Tetrahydrofolic acid

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MedKoo CAT#: 318854

CAS#: 135-16-0

Description: Tetrahydrofolic acid, or tetrahydrofolate, is a folic acid derivative. Tetrahydrofolic acid is a cofactor in many reactions, especially in the metabolism of amino acids and nucleic acids. Tetrahydrofolic acid acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes.

Chemical Structure

Tetrahydrofolic acid
CAS# 135-16-0

Theoretical Analysis

MedKoo Cat#: 318854
Name: Tetrahydrofolic acid
CAS#: 135-16-0
Chemical Formula: C19H23N7O6
Exact Mass: 445.17098
Molecular Weight: 445.436
Elemental Analysis: C, 51.23; H, 5.20; N, 22.01; O, 21.55

Price and Availability

Size Price Availability Quantity
100.0mg USD 650.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1450.0 2 Weeks
1.0g USD 1950.0 2 Weeks
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Synonym: 5,6,7,8-tetrahydrofolic acid; Tetrahydropteroylglutamic acid; th-folate; folate-H4; Tetrahydrofolic acid.

IUPAC/Chemical Name: (2S)-2-{[4-({[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid


InChi Code: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12+/m1/s1

SMILES Code: O=C(O)[C@@H](NC(C1=CC=C(NC[C@H]2NC3=C(NC(N)=NC3=O)NC2)C=C1)=O)CCC(O)=O

Appearance: Solid powder

Purity: >60% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 445.436 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: García-Molina F, Muñoz-Muñoz JL, Martínez-Ortiz F, García-Ruíz PA, Tudela J, García-Cánovas F, Rodríguez-López JN. Tetrahydrofolic Acid is a potent suicide substrate of mushroom tyrosinase. J Agric Food Chem. 2011 Feb 23;59(4):1383-91. doi: 10.1021/jf1035433. Epub 2011 Jan 25. PubMed PMID: 21265541.

2: Marsilje TH, Hedrick MP, Desharnais J, Capps K, Tavassoli A, Zhang Y, Wilson IA, Benkovic SJ, Boger DL. 10-(2-benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: a potential inhibitor of GAR transformylase and AICAR transformylase. Bioorg Med Chem. 2003 Oct 1;11(20):4503-9. PubMed PMID: 13129586.

3: Zhang Y, Desharnais J, Marsilje TH, Li C, Hedrick MP, Gooljarsingh LT, Tavassoli A, Benkovic SJ, Olson AJ, Boger DL, Wilson IA. Rational design, synthesis, evaluation, and crystal structure of a potent inhibitor of human GAR Tfase: 10-(trifluoroacetyl)-5,10-dideazaacyclic-5,6,7,8-tetrahydrofolic acid. Biochemistry. 2003 May 27;42(20):6043-56. PubMed PMID: 12755606.

4: Marsilje TH, Labroli MA, Hedrick MP, Jin Q, Desharnais J, Baker SJ, Gooljarsingh LT, Ramcharan J, Tavassoli A, Zhang Y, Wilson IA, Beardsley GP, Benkovic SJ, Boger DL. 10-Formyl-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid (10-formyl-DDACTHF): a potent cytotoxic agent acting by selective inhibition of human GAR Tfase and the de novo purine biosynthetic pathway. Bioorg Med Chem. 2002 Aug;10(8):2739-49. PubMed PMID: 12057663.

5: Borrell JI, Teixidó J, Matallana JL, Martínez-Teipel B, Colominas C, Costa M, Balcells M, Schuler E, Castillo MJ. Synthesis and biological activity of 7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF). J Med Chem. 2001 Jul 5;44(14):2366-9. PubMed PMID: 11428931.

6: Schleyer E, Rudolph KL, Braess J, Unterhalt M, Ehninger G, Hiddemann W, Kern W. Impact of the simultaneous administration of the (+)- and (-)-forms of formyl-tetrahydrofolic acid on plasma and intracellular pharmacokinetics of (-)-tetrahydrofolic acid. Cancer Chemother Pharmacol. 2000;45(2):165-71. PubMed PMID: 10663632.

