Folate

Folic acid
Skeletal formula
Clinical data
Pronunciation/ˈfoʊlɪk, ˈfɒlɪk/
Trade namesFolicet, Folvite
Other namesWills factor, FA, N-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid, pteroyl-L-glutamic acid, folacin, vitamin B9;[1] formerly, vitamin Bc and vitamin M[2]
AHFS/Drugs.comMonograph
MedlinePlusa682591
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, intramuscular, intravenous, subcutaneous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S2
  • US: ℞-only / OTC
Pharmacokinetic data
Bioavailability50–100%[3]
MetabolismLiver[3]
ExcretionUrine[3]
Identifiers
  • (2S)-2-[[4-[(2-Amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid[4]
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.381 Edit this at Wikidata
Chemical and physical data
FormulaC19H19N7O6
Molar mass441.404 g·mol−1
3D model (JSmol)
Density1.6±0.1 g/cm3 [5]
Melting point250 °C (482 °F) (decomposition)
Solubility in water1.6mg/L (25 °C)
  • n1c2C(=O)NC(N)=Nc2ncc1CNc3ccc(cc3)C(=O)N[C@H](C(O)=O)CCC(O)=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
  • Key:OVBPIULPVIDEAO-LBPRGKRZSA-N

Folate, also known as vitamin B9 and folacin,[6] is one of the B vitamins.[3] Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and storage.[7] Folate is required for the body to make DNA and RNA and metabolise amino acids necessary for cell division and maturation of blood cells.[1][8] As the human body cannot make folate, it is required in the diet, making it an essential nutrient.[9] It occurs naturally in many foods.[6][1] The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements.[1]

Folate in the form of folic acid is used to treat anemia caused by folate deficiency.[3] Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby.[3][10] NTDs include anencephaly and spina bifida, among other defects. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs.[1] More than 80 countries use either mandatory or voluntary fortification of certain foods with folic acid as a measure to decrease the rate of NTDs.[11] Long-term supplementation with relatively large amounts of folic acid is associated with a small reduction in the risk of stroke[12] and an increased risk of prostate cancer.[13] There are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency.[1]

Not consuming enough folate can lead to folate deficiency.[1] This may result in a type of anemia in which red blood cells become abnormally large.[1] Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair.[1] Folate deficiency in children may develop within a month of poor dietary intake.[14] In adults, normal total body folate is between 10 and 30 mg with about half of this amount stored in the liver and the remainder in blood and body tissues.[1] In plasma, the natural folate range is 150 to 450 nM.[15]

Folate was discovered between 1931 and 1943.[16] It is on the World Health Organization's List of Essential Medicines.[17] In 2022, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions.[18][19] The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables.[20]

  1. ^ a b c d e f g h i j Cite error: The named reference NIH was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Welch1983 was invoked but never defined (see the help page).
  3. ^ a b c d e f "Folic Acid". Drugs.com. American Society of Health-System Pharmacists. 1 January 2010. Archived from the original on 8 August 2017. Retrieved 1 September 2016.
  4. ^ "Folic Acid". The PubChem Project. Archived from the original on 7 April 2014.
  5. ^ "Folic Acid". ChemSrc. Archived from the original on 28 August 2021. Retrieved 12 April 2018.
  6. ^ a b "Folate". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2014. Archived from the original on 19 August 2021. Retrieved 17 March 2018. Folate is a water-soluble B-vitamin, which is also known as vitamin B9 or folacin.
  7. ^ Choi JH, Yates Z, Veysey M, Heo YR, Lucock M (December 2014). "Contemporary issues surrounding folic Acid fortification initiatives". Prev Nutr Food Sci. 19 (4): 247–60. doi:10.3746/pnf.2014.19.4.247. PMC 4287316. PMID 25580388.
  8. ^ West AA, Caudill MA, Bailey LB (2020). "Folate". In BP Marriott, DF Birt, VA Stallings, AA Yates (eds.). Present Knowledge in Nutrition, Eleventh Edition. London, United Kingdom: Academic Press (Elsevier). pp. 273–88. ISBN 978-0-323-66162-1.
  9. ^ Pommerville JC (2009). Alcamo's Fundamentals of Microbiology: Body Systems. Jones & Bartlett Publishers. p. 511. ISBN 978-0-7637-8712-7. Archived from the original on 8 September 2017.
  10. ^ Bibbins-Domingo K, Grossman DC, Curry SJ, Davidson KW, Epling JW, García FA, et al. (January 2017). "Folic Acid Supplementation for the Prevention of Neural Tube Defects: US Preventive Services Task Force Recommendation Statement". JAMA. 317 (2): 183–189. doi:10.1001/jama.2016.19438. PMID 28097362. S2CID 205077749.
  11. ^ Cite error: The named reference Wald2018 was invoked but never defined (see the help page).
  12. ^ Li Y, Huang T, Zheng Y, Muka T, Troup J, Hu FB (August 2016). "Folic Acid Supplementation and the Risk of Cardiovascular Diseases: A Meta-Analysis of Randomized Controlled Trials" (PDF). Journal of the American Heart Association. 5 (8): e003768. doi:10.1161/JAHA.116.003768. PMC 5015297. PMID 27528407. Archived (PDF) from the original on 27 April 2021. Retrieved 4 November 2018.
  13. ^ Cite error: The named reference Wien2012 was invoked but never defined (see the help page).
  14. ^ Marino BS, Fine KS (2009). Blueprints Pediatrics. Lippincott Williams & Wilkins. p. 131. ISBN 978-0-7817-8251-7. Archived from the original on 8 September 2017.
  15. ^ Fardous AM, Heydari AR (November 2023). "Uncovering the Hidden Dangers and Molecular Mechanisms of Excess Folate: A Narrative Review". Nutrients. 15 (21): 4699. doi:10.3390/nu15214699. PMC 10648405. PMID 37960352.
  16. ^ Pond WG, Nichols BL, Brown DL (2009). Adequate Food for All: Culture, Science, and Technology of Food in the 21st Century. CRC Press. p. 148. ISBN 978-1-4200-7754-4. Folic acid's discovery started in 1931...
  17. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  18. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  19. ^ "Folic Acid Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Archived from the original on 8 July 2020. Retrieved 30 August 2024.
  20. ^ Chambers Concise Dictionary. Allied Publishers. 2004. p. 451. ISBN 978-81-86062-36-4. Archived from the original on 8 September 2017.