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MedKoo Cat#: 581880 | Name: Monocaprin
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Description:

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

Monocaprin also is known as Monoctanoin component B, 1-Decanoyl-rac-glycerol. It is a monoacylglyecrol with antibacterial activity. Studies show that 1-Decanoyl-rac-glycerol maybe potential apoptotic agents in T-cells.

Chemical Structure

Monocaprin
Monocaprin
CAS#2277-23-8

Theoretical Analysis

MedKoo Cat#: 581880

Name: Monocaprin

CAS#: 2277-23-8

Chemical Formula: C13H26O4

Exact Mass: 246.1830

Molecular Weight: 246.35

Elemental Analysis: C, 63.38; H, 10.64; O, 25.98

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
250mg USD 400.00 2 Weeks
1g USD 650.00 2 Weeks
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Related CAS #
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Synonym
Monocaprin; Monoctanoin component B; Glycerol 1-monocaprinate; 1-Monodecanoin;
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
OCC(COC(CCCCCCCCC)=O)O
Appearance
Liquid
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
Product Data
Instruction
View handling instruction
Biological target:
Monocaprin also is known as Monoctanoin component B, 1-Decanoyl-rac-glycerol.
In vitro activity:
Monocaprin had antibacterial activity under neutral and alkaline conditions (pH 7.0 to 9.0) but had no inhibitory effect on S. aureus, B. subtilis, and E. coli under weakly acidic conditions (pH 6.0). The antibacterial mechanism of monocaprin against gram-positive strains (S. aureus and B. subtilis) resulted from destruction of the cell membrane. In contrast, the antibacterial activity of monocaprin against gram-negative strains (P. aeruginosa and E. coli) was attributed to damage to lipopolysaccharides in the cell walls. Reference: J Food Prot. 2020 Feb 1;83(2):331-337. https://pubmed.ncbi.nlm.nih.gov/31961233/
In vivo activity:
TBD

