18499-84-8

Usage

Uses

Flavokermes Acid is an anthroquinone and natural yellow dye which may also display significant inhibition of lipid peroxidation.

InChI:InChI=1/C16H10O7/c1-5-11-8(4-10(19)12(5)16(22)23)14(20)7-2-6(17)3-9(18)13(7)15(11)21/h2-4,17-19H,1H3,(H,22,23)

Upstream product

• 69119-25-1 ethyl 3-chloro-7-methoxy-5-methyl-1,4-naphthoquinone-6-carboxylate 
• 867022-57-9 (S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid 
• 155884-01-8 (2-(2H-tetrazol-5-yl)phenyl)boronic acid 
• 137863-17-3 methyl N-((2’-(1H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)methyl)-N-pentanoyl-L-valinate 
• 50-99-7 D-glucose 
• 137863-90-2 methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate 
• 1080555-76-5 C₂₄H₂₇N₅O₃ 
• 1080555-70-9 C₃₃H₃₇N₅O₃ 
• 852212-82-9 (S)-4-isopropyl-3-pentanoyl-2-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-yl]oxazolidin-5-one 
• 69119-27-3 ethyl 3,6,8-trimethoxy-1-methylanthraquinone-2-carboxylate 

Downstream Products

• 53254-85-6 3,6,8-trihydroxy-1-methyl-9,10-anthraquinone-2-carboxylic acid methyl ester 
• 18499-92-8 2-carboxy-1-methyl-3,5,6,8-tetrahydroxy-anthraquinone 

Relevant academic research and scientific papers

Production of Carminic Acid by Metabolically Engineered Escherichia coli

Carminic acid is an aromatic polyketide found in scale insects (i.e., Dactylopius coccus) and is a widely used natural red colorant. It has long been produced by the cumbersome farming of insects followed by multistep purification processes. Thus, there has been much interest in producing carminic acid by the fermentation of engineered bacteria. Here we report the complete biosynthesis of carminic acid from glucose in engineered Escherichia coli. We first optimized the type II polyketide synthase machinery from Photorhabdus luminescens, enabling a high-level production of flavokermesic acid upon coexpression of the cyclases ZhuI and ZhuJ from Streptomyces sp. R1128. To discover the enzymes responsible for the remaining two reactions (hydroxylation and C-glucosylation), biochemical reaction analyses were performed by testing enzyme candidates reported to perform similar reactions. The two identified enzymes, aklavinone 12-hydroxylase (DnrF) from Streptomyces peucetius and C-glucosyltransferase (GtCGT) from Gentiana triflora, could successfully perform hydroxylation and C-glucosylation of flavokermesic acid, respectively. Then, homology modeling and docking simulations were performed to enhance the activities of these two enzymes, leading to the generation of beneficial mutants with 2-5-fold enhanced conversion efficiencies. In addition, the GtCGT mutant was found to be a generally applicable C-glucosyltransferase in E. coli, as was showcased by the successful production of aloesin found in Aloe vera. Simple metabolic engineering followed by fed-batch fermentation resulted in 0.63 ± 0.02 mg/L of carminic acid production from glucose. The strategies described here will be useful for the design and construction of biosynthetic pathways involving unknown enzymes and consequently the production of diverse industrially important natural products.

New impurity of valsartan and synthesis method

The invention discloses a new impurity of valsartan and a synthesis method of the impurity. The method comprises the following steps of: adopting the valsartan to carry out high-temperature reaction in a solvent by using strong base, then adding acid for

A facile synthesis of 5-(4'-substituted)-[1,1'-biphenyl]-2-yl)-1H-tetrazole: A key intermediate for synthesis of angiotensin II receptor antagonist

A convenient commercial scale synthesis of 5-(4'-(substituted)-[1,1'-biphenyl]-2-yl)-1H-tetrazole 1 a common intermediate for so many angiotensin II receptors antagonists, has been achieved with high purity using a simple synthetic protocol. The advantage

A method for preparing methyl valsartan

The invention provides a preparation method of valsartan. The preparation method has the technical effects that amide methyl ester and sodium azide are used as raw materials and are catalyzed by amine salt to carry out tetrazole formation reaction; side effects are minimized by controlling the reaction course; main products are furthest generated; unreacted raw materials are recycled and reused; the yield in the preparation method is increased by more than 10% relative to the yields in existing processes; compared with the existing processes, the method has the effect that plenty of high-toxicity wastewater is no longer generated, and is easy to be widely popularized industrially.

DEPROTECTION METHOD FOR TETRAZOLE COMPOUND

The present invention relates to a method of deprotecting a tetrazole compound, useful as an intermediate for angiotensin II receptor blockers, and provides a novel production method of angiotensin II receptor blockers. Provided is a production method of a compound represented by the formula [3] or [4] or a salt thereof, including (i) reducing a compound represented by the formula [1] or [2] or a salt thereof in the presence of a metal catalyst and an alkaline earth metal salt, or (ii) reacting the compound with a particular amount of Br?nsted acid: wherein each symbol is as defined in the present specification.

PROCESS FOR THE PREPARATION OF VALSARTAN

The present invention relates to a process for preparing valsartan from a compound of general formula (I), wherein R is cumyl, trityl or t-butyl. The process comprises a first step, wherein the protective group is eliminated and thereafter the oxazolidinone ring is opened by catalytic hydrogenationin the presence of an organic base. Finally, Valsartanor a pharmaceutically acceptable salt thereofis isolated.

Synthesis of valsartan via decarboxylative biaryl coupling

(Chemical Equation Presented) An efficient synthesis of the angiotensin II inhibitor valsartan (Diovan) is presented. Two routes were evaluated, both making use of an advanced version of our decarboxylative coupling for the construction of the biaryl moiety. Thus, in the presence of a catalyst system consisting of copper(II) oxide, 1,10-phenanthroline, and palladium(II) bromide, 2-cyanocarboxylic acid was coupled with 1-bromo(4-dimethoxymethyl)benzene in 80% yield and with 4-bromotoluene in 71% yield. The valsartan synthesis using 1-bromo(4-dimethoxymethyl)benzene was completed in four steps overall with a total yield of 39%, via a novel route that presents substantial economical and ecological advantages over the literature process, as it is more concise and stoichiometric amounts of expensive organometallic reagents are avoided.

Chemistry of the Coccoidea. VIII. Synthesis of the Ancient Dyestuff Kermesic Acid and of Related Anthraquinones

The insect anthraquinones kermesic acid (3) and laccaic acid D (2) have been synthesized efficiently, as have the plant anthraquinones aloesaponarin-I (4) and -II (33).The syntheses were based on regiospecific Diels-Alder addition of the silyloxy dienes (10) and (11) to simpler quinones.Regiospecificity was controlled by 2(3)-chloro groups in the dienophiles or, for addition to certain naphthoquinones, by a hydroxy group peri to carbonyl.