Synonym name: 2,3-Dihydroxypropyl tetradecanoate; alpha-Monomyristin; Glycerol 1-myristate; 1-Myristoylglycerol; 1-O-Tetradecanoylglycerol
Catalogue No.: BP0032
Cas No.: 589-68-4
Formula: C₁₇H₃₄O₄
Mol Weight: 302.455
Botanical Source: the fruit of Serenoa repens

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.

For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.

HPLC of 1-Monomyristin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

1-Monomyristin (CAS No. 589-68-4), as a natural lipid compound, has attracted widespread attention in the field of natural product pharmacology in recent years. Its structure belongs to the 1-monoglyceride class, characterized by the esterification of a glycerol skeleton and tetraderethoracic saturated fatty acids (myristic acid) to form a monoester. This compound was originally isolated from Serenoa repens and has shown various biological activities, especially in lipid metabolism regulation, antibacterial and antifungal properties, and neuroprotection, showing potential pharmacological value. With the rising incidence of metabolic diseases such as non-alcoholic fatty liver disease (NAFLD), 1-myristic monoglycerides have become a research hotspot due to their regulatory effects on related molecular targets.

This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of 1-myristic acid monoglyceride, druggability evaluation, and clinical application prospects, striving to provide scientific basis and theoretical support for further research and development of this compound.

Chemical structure and physicochemical properties

The chemical structure of 1-myristic acid monoglyceride is formed by esterification of the 1-position hydroxyl group of a glycerol molecule with myristic acid (a tetradectorico-saturated fatty acid). The molecular formula is C17H34O4, and the molecular weight is 302.45. Its structural features include:

• The glycerol backbone has esterification at position 1, and hydroxyl groups at positions 2 and 3 are free, imparting certain polarity and water solubility.
• Myristic acid long-chain fatty acid acyl group has strong hydrophobicity, a LogP value of about 4.5, showing high lipid solubility.
• The total polar surface area (TPSA) is 60.69 Ų, with 4 hydrogen bond receptors, indicating certain advantages in cell membrane permeability.
• This compound has low blood-brain barrier permeability, suggesting it mainly acts on peripheral tissues.

In terms of physicochemical properties, 1-myristic acid monoglyceride has good stability and is easily soluble in organic solvents such as ethanol and ethyl acetate, but has poor water solubility. The length of the fatty acid chain in its structure and the ester bonds in its glycerol framework determine its affinity and metabolic stability in biofilms.

Plant Origins and Extraction Methods

1-Myristic acid monoglycerides are mainly extracted from the fruit of saw palmetto (Serenoa repens). Saw palmetto is a palm plant widely distributed in North America, traditionally used to treat benign prostatic hyperplasia and urinary system diseases. It is rich in lipid content, containing various monoglycerides and fatty acids.

Extraction methods typically include:

1. Solvent extraction: Organic solvents such as ethanol, methanol, or ethyl acetate are used to extract dried and crushed saw palmetto fruit to extract fat-soluble components.
2. Liquid-liquid distribution: enriches lipid substances through the distribution of water and organic solvents.
3. Chromatographic separation: Extracts are separated and purified using silica gel column chromatography or high-performance liquid chromatography (HPLC) to obtain high-purity monoglycerides of 1-myristic acid.
4. Identification: Confirm the structure using techniques such as mass spectrometry (MS) and nuclear magnetic resonance (NMR).

In recent years, supercritical CO2 extraction technology has also been applied to extract saw palmetto lipid components, offering high efficiency and environmental friendliness, making industrial production of 1-myristic acid monoglycerides possible.

Pharmacological activity research

The pharmacological activities of 1-myristic monoglyceride include lipid metabolism regulation, antibacterial and antifungal effects, and neuroprotection.

Regulation of lipid metabolism

Studies have shown that 1-myristic acid monoglyceride can inhibit the hydrolysis of 2-oleacylglycerol (IC50=32 μM) and the activity of fatty acid amide hydrolase (FAAH) (IC50=18 μM). FAAH is an enzyme that degrades endogenous fatty acid amide signaling molecules, involved in regulating neuroinflammation and metabolic homeostasis. Its inhibitory effect helps increase endogenous fatty acid amide levels, exerting anti-inflammatory and neuroprotective effects.

Additionally, this compound has regulatory potential for targets related to nonalcoholic fatty liver disease (NAFLD) such as AMPK, NFE2L2, and NR1H4, suggesting potential value in improving liver lipid metabolism disorders and reducing liver inflammation and oxidative stress.

Antibacterial and antifungal activity

Monoglyceride 1-myristic acid exhibits significant inhibitory effects on various pathogenic microorganisms, especially against Staphylococcus aureus and Actinomyces spp., and also shows antifungal activity against Candida albicans. Its mechanism of action may be related to damaging microbial cell membrane integrity and interfering with lipid metabolism.

Neuroprotection and anti-inflammation

By inhibiting FAAH activity, 1-myristic acid monoglyceride can regulate endogenous fatty acid amide signaling pathways, exerting neuroprotective and anti-inflammatory effects. Related studies show that it may alleviate neuroinflammation and pain responses, showing potential as an adjunctive therapy for neurological diseases.

