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01769

Sigma-Aldrich

Folic acid

Synonym(s):
Acidum folicum, PteGlu, Vitamin M, Pteroyl-L-glutamic acid
Empirical Formula (Hill Notation):
C19H19N7O6
CAS Number:
Molecular Weight:
441.40
Beilstein:
100781
EC Number:
MDL number:
eCl@ss:
34058014
PubChem Substance ID:

biological source

synthetic

Agency/Method

USP/NF

assay

96.0-102.0% anhydrous basis

form

powder

color

yellow

mp

250 °C

solubility

cold water: very slightly soluble 0.0016 mg/ml at 25 degrees C
boiling water: soluble 1%
1-butanol: partially soluble
acetone: insoluble
benzene: insoluble
chloroform: insoluble
diethyl ether: insoluble
dilute HCl: soluble (Hot)
ethanol: partially soluble
methanol: slightly soluble
sulfuric acid: soluble

storage temp.

2-8°C

SMILES string

NC(N1)=NC(C2=C1N=CC(CNC3=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C3)=N2)=O

InChI

1S/C19H19N7O6/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/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1

InChI key

OVBPIULPVIDEAO-LBPRGKRZSA-N

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Application

Folic acid was injected in control and manifest diabetic pregnant rats for studying whether folic acid supplementation can moderate diabetes and glucose-induced dysmorphogenesis in rat embryos. It can also be used in the synthesis of N10-trifluoroacetylpteroic acid.

Biochem/physiol Actions

Folic acid also referred to as folate, vitamin M or vitamin Bc is a form of water-soluble vitamin B9. Folic acid therapy can reduce elevated plasma levels of arginine and asymmetric dimethylarginine (ADMA) in hyperhomocysteinaemic subjects. Folic acid used as a food supplement in early pregnancy can diminish the risk of neural tube defects.

Preparation Note

Folic acid dissolves in hot dil HCl, H2SO4 and about 1% boiling water. It is slightly soluble in methanol and shows very slight solubility in cold water (0.0016 mg/ml at 25°C). Additionally, the product appreciably dissolves in ethanol and butanol and has relative solubility in acetic acid, phenol, pyridine, solutions of alkali hydroxides and carbonates. It is insoluble in acetone, benzene, ether and chloroform.

Certificate of Analysis

Certificate of Origin

A Milunsky et al.
JAMA, 262(20), 2847-2852 (1989-11-24)
We examined the relation of multivitamin intake in general, and folic acid in particular, to the risk of neural tube defects in a cohort of 23,491 women undergoing maternal serum alpha-fetoprotein screening or amniocentesis around 16 weeks of gestation. Complete...
Parri Wentzel et al.
Diabetes, 54(2), 546-553 (2005-01-29)
Maternal administration of folic acid diminishes the risk of neural tube defects (NTDs) in offspring, but whether folic acid exerts a similar effect in diabetic pregnancy is unknown. The aim was to investigate whether maldevelopment in rat embryos caused by...
Ruben M Sandoval et al.
American journal of physiology. Cell physiology, 287(2), C517-C526 (2004-04-23)
Intravital two-photon microscopy was used to follow the uptake and trafficking of fluorescent conjugates of folic acid in the rat kidney. Intravenously administered folate-linked dye molecules quickly filled the plasma volume but not cellular components of the blood. Glomerular filtration...
Kirsten B Holven et al.
The British journal of nutrition, 89(3), 359-363 (2003-03-12)
Asymmetric dimethylarginine (ADMA), an endogenous inhibitor of NO synthase, has been suggested to be a novel risk factor for endothelial dysfunction. It has previously been reported that hyperhomocysteinaemia may be associated with impaired endothelium-dependent vasodilation and reduced plasma level of...
Susanna Kariluoto et al.
International journal of food microbiology, 176, 38-48 (2014-02-25)
The objective was to study folate production of yeast strains, bacteria isolated from oat bran, and selected lactic acid bacteria as well as one propionibacterium in oat and barley based models. Simultaneously, we aimed at sustaining the stability of viscosity...

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