An intermediate in the microbial metabolism of aromatic compounds
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Benzoyl-Coenzyme A (sodium salt)

Item No. 27859

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-benzoate coenzyme A, sodium salt
Synonyms
  • Benzoyl-CoA
Molecular Formula
C28H40N7O17P3S • XNa
Formula Weight
871.6
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 50 mg/ml
λmax
261 nm
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@H](COP(OP(OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(C4=CC=CC=C4)=O)=O)=O)(O)=O)(O)=O)[C@H]1OP(O)(O)=O.[Na]
InChi Code
InChI=1S/C28H40N7O17P3S.Na/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35;/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43);/t17-,20-,21-,22+,26-;/m1./s1
InChi Key
XIPUXHYWTIVYBZ-MEFCJLEQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $74

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    5 mg

    $327

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    10 mg

    $613

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    Product Description

    Benzoyl-coenzyme A (benzoyl-CoA) is an intermediate in the microbial metabolism of aromatic compounds.1,2 It can be produced via anaerobic metabolism of benzoate, toluene, and phenylalanine, among others, in the environment as well as the gut microbiome.1 In proteobacteria, conversion of benzoate to benzoyl-CoA by a benzoate-CoA ligase can occur under both aerobic and anaerobic conditions.2 Benzoyl-CoA is also a precursor in the biosynthesis of the antibiotic enterocin (Item No. 20592) in Salinospora.3 Benzoyl-CoA has been used as a substrate to measure the enzyme kinetics of human recombinant glycine N-acyltransferase (GLYAT), which catalyzes the formation of hippuric acid from benzoyl-CoA and glycine.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Porter, A.W., and Young, L.Y. Benzoyl-CoA, a universal biomarker for anaerobic degradation of aromatic compounds. Adv. Appl. Microbiol. 88, 167-203 (2014).

    2. Valderrama, J.A., Durante-Rodríguez, G., Blázquez, B., et al. Bacterial degradation of benzoate: Cross-regulation between aerobic and anaerobic pathways. The Journal of Biological Chemisty 287(13), 10494-10508 (2012).

    3. Thonburg, C.K., Wortas-Strom, S., Nosrati, M., et al. Kinetically and crystallographically guided mutations of a benzoate CoA ligase (BadA) elucidate mechanism and expand substrate permissivity. Biochemistry 54(40), 6230-6242 (2015).

    4. van der Sluis, R., Ungerer, V., Nortje, C., et al. New insights into the catalytic mechanism of human glycine N-acyltransferase. J. Biochem. Mol. Toxicol. 31(11), e21963 (2017).