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MedKoo Cat#: 597204 | Name: Homofolic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Homofolic acid is an analog of folic acid.

Chemical Structure

Homofolic acid
Homofolic acid
CAS#3566-25-4

Theoretical Analysis

MedKoo Cat#: 597204

Name: Homofolic acid

CAS#: 3566-25-4

Chemical Formula: C20H21N7O6

Exact Mass: 455.1553

Molecular Weight: 455.43

Elemental Analysis: C, 52.75; H, 4.65; N, 21.53; O, 21.08

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Homofolic acid; Homofolate; 9-Methylfolic acid; NSC 79249; NSC-79249; NSC79249;
IUPAC/Chemical Name
(4-((2-(2-amino-4-oxo-1,4-dihydropteridin-6-yl)ethyl)amino)benzoyl)-L-glutamic acid
InChi Key
QXARTGUOGAZGKO-ZDUSSCGKSA-N
InChi Code
InChI=1S/C20H21N7O6/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/h1-4,9,13,22H,5-8H2,(H,25,30)(H,28,29)(H,32,33)(H3,21,23,26,27,31)/t13-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCCC2=CN=C3NC(N)=NC(C3=N2)=O)C=C1)=O
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 455.43 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
1: Bazzano LA, Reynolds K, Holder KN, He J. Effect of folic acid supplementation on risk of cardiovascular diseases: a meta-analysis of randomized controlled trials. JAMA. 2006 Dec 13;296(22):2720-6. Erratum in: JAMA. 2007 Mar 7;297(9):952. PubMed PMID: 17164458. 2: Henderson GB, Strauss BP. Growth inhibition by homofolate in tumor cells utilizing a high-affinity folate binding protein as a means for folate internalization. Biochem Pharmacol. 1990 Jun 15;39(12):2019-25. PubMed PMID: 2353941. 3: Thorndike J, Gaumont Y, Kisliuk RL, Sirotnak FM, Murthy BR, Nair MG, Piper JR. Inhibition of glycinamide ribonucleotide formyltransferase and other folate enzymes by homofolate polyglutamates in human lymphoma and murine leukemia cell extracts. Cancer Res. 1989 Jan 1;49(1):158-63. PubMed PMID: 2521177. 4: 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. 5: Diddens H, Niethammer D, Jackson RC. Resistance of human tumor cell lines to antifolates. Cancer Treat Rev. 1984 Mar;11 Suppl A:37-41. PubMed PMID: 6234060. 6: Diddens H, Niethammer D, Jackson RC. Patterns of cross-resistance to the antifolate drugs trimetrexate, metoprine, homofolate, and CB3717 in human lymphoma and osteosarcoma cells resistant to methotrexate. Cancer Res. 1983 Nov;43(11):5286-92. PubMed PMID: 6225514. 7: Nair MG, Otis EB, Kisliuk RL, Gaumont Y. Folate analogues. 20. Synthesis and antifolate activity of 1',2',3',4',5',6'-hexahydrohomofolic acid. J Med Chem. 1983 Feb;26(2):135-40. PubMed PMID: 6827531. 8: Hoffman JM, Pietruszkiewicz AM, Habecker CN, Phillips BT, Bolhofer WA, Cragoe EJ Jr, Torchiana ML, Lumma WC Jr, Baldwin JJ. Conformational requirements for histamine H2-receptor inhibitors: a structure-activity study of phenylene analogues related to cimetidine and tiotidine. J Med Chem. 1983 Feb;26(2):140-4. PubMed PMID: 6131129. 9: Grossowicz N, Waxman S. Biotransformation of homofolate from a growth inhibitor to a growth-promoting derivative. Chemotherapy. 1983;29(6):436-41. PubMed PMID: 6418446. 10: Domin BA, Cheng YC, Nair MG. Effect of 11-oxahomofolate and its reduced derivatives on human dihydrofolate reductase and on human cells having different amounts of dihydrofolate reductase. Biochem Pharmacol. 1982 Jan 15;31(2):255-6. PubMed PMID: 7059366. 11: Nair MG, Chen SY, Kisliuk RL, Gaumont Y, Strumpf D. Folate analogues altered in the C9-N10 bridge region. 16. Synthesis and antifolate activity of 11-thiohomoaminopterin. J Med Chem. 1980 Aug;23(8):899-903. PubMed PMID: 6772788. 12: Nair MG, Saunders C, Chen SY, Kisliuk RL, Gaumont Y. Folate analogues altered in the C9--N10 bridge region. 14. 11-Oxahomofolic acid, a potential antitumor agent. J Med Chem. 1980 Jan;23(1):59-65. PubMed PMID: 6767031. 13: Spector R. Identification of folate binding macromolecule in rabbit choroid plexus. J Biol Chem. 1977 May 25;252(10):3364-70. PubMed PMID: 16898. 14: Plante LT, Crawford EJ, Friedkin M. Polyglutamyl and polylysyl derivatives of the lysine analogues of folic acid and homofolic acid. J Med Chem. 1976 Nov;19(11):1295-9. PubMed PMID: 794472. 15: Plante LT, Crawford EJ, Friedkin M. Enzyme studies with new analogues of folic acid and homofolic acid. J Biol Chem. 1967 Apr 10;242(7):1466-76. PubMed PMID: 5337042.