Synonym
Tetrahydrohomofolic acid; Homofolic acid, tetrahydro-; H4HF; THHF; Tetrahydrohomofolate;
IUPAC/Chemical Name
(4-((2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropteridin-6-yl)ethyl)amino)benzoyl)-L-glutamic acid
InChi Key
SVEJTXIHPDUQLZ-ABLWVSNPSA-N
InChi Code
InChI=1S/C20H25N7O6/c21-20-26-16-15(18(31)27-20)24-12(9-23-16)7-8-22-11-3-1-10(2-4-11)17(30)25-13(19(32)33)5-6-14(28)29/h1-4,12-13,22,24H,5-9H2,(H,25,30)(H,28,29)(H,32,33)(H4,21,23,26,27,31)/t12?,13-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCCC2NC3=C(O)N=C(N)N=C3NC2)C=C1)=O
Purity
>98% (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
Shelf Life
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
459.46
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.
| 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 |
1: Slieker LJ, Benkovic SJ. Inhibition of HKSV28 cell growth by 5,11-methenyl-tetrahydrohomofolate. Mol Pharmacol. 1984 Mar;25(2):294-302. PubMed PMID: 6700575.
2: Wasserman GF, Benkovic PA, Young M, Benkovic SJ. Kinetic relationships between the various activities of the formyl-methenyl-methylenetetrahydrofolate synthetase. Biochemistry. 1983 Mar 1;22(5):1005-13. PubMed PMID: 6601493.
3: Fong KL, Ho DH, Benjamin RS, Yang F, Sickler J, Brown NS, Bodey GP. A radioimmunoassay for 5-methyltetrahydrohomofolate. J Pharmacol Exp Ther. 1981 Aug;218(2):344-7. PubMed PMID: 6265623.
4: Mishra LC, Mead JA. On the biochemical mechanism of action of tetrahydrohomofolic acid. Biochem Pharmacol. 1972 Feb 15;21(4):579-81. PubMed PMID: 5014514.
5: Mishra LC, Parmar AS, Mead JA. Chemical transformations of tetrahydrohomofolic acid in vitro and in vivo. Chem Biol Interact. 1972 Jan;4(2):97-102. PubMed PMID: 5058329.
6: Mishra LC, Parmar AS, Mead JA. Distribution studies of tetrahydrohomofolic acid (NSC 89473) in mice. Cancer Res. 1970 Mar;30(3):642-9. PubMed PMID: 5425289.
7: Kisliuk RL, Friedkin M, Reid V, Crawford EJ, Schmidt LH, Rossan R, Lewis D, Harrison J, Sullivan R. The toxicity of tetrahydrohomofolic acid in normal and malaria-infected monkeys. J Pharmacol Exp Ther. 1968 Feb;159(2):416-21. PubMed PMID: 4966294.
8: Tong GL, Lee WW, Goodman L. Synthesis of a pyrimidine analog of tetrahydrohomofolic acid. J Med Chem. 1966 Jul;9(4):590-3. PubMed PMID: 5968029.
