5-Bromo-4-chloro-3-indolyl β-D-galactopyranoside (X-Gal) - ≥98% , CAS No.7240-90-6

CAS: 7240-90-6 Cat. No.: X108836 Molecular Weight: 408.63 Beilstein Registry Number: 1402009 EC Number: 230-640-8

GRADE & PURITY ≥98%

Synonyms

V595OG374W | X-Gal | 5-Bromo-4-chloro-3-indolyl beta-galactoside | C14H15BrClNO6 | CHEBI:75055 | BCIG | 5-Bromo-4-chloro-3-(beta-D-galactopyranosyloxy)indole | 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside | 5-Bromo-4-chloro-3-indolyl beta-D-galactopyrano

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

Synonyms

V595OG374W | X-Gal | 5-Bromo-4-chloro-3-indolyl beta-galactoside | C14H15BrClNO6 | CHEBI:75055 | BCIG | 5-Bromo-4-chloro-3-(beta-D-galactopyranosyloxy)indole | 5-Bromo-4-chloro-3-indolyl-beta-D-galactoside | 5-Bromo-4-chloro-3-indolyl beta-D-galactopyrano

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

5-Bromo-4-chloro-3-indolyl b-D-galactopyranoside (X-Gal) is a histochemical substrate for β-galactosidase. X-Gal is cleaved by β-galactosidase to yield an insoluble blue preceipitate. X-Gal is used to detect DNA insertions into the lacZ region of plasmid

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: OPIFSICVWOWJMJ-AEOCFKNESA-N
• 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
• Isomeric SMILES: C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)Cl)Br
• WGK Germany: 3
• Molecular Weight: 408.63
• Beilstein: 1402009
• Reaxy-Rn: 32869881
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=32869881&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 O-glycosyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: O-glycosyl compounds
• Alternative Parents: Hexoses Indoles Substituted pyrroles Aryl bromides Aryl chlorides Oxanes Benzenoids Heteroaromatic compounds Secondary alcohols Acetals Polyols Azacyclic compounds Oxacyclic compounds Organopnictogen compounds Primary alcohols Organonitrogen compounds Hydrocarbon derivatives Organochlorides Organobromides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hexose monosaccharide - O-glycosyl compound - Indole - Indole or derivatives - Aryl bromide - Aryl chloride - Aryl halide - Monosaccharide - Oxane - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Secondary alcohol - Oxacycle - Polyol - Azacycle - Organoheterocyclic compound - Acetal - Primary alcohol - Organohalogen compound - Hydrocarbon derivative - Organopnictogen compound - Organobromide - Organochloride - Organic nitrogen compound - Organonitrogen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
• External Descriptors: organobromine compound - organochlorine compound - beta-D-galactoside - indolyl carbohydrate - D-aldohexose derivative

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMF (5% w/v), DMSO (20 mg/ml), and water (partly miscible).
• Sensitivity: Air & Heat & Light & moisture sensitive
• Specific Rotation[α]: -66 ° (C=1, DMF)
• Melt Point(°C): 236°C
• Molecular Weight: 408.630 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 406.977 Da
• Monoisotopic Mass: 406.977 Da
• Topological Polar Surface Area: 115.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 421.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chunxu Chen, Tianhui Li, Guijie Chen, Dan Chen, Yujia Peng, Bing Hu, Yi Sun, Xiaoxiong Zeng.  (2020)  Commensal Relationship of Three Bifidobacterial Species Leads to Increase of Bifidobacterium in Vitro Fermentation of Sialylated Immunoglobulin G by Human Gut Microbiota.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:32806107] [10.1021/acs.jafc.0c03628]

2. Zhi-P. Cai, Louis P. Conway, Ying Y. Huang, Wen J. Wang, Pedro Laborda, Ting Wang, Ai M. Lu, Hong L. Yao, Kun Huang, Sabine L. Flitsch, Li Liu, Josef Voglmeir.  (2019)  Enzymatic Synthesis of Trideuterated Sialosides.  MOLECULES,  24  (7): (1368).  [PMID:30965582] [10.3390/molecules24071368]

3. Xiaochong Zhu, Jieyuan Wu, Shizhong Li, La Xiang, Jian-Ming Jin, Chaoning Liang, Shuang-Yan Tang.  (2024)  Artificial Biosynthetic Pathway for Efficient Synthesis of Vanillin, a Feruloyl-CoA-Derived Natural Product from Eugenol.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:38501643] [10.1021/acs.jafc.3c08723]

4. Zi-Xuan Hu, Shu-Rui Li, Qing-Jun Xia, Ting Wang, Josef Voglmeir, Göran Widmalm, Li Liu.  (2024)  Enzymatic synthesis of N-formylated sialosides via a five-enzyme cascade.  ORGANIC & BIOMOLECULAR CHEMISTRY,  22  (36): (7485-7491).  [PMID:39189395] [10.1039/D4OB00874J]

5. Xiaoyu Cui, Liqing Feng, Jiayin Li, Shan Gao, Shunping Yan, Ting Pan.  (2026)  Chloroplast vesiculation fine-tunes seed germination by antagonizing ABA signaling through dual degradation of ABI5 and XIW1.  PLANT JOURNAL,  125  (1): (e70669).  [PMID:41525299] [10.1111/tpj.70669]