Monolaurin

From Wikipedia, the free encyclopedia
  (Redirected from Glyceryl laurate)
Jump to navigation Jump to search
Monolaurin
Glyceryl laurate.png
Names
IUPAC name
2,3-Dihydroxypropyl dodecanoate
Other names
Glyceryl laurate; Monolauroylglycerin; Glycerol monolaurate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.043.929
UNII
Properties
C15H30O4
Molar mass 274.40 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Monolaurin, also known as glycerol monolaurate, glyceryl laurate or 1-lauroyl-glycerol, is a monoglyceride. It is the mono-ester formed from glycerol and lauric acid. Its chemical formula is C15H30O4.

Uses[edit]

Monolaurin is most commonly used as a surfactant in cosmetics, such as deodorants. As a food additive it is also used as an emulsifier or preservative. Monolaurin is also taken as a dietary supplement.

Occurrence[edit]

Monolaurin is found in coconut oil and may be similar to other monoglycerides found in human breast milk.[1]

Lauric acid can be ingested in coconut oil and the human body converts it into monolaurin, but researchers are unsure of the conversion rates.[2] Because of this, it’s impossible to say how much coconut oil one would need to ingest to receive a therapeutic dose of monolaurin, however some articles suggest it may be upwards of 100-300mL/day making ingesting coconut oil unrealistic compared to monolaurin capsules.[3]

Pharmacology[edit]

Monolaurin in capsule form as a dietary supplement

Monolaurin has antibacterial, antiviral, and other antimicrobial effects in vitro,[4][5][6][7][8][9] but its clinical usefulness has not been established. Monolaurin is currently sold as a dietary supplement and is categorized in the United States by the Food and Drug Administration as generally recognized as safe (GRAS).[10]

Monolaurin is known to inactivate lipid-coated viruses by binding to the lipid-protein envelope of the virus, thereby preventing it from attaching and entering host cells, making infection and replication impossible.[11] Other studies show that Monolaurin disintegrates the protective viral envelope, killing the virus.[12][13] Monolaurin has been studied to inactivate many pathogens including Herpes simplex virus[14] and Chlamydia trachomatis.[15]

Monolaurin also shows promising effects against bacteria (both gram-positive and gram-negative), yeast, fungi, and protozoa. Bacteria including E. Coli,[16] yeast including Candida alibcans,[17] Helicobacter pylori (H. pylori),[18] Giardia lamblia,[citation needed] Staphylococcus aureus (Staph),[19] and other microbials have all been neutralized by monolaurin in scientific studies. Monolaurin also presented antibacterial and anti-biofilm properties against Borrelia burgdorferi and Borrelia garinii, the bacterium which cause Lyme Disease in humans.[20]

Furthermore, monolaurin does not seem to contribute to drug resistance,[21] and may be taken as a preventative measure to avoid infection.[citation needed]

References[edit]

