480-64-8

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dihydroxy-6-methylbenzoic acid is used as a neuroprotective agent for its ability to block PAF-mediated neuronal apoptosis. It plays a crucial role in preventing PARP cleavage and cytotoxicity in various cell types, making it a potential candidate for the development of treatments targeting neurodegenerative diseases.
Used in Antioxidant Applications:
As an antioxidant, 2,4-Dihydroxy-6-methylbenzoic acid is used to neutralize free radicals, such as DPPH radicals, with an IC50 value of 5 mM. Its antioxidant properties make it a valuable compound for the development of products aimed at reducing oxidative stress and promoting overall health.
Used in Chemical Synthesis:
Orsellinic acid can be utilized as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique structure and functional groups make it a versatile building block for creating a wide range of molecules with diverse applications.

Biosynthesis

One of the simplest polyketide derivatives, orsellinic acid is widely distributed in fungi. It is biosynthesised from an acetate starter unit and three malonyl units, as shown in Figure. Intramolecular condensation of the polyketide chain gives orsellinic acid without further modification. The biosynthesis of orsellinic acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3566, 1965 DOI: 10.1021/jo01021a507

InChI:InChI=1/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 548-89-0 gyrophoric acid 
• 4860-88-2 4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione 
• 67-56-1 methanol 
• 110064-65-8 isoelecanoric acid 
• 487-69-4 2,4-dihydroxy-6-methylbenzaldehyde 
• 866997-22-0 2,4-bis-ethoxycarbonyloxy-6-methyl-benzoic acid 
• 860752-66-5 2,4-bis-methoxycarbonyloxy-6-methyl-benzoic acid 
• 480-56-8 lecanoric acid 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 78-92-2 iso-butanol 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 520-43-4 2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester 
• 3187-58-4 methyl orsellinate 
• 504-15-4 orcinol 
• 3163-24-4 2,4,6-tribromo-3,5-dihydroxytoluene 
• 92455-24-8 Dibromorsellinsaeure 
• 156998-32-2 4-[1-(4-Hydroxy-phenyl)-ethyl]-5-methyl-benzene-1,3-diol 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 124-38-9 carbon dioxide 
• 867367-94-0 2,4-Dihydroxy-6-methyl-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester 
• 867367-96-2 2,4-Dihydroxy-6-methyl-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester 
• 256327-77-2 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-allyloxy-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester 
• 256327-71-6 4-benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid 6-(4-benzyloxy-5-hydroxy-2-methyl-6-phenylselanyl-tetrahydro-pyran-3-yloxy)-4-(5-methoxy-4,6-dimethyl-4-nitro-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester 
• 256327-65-8 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester 
• 256327-68-1 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R)-5-acetoxy-4-benzyloxy-2-methyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

An orsellinic acid glucoside from Syzygium aromatica

The buds of Syzygium aromatica yielded two triterpenoid acids, oleanolic acid and crategolic acid, and a new phenolic glucoside, orsellinic-2-O-β-D- glucopyranoside, from its methanolic extract. The structure was elucidated by spectroscopic methods and acid hydrolysis.

CRUSTINIC ACID, A TRIDEPSIDE FROM UMBILICARIA CRUSTULOSA

The structure of crustinic acid extracted from Umbilicaria crustulosa has been elucidated as 4,6-dihydroxy-3-carboxy-2-methylphenyl lecanorate by spectroscopic and chemical means.Key Word Index - Umbilicaria crustulosa; Umbilicariaceae; crustinic acid; tridepside; lichen substance.

Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase

We have recently reported on the development and trypanocidal activity of a class of inhibitors of Trypanosome Alternative Oxidase (TAO) that are targeted to the mitochondrial matrix by coupling to lipophilic cations via C14 linkers to enable optimal interaction with the enzyme's active site. This strategy resulted in a much-enhanced anti-parasite effect, which we ascribed to the greater accumulation of the compound at the location of the target protein, i.e. the mitochondrion, but to date this localization has not been formally established. We therefore synthesized a series of fluorescent analogues to visualize accumulation and distribution within the cell. The fluorophore chosen, julolidine, has the remarkable extra feature of being able to function as a viscosity sensor and might thus additionally act as a probe of the cellular glycerol that is expected to be produced when TAO is inhibited. Two series of fluorescent inhibitor conjugates incorporating a cationic julolidine-based viscosity sensor were synthesized and their photophysical and biological properties were studied. These probes display a red emission, with a high signal-to-noise ratio (SNR), using both single- and two-photon excitation. Upon incubation with T. brucei and mammalian cells, the fluorescent inhibitors 1a and 2a were taken up selectively in the mitochondria as shown by live-cell imaging. Efficient partition of 1a in functional isolated (rat liver) mitochondria was estimated to 66 ± 20% of the total. The compounds inhibited recombinant TAO enzyme in the submicromolar (1a, 2c, 2d) to low nanomolar range (2a) and were effective against WT and multidrug-resistant trypanosome strains (B48, AQP1-3 KO) in the submicromolar range. Good selectivity (SI > 29) over mammalian HEK cells was observed. However, no viscosity-related shift could be detected, presumably because the glycerol was produced cytosolically, and released through aquaglyceroporins, whereas the probe was located, virtually exclusively, in the trypanosome's mitochondrion.

Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base

The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.

Hansforesters A-M, polyesters from the sponge-associated fungus Hansfordia sinuosae with antibacterial activities

Bioassay-guided fractionation and chromatographic separation of a sponge-derived fungus Hansfordia sinuosae, resulted in the isolation of thirteen new polyesters namely hansforesters A-M (1-13), along with five known analogues involving ascotrichalactone A, ascotrichester B, 15G256π, 6R-hydroxymellein, and (?)orthosporin. The structures of the new compounds were determined through extensive spectroscopic analysis, in addition to the chemical conversion for the configurational assignment. The polyesters incorporating the motifs of orsellinic acid, 2,4-dihydroxy-6-acetonylbenzoic acid, and orcinotriol were found from nature for the first time. Hansforester A (1) and ascotrichalactone A exhibited potent inhibition against a panel of bacterial strains, including the agricultural pathogenic bacteria, Pseudomonas lachrymans, Agrobacterium tumefaciens, Xanthomonas vesicatoria, and Ralstonia solanacearum, with the MIC values of 15.6 μM, and the human infected bacterium Staphylococcus aureus with the MIC values of 3.9 μM. These findings suggested that hansforester A and ascotrichalactone A are the potential leads to be developed as the antibacterial agents for the treatment of agriculture bacterial pathogens.

New orsellinic acid esters from fungus chaetomium globosporum

Seven new orsellinic acid esters, 1-7, and four known compounds were isolated from the solid, fermented rice culture of Chaetomium globosporum (cib-132). Their structures were elucidated by 1D- and 2D-NMR spectra, and the relative configuration of compoun

Assembly of melleolide antibiotics involves a polyketide synthase with cross-coupling activity

Summary Little is known about polyketide biosynthesis in mushrooms (basidiomycota). In this study, we investigated the iterative type I polyketide synthase (PKS) ArmB of the tree pathogen Armillaria mellea, a producer of cytotoxic melleolides (i.e., polyketides esterified with various sesquiterpene alcohols). Heterologously produced ArmB showed orsellinic acid (OA) synthase activity in vitro. Further, we demonstrate cross-coupling activity of ArmB, which forms OA esters with various alcohols. Using a tricyclic Armillaria sesquiterpene alcohol, we reconstituted the biosynthesis of melledonol. Intermolecular transesterification reactions may represent a general mechanism of fungal PKSs to create structural diversity of small molecules. Phylogenetic network construction of thioesterase domains of both basidiomycetes and ascomycetes suggests that the fungal nonreducing PKS family has likely evolved from an ancient OA synthase and has gained versatility by adopting Claisen-like cyclase or transferase activity.

Protoilludance Norsesquiterpenoid Esters and Uses Thereof

Disclosed herein are novel protoilludane norsesquiterpenoid ester compounds isolated from mycelium of Armillaria mellea that are useful for treating tumors or proliferative diseases such as breast cancers, lung cancers, colon cancers or leukemia.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Total synthesis of graphislactone G

We present a total synthesis of the fungal natural product graphislactone G, a chlorinated resorcylic lactone. The key step is a Suzuki coupling used for the construction of the central biaryl bond. Graphislactone G was prepared in 13 steps with 22% yield