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Sigma-Aldrich

N10-(Trifluoroacetyl)pteroic acid

95%

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Synonym(s):
4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl](2,2,2-trifluoroacetyl)amino]benzoic acid, N10-Trifluoroacetylpteroic acid
Empirical Formula (Hill Notation):
C16H11F3N6O4
CAS Number:
37793-53-6
Molecular Weight:
408.29
MDL number:
MFCD00006707
UNSPSC Code:
12352100
PubChem Substance ID:
24888548
NACRES:
NA.22

Quality Level

200

Assay

95%

form

solid

mp

270 °C (dec.) (lit.)

SMILES string

Nc1nc(O)c2nc(CN(c3ccc(cc3)C(O)=O)C(=O)C(F)(F)F)cnc2n1

InChI

1S/C16H11F3N6O4/c17-16(18,19)14(29)25(9-3-1-7(2-4-9)13(27)28)6-8-5-21-11-10(22-8)12(26)24-15(20)23-11/h1-5H,6H2,(H,27,28)(H3,20,21,23,24,26)

InChI key

IJGIHDXKYQLIMA-UHFFFAOYSA-N

Related Categories

Application

N10-(Trifluoroacetyl)pteroic acid is a structural component of folic acid. It can be used as a precursor to synthesize folic acid derivatives, γ-azido modified folic acid, and pteroyl-γ-glutamate-cysteine.

Other Notes

Remainder DMF

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Pteroyl-γ-glutamate-cysteine synthesis and its application in folate receptor-mediated cancer cell targeting using folate-tethered liposomes.
Zhang Y, et al.
Analytical Biochemistry, 332(1), 168-177 (2004)
The facile synthesis of multifunctional PAMAM dendrimer conjugates through copper-free click chemistry.
Huang B, et al.
Bioorganic & Medicinal Chemistry Letters, 22(9), 3152-3156 (2012)
Self?Assembly of Folic Acid Derivatives: Induction of Supramolecular Chirality by Hierarchical Chiral Structures.
Kamikawa Y, et al.
Chemistry?A European Journal , 10(23), 5942-5951 (2004)
Chun-Yen Ke et al.
Journal of the American Chemical Society, 127(20), 7421-7426 (2005-05-19)
The cell membrane folate receptor is a potential molecular target for tumor-selective drug delivery. To probe structural requirements for folate receptor targeting with low molecular weight radiometal chelates, specifically the role of the amino acid fragment of folic acid (pteroylglutamic

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