Monomyristin

Names

[ CAS No. ]:
589-68-4

[ Name ]:
Monomyristin

[Synonym ]:
Myristic acid 1-monoglyceride
Tetradecanoic acid, 2,3-dihydroxypropyl ester
MFCD00046760
2,3-Dihydroxypropyl myristate
1-monomyristoylglycerol
UNII:SMJ2192F1R
rac-Glycerol 1-myristate

Biological Activity

[Description]:

1-Monomyristin, extracted from Serenoa repens, inhibits the hydrolysis of 2-oleoylglycerol (IC50=32 μM) and fatty acid amide hydrolase (FAAH) activity (IC50=18 μM). 1-Monomyristin shows antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also antifungal activity against Candida albicans[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Metabolic Enzyme/Protease >> FAAH

Signaling Pathways >> Neuronal Signaling >> FAAH

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

IC50: 18 μM (FAAH)[2]

[References]

[1]. Shimada H, et al. Biologically active acylglycerides from the berries of saw-palmetto (Serenoa repens). J Nat Prod. 1997 Apr;60(4):417-8.

[2]. Vandevoorde S, et al. Influence of the degree of unsaturation of the acyl side chain upon the interaction of analogues of 1-arachidonoylglycerol with monoacylglycerol lipase and fatty acid amide hydrolase. Biochem Biophys Res Commun. 2005 Nov 11;337(1):104-9.

[3]. Jumina, et al. Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents. Molecules. 2018 Nov 29;23(12). pii: E3141

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
424.8±25.0 °C at 760 mmHg

[ Melting Point ]:
68-70ºC

[ Molecular Formula ]:
C₁₇H₃₄O₄

[ Molecular Weight ]:
302.449

[ Flash Point ]:
141.3±16.7 °C

[ Exact Mass ]:
302.245697

[ PSA ]:
66.76000

[ LogP ]:
5.10

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.468

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2915900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2915900090

[ Summary ]:
2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%

Articles

Adsorption of 1-Monoglycerides at the Hexane/Water Interface.

J. Colloid. Interface Sci. 220 , 374-379, (1999)

The interfacial tension of a hexane solution of 1-monolaurin against water was measured as a function of temperature and concentration under atmospheric pressure. The thermodynamic quantity changes as...

Structure of nonionic surfactant (glycerol alpha-monomyristate) micelles in organic solvents: a SAXS study.

J. Phys. Chem. B 113 , 6290-6298, (2009)

In this paper we present the study of reverse micellar aggregates formed by glycerol alpha-monomyristate (C(14)G(1)) in different organic solvents. We have investigated the structure (mainly shape and...

Absorption properties of micellar lipid metabolites into Caco2 cells.

Lipids 42 , 613-619, (2007)

To elucidate the absorption characteristics of dietary lipids in the human intestine, we investigated the cellular uptake of lipid metabolites using a differential monolayer of the Caco2 cells. As lip...