Product name: D-α-Tocopherol
Synonym name: Emipherol;Eprolin; Eprolin S;Esorb;Viteolin; D-Alpha-Tocopherol; α-Tocopherol; α-Vitamin E
Catalogue No.: SBP02699
Cas No.: 59-02-9
Formula: C₂₉H₅₀O₂
Mol Weight: 430.717
Botanical Source:
Type of Compound: Tocopherols

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams
Inquire for bulk scale.

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

HPLC of D-α-Tocopherol

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

Introduction/Overview

α-Tocopherol (α-Tocopherol), the most bioactive natural isomer in the vitamin E family, has long attracted widespread attention in pharmacology, nutrition, and natural product research due to its outstanding antioxidant properties and diverse biological functions. Its natural stereoisomer (R, R,R)-α-tocopherol is widely found in various vegetable oils such as sunflower oil and olive oil, and is one of the essential trace nutrients for the human body. α-tocopherol not only plays a key role in protecting lipids in cell membranes but also exhibits multiple pharmacological activities including antiviral, anticoagulant, immunomodulatory, and anti-atherosclerosis, with its mechanism of action closely related to multiple molecular targets. This paper will systematically review the chemical structure and physicochemical properties of α-tocopherol, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and, combined with its potential applications in cardiovascular and related diseases, explore its clinical development prospects and future research directions.

Chemical structure and physicochemical properties

The chemical name of α-tocopherol is (R,R,R)-α-tocopherol, with a molecular formula of C29H50O2 and a molecular weight of 430.7 Da. Its structure consists of a 6-hydroxychromoquinone ring with three chiral centers and a saturated side chain (a long-chain isoprene unit rich in methyl substitution). This molecule has two hydrogen bond acceptor sites and a polar surface area (TPSA) of about 29.46 Ų, showing relatively low polarity. A LogP value as high as 10 indicates high hydrophobicity, easily soluble in lipid environments, but poorly soluble in water. Its high hydrophobicity facilitates its localization in the lipid bilayer of cell membranes, exerting antioxidant protective effects.

The stereochemical configuration of α-tocopherol is crucial for its biological activity; naturally occurring (R,R,R)-isomers exhibit stronger bioactivity and bioavailability than their enantiomerics (S,S,S). This compound has a half-life of up to 48 hours, indicating a relatively long duration in the body. Toxicological evaluation showed that the LD50 of α-tocopherol is about 2000 mg/kg, with negative results in hepatotoxicity, hERG channel inhibition, and Ames-induced mutagenic tests, indicating high safety.

Plant Origins and Extraction Methods

α-Tocopherol is mainly found in various vegetable oils, especially sunflower oil and olive oil. In plants, it acts as an important fat-soluble antioxidant, protecting plant cell membranes from oxidative damage. Besides vegetable oils, nuts, grains, and leafy green vegetables also contain certain amounts of α-tocopherol.

Traditional methods for extracting α-tocopherol include solvent extraction, cold pressing, and distillation. Modern extraction technologies focus more on improving extraction efficiency and purity, with commonly used methods including supercritical CO2 extraction, molecular distillation, and high-performance liquid chromatography (HPLC) purification. Supercritical CO2 extraction has become the mainstream technology for industrial-scale extraction of α-tocopherol due to its environmental friendliness, good selectivity, and lack of solvent residue. In addition, enzyme-assisted extraction technology is gradually being applied to improve extraction rates and reduce energy consumption.

Pharmacological activity research

α-tocopherol, as a potent fat-soluble antioxidant, mainly protects cell membrane lipids from oxidative damage by scavenging free radicals and blocking lipid peroxidation chain reactions, thereby exerting its biological effects. Its pharmacological activities cover antioxidant, anti-inflammatory, immunomodulatory, antiviral, anti-atherosclerosis, and anticoagulant effects.

1. Antioxidant effects
   α-Tocopherol can effectively capture lipid peroxidation free radicals, terminate the lipid peroxidation reaction chain, and protect cell membranes and low-density lipoprotein (LDL) from oxidative damage. Its antioxidant effects not only maintain the integrity of cell membranes but also regulate cell signal transduction, preventing oxidative stress-related diseases.

2. Anti-inflammatory and immunomodulatory
   Research shows that α-tocopherol can inhibit the release of inflammatory mediators, lower levels of pro-inflammatory cytokines, regulate immune cell function, and enhance the body's immune response. Its regulation of macrophages, T cells, and natural killer cell functions helps improve chronic inflammatory states.

3. Antiviral effects
   α-tocopherol exhibits potential antiviral activity by regulating cell membrane fluidity and antioxidant mechanisms, inhibiting the replication and infection processes of various viruses.

4. Cardiovascular protective effects
   As an anti-atherosclerosis, α-tocopherol lowers cardiovascular disease risk by reducing oxidative LDL deposition, inhibiting platelet aggregation, and improving vascular endothelial function. Its anticoagulant effect helps prevent thrombosis and maintains hemorheological stability.

Mechanism of action and molecular targets

The multi-biological effects of α-tocopherol are closely related to its action on various molecular targets, especially prominent in the prevention and treatment of cardiovascular diseases. Its main targets include:

• BACE1 (β-secretase 1):α-tocopherol may regulate BACE1 activity, influence oxidative stress-related signaling