Glyceryl monocaprate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581926

CAS#: 26402-22-2

Description: Glyceryl monocaprate is active against bacteria such as candida albicans and campylobacter.


Chemical Structure

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Glyceryl monocaprate
CAS# 26402-22-2

Theoretical Analysis

MedKoo Cat#: 581926
Name: Glyceryl monocaprate
CAS#: 26402-22-2
Chemical Formula: C13H26O4
Exact Mass: 0.00
Molecular Weight: 246.347
Elemental Analysis: C, 63.38; H, 10.64; O, 25.98

Price and Availability

Size Price Availability Quantity
1g USD 350 2 Weeks
5g USD 750 2 Weeks
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Synonym: Glyceryl monocaprate; 1-Decanoyl-rac-glycerol; Glyceryl caprate; Decanoic acid, monoester with glycerol; Decanoic acid, monoester with 1,2,3-propanetriol

IUPAC/Chemical Name: 2,3-dihydroxypropyl decanoate

InChi Key: LKUNXBRZDFMZOK-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H26O4/c1-2-3-4-5-6-7-8-9-13(16)17-11-12(15)10-14/h12,14-15H,2-11H2,1H3

SMILES Code: CCCCCCCCCC(=O)OCC(CO)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Glyceryl monocaprate (Monolaurin) is a 1-monoglyceride of capric acid against gram-positive bacterial infections. Glyceryl monocaprate (Monolaurin) has inhibitory effect on Herpes Simplex Virus (HSV).
In vitro activity: Cells treated with GML (glyceryl monocaprate) had reduced responses to BCR (B cell antigen receptor) stimulation, with significantly less phosphorylation of both CD79 and AKT in GML treated cells compared to vehicle control treated cells (Fig. 4A,B). Inhibition of CD79 and AKT phosphorylation in GML-treated B cells demonstrates GML inhibits early BCR dependent signaling cascades. Reference: Sci Rep. 2022 Aug 5;12(1):13506. https://pubmed.ncbi.nlm.nih.gov/35931746/
In vivo activity: Dietary GML (glyceryl monocaprate) restored serum LPS levels (P = 0.031) and jejunal VH (P = 0.030) in LPS-challenged birds. GML supplementation increased the jejunal p-AMPK (P = 0.021) and total AMPK (P = 0.001) contents of challenged birds compared to the LPS group. The ratio of p-AMPK and total AMPK was higher in the GML groups than in the other 3 groups (P = 0.027). These results suggested that GML supplementation promoted the activation of AMPK signaling and ensured recovery of intestinal barrier function that had been injured by LPS challenge. Reference: Anim Nutr. 2022 Jun 19;10:347-359. https://pubmed.ncbi.nlm.nih.gov/35919246/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 45.3 184.03
Ethanol 49.0 198.91