7: Hullán L, Trézl L, Szarvas T, Csiba A. The hydrazine derivative aminoguanidine inhibits the reaction of tetrahydrofolic acid with hydroxymethylarginine biomolecule. Acta Biol Hung. 1998;49(2-4):265-73. PubMed PMID: 10526969.

8: Baggott JE, Robinson CB, Eto I, Johanning GL, Cornwell PE. Iron compounds catalyze the oxidation of 10-formyl-5,6,7,8 tetrahydrofolic acid to 10-formyl-7,8 dihydrofolic acid. J Inorg Biochem. 1998 Sep;71(3-4):181-7. PubMed PMID: 9833324.

9: Borrell JI, Teixidó J, Martínez-Teipel B, Matallana JL, Copete MT, Llimargas A, García E. Synthesis and biological activity of 4-amino-7-oxo-substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid and 5,10-dideaza-5, 6,7,8-tetrahydrofolic acid. J Med Chem. 1998 Aug 27;41(18):3539-45. PubMed PMID: 9719607.

10: Bailey SW, Ayling JE. Total chemical synthesis of chirally pure (6S)-tetrahydrofolic acid. Methods Enzymol. 1997;281:3-16. PubMed PMID: 9250961.

11: Taylor EC, Chaudhari R, Lee K. A simplified and efficient synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF). Invest New Drugs. 1996;14(3):281-5. PubMed PMID: 8958183.

12: Wedge SR, Laohavinij S, Taylor GA, Boddy A, Calvert AH, Newell DR. Clinical pharmacokinetics of the antipurine antifolate (6R)-5,10- dideaza-5,6,7,8-tetrahydrofolic acid (Lometrexol) administered with an oral folic acid supplement. Clin Cancer Res. 1995 Dec;1(12):1479-86. PubMed PMID: 9815947.

13: Czejka MJ, Schenk T, Scheithauer W. Red blood cell partitioning of N5-methyl-tetrahydrofolic acid after i.v. administration. Arch Pharm (Weinheim). 1992 Nov;325(11):741-2. PubMed PMID: 1485839.

14: Bigham EC, Hodson SJ, Mallory WR, Wilson D, Duch DS, Smith GK, Ferone R. Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents. J Med Chem. 1992 Apr 17;35(8):1399-410. PubMed PMID: 1573633.

15: van Tellingen O, Sips JH, Beijnen JH, Schornagel JH, Nooyen WJ. Bioanalysis of the investigational anti-tumour drug 5,10-dideaza-5,6,7,8-tetrahydrofolic acid by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1992 Apr 15;576(1):158-62. PubMed PMID: 1500451.

16: Shih C, Gossett LS, Worzalla JF, Rinzel SM, Grindey GB, Harrington PM, Taylor EC. Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid. J Med Chem. 1992 Mar 20;35(6):1109-16. PubMed PMID: 1552503.

17: Natsuhori M, Shimoda M, Kokue E, Hayama T, Takahashi Y. Tetrahydrofolic acid as the principal congener of plasma folates in pigs. Am J Physiol. 1991 Jul;261(1 Pt 2):R82-6. PubMed PMID: 1858958.

18: Pizzorno G, Moroson BA, Cashmore AR, Beardsley GP. (6R)-5,10-Dideaza-5,6,7,8-tetrahydrofolic acid effects on nucleotide metabolism in CCRF-CEM human T-lymphoblast leukemia cells. Cancer Res. 1991 May 1;51(9):2291-5. PubMed PMID: 1707749.

19: Taber LD, O'Brien P, Bowsher RR, Sportsman JR. Competitive particle concentration fluorescence immunoassay for measuring 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (lometrexol) in serum. Clin Chem. 1991 Feb;37(2):254-60. PubMed PMID: 1993335.

20: 5,10-Dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF): a potent inhibitor of purine biosynthesis. Nutr Rev. 1990 Nov;48(11):421-3. Review. PubMed PMID: 2080047.