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Synonym name: Triolein; Olein
Catalogue No.: BP0677
Cas No.: 122-32-7
Formula: C57H104O6
Mol Weight: 885.453
Botanical Source: olive oil and other vegetable oils
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 Glycerol trioleate
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
78.9000
14.0000
14.0000
.0000
2.6512
1.4926
High
97.2757
3.0933
Yes
Yes
Yes
Yes
No
No
0.0
No
No
No
No
Glycerol trioleate (CAS No.: 122-32-7), also known as trioleol trioleate, is a natural triglyceride formed by the combination of glycerol molecules and trioleic acid through ester bonds. As an important lipid molecule, triglycerides are not only widely found in vegetable oils but also serve as important carriers for energy storage and signal transduction in living organisms. In recent years, with the rapid development of natural product pharmacology, triglycerides have gradually attracted the attention of researchers in fields such as neurological diseases due to their unique bioactivity and multi-target effects. Its potential roles in neuroprotection, anti-inflammation, and metabolic regulation, especially in interactions with targets related to neurodegenerative diseases, provide both the theoretical foundation and practical feasibility for its development into novel therapeutic drugs.
This paper reviews the chemical structure and physicochemical properties of triglycerides, plant origins, and extraction methods, systematically reviews research progress on their pharmacological activity, delves into their mechanisms of action and molecular targets, evaluates pharmacokinetics and safety in combination with druggability parameters, and finally looks ahead to their clinical application prospects, providing scientific basis and reference for subsequent research and development.
The molecular structure of glycerol trioleate consists of a glycerol backbone connected by three oleic acid molecules via ester bonds. Oleic acid (cis-9-octaenoic acid) is a monounsaturated fatty acid whose molecule contains a cis-double bond, giving it a certain degree of flexibility and biological activity. Glycerol trioleate has a molecular formula of C57H104O6 and a molecular weight of 885.4530, with high hydrophobicity (LogP about 14.0), indicating extremely low water solubility (almost zero), making it more suitable for distribution in lipid environments.
Its topological pole surface area (TPSA) is 78.9 Ų, reflecting the exposure area of polar groups in the molecule. Although not high, it is sufficient to support its certain affinity in biofilms. Triglycerides have a high blood-brain barrier penetration ability, which is of great significance for their application in neurological diseases. Additionally, it inhibits the hERG channel, suggesting that cardiotoxicity risk should be prioritized in drug safety assessment. The Ames test result was 0, indicating no significant genetic mutation carcinogenic risk.
In the laboratory, triglycerides are commonly used as sample preparation and gel formation agents for polyacrylamide gel electrophoresis, demonstrating good physicochemical stability and biocompatibility.
Triglycerides are widely found in various vegetable oils, especially olive oil, sunflower oil, rapeseed oil, and other oils rich in oleic acid. Its natural source mainly depends on the biosynthesis pathway of plant fatty acids. After oleic acid is synthesized through the catalytic action of fatty acid synthase and fatty acid desaturation, it further combines with glycerol to form triglycerides.
Traditional methods for extracting glycerol trioleate mainly include solvent extraction and supercritical fluid extraction. Solvent extraction generally uses organic solvents such as hexane and ethanol, obtaining vegetable oils through extraction steps, filtration, and concentration, followed by purification of triglycerol esters through distillation and chromatography techniques. In recent years, supercritical CO2 extraction technology has become an ideal method for extracting high-purity triglycerides due to its green and environmentally friendly nature, strong selectivity, and gentle operation.
In addition, bioenzymatic extraction and synthesis are also gradually receiving attention. Using lipase to catalyze the esterification reaction between glycerol and oleic acid not only improves product purity but also enables precise control of product structure, making it suitable for preparing pharmaceutical-grade triglycerides.
Pharmacological studies on triglycerides mainly focus on their protective effects in neurological diseases and their potential to regulate lipid metabolism. As one of the two components of Lorenzo's oil, triglycerides play a key role in treating X-linked leukodystrophy (X-ALD). Lorenzooil slows the progression of neurodegenerative diseases by regulating the metabolism of long-chain fatty acids in the nervous system. Triglycerides, as an important component, participate in this metabolic regulation process.
In vitro and in vivo experiments, triglycerides have demonstrated anti-inflammatory, antioxidant, and neuroprotective activities. By regulating fatty acid metabolism-related enzymes and receptors, it influences nerve energy metabolism and membrane lipid composition, promoting neuronal survival and functional recovery. Additionally, triglycerides have shown metabolic regulation in Caenorhabditis elegan models, suggesting that they may influence organism health through conserved lipid metabolism pathways.
Although there is limited direct pharmacological research on triglyceride itself, its functional correlation with oleic acid provides theoretical support for its potential biological activity. Oleic acid has been shown to regulate inflammatory responses, improve neural function, and protect cell membrane integrity. Triglycerides, as carriers and storage forms of oleic acid, may exert similar biological effects by releasing oleic acid and its metabolites.