Preparing Stock Solutions

The following data is based on the product molecular weight 246.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Fosdick MG, Loftus S, Phillips I, Zacharias ZR, Houtman JCD. Glycerol monolaurate inhibition of human B cell activation. Sci Rep. 2022 Aug 5;12(1):13506. doi: 10.1038/s41598-022-17432-4. PMID: 35931746; PMCID: PMC9355977. 2. Welch JL, Xiang J, Okeoma CM, Schlievert PM, Stapleton JT. Glycerol Monolaurate, an Analogue to a Factor Secreted by Lactobacillus, Is Virucidal against Enveloped Viruses, Including HIV-1. mBio. 2020 May 5;11(3):e00686-20. doi: 10.1128/mBio.00686-20. PMID: 32371599; PMCID: PMC7201201. 3. Kong L, Wang Z, Xiao C, Zhu Q, Song Z. Glycerol monolaurate attenuated immunological stress and intestinal mucosal injury by regulating the gut microbiota and activating AMPK/Nrf2 signaling pathway in lipopolysaccharide-challenged broilers. Anim Nutr. 2022 Jun 19;10:347-359. doi: 10.1016/j.aninu.2022.06.005. PMID: 35919246; PMCID: PMC9307562. 4. Zhang Q, Yi D, Ji C, Wu T, Wang M, Guo S, Wang L, Zhao D, Hou Y. Monolaurin Confers a Protective Effect Against Porcine Epidemic Diarrhea Virus Infection in Piglets by Regulating the Interferon Pathway. Front Immunol. 2022 Jan 13;12:797476. doi: 10.3389/fimmu.2021.797476. PMID: 35095875; PMCID: PMC8793282.
In vitro protocol: 1. Fosdick MG, Loftus S, Phillips I, Zacharias ZR, Houtman JCD. Glycerol monolaurate inhibition of human B cell activation. Sci Rep. 2022 Aug 5;12(1):13506. doi: 10.1038/s41598-022-17432-4. PMID: 35931746; PMCID: PMC9355977. 2. Welch JL, Xiang J, Okeoma CM, Schlievert PM, Stapleton JT. Glycerol Monolaurate, an Analogue to a Factor Secreted by Lactobacillus, Is Virucidal against Enveloped Viruses, Including HIV-1. mBio. 2020 May 5;11(3):e00686-20. doi: 10.1128/mBio.00686-20. PMID: 32371599; PMCID: PMC7201201.
In vivo protocol: 1. Kong L, Wang Z, Xiao C, Zhu Q, Song Z. Glycerol monolaurate attenuated immunological stress and intestinal mucosal injury by regulating the gut microbiota and activating AMPK/Nrf2 signaling pathway in lipopolysaccharide-challenged broilers. Anim Nutr. 2022 Jun 19;10:347-359. doi: 10.1016/j.aninu.2022.06.005. PMID: 35919246; PMCID: PMC9307562. 2. Zhang Q, Yi D, Ji C, Wu T, Wang M, Guo S, Wang L, Zhao D, Hou Y. Monolaurin Confers a Protective Effect Against Porcine Epidemic Diarrhea Virus Infection in Piglets by Regulating the Interferon Pathway. Front Immunol. 2022 Jan 13;12:797476. doi: 10.3389/fimmu.2021.797476. PMID: 35095875; PMCID: PMC8793282.

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1: Wong K, Flanagan J, Jalbert I, Tan J. The effect of Blephadex™ Eyelid Wipes on Demodex mites, ocular microbiota, bacterial lipase and comfort: a pilot study. Cont Lens Anterior Eye. 2019 Jun 22. pii: S1367-0484(19)30031-1. doi: 10.1016/j.clae.2019.06.001. [Epub ahead of print] PubMed PMID: 31239200.

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4: Chinatangkul N, Tubtimsri S, Panchapornpon D, Akkaramongkolporn P, Limmatvapirat C, Limmatvapirat S. Design and characterisation of electrospun shellac-polyvinylpyrrolidone blended micro/nanofibres loaded with monolaurin for application in wound healing. Int J Pharm. 2019 May 1;562:258-270. doi: 10.1016/j.ijpharm.2019.03.048. Epub 2019 Mar 22. PubMed PMID: 30910635.

5: Lopes LQS, de Almeida Vaucher R, Giongo JL, Gündel A, Santos RCV. Characterisation and anti-biofilm activity of glycerol monolaurate nanocapsules against Pseudomonas aeruginosa. Microb Pathog. 2019 May;130:178-185. doi: 10.1016/j.micpath.2019.03.007. Epub 2019 Mar 9. PubMed PMID: 30862561.

6: Fortuoso BF, Dos Reis JH, Gebert RR, Barreta M, Griss LG, Casagrande RA, de Cristo TG, Santiani F, Campigotto G, Rampazzo L, Stefani LM, Boiago MM, Lopes LQ, Santos RCV, Baldissera MD, Zanette RA, Tomasi T, Da Silva AS. Glycerol monolaurate in the diet of broiler chickens replacing conventional antimicrobials: Impact on health, performance and meat quality. Microb Pathog. 2019 Apr;129:161-167. doi: 10.1016/j.micpath.2019.02.005. Epub 2019 Feb 5. PubMed PMID: 30735801.

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8: Zhao M, Cai H, Liu M, Deng L, Li Y, Zhang H, Feng F. Dietary glycerol monolaurate supplementation for the modification of functional properties of egg white protein. J Sci Food Agric. 2019 Jun;99(8):3852-3859. doi: 10.1002/jsfa.9607. Epub 2019 Feb 27. PubMed PMID: 30680726.

