Folinic acid

Base Information

• Chemical Name: Folinic acid
• CAS No.: 58-05-9
• Molecular Formula: C20H23N7O7
• Molecular Weight: 473.445
• Mol file: 58-05-9.mol

Synonyms:Glutamicacid, N-[p-[[(2-amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-,L- (8CI);L-Glutamic acid,N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-(9CI);(6R,S)-5-Formyltetrahydrofolate;5-Formyl-5,6,7,8-tetrahydrofolic acid;5-Formyltetrahydrofolic acid;5-Formyltetrahydropteroylglutamic acid;CF;Folinic acid;Folinic acid-SF;Leucal;Leucoverin;Leucovorin;Levoleucovorin;N5-Formyl-5,6,7,8-tetrahydrofolic acid;N5-Formyltetrahydrofolic acid;Welcovorin;l-Leucovorin;

Chemical Property of Folinic acid

Chemical Property:

• Appearance/Colour: Crystals from water with 3 mol of water of crystallization.
• Melting Point: 245ºC (decomp)
• Refractive Index: 1.748
• Boiling Point: 573.92°C (rough estimate)
• PKA: 3.1, 4.8, 10.4(at 25℃)
• PSA: 219.84000
• Density: 1.68 g/cm³
• LogP: 1.15290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility.: >1350g/L(25 oC)

Purity/Quality:

99% ^*data from raw suppliers

LeucovorinCalciumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Folinic acid, chemical name N-[4-[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridyl) Methyl]amino]benzoyl-L-glutamic acid has been widely used in cancer combined chemotherapy. Folinic acid enters the human body through the ingestion and absorption pathway of folate. Folinic acid (calcium folinate) is a special form of reduced folic acid (folate).
• Uses: 1. It is mainly used as an antidote for folic acid antagonists (such as methotrexate, pyrimethamine or trimethoprim, etc.).2. It is used to prevent severe toxic effects caused by methotrexate overdose or high-dose treatment.3. Megaloblastic anemia caused by folic acid deficiency.4. When combined with fluorouracil, it is used to treat advanced colon cancer and rectal cancer. Folinic Acid is used in combination with 5-fluorouracil in the treatment of colorectal cancers. It also functions as a useful antidotal therapy medication for decreasing the toxic effect of methotrexate overdosing.

Technology Process of Folinic acid

There total 28 articles about Folinic 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:

Leucovorin Calcium (6035-45-6) → folinic acid (58-05-9)

Guidance literature:

With hydrogenchloride; In water; at 6 - 10 ℃; for 4h; pH=2.8 - 3.2;

Reference yield:

→ folinic acid (58-05-9)

Guidance literature:

Reference yield:

N-<4-<<2(S)--3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid (142811-49-2) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

2: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

4: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

upstream raw materials:

tetrahydrofolic acid

formic acid

chloral

N-methyl-N-phenylformamide

Downstream raw materials:

(6RS)-5,10-diformyl-5,6,7,8-tetrahydrofolic acid

N₅,N₁₀-methenyl-tetrahydrofolic acid

folate

Refernces

• 1、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.
• 2、 -. "METHOD FOR THE PRODUCTION OF CRYSTALLINE (6RS)-N(5)-FORMYL-5,6,7,8-TETRAHYDROFOLIC ACID". Page/Page column 9-11. . Retrieved 2008/06/13.