3187-58-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL ORSELLINATE is used as a synthetic intermediate for the production of Grifolic Acid (G786500), a selective partial GPR120 agonist. METHYL ORSELLINATE plays a crucial role in the development of drugs targeting specific receptors, which can be beneficial for treating various medical conditions.
Grifolic Acid, synthesized using METHYL ORSELLINATE, is known to induce ERK and [Ca2+]i responses in cells expressing GPR120. It does not have any effects on cells expressing GPR40, making it a selective agonist with potential therapeutic applications.

InChI:InChI=1/C9H10O4/c1-5-3-6(10)4-7(11)8(5)9(12)13-2/h3-4,10-11H,1-2H3

Upstream product

• 480-56-8 lecanoric acid 
• 548-89-0 gyrophoric acid 
• 67-56-1 methanol 
• 106-99-0 buta-1,3-diene 
• 480-64-8 orsellinic acid 
• 77-78-1 dimethyl sulfate 
• 674-82-8 4-methyleneoxetan-2-one 
• 105-45-3 acetoacetic acid methyl ester 
• 23066-87-7 methyl 3,5,7-trioxooctanoate 
• 4030-18-6 N-(acetyl)pyrrolidine 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 2466-76-4 N-Acetylimidazole 
• 102342-54-1 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene 
• 61996-35-8 2-[(N-acetyl-N-methyl)amino]pyridine 

Downstream Products

• 520-43-4 2-hydroxy-4-methoxy-6-methyl-benzoic acid methyl ester 
• 34874-90-3 methyl haematommate 
• 64400-53-9 methyl isohaematommate 
• 80145-01-3 methyl 4-O-benzyl-2-O-methyllecanorate 
• 130998-50-4 2-Hydroxy-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid methyl ester 
• 118607-91-3 potassium methyl orsenillate 
• 22375-05-9 methyl 4-benzyloxy-2-hydroxy-6-methylbenzoate 
• 58061-98-6 methyl 2,4-bis(benzyloxy)-6-methylbenzoate 
• 82752-88-3 methyl 2,4-bis(methoxymethoxy)-6-methylbenzoate 
• 78023-86-6 methyl 2-hydroxy-4-isopropyloxy-6-methylbenzoate 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 300719-60-2 Methyl 2,4-bis(benzyloxymethoxy)-6-methylbenzoate 
• 300719-64-6 Methyl 2-hydroxy-4-[13C]methoxy-6-methylbenzoate 
• 118040-61-2 methyl 2,4-dihydroxy-6-methyl-3-(3-methyl-but-2-enyl)-benzoate 

Relevant academic research and scientific papers

Total synthesis of isocladosporin and 3-epi-isocladosporin

A convergent total synthesis of isocladosporin and 3-epi-isocladosporin is reported starting from commercially available homoallyl alcohol in 10 longest linear steps with 28% overall yield. The key steps involved in the synthesis are cross-metathesis, tan

Chemical Studies on the Lichen. I. The Structure of Isolecanoric Acid, a New ortho-Depside Isolated from Parmelia tinctorum Despr.

A new ortho-depside, isolecanoric acid was isolated from Parmelia tinctorum Despr. and 2-(2,4-dihydroxy-6-methylbenzoyloxy)-4-hydroxy-6-methylbenzoic acid was assigned to this substance from studies on the hydrolysis products and from analyses of the 1H and 13C NMR spectra.This substance is the first ortho-depside isolated from the genus Lichen.

Biomimetic Total Syntheses of Sanctis A-B with Structure Revision

The first concise total syntheses of sanctis A and B were reported, and it enabled revision of the structure of sanctis B through single-crystal X-ray diffraction. The established synthetic approach mainly mimics a biosynthetic olefin isomerization/hemiac

Photolytic Studies on the Generation and Trapping of 6-Oxomethylidenecyclohexa-2,4-diene-1-one Derivatives with Various Nucleophiles

α-Oxoketenes and cyclohexadiene α-oxoketenes are reactive intermediates, particularly the latter due to their high re-aromatization potential. In this communication, we report photolytic studies on the generation of such species from 4-OMe and 4-OMOM protected resorcylate dioxinones and their trapping to give resorcylate esters and amides as well as the formation of adducts with enol-ethers as trapping reagents.

