Folic acid

Base Information

• Chemical Name: Folic acid
• CAS No.: 59-30-3
• Molecular Formula: C19H19N7O6
• Molecular Weight: 441.403
• Hs Code.: 29362900
• Mol file: 59-30-3.mol

Synonyms:

Chemical Property of Folic acid

Chemical Property:

• Appearance/Colour: orange to yellow crystalline powder
• Melting Point: 250 °C
• Refractive Index: 1.6800 (estimate)
• Boiling Point: 552.35°C (rough estimate)
• PKA: pKa 2.5 (Uncertain)
• PSA: 213.28000
• Density: 1.68 g/cm³
• LogP: 1.00030
• Storage Temp.: 2-8°C
• Solubility.: boiling water: soluble1%
• Water Solubility.: 1.6 mg/L (25 ºC)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 441.13968135
• Heavy Atom Count: 32
• Complexity: 767

Purity/Quality:

98%-101.0% ^*data from raw suppliers

Folic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 33-62-68
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)N=C(N3)N
• Isomeric SMILES: C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)N=C(N3)N
• Discovery and History: Folic acid's discovery is attributed to Lucy Wills, a medical researcher who identified its role in preventing severe anemia in pregnant textile workers in India in 1930. Initially known as "the Wills Factor," it was later designated as vitamin M, vitamin Bc, Lactobacillus casei growth factor, and eventually vitamin B9. Folic acid was isolated from spinach in 1941, and its industrial synthesis was developed in 1945.
• Chemical Structure: Folic acid has the chemical formula C19H19N7O6 and consists of a heterocyclic pterin structure with a methyl group in the sixth position bound to para-aminobenzoic and glutamic acids. It is also known as pteroylglutamic acid and belongs to the folate group, which includes its derivatives like dihydro-, tetrahydro-, methyl-, and formyl-compounds conjugated with para-aminobenzoyl-glutamate.
• Biological Functions: Folic acid plays a crucial role in various biological processes, including early neurodevelopment and the prevention of neural tube defects, particularly spina bifida. It is involved in homocysteine metabolism, where supplementation can lower serum homocysteine levels and reduce the risk of ischemic heart disease and stroke. National health agencies recommend daily supplementation of folic acid for women of childbearing age to reduce the risk of neural tube defects during pregnancy.
• Fortification and Recommendations: The US Public Health Service recommends that all individuals capable of becoming pregnant consume 400 渭g/day of folic acid to prevent neural tube defects. Fortification of foods with folic acid has been recognized as an effective strategy in populations with limited access to folic acid-rich foods or supplements, ensuring adequate intake for neural tube defect prevention.

Technology Process of Folic acid

There total 56 articles about Folic 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: 85.0%

N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1,532-63-8) + 2,5,6-triamino-1,4-dihydropyrimidin-4-one hydrochloride → folate (59-30-3)

Guidance literature:

With 1,1,1-trichloroacetone; sodium sulfite; In water; at 40 - 50 ℃; for 1h; pH=3 - 4; pH-value; Temperature;

Reference yield: 84.0%

→ folate (59-30-3)

Guidance literature:

Reference yield: 83.2%

1,1,3-trichloroacetone (921-03-9) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1,532-63-8) + 2,4,5-triamino-6-hydroxypyrimidine sulfate (35011-47-3) → folate (59-30-3)

Guidance literature:

With sodium metabisulfite; at 20 - 30 ℃; for 2h; Temperature; Ionic liquid;

upstream raw materials:

2,5,6-triamino-3,4-dihydro-4-pyrimidinone

1,1,3-trichloroacetone

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

1,1,3-tribromoacetone

Downstream raw materials:

5-(-)-menthyloxycarbonyl-(6R)-tetrahydrofolic acid

tetrahydrofolic acid

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

6-methyl-5,6,7,8-tetrahydropterin hydrochloride

Refernces

Novel synthesis of [¹⁸F]-fluorobenzene and pyridinecarbohydrazide-folates as potential PET radiopharmaceuticals

10.1002/jlcr.1022

The study presents the novel synthesis of [18F]-fluorobenzene and pyridinecarbohydrazide-folates as potential PET radiopharmaceuticals for visualizing folate receptors that are over-expressed in many cancers. Two synthetic approaches were utilized, starting from nucleophilic displacement reactions on ethyl-trimethylammonium-benzoate and pyridine carboxylate precursors. Key chemicals used included [18F]-fluoride as the starting material, ethyl [18F]-fluorinated benzene and pyridine esters as intermediates, hydrazine for the production of [18F]-fluorobenzene and pyridine carbohydrazides, and NHS-folate for coupling with the intermediates. The purpose of these chemicals was to develop radiolabeled folate conjugates that could target and image folate receptor-positive tumor cells, with the first synthetic approach showing promise as a rapid, simple method for radiofluorination of folic acid with high radiochemical yield and short synthesis time.

Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: Synthesis and in vitro biological evaluation

10.1021/jm00087a012

This research aimed to synthesize and evaluate a series of 5-deazafolate and 5-deazatetrahydrofolate analogues as potential inhibitors of folylpolyglutamate synthetase (FPGS) and glycinamide ribonucleotide formyltransferase (GARFT), enzymes involved in folate metabolism and purine biosynthesis, respectively. The researchers synthesized analogues by replacing the glutamic acid side chain with homocysteic acid (HCysA), 2-amino-4-phosphonobutanoic acid (APBA), and ornithine (Om). The compounds were tested for their inhibitory effects on mouse liver FPGS and GARFT. The results showed that the analogues with HCysA and monoethyl APBA side chains were less active as FPGS inhibitors, while Orn and APBA analogues exhibited competitive inhibition kinetics and were more potent, with Ki values as low as 30 nM.

Chemical Conversion of Folic Acid to Pteroic Acid

10.1021/jo00331a016

The study presents a chemical method for converting folic acid to pteroic acid, a valuable intermediate for synthesizing folic acid analogues and derivatives. The process involves treating folic acid with acetic anhydride to form a mixture of acetylated azlactones, which are then cleaved with mild base to yield mainly acetylated pteroic acids. Further treatment with hot base removes the acetyl groups, resulting in pteroic acid with a yield of 55-60% contaminated with folic acid. The study also discusses various side reactions and byproducts, including the formation of a pyrazine derivative from the hydrolysis of the glutamic acid moiety and the opening of the pyrimidine ring. The authors detail the experimental procedures, including HPLC analysis, UV absorption spectra, mass spectrometry, and proton NMR spectra, and provide a method for separating folic and pteroic acids using column chromatography. The research was supported by a grant from the National Cancer Institute, National Institutes of Health.

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