with S-Gal and IPTG.
Reconstitution
Add to agar media pre-autoclaving at a recommended concentration of 300 mg S-Gal/L of media, along with 500mg/L Ferric Ammonium Citrate (F5879). Stock solutions of S-Gal can be made by dissolving at 50mg/ml in dimethyl formamide and storing at -20 °C.
Legal Information
S-GAL is a registered trademark of Sigma-Aldrich Co. LLC