Monolaurin

Monolaurin
Names
IUPAC name
Dodecanoic acid 2,3-dihydroxypropyl ester
Other names
Glyceryl laurate; Monolauroylglycerin; Glycerol monolaurate
Identifiers
27215-38-9 YesY
ChEMBL ChEMBL510533 YesY
ChemSpider 14181 YesY
Jmol interactive 3D Image
PubChem 14871
UNII Y98611C087 YesY
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).
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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

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

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

Pharmacology

Monolaurin in capsule form as a dietary supplement

Monolaurin has antibacterial, antiviral, and other antimicrobial effects in vitro.[2][3][4][5][6][7] It may therefore be useful in the treatment or prevention of various infections, but its clinical usefulness has not been established.

Monolaurin is currently sold as a dietary supplement under various brands, generally under the category of digestive and immune system support.

Monolaurin is believed 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.[8] Other studies show that Monolaurin disintegrates the protective viral envelope, killing the virus.[9][10] Monolaurin has been studied to inactivate many enveloped viruses including Herpes simplex virus[11] and Chlamydia trachomatis.[12]

Monolaurin also shows promising effects against bacteria (both gram-positive and gram-negative), yeast, fungi, and protozoa. Bacteria including E. Coli,[13] yeast including Candida alibcans,[14] Helicobacter Pylori (H. Pylori),[15] Giardia lamblia,[16] Staphylococus aureus (Staph),[17] and other microbials have all been neutralized by monolaurin in scientific studies.

Furthermore, monolaurin does not seem to contribute to drug resistance,[18] may be taken as a preventative measure to avoid infection,[19] and has been listed in the FDA's GRAS (Generally Regarded As Safe) list.

References

  1. ↑ Hegde, BM (2006). "View Point: Coconut Oil – Ideal Fat next only to Mother's Milk (Scanning Coconut's Horoscope)" (pdf). JIACM 7: 16–19.
  2. ↑ 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 2785041. PMID 19262509.
  3. ↑ 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.
  4. ↑ 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 : JDD 6 (10): 991–998. PMID 17966176.
  5. ↑ Isaacs, C. E. (2001). "The antimicrobial function of milk lipids". Advances in nutritional research 10: 271–285. PMID 11795045.
  6. ↑ 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.
  7. ↑ 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 205630. PMID 8021206.
  8. ↑ Isaacs, C. E.; Kim, K. S.; Thormar, H. (1994-06-06). "Inactivation of enveloped viruses in human bodily fluids by purified lipids". Annals of the New York Academy of Sciences 724: 457–464. doi:10.1111/j.1749-6632.1994.tb38947.x. ISSN 0077-8923. PMID 8030973.
  9. ↑ Thormar, H.; Isaacs, C. E.; Brown, H. R.; Barshatzky, M. R.; Pessolano, T. (1987-01-01). "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. ISSN 0066-4804. PMC 174645. PMID 3032090.
  10. ↑ Arora, Rajesh; Chawla, R.; Marwah, Rohit; Arora, P.; Sharma, R. K.; Kaushik, Vinod; Goel, R.; Kaur, A.; Silambarasan, M. (2011-01-01). "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 : eCAM 2011: 1–16. doi:10.1155/2011/586506. ISSN 1741-427X. PMC 2957173. PMID 20976081.
  11. ↑ Sands, J.; Auperin, D.; Snipes, W. (1979-01-01). "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. ISSN 0066-4804. PMC 352602. PMID 218499.
  12. ↑ Bergsson, Gudmundur; Arnfinnsson, Jóhann; Karlsson, Sigfús M.; Steingrímsson, Ólafur; Thormar, Halldor (1998-09-01). "In Vitro Inactivation of Chlamydia trachomatis by Fatty Acids and Monoglycerides". Antimicrobial Agents and Chemotherapy 42 (9): 2290–2294. ISSN 0066-4804. PMC 105821. PMID 9736551.
  13. ↑ Kabara JJ. The Pharmacological Effect of Lipids. Champaign, Ill, USA: American Oil Chemist’s Society; 1978. Page 92
  14. ↑ Bergsson, G.; Arnfinnsson, J.; Steingrímsson O, null; Thormar, H. (2001-11-01). "In vitro killing of Candida albicans by fatty acids and monoglycerides". Antimicrobial Agents and Chemotherapy 45 (11): 3209–3212. doi:10.1128/AAC.45.11.3209-3212.2001. ISSN 0066-4804. PMC 90807. PMID 11600381.
  15. ↑ Petschow, B. W.; Batema, R. P.; Ford, L. L. (1996-02-01). "Susceptibility of Helicobacter pylori to bactericidal properties of medium-chain monoglycerides and free fatty acids.". Antimicrobial Agents and Chemotherapy 40 (2): 302–306. ISSN 0066-4804. PMC 163106. PMID 8834870.
  16. ↑ Fahmy ZH, Aly E, Shalsh I, Mohamed AH. The effect of medium chain saturated fatty acid (monolaurin) on levels of the cytokines on experimental animal in Entamoeba histolytica and Giardia lamblia infection. African Journal of Pharmacy and Pharmacology. January 2014.
  17. ↑ Ruzin, A.; Novick, R. P. (2000-05-01). "Equivalence of lauric acid and glycerol monolaurate as inhibitors of signal transduction in Staphylococcus aureus". Journal of Bacteriology 182 (9): 2668–2671. doi:10.1128/jb.182.9.2668-2671.2000. ISSN 0021-9193. PMC 111339. PMID 10762277.
  18. ↑ Carpo, Beatriz G.; Verallo-Rowell, Vermén M.; Kabara, Jon (2007-10-01). "Novel antibacterial activity of monolaurin compared with conventional antibiotics against organisms from skin infections: an in vitro study". Journal of drugs in dermatology: JDD 6 (10): 991–998. ISSN 1545-9616. PMID 17966176.
  19. ↑ Fahmy ZH, Aly E, Shalsh I, Mohamed AH. The effect of medium chain saturated fatty acid (monolaurin) on levels of the cytokines on experimental animal in Entamoeba histolytica and Giardia lamblia infection. African Journal of Pharmacy and Pharmacology. January 2014.
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