(2S,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 130195
• Molecular Formular: C14H15BrClNO6
• Molecular Mass: 408.629
• Monoisotopic Mass: 406.97712689
• SMILES: Brc1ccc2c(c(O[C@@H]3O[C@@H]([C@H](O)[C@H](O)[C@H]3O)CO)c[nH]2)c1Cl
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11+,12+,13-,14-/m1/s1
• InChIKey: OPIFSICVWOWJMJ-AEOCFKNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: X-gal
• Synonyms: 5-BROMO-4-CHLORO-3-INDOLYL-BETA-D-GALACTOPYRANOSIDE; X-gal; 5-Bromo-4-chloro-3-indolyl β-D-galactoside; BCIG; X-Gal; 5-Bromo-4-chloro-3-indolyl β-D-galactopyranoside; 5-Bromo-4-chloro-3-indolyl-beta-D-galactopyranoside; 5-溴-4-氯-3-吲哚-β-D-半乳糖苷; 5-溴-4-氯-3-吲哚β-D-吡喃半乳糖苷; 5-Bromo-4-chloro-3-indolyl β-D-galactopyranoside; 5-溴-4-氯-3-吲哚基-β-D-吡喃半乳糖苷

Database IDs

• CAS Number: 7240-90-6
• EC Number: 230-640-8
• MDL Number: MFCD00005666
• Beilstein Number: 1402009
• PubChem SID: 162224479; 24892124; 24891761; 24891889
• PubChem CID: 65181
• Chemspider ID: 58680
• MeSH Name: X-gal
• Wikipedia Title: X-gal

CALCULATED PROPERTIES

• Acid pKa: 12.199782
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.8731716
• LogD (pH = 7.4): 0.87316483
• Log P: 0.8731717
• Molar Refractivity: 83.6974 cm^3
• Polarizability: 34.64774 Å^3
• Polar Surface Area: 115.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL
• Apperance: powder; tablet
• Melting Point: ca 236°C dec.
• Optical Rotation: [α]20/D -62±2°, c = 1% in DMF/H2O 1:1; -60 (c=1 in 50% DMF)

Safety Information

• Storage Warning: Moisture & Light Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); ≥98.0% (TLC); 98%; 98+%
• Grade: for molecular biology
• Suitability: suitable as substrate for β-galactosidase test; suitable for identification of lac+ bacterial colonies
• Impurities: DNases, none detected; phosphatases, none detected; proteases, none detected; RNases, none detected
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C14H15BrClNO6

DETAILS

Sigma Aldrich - B9146

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.
Reconstitution
A stock solution (100 mg/ml) is prepared by dissolving X-Gal in dimethylformamide and should be stored at -20 °C and protected from light. Sterilization is not required.

Sigma Aldrich - B6024

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.
Quantity
Contains 5 mg substrate per tablet
Reconstitution
A stock solution (100 mg/ml) is prepared by dissolving X-Gal in dimethylformamide and should be stored at -20°C and protected from light. Sterilization is not required.

Sigma Aldrich - 857211

Application
Histochemical substrate for β-galactosidase.1

Sigma Aldrich - 16665

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.
Other Notes
Substrate for β-galactosidase1,2

Sigma Aldrich - 16664

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.

Sigma Aldrich - B4252

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.

Sigma Aldrich - 03-3734

Application
X-Gal is a chromogenic substrate for β-galactosidase that produces a rich blue color that can easily be detected visually over background. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.
Suitability
for biological purposes