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2-hydroxy-6-Methylbenzoic Acid Sale

(Synonyms: 2-羟基-6-甲基苯甲酸) 目录号 : GC40944

A precursor for various antibiotic and anticancer agents

2-hydroxy-6-Methylbenzoic Acid Chemical Structure

Cas No.:567-61-3

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产品描述

2-hydroxy-6-Methylbenzoic acid is a constituent of G. anandria, a well-known traditional Chinese medicinal herb, and also produced in various fungi, including P. patulum, where it is a precursor to the toxin patulin . This polyketide is a key structural moiety for many different antibiotic and anticancer agents, including chlorothricin , maduropeptin, neocarzinostatin, and terreic acid.

Chemical Properties

Cas No. 567-61-3 SDF
别名 2-羟基-6-甲基苯甲酸
Canonical SMILES CC1=C(C(O)=O)C(O)=CC=C1
分子式 C8H8O3 分子量 152.1
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 6.5746 mL 32.8731 mL 65.7462 mL
5 mM 1.3149 mL 6.5746 mL 13.1492 mL
10 mM 0.6575 mL 3.2873 mL 6.5746 mL
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Research Update

Isolation and structure of mycobactin T, a growth factor from Mycobacterium tuberculosis

Biochem J 1965 Oct;97(1):166-75.PMID:16749098DOI:10.1042/bj0970166.

1. A growth factor for Mycobacterium johnei has been isolated from Mycobacterium tuberculosis as an iron complex; it has been named ferric mycobactin T. 2. Ferric mycobactin T as isolated is a mixture of at least four closely related components differing only in their fatty acid side chains. 3. Mycobactin T resembles mycobactin P in structure but differs in the following respects: (a) the aromatic acid residue is salicylic acid in place of 2-hydroxy-6-Methylbenzoic Acid; (b) the hydroxy acid residue is (+)-beta-hydroxybutyric acid in place of (-)-3-hydroxy-2-methylpentanoic acid; (c) its components have fatty acid side chains that are mostly different from the side chains of the components in mycobactin P preparations. One minor component in mycobactin T has probably a cis-octadec-2-enoyl side chain. The major side-chain components correspond to acids of chain length C(18)-C(21) that are not n-saturated or n-Delta(2)-unsaturated acids. 4. The differences in biosynthesis between mycobactins T and P are discussed.

Neotropical ant gardens II. Bioassays of seed compounds

J Chem Ecol 1990 Oct;16(10):2993-3013.PMID:24263271DOI:10.1007/BF00979490.

A number of volatile compounds occur on the seeds of taxonomically unrelated ant-garden epiphytes in western Amazonia. In field trials in southeastern Peru, we assayed the responses of ant-garden ants (Camponotus femoratus) to these and structurally similar compounds applied to artificial "seeds" made from zeolite molecular sieves. Benzothiazole,2, present on seeds of eight ant-garden epiphytes, repelled ants over the range of concentrations tested, as did 1-(2-hydroxy-6-methylphenyl)ethanone,3, occurring on seeds of six ant-garden epiphytes. 2-hydroxy-6-Methylbenzoic Acid, methyl ester (methyl-6-methylsalicylate, 6-MMS),1, found on seeds of at least nine ant-garden epiphytes, was mildly repellent at high concentration, but stimulated excitement, seed handling, and (rarely) seed carrying at lower concentrations. Vanillin,5, a seed compound of four ant-garden epiphytes, and limonene,6, a monoterpene from seeds of three ant-garden epiphytes, both stimulated excitement, alarm, seed handling, and (rarely) seed carrying. Identified from seeds of seven ant-garden epiphytes, 1-(2,4-dihydroxyphenyl)ethanone,4, elicited little or no response. Among 70 compounds tested (mainly aromatic compounds), those found on seeds of ant-garden epiphytes or having structural features in common with such compounds were the most attractive to the ants. Although not present on epiphyte seeds, 2-hydroxy-3-methoxybenzenemethanol,10, consistently stimulated seed transport to the nest in one year, but did so only rarely in subsequent years. Some of the volatile compounds on seeds of ant-garden epiphytes probably play a role in ant attraction to epiphyte seeds, but evidence remains ambiguous. Finally,Ca. femoratus responded to one test compound [1-(2-hydroxy-4-methoxyphenyl)ethanone,60] (absent from epiphyte seeds) by descending from the vegetation to the ground.

Chemical composition and biological activities of Gerbera anandria

Molecules 2014 Apr 2;19(4):4046-57.PMID:24699147DOI:10.3390/molecules19044046.

Gerbera anandria (Compositae) was extracted with 75% ethanol and the residue was fractionated using light petroleum, chloroform and ethyl acetate. The constituents of the extracts were separated by column chromatography employing solvents of different polarity. Column chromatography of the light petroleum fraction resulted in the isolation of methyl hexadecanoate, while the chloroform fraction afforded xanthotoxin, 2-hydroxy-6-Methylbenzoic Acid, 7-hydroxy-1(3H)-isobenzofuranone, a mixture of β-sitosterol and stigmasterol, and 8-methoxysmyrindiol and the ethyl acetate fraction gave gerberinside, apigenin-7-O-β-d-glucopyranoside and quercetin. A new coumarin, 8-methoxysmyrindiol, was found. The chemical structures of the isolated compounds were established by MS and NMR (HSQC, HMBC). Free radical scavenging and cytotoxic activities of crude extracts and 8-methoxysmyrindiol were further investigated. The ethyl acetate phase exerted the strongest DPPH free radical scavenging activity in comparison to the other fractions. The coumarin 8-methoxysmyrindiol demonstrated cytotoxicity against multiple human cancer cell lines, with the highest potency in HepG2 cells.

Heteroatom-containing antibacterial phenolic metabolites from a terrestrial Ampelomyces fungus

Biosci Biotechnol Biochem 2008 Jul;72(7):1746-9.PMID:18603789DOI:10.1271/bbb.80043.

Two new sulfur-containing phenolic compounds, 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one (1) and 2,5-dihydroxy-3-methanesulfinylbenzyl alcohol (2), along with two known compounds, 3-chloro-2,5-dihydroxybenzyl alcohol (3) and 2-hydroxy-6-Methylbenzoic Acid (4), were isolated from the mycelial solid culture of a soil-derived Ampelomyces fungus by antibacterial assay-guided fractionation. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1-3 showed structure and microbial dependent antibacterial activities.