6-Methylsalicylic acid
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| Category | Others |
| Catalog number | BBF-05171 |
| CAS | 567-61-3 |
| Molecular Weight | 152.15 |
| Molecular Formula | C8H8O3 |
| Purity | > 95 % by HPLC |
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Description
It is the core salicylic acid unit in the biosynthesis of many secondary metabolites in actinomycetes, fungi and lichens. This polyketone is a key structural part of many different antibiotics and anticancer drugs, such as chlorothricin, maduropeptin, neocarzinostatin and terreic acid.
Specification
| Synonyms | 6-Hydroxy-o-toluic acid; 2,6-Cresotic acid; 6-MSA; 6-Methyl-2-hydroxybenzenecarboxylate; 6-hydroxy-2-methylbenzoic acid; NSC 403256 |
| Storage | Store at -20 ℃ |
| IUPAC Name | 2-hydroxy-6-methylbenzoic acid |
| Canonical SMILES | CC1=C(C(=CC=C1)O)C(=O)O |
| InChI | InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11) |
| InChI Key | HCJMNOSIAGSZBM-UHFFFAOYSA-N |
Properties
| Appearance | Crystalline solid |
| Boiling Point | 300.4±30.0 ℃ (Predicted) |
| Melting Point | 141.5-142 ℃ |
| Density | 1.304±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol |
| LogP | 1.39880 |
Reference Reading
1. Insights into 6-Methylsalicylic Acid Bio-assembly by Using Chemical Probes
James S Parascandolo, Judith Havemann, Helen K Potter, Fanglu Huang, Elena Riva, Jack Connolly, Ina Wilkening, Lijiang Song, Peter F Leadlay, Manuela Tosin Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3463-7. doi: 10.1002/anie.201509038. Epub 2016 Feb 2.
Chemical probes capable of reacting with KS (ketosynthase)-bound biosynthetic intermediates were utilized for the investigation of the model type I iterative polyketide synthase 6-methylsalicylic acid synthase (6-MSAS) in vivo and in vitro. From the fermentation of fungal and bacterial 6-MSAS hosts in the presence of chain termination probes, a full range of biosynthetic intermediates was isolated and characterized for the first time. Meanwhile, in vitro studies of recombinant 6-MSA synthases with both nonhydrolyzable and hydrolyzable substrate mimics have provided additional insights into substrate recognition, providing the basis for further exploration of the enzyme catalytic activities.
2. Insights into 6-Methylsalicylic Acid Bio-assembly by Using Chemical Probes
James S Parascandolo, Judith Havemann, Helen K Potter, Fanglu Huang, Elena Riva, Jack Connolly, Ina Wilkening, Lijiang Song, Peter F Leadlay, Manuela Tosin Angew Chem Weinheim Bergstr Ger. 2016 Mar 1;128(10):3524-3528. doi: 10.1002/ange.201509038. Epub 2016 Feb 2.
Chemical probes capable of reacting with KS (ketosynthase)-bound biosynthetic intermediates were utilized for the investigation of the model type I iterative polyketide synthase 6-methylsalicylic acid synthase (6-MSAS) in vivo and in vitro. From the fermentation of fungal and bacterial 6-MSAS hosts in the presence of chain termination probes, a full range of biosynthetic intermediates was isolated and characterized for the first time. Meanwhile, in vitro studies of recombinant 6-MSA synthases with both nonhydrolyzable and hydrolyzable substrate mimics have provided additional insights into substrate recognition, providing the basis for further exploration of the enzyme catalytic activities.
3. The gene PatG involved in the biosynthesis pathway of patulin, a food-borne mycotoxin, encodes a 6-methylsalicylic acid decarboxylase
Selma P Snini, Souria Tadrist, Joelle Laffitte, Emilien L Jamin, Isabelle P Oswald, Olivier Puel Int J Food Microbiol. 2014 Feb 3;171:77-83. doi: 10.1016/j.ijfoodmicro.2013.11.020. Epub 2013 Nov 27.
Patulin is a mycotoxin produced by fungal genera such as Aspergillus, Penicillium and Byssochlamys. It induces neurological, gastrointestinal and immunological effects, which is why patulin belongs to a short list of mycotoxins whose level in food is regulated in many countries around the world. Recently, a cluster gathering 15 genes involved in the biosynthesis of patulin has been identified in Aspergillus clavatus, but so far, only 4 genes encoding 6-methylsalicylic acid synthase, m-cresol hydroxylase, m-hydroxybenzyl alcohol hydroxylase and isoepoxydon dehydrogenase have been characterized. Previous studies have shown the involvement of a decarboxylase in the transformation of 6-methylsalicylic acid, the first stable patulin precursor, into m-cresol. In this study a putative decarboxylase gene, PatG, was identified in the genome sequence of A. clavatus. This gene is located near two P450 cytochrome genes PatH and PatI responsible respectively for the hydroxylation of m-cresol and m-hydroxybenzyl alcohol. This decarboxylase encoded by PatG (ACLA_093620) consists of 325 amino acids. The search for putative conserved domain revealed that the gene product belongs to the AminoCarboxyMuconate Semialdehyde Decarboxylase (ACMSD) related protein family. This family includes decarboxylases such as the γ-resorcylate decarboxylase or o-pyrocatechuate decarboxylase. The substrates of these enzymes display strong structural similarities with 6-methylsalicylic acid. PatG was strongly expressed during patulin production whereas it was very weakly expressed in non-patulin permissive conditions. The coding sequence was used to enable heterologous expression of functional enzymes in Saccharomyces cerevisiae. The presence of decarboxylase was confirmed by Western blot. The bioconversion assays showed that PATG catalyzed the decarboxylation of 6-methylsalicylic acid into m-cresol. These results confirm for the first time that 6-methylsalicylic acid is the substrate for PATG, the 6-methylsalicylic acid decarboxylase. With this study, the four genes involved in the four first steps of patulin biosynthesis pathway (acetate→gentisyl alcohol) are now identified.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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