Mechanism of action and molecular targets

The pharmacological effects of 1-myristic acid monoglyceride involve multiple molecular targets and signaling pathways, mainly including:

• AMPK (PRKAA1): As a key regulator of cellular energy metabolism, AMPK activation helps promote fatty acid oxidation and inhibit fat synthesis. 1-Myristic acid monoglycerides improve lipid metabolism disorders by regulating AMPK activity.
• NFE2L2 (Nrf2): regulates cellular antioxidant responses and reduces oxidative stress. This compound activates the Nrf2 signaling pathway, enhancing cellular antioxidant capacity.
• NR1H4 (FXR): Member of the nuclear receptor family, regulates bile acid metabolism and lipid homeostasis. 1-Monoglyceride myristic acid may regulate liver lipid metabolism by affecting FXR activity.
• FAAH: Fatty acid amide hydrolase, regulates endogenous fatty acid amide levels. Its inhibitory effect enhances endogenous anti-inflammatory factors and reduces inflammatory responses.
• 2-oleacylglycerol hydrolase: participates in triglyceride breakdown and regulates fatty acid supply. Inhibiting this enzyme activity helps regulate lipid metabolic balance.
• TLR2 (Toll-like receptor 2): participates in immune inflammatory responses and regulates host defenses. 1-Monoglyceride myristic acid may reduce chronic inflammation by modulating TLR2 signaling.
• LPAR1/LPAR2 (hemolysphospholipid acid receptors) and ENPP2 (autocrine hemolysphospholipid acid synthase): regulate cell proliferation, migration, and inflammatory responses, and participate in lipid signal transduction.

In summary, 1-myristic monoglyceride regulates lipid metabolism, anti-inflammatory, and antibacterial processes through multi-target and multi-pathway synergistic effects, laying the foundation for its application in metabolic and infectious diseases.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, 1-myristic acid monoglycerides exhibit good medicinal properties:

• Molecular weight: 302.45, which fits the ideal range for small molecule drugs.
• Lipophilic (LogP=4.5): moderately high in the range, facilitating penetration of cell membranes, but excessively high may affect water solubility and bioavailability.
• The polar surface area (TPSA=60.69) and the number of hydrogen bond acceptors (4) indicate that it has good membrane permeability.
• The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects.
• Safety indicators: No hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and Ames-induced mutagenic test negative, indicating relatively high safety.

Pharmacokinetics, limited studies suggest high lipophilusity and good oral absorption, but possibly a first-pass effect. Metabolic pathways may involve hepatic lipase-mediated hydrolysis and β-oxidative metabolism. In the future, further systematic research is needed on its in vivo absorption, distribution, metabolism, and excretion (ADME) characteristics to guide clinical development.

Prospects and outlooks for clinical applications

Monoglyceride 1-myristic acid, as a natural lipid compound, has broad clinical application potential due to its multi-target regulatory capabilities and good safety.

Non-alcoholic fatty liver disease (NAFLD)

NAFLD, as a metabolic liver disease with rapidly rising incidence worldwide, lacks effective specific drugs. Monoglyceride 1-myristic acid improves liver lipid metabolism and oxidative stress by modulating key targets such as AMPK, Nrf2, and FXR, demonstrating potential for treating NAFLD. In the future, animal models and clinical trials can be combined to verify efficacy and safety.

Antibacterial and antifungal treatments

In the face of antibiotic resistance, developing new natural antimicrobial agents is especially important. Monoglyceride 1-myristic acid inhibitory effects on Staphylococcus aureus, Actus aggregation, and Candida albicans suggest its potential as an adjunct anti-infective agent or for local infection treatment.

Neuroprotection and anti-inflammation

Inhibiting FAAH activity gives it promising applications in neurological diseases, chronic pain, and inflammatory diseases. In the future, its mechanisms of action and clinical value in neurodegenerative diseases and neuroinflammation can be explored.

Industrialization and formulation development

Based on its physicochemical properties, 1-myristic monoglyceride is suitable for developing novel drug delivery systems such as liposomes and nanoparticles to improve bioavailability and targeting. At the same time, optimization of green extraction technologies and synthesis methods will promote their large-scale production and clinical application.

Conclusion

As a natural monoglyceride with multiple biological activities, 1-myristic acid monoglyceride shows broad application potential in lipid metabolism regulation, antibacterial and antifungal properties, and neuroprotection. Its mechanism of action involves multi-target coordinated regulation, with good safety and excellent druggability, providing new approaches for the treatment of metabolic and infectious diseases.

Future research should focus on systematically elucidating its pharmacokinetic characteristics, in-depth analysis of its mechanisms of action, and developing drug formulations based on clinical needs. Through multidisciplinary integration, 1-myristic monoglyceride is expected to become an important drug candidate in the field of natural product pharmacology, promoting the application and development of natural lipid compounds in modern medicine.