  1. ^ Hegde, BM (2006). "View Point: Coconut Oil – Ideal Fat next only to Mother's Milk (Scanning Coconut's Horoscope)" (pdf). Journal of the Indian Academy of Clinical Medicine. 7: 16–19. 
  2. ^ "Monolaurin: Benefits, Dosage, and Side Effects". www.healthline.com. Retrieved 2017-12-02. 
  3. ^ "Pharmacological effects of coconut oil vs. monoglycerides" (PDF). inform Volume 16. June 2005. 
  4. ^ Li, Q; Estes, J. D.; Schlievert, P. M.; Duan, L; Brosnahan, A. J.; Southern, P. J.; Reilly, C. S.; Peterson, M. L.; Schultz-Darken, N; Brunner, K. G.; Nephew, K. R.; Pambuccian, S; Lifson, J. D.; Carlis, J. V.; Haase, A. T. (2009). "Glycerol monolaurate prevents mucosal SIV transmission". Nature. 458 (7241): 1034–8. doi:10.1038/nature07831. PMC 2785041Freely accessible. PMID 19262509. 
  5. ^ Preuss, H. G.; Echard, B.; Enig, M.; Brook, I.; Elliott, T. B. (2005). "Minimum inhibitory concentrations of herbal essential oils and monolaurin for gram-positive and gram-negative bacteria". Molecular and Cellular Biochemistry. 272 (1–2): 29–34. doi:10.1007/s11010-005-6604-1. PMID 16010969. 
  6. ^ Carpo, B. G.; Verallo-Rowell, V. M.; Kabara, J. (2007). "Novel antibacterial activity of monolaurin compared with conventional antibiotics against organisms from skin infections: an in vitro study". Journal of Drugs in Dermatology. 6 (10): 991–998. PMID 17966176. 
  7. ^ Isaacs, C. E. (2001). "The antimicrobial function of milk lipids". Advances in Nutritional Research. 10: 271–285. PMID 11795045. 
  8. ^ Lieberman, Shari; Enig, Mary G.; Preuss, Harry G. (2006). "A Review of Monolaurin and Lauric Acid:Natural Virucidal and Bactericidal Agents". Alternative and Complementary Therapies. 12 (6): 310–314. doi:10.1089/act.2006.12.310. 
  9. ^ Projan, S. J.; Brown-Skrobot, S.; Schlievert, P. M.; Vandenesch, F.; Novick, R. P. (1994). "Glycerol monolaurate inhibits the production of beta-lactamase, toxic shock toxin-1, and other staphylococcal exoproteins by interfering with signal transduction". Journal of Bacteriology. 176 (14): 4204–4209. PMC 205630Freely accessible. PMID 8021206. 
  10. ^ "CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. 
  11. ^ Isaacs, CE; Kim, KS; Thormar, H (6 June 1994). "Inactivation of enveloped viruses in human bodily fluids by purified lipids". Annals of the New York Academy of Sciences. 724: 457–64. PMID 8030973. 
  12. ^ Thormar, H; Isaacs, C E; Brown, H R; Barshatzky, M R; Pessolano, T (1 January 1987). "Inactivation of enveloped viruses and killing of cells by fatty acids and monoglycerides". Antimicrobial Agents and Chemotherapy. 31 (1): 27–31. doi:10.1128/aac.31.1.27. PMID 3032090. 
  13. ^ Arora, R; Chawla, R; Marwah, R; Arora, P; Sharma, RK; Kaushik, V; Goel, R; Kaur, A; Silambarasan, M; Tripathi, RP; Bhardwaj, JR (2011). "Potential of Complementary and Alternative Medicine in Preventive Management of Novel H1N1 Flu (Swine Flu) Pandemic: Thwarting Potential Disasters in the Bud". Evidence-based Complementary and Alternative Medicine. 2011: 586506. doi:10.1155/2011/586506. PMC 2957173Freely accessible. PMID 20976081. 
  14. ^ Sands, J; Auperin, D; Snipes, W (January 1979). "Extreme sensitivity of enveloped viruses, including herpes simplex, to long-chain unsaturated monoglycerides and alcohols". Antimicrobial Agents and Chemotherapy. 15 (1): 67–73. doi:10.1128/aac.15.1.67. PMID 218499. 
  15. ^ Bergsson, G; Arnfinnsson, J; Karlsson, SM; Steingrímsson, O; Thormar, H (September 1998). "In vitro inactivation of Chlamydia trachomatis by fatty acids and monoglycerides". Antimicrobial Agents and Chemotherapy. 42 (9): 2290–4. PMID 9736551. 
  16. ^ Bergsson, G; Arnfinnsson, J; Steingrímsson, O; Thormar, H (November 2001). "In vitro killing of Candida albicans by fatty acids and monoglycerides". Antimicrobial Agents and Chemotherapy. 45 (11): 3209–12. doi:10.1128/AAC.45.11.3209-3212.2001. PMID 11600381. 
  17. ^ Bergsson, G; Arnfinnsson, J; Steingrímsson, O; Thormar, H (November 2001). "In vitro killing of Candida albicans by fatty acids and monoglycerides". Antimicrobial Agents and Chemotherapy. 45 (11): 3209–12. doi:10.1128/AAC.45.11.3209-3212.2001. ISSN 0066-4804. PMC 90807Freely accessible. PMID 11600381. 
  18. ^ Petschow, BW; Batema, RP; Ford, LL (February 1996). "Susceptibility of Helicobacter pylori to bactericidal properties of medium-chain monoglycerides and free fatty acids". Antimicrobial Agents and Chemotherapy. 40 (2): 302–6. PMID 8834870. 
  19. ^ Ruzin, A; Novick, RP (May 2000). "Equivalence of lauric acid and glycerol monolaurate as inhibitors of signal transduction in Staphylococcus aureus". Journal of Bacteriology. 182 (9): 2668–71. PMID 10762277. 
  20. ^ Goc, A; Niedzwiecki, A; Rath, M (December 2015). "In vitro evaluation of antibacterial activity of phytochemicals and micronutrients against Borrelia burgdorferi and Borrelia garinii". Journal of Applied Microbiology. 119 (6): 1561–72. doi:10.1111/jam.12970. PMID 26457476. 
  21. ^ Carpo, BG; Verallo-Rowell, VM; Kabara, J (October 2007). "Novel antibacterial activity of monolaurin compared with conventional antibiotics against organisms from skin infections: an in vitro study". Journal of Drugs in Dermatology. 6 (10): 991–8. ISSN 1545-9616. PMID 17966176.