9: Chan WY, Khazandi M, Hickey EE, Page SW, Trott DJ, Hill PB. In vitro antimicrobial activity of seven adjuvants against common pathogens associated with canine otitis externa. Vet Dermatol. 2019 Apr;30(2):133-e38. doi: 10.1111/vde.12712. Epub 2018 Dec 13. PubMed PMID: 30548715.

10: Silva VO, Pereira LJ, Pasetto S, da Silva MP, Meyers JC, Murata RM. Effects of Monolaurin on Oral Microbe-Host Transcriptome and Metabolome. Front Microbiol. 2018 Nov 6;9:2638. doi: 10.3389/fmicb.2018.02638. eCollection 2018. PubMed PMID: 30467497; PubMed Central PMCID: PMC6237204.

11: Rozenbaum RT, Su L, Umerska A, Eveillard M, Håkansson J, Mahlapuu M, Huang F, Liu J, Zhang Z, Shi L, van der Mei HC, Busscher HJ, Sharma PK. Antimicrobial synergy of monolaurin lipid nanocapsules with adsorbed antimicrobial peptides against Staphylococcus aureus biofilms in vitro is absent in vivo. J Control Release. 2019 Jan 10;293:73-83. doi: 10.1016/j.jconrel.2018.11.018. Epub 2018 Nov 19. PubMed PMID: 30465823.

12: Schlievert PM, Kilgore SH, Kaus GM, Ho TD, Ellermeier CD. Glycerol Monolaurate (GML) and a Nonaqueous Five-Percent GML Gel Kill Bacillus and Clostridium Spores. mSphere. 2018 Nov 21;3(6). pii: e00597-18. doi: 10.1128/mSphereDirect.00597-18. PubMed PMID: 30463926; PubMed Central PMCID: PMC6249644.

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14: Valle-González ER, Jackman JA, Yoon BK, Park S, Sut TN, Cho NJ. Characterizing How Acidic pH Conditions Affect the Membrane-Disruptive Activities of Lauric Acid and Glycerol Monolaurate. Langmuir. 2018 Nov 13;34(45):13745-13753. doi: 10.1021/acs.langmuir.8b02536. Epub 2018 Nov 5. PubMed PMID: 30343569.

15: Ponphaiboon J, Limmatvapirat S, Chaidedgumjorn A, Limmatvapirat C. Optimization and comparison of GC-FID and HPLC-ELSD methods for determination of lauric acid, mono-, di-, and trilaurins in modified coconut oil. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Nov 1;1099:110-116. doi: 10.1016/j.jchromb.2018.09.023. Epub 2018 Sep 24. PubMed PMID: 30265940.

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17: Yang H, Li X, Lu G. Effect of Carnauba Wax-Based Coating Containing Glycerol Monolaurate on Decay and Quality of Sweet Potato Roots during Storage. J Food Prot. 2018 Oct;81(10):1643-1650. doi: 10.4315/0362-028X.JFP-18-017. PubMed PMID: 30204002.

18: Seleem D, Freitas-Blanco VS, Noguti J, Zancope BR, Pardi V, Murata RM. In Vivo Antifungal Activity of Monolaurin against Candida albicans Biofilms. Biol Pharm Bull. 2018;41(8):1299-1302. doi: 10.1248/bpb.b18-00256. PubMed PMID: 30068882.

19: Yu D, Regenstein JM, Zang J, Jiang Q, Xia W, Xu Y. Inhibition of microbial spoilage of grass carp (Ctenopharyngodon idellus) fillets with a chitosan-based coating during refrigerated storage. Int J Food Microbiol. 2018 Nov 20;285:61-68. doi: 10.1016/j.ijfoodmicro.2018.07.010. Epub 2018 Jul 10. PubMed PMID: 30031352.

20: Sun G, Lei L, Chen H, Li B, Cao Y, Li Y. Tailoring of structured hydroxypropyl methylcellulose-stabilized emulsions for encapsulation of nobiletin: modification of the oil and aqueous phases. Food Funct. 2018 Jul 17;9(7):3657-3664. doi: 10.1039/c7fo02068f. PubMed PMID: 29808200.