5,6,7,8-tetrahydrofolic acid

Base Information

• Chemical Name: 5,6,7,8-tetrahydrofolic acid
• CAS No.: 29347-89-5
• Molecular Formula: C19H23 N7 O6
• Molecular Weight: 445.435
• Mol file: 29347-89-5.mol

Synonyms:DL-Glutamicacid, N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-;Glutamic acid,N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-(9CI); Glutamic acid,N-[p-[[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-,DL- (8CI); DL-5,6,7,8-Tetrahydrofolic acid

Chemical Property of 5,6,7,8-tetrahydrofolic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: °C
• PSA: 211.56000
• Density: 1.7g/cm³
• LogP: 1.03910

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,6,7,8-tetrahydrofolic acid

There total 25 articles about 5,6,7,8-tetrahydrofolic 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:

folic acid (59-30-3) → (6S,S)-5,6,7,8-tetrahydrofolic acid (135-16-0,15582-28-2,29347-89-5,71963-69-4,74708-38-6) + (6R,S)-5,6,7,8-tetrahydrofolic acid (74708-38-6)

Guidance literature:

With hydrogen; silica gel; (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In phosphate buffer; at 80 ℃; for 24h; under 37503 Torr; pH=7.0; Further Variations:; Reagents; Product distribution;

DOI:10.1007/s007060070017

Reference yield:

folate (59-30-3) → (6S,S)-5,6,7,8-tetrahydrofolic acid (135-16-0,15582-28-2,29347-89-5,71963-69-4,74708-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / 50 percent NaOH, sodium dithionite / H₂O / 3.33 h / Ambient temperature

2: NaOH, EDTA, MgCl₂*6H₂O, dithiotreitol, adenosine triphosphate, glucose hydrate, NADP⁽¹⁺⁾, diammonium acetyl phosphate / H₂O / 168 h / Ambient temperature; protection from light; enzyme-catalyzed reduction with dihydrofolate reductase, glucose 6-phosphate dehydrogenase hexokinase and acetate kinase

With sodium hydroxide; sodium dithionite; D-glucose monohydrate; ethylenediaminetetraacetic acid; ethanoylphosphate diammonium salt; nicotinamide adenine dinucleotide phosphate; ATP; magnesium chloride; diothiothreitol; In water;

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

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,S)-5,6,7,8-tetrahydrofolic acid (135-16-0,15582-28-2,29347-89-5,71963-69-4,74708-38-6)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00042a030

upstream raw materials:

dihydrofolic acid

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

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

folic acid

Downstream raw materials:

<6S>-N⁵-formyltetrahydrofolic acid

(6R)-5,10-methylylidenetetrahydrofolic acid chloride

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

(6S)-N-[4-[[(2-amino-1,4,5,6,7,8-hexahydro-4-oxo-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid

Refernces

• 1、 Ryabokon' et al.. "". . . Retrieved 1975.
• 2、 Angelastro, Antonio,Dawson, William M.,Luk, Louis Y. P.,Loveridge, E. Joel,Allemann, Rudolf K.. "Chemoenzymatic Assembly of Isotopically Labeled Folates". supporting information. p. 13047 - 13054. Retrieved 2017/09/26.
• 3、 Pugin, Benoit,Groehn, Viola,Moser, Rudolf,Blaser, Hans-Ulrich. "Aqueous diastereoselective hydrogenation of folic acid to tetrahydrofolic acid in the presence of water-soluble Rh and Ir diphosphine complexes". . p. 544 - 549. Retrieved 2007/10/03.