Monolaurin

Monolaurin
Names

IUPAC name Dodecanoic acid 2,3-dihydroxypropyl ester
Other names Glyceryl laurate; Monolauroylglycerin; Glycerol monolaurate
Identifiers
CAS Registry Number	27215-38-9^Y
ChEMBL	ChEMBL510533^Y
ChemSpider	14181^Y
InChI InChI=1S/C15H30O4/c1-2-3-4-5-6-7-8-9-10-11-15(18)19-13-14(17)12-16/h14,16-17H,2-13H2,1H3^Y Key: ARIWANIATODDMH-UHFFFAOYSA-N^Y InChI=1/C15H30O4/c1-2-3-4-5-6-7-8-9-10-11-15(18)19-13-14(17)12-16/h14,16-17H,2-13H2,1H3 Key: ARIWANIATODDMH-UHFFFAOYAD
Jmol-3D images	Image
PubChem	14871
SMILES O=C(OCC(O)CO)CCCCCCCCCCC
UNII	Y98611C087^Y
Properties
Molecular formula	C₁₅H₃₀O₄
Molar mass	274.40 g·mol⁻¹
Except where noted otherwise, data is 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

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

Occurrence

Monolaurin is found in coconut oil and naturally occurs in human breast milk.^[1]

Pharmacology

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.

References

↑ Hegde, BM (2006). "View Point: Coconut Oil – Ideal Fat next only to Mother's Milk (Scanning Coconut's Horoscope)" (PDF). JIACM 7: 16–19.
↑ 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.
↑ 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.
↑ 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.
↑ Isaacs, C. E. (2001). "The antimicrobial function of milk lipids". Advances in nutritional research 10: 271–285. PMID 11795045.
↑ 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. doi:10.1089/act.2006.12.310.
↑ 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.