The mechanism of action of triglycerides in neurological diseases involves multiple molecular targets, reflecting their multi-target and multi-pathway regulatory characteristics. The main related targets include:
BACE1 (β-secretase 1): BACE1 is a key enzyme in Alzheimer's disease (AD) that cleaves amyloid precursor protein (APP) to produce β-amyloid protein. Triglycerides may influence BACE1 activity by modulating the lipid environment, reducing the production of harmful β-amyloid protein.
MAPT (microtubule-associated protein Tau): Abnormal phosphorylation of Tau protein is a hallmark of neurodegenerative diseases. Triglycerides may affect the stability and function of tau protein by regulating the composition of cell membrane lipids.
LPAR1 (lipid-lytic phospholipid acid receptor 1): As a receptor for lipid signaling, LPAR1 is involved in neuroprotection and inflammatory responses. Triglyceride metabolites may activate or modulate LPAR1-mediated signaling pathways.
ENPP2 (Exocrine Phospholipase D): Involved in the production of lysophosphatid acid, regulates neuronal proliferation and migration; metabolism of triglycerides may affect ENPP2 activity.
FAAH (fatty acylethanolamine hydrolase): regulates the endocannabinoid system, participating in neuroprotection and anti-inflammation; triglycerides may affect FAAH function by modulating lipid metabolism.
ACE (Acetylcholinesterase): Regulates the degradation of the neurotransmitter acetylcholine, affecting nerve signal transduction.
NFKB1 (nuclear factor κB1): A key inflammatory signal transduction factor, triglycerides may inhibit NFKB1 activation by modulating lipid-mediated signaling pathways, thereby reducing neuroinflammation.
MGLL (Monoacylglycerol Lipase): Involved in lipid metabolism and regulation of endogenous cannabinoids.
FABP3 (fatty acid-binding protein 3): regulates the transport and signal transduction of fatty acids within neurons.
GRIN1 (NMDA receptor subunit 1): Regulates glutamate-mediated excitatory neurotransmission, affecting neuroplasticity and survival.
Through the coordinated regulation of these targets, triglycerides participate in lipid metabolism, signal transduction, inflammation regulation, and neuroprotection in the nervous system, demonstrating their biological value as multifunctional lipid molecules.
The druggability evaluation of triglycerides shows that they have certain advantages and challenges. Its high molecular weight (885.4530) and extremely high hydrophobicity (LogP=14) limit its water solubility, which may affect oral absorption and internal distribution. However, its high blood-brain barrier penetration capability makes its application possible in central nervous system diseases.
In terms of safety, triglycerides inhibit hERG channels, suggesting potential cardiotoxicity risks and requiring strict cardiac safety monitoring during drug development. The Ames test result was negative, indicating no significant genotoxicity risk.
Pharmacokinetic studies are still incomplete, but it is speculated that oleic acid and glycerol are mainly released in the body through the hydrolysis of lipase, which then enters lipid metabolism pathways. Its lipophilic characteristics may lead to accumulation in adipose tissue and cell membranes, affecting its distribution and clearance. In the future, in vivo and in vitro experimental systems will be used to evaluate its absorption, distribution, metabolism, and excretion (ADME) characteristics to guide dosage formulation design and administration protocol optimization.
Triglycerides, as an important component of Lorenzoolin, have shown clinical value in adjunctive treatment of X-ALD. By regulating abnormal fatty acid metabolism in the nervous system, it delays disease progression and offers new ideas for treating lipid metabolism-related neurological diseases.
In the future, with deeper understanding of their mechanisms of action, triglycerides are expected to expand into the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Its multi-target action makes it an ideal candidate molecule for developing compound drugs that regulate lipid metabolism and neuroprotection.
Moreover, the potential of triglycerides to regulate neuroinflammation and improve neurological dysfunction also opens up applications in neuropsychiatric disorders and brain injury repair. By combining nanotechnology with the development of liposomal drug delivery systems, it is expected to overcome limitations such as poor water solubility and low bioavailability, enhancing its clinical application value.
Future research should focus on:
Triglycerides, as natural triglyceride molecules, show broad application prospects in the treatment of neurological diseases due to their unique chemical structure and biological functions. Its multi-target regulation of lipid metabolism and neuroprotective mechanisms provides a theoretical basis for the development of novel neuroprotective agents. Despite challenges such as poor water solubility and potential cardiotoxicity, with advances in drug delivery technologies and molecular modification strategies, triglycerides are expected to become important drug candidates for the treatment of neurodegenerative diseases in the future.
Systematic and in-depth pharmacological mechanism research and clinical evaluation will be key to moving triglycerides from the laboratory to clinical practice. In the future, combined with multidisciplinary research, triglycerides are expected to bring new therapeutic hope for patients with neurological diseases.
Shenshuai
Wenjing
Hedandan
