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%,99%, ^*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:

• Uses: antidote to methotrexate toxicity Dihydrofolic Acid is an intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). Folic acid (FA) and Dihydrofolic acid (FAH2) are substrates of dihydrofolate reductase(s) which reduce them to tetrahydrofolate (THF). Dihydrofolic Acid is an intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). Folic acid (FA) and Dihydrofolic acid (FAH2) are substrates of dihydrofolate reductase(s) which reduce them to tetrahydrofolate (THF).

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:

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

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

(6-R,S)-5,6,7,8-tetrahydrofolate

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

Refernces

• 1、 -. "Method for preparing L-5-calcium methyl tetrahydrofolate through enzymic method". Page/Page column 5-8. . Retrieved 2019/05/04.
• 2、 Zhao, Fei,Wang, Xu-De,Erber, Luke N.,Luo, Ming,Guo, Ai-Zhen,Yang, Shan-Shan,Gu, Jing,Turman, Breanna J.,Gao, Yun-Rong,Li, Dong-Fang,Cui, Zong-Qiang,Zhang, Zhi-Ping,Bi, Li-Jun,Baughn, Anthony D.,Zhang, Xian-En,Deng, Jiao-Yu. "Binding pocket alterations in dihydrofolate synthase confer resistance to para-aminosalicylic acid in clinical isolates of Mycobacterium tuberculosis". . p. 1479 - 1487. Retrieved 2014/03/21.