Biomimetic synthesis and anti-inflammatory evaluation of violacin A analogues

Violacin A, a chromanone derivative, isolated from a fermentation broth of Streptomyces violaceoruber, has excellent anti-inflammatory potential. Herein, a biogenetically modeled approach to synthesize violacin A and twenty-five analogues was described, which involved the preparation of aromatic polyketide precursor through Claisen condensation and its spontaneous cyclization. The inhibitory effect on nitric oxide (NO) production of all synthetic molecules was evaluated by lipopolysaccharide (LPS)-induced Raw264.7 cells. The results revealed that introduction of aliphatic amine moieties on C-7 obviously improved the anti-inflammation effect of violacin A, and also the aromatic ether instead of ketone group at side chain was favorable to increase the activity. Among them, analogue 7a and 16d were screened as the most effective anti-inflammatory candidates. Molecular mechanism research revealed that 7a and 16d acquired anti-inflammatory ability due to the inhibition of NF-κB signaling pathway.

CANNABIDIOL-TYPE CANNABINOID COMPOUND

The present invention relates to a cannabidiol (CBD) type cannabinoid compound for use as a medicament. The CBD-type cannabinoid, cannabidiol-C1 (CBD-C1), is a naturally occurring cannabinoid that can be found in minor quantities in the cannabis plant. Furthermore, the 5 cannabinoid can be produced by synthetic means and a method for the production of CBD-C1 is described herein. In addition, disclosed herein are data which demonstrate the efficacy of CBD-C1 in models of disease.

Novel benzyl phenyl sulfide derivatives as antibacterial agents against methicillin-resistant Staphylococcus aureus

Methicillin-resistant Staphylococcus aureus (MRSA) infection is a major threat to human health due to its resistance to almost all classes of antibiotics. Discovery of novel antibacterial agents with new structures which combat the pathogens responsible f

Benzyl aryl thioether derivative as well as preparation method and application thereof

The invention belongs to the field of medicines and discloses a benzyl aryl thioether derivative as well as a preparation method and an application thereof. The benzyl aryl thioether derivative has astructure shown in the following description, wherein R1

Asymmetric synthesis of natural cis-dihydroarenediols using tetrahydroxynaphthalene reductase and its biosynthetic implications

Asymmetric reduction of hydroxynaphthoquinones to secondary metabolites, (3S,4R)-3,4,8- A nd (2S,4R)-2,4,8-trihydroxy-1-tetralone, a putative biosynthetic diketo intermediate and a probable natural analogue, (3S,4R)-7-acetyl-3,4,8-trihydroxy-6-methyl-3,4-

Inhibition of mushroom tyrosinase activity by orsellinates

Several applications have been proposed for tyrosinase inhibitors in the pharmaceutical, food bioprocessing, and environmental industries. However, only a few compounds are known to serve as effective tyrosinase inhibitors. This study evaluated the tyrosinase-related activity of resorcinol (1), orcinol (2) lecanoric acid (3), and derivatives of this acid (4-15). Subjected to alcoholysis, lecanoric acid (3), a depside isolated from the lichen Parmotrema tinctorum, produces orsellinic acid (2,4-dihydroxy-6-methylbenzoic acid) (4) and orsellinates (2,4-dihydroxy-6-methyl benzoates) (5-15). At 0.50 mM, methyl (5), ethyl (6), n-propyl (7), tert-butyl (11), and n-cetyl orsellinates (15) acted as tyrosinase activators, whereas n-butyl (8), iso-propyl (9), sec-butyl (10), n-pentyl (12), n-hexyl (13), and n-octyl orsellinates (14) behaved as inhibitors. Tyrosinase inhibition rose with chain elongation-n-butyl (8) n-pentyl (12) n-hexyl (13) n-octyl orsellinates (14)-suggesting that the enzyme site can accept an eight-carbon alkyl chain. A kinetic study of n-octyl orsellinate (14) revealed uncompetitive inhibition of tyrosinase, with an inhibition constant of 0.99 mM.