DIHYDROFOLIC ACID

Base Information

• Chemical Name: DIHYDROFOLIC ACID
• CAS No.: 4033-27-6
• Molecular Formula: C19H21 N7 O6
• Molecular Weight: 443.419
• Mol file: 4033-27-6.mol

Synonyms:Glutamicacid, N-[p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-,L- (6CI,7CI,8CI); L-Glutamic acid,N-[4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-(9CI); 7,8-Dihydro-L-folic acid; 7,8-Dihydrofolic acid; Dihydrofolic acid; NSC165989

Chemical Property of DIHYDROFOLIC ACID

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: pKa 1.38(H2O t=25 I=0.10) (Occasionally);3.84(H2O t=25 I=0.10) (Occasionally)
• Flash Point: °C
• PSA: 211.89000
• Density: 1.69g/cm³
• LogP: 0.62870
• Storage Temp.: −20°C
• Solubility.: 0.1 M NaOH: 10 mg/mL, slightly hazy, orange

Purity/Quality:

≥ 98% ^*data from raw suppliers

Dihydrofolic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Dihydrofolic acid (DHF) is a key intermediate in folate metabolism and serves as a substrate for dihydrofolate reductase (DHFR), an enzyme targeted by antimalarial drugs such as pyrimethamine and WR99210. Inhibition of DHFR disrupts nucleotide synthesis, impairing parasite growth. The study highlights the development of hybrid inhibitors (e.g., BT1) that effectively target both wild-type and mutant forms of Plasmodium falciparum DHFR, addressing resistance mechanisms while maintaining high selectivity and efficacy. DHF's role in this pathway underscores its importance as a metabolic checkpoint in antimalarial drug design.

Technology Process of DIHYDROFOLIC ACID

There total 17 articles about DIHYDROFOLIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

folic acid (59-30-3) → (S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid (4033-27-6)

Guidance literature:

With sodium hydroxide; sodium dithionite; ascorbic acid; In water; pH 4.5;

DOI:10.1002/hlca.19800630850

Reference yield: 77.0%

folate (59-30-3) → dihydrofolic acid (15574-38-6,4033-27-6)

Guidance literature:

With sodium hydroxide; sodium dithionite; In water; for 3.33333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87409-3

Reference yield: 30.0%

D-Glucose (2280-44-6) + 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1,532-63-8) → (S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid (4033-27-6)

Guidance literature:

D-Glucose; With cysteine disulfide; pyruvate kinase from rabbit muscle; glutaredoxin 2; glucose-6-phosphate dehydrogenase from L_. mesenteroides; glutathione reductase from baker’s yeast; hexokinase type F-300 from S_. cerevisiae; myokinase from rabbit muscle; phosphoriboisomerase type I from spinach; NADP; phospho(enol)pyruvic acid mono potassium salt; ATP; In aq. buffer; at 37 ℃; pH=7; Glovebox; Inert atmosphere; Enzymatic reaction;

With guanylate kinase; ribose-phosphate pyrophosphokinase; xanthine guanine phosphoribosyl transferase; In aq. buffer; for 0.25h; Glovebox; Inert atmosphere; Enzymatic reaction;

2-amino-1,9-dihydro-6H-purin-6-one; N-(4-aminobenzoyl)-L-glutamic acid; Further stages;

DOI:10.1021/jacs.7b06358

upstream raw materials:

folic acid

N-<4-<<2(S)-amino-3-<(2,5-diamino-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid

N-(4-aminobenzoyl)-L-glutamic acid

5-aminoimidazole-4-carboxamide ribonucleotide

Downstream raw materials:

5,10-bis(uracil-5-ylmethyl)tetrahydropteroylglutamic acid

5,10-bis(uracil-5-ylmethyl)<6-2H₁>tetrahydropteroylglutamic acid

tetrahydrofolic acid

(6S,S)-5,6,7,8-tetrahydrofolic acid

Refernces

Hybrid Inhibitors of Malarial Dihydrofolate Reductase with Dual Binding Modes That Can Forestall Resistance

10.1021/acsmedchemlett.8b00389

The research aims to develop hybrid inhibitors of Plasmodium falciparum dihydrofolate reductase (PfDHFR) that can effectively combat malaria and forestall the emergence of drug resistance in the parasite. The purpose of this study is to design and synthesize compounds that can inhibit both wild-type and multiple mutant forms of PfDHFR, which is a key enzyme in folate metabolism and a target for antimalarial drugs. The chemicals used in this process include pyrimethamine (Pyr), a known inhibitor of PfDHFR, and WR99210, a compound with flexible side chains that can avoid steric clashes with mutant PfDHFR. The researchers synthesized hybrid inhibitors BT1, BT2, and BT3, which incorporate both rigid and flexible diaminopyrimidine moieties. These compounds were tested for their inhibition constants, anti-plasmodial activities, and toxicities against mammalian cells. The results showed that BT1, in particular, had high selectivity and efficacy against both wild-type and mutant PfDHFRs, making it a promising candidate for further development as an antimalarial drug that could potentially overcome resistance issues.

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