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. Wang W, Wang R, Zhang G, Chen F, Xu B. In Vitro Antibacterial Activities and Mechanisms of Action of Fatty Acid Monoglycerides Against Four Foodborne Bacteria. J Food Prot. 2020 Feb 1;83(2):331-337. doi: 10.4315/0362-028X.JFP-19-259. PMID: 31961233. 2. Thorgeirsdóttir TO, Kristmundsdóttir T, Thormar H, Axelsdóttir I, Holbrook WP. Antimicrobial activity of monocaprin: a monoglyceride with potential use as a denture disinfectant. Acta Odontol Scand. 2006 Feb;64(1):21-6. doi: 10.1080/00016350500326245. PMID: 16428178.
In vitro protocol:
1. Wang W, Wang R, Zhang G, Chen F, Xu B. In Vitro Antibacterial Activities and Mechanisms of Action of Fatty Acid Monoglycerides Against Four Foodborne Bacteria. J Food Prot. 2020 Feb 1;83(2):331-337. doi: 10.4315/0362-028X.JFP-19-259. PMID: 31961233. 2. Thorgeirsdóttir TO, Kristmundsdóttir T, Thormar H, Axelsdóttir I, Holbrook WP. Antimicrobial activity of monocaprin: a monoglyceride with potential use as a denture disinfectant. Acta Odontol Scand. 2006 Feb;64(1):21-6. doi: 10.1080/00016350500326245. PMID: 16428178.
In vivo protocol:
TBD
1: Churchward CP, Calder A, Snyder LAS. Mutations in Neisseria gonorrhoeae grown in sub-lethal concentrations of monocaprin do not confer resistance. PLoS One. 2018 Apr 5;13(4):e0195453. doi: 10.1371/journal.pone.0195453. eCollection 2018. PubMed PMID: 29621310; PubMed Central PMCID: PMC5886539. 2: Churchward CP, Alany RG, Kirk RS, Walker AJ, Snyder LAS. Prevention of Ophthalmia Neonatorum Caused by Neisseria gonorrhoeae Using a Fatty Acid-Based Formulation. MBio. 2017 Jul 25;8(4). pii: e00534-17. doi: 10.1128/mBio.00534-17. PubMed PMID: 28743809; PubMed Central PMCID: PMC5527305. 3: Yoon BK, Jackman JA, Kim MC, Sut TN, Cho NJ. Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin. Langmuir. 2017 Mar 21;33(11):2750-2759. doi: 10.1021/acs.langmuir.6b03944. Epub 2017 Mar 13. PubMed PMID: 28263610. 4: Park KM, Lee JH, Hong SC, Kwon CW, Jo M, Choi SJ, Kim K, Chang PS. Selective production of 1-monocaprin by porcine liver carboxylesterase-catalyzed esterification: Its enzyme kinetics and catalytic performance. Enzyme Microb Technol. 2016 Jan;82:51-57. doi: 10.1016/j.enzmictec.2015.08.014. Epub 2015 Aug 28. PubMed PMID: 26672448. 5: Skulason S, Holbrook WP, Thormar H, Gunnarsson GB, Kristmundsdottir T. A study of the clinical activity of a gel combining monocaprin and doxycycline: a novel treatment for herpes labialis. J Oral Pathol Med. 2012 Jan;41(1):61-7. doi: 10.1111/j.1600-0714.2011.01037.x. Epub 2011 Apr 30. PubMed PMID: 21535163. 6: Thormar H, Hilmarsson H, Thrainsson JH, Georgsson F, Gunnarsson E, Dadadottir S. Treatment of fresh poultry carcases with emulsions of glycerol monocaprate (monocaprin) to reduce contamination with Campylobacter and psychrotrophic bacteria. Br Poult Sci. 2011 Feb;52(1):11-9. doi: 10.1080/00071668.2010.537308. PubMed PMID: 21337193. 7: Thormar H, Hilmarsson H. Killing of Campylobacter on contaminated plastic and wooden cutting boards by glycerol monocaprate (monocaprin). Lett Appl Microbiol. 2010 Sep;51(3):319-24. doi: 10.1111/j.1472-765X.2010.02898.x. Epub 2010 Jul 8. PubMed PMID: 20666986. 8: Park KM, Kwon OT, Ahn SM, Lee J, Chang PS. Characterization and optimization of carboxylesterase-catalyzed esterification between capric acid and glycerol for the production of 1-monocaprin in reversed micellar system. N Biotechnol. 2010 Feb 28;27(1):46-52. doi: 10.1016/j.nbt.2009.11.004. Epub 2009 Nov 28. PubMed PMID: 19931658. 9: Batovska DI, Todorova IT, Tsvetkova IV, Najdenski HM. Antibacterial study of the medium chain fatty acids and their 1-monoglycerides: individual effects and synergistic relationships. Pol J Microbiol. 2009;58(1):43-7. PubMed PMID: 19469285. 10: Reis P, Holmberg K, Debeche T, Folmer B, Fauconnot L, Watzke H. Lipase-catalyzed reactions at different surfaces. Langmuir. 2006 Sep 12;22(19):8169-77. PubMed PMID: 16952258. 11: Thorgeirsdóttir TO, Thormar H, Kristmundsdóttir T. Viscoelastic properties of a virucidal cream containing the monoglyceride monocaprin: effects of formulation variables: a technical note. AAPS PharmSciTech. 2006 May 12;7(2):E44. PubMed PMID: 16796361; PubMed Central PMCID: PMC2750295. 12: Hilmarsson H, Thormar H, Thráinsson JH, Gunnarsson E, Dadadóttir S. Effect of glycerol monocaprate (monocaprin) on broiler chickens: an attempt at reducing intestinal Campylobacter infection. Poult Sci. 2006 Apr;85(4):588-92. Erratum in: Poult Sci. 2006 Jun;85(6):1121. Dadadóttir, S [added]. PubMed PMID: 16615341. 13: Thorgeirsdóttir TO, Kristmundsdóttir T, Thormar H, Axelsdóttir I, Holbrook WP. Antimicrobial activity of monocaprin: a monoglyceride with potential use as a denture disinfectant. Acta Odontol Scand. 2006 Feb;64(1):21-6. PubMed PMID: 16428178. 14: Thorgeirsdóttir TO, Hilmarsson H, Thormar H, Kristmundsdóttir T. Development of a virucidal cream containing the monoglyceride monocaprin. Pharmazie. 2005 Dec;60(12):897-9. PubMed PMID: 16398264. 15: Thormar H, Hilmarsson H, Bergsson G. Stable concentrated emulsions of the 1-monoglyceride of capric acid (monocaprin) with microbicidal activities against the food-borne bacteria Campylobacter jejuni, Salmonella spp., and Escherichia coli. Appl Environ Microbiol. 2006 Jan;72(1):522-6. PubMed PMID: 16391087; PubMed Central PMCID: PMC1352223. 16: Thorgeirsdóttir TO, Kjøniksen AL, Knudsen KD, Kristmundsdóttir T, Nyström B. Viscoelastic and structural properties of pharmaceutical hydrogels containing monocaprin. Eur J Pharm Biopharm. 2005 Feb;59(2):333-42. PubMed PMID: 15661506. 17: Da Silva MA, Medeiros VC, Langone MA, Freire DM. Synthesis of monocaprin catalyzed by lipase. Appl Biochem Biotechnol. 2003 Spring;105 -108:757-67. PubMed PMID: 12721413. 18: Kristmundsdóttir T, Sigurdsson P, Thormar H. Effect of buffers on the properties of microbicidal hydrogels containing monoglyceride as the active ingredient. Drug Dev Ind Pharm. 2003 Feb;29(2):121-9. PubMed PMID: 12648008. 19: Brown JR, Collett JH, Attwood D, Ley RW, Sims EE. Influence of monocaprin on the permeability of a diacidic drug BTA-243 across Caco-2 cell monolayers and everted gut sacs. Int J Pharm. 2002 Oct 1;245(1-2):133-42. PubMed PMID: 12270250. 20: Bergsson G, Arnfinnsson J, Steingrímsson O, Thormar H. Killing of Gram-positive cocci by fatty acids and monoglycerides. APMIS. 2001 Oct;109(10):670-8. PubMed PMID: 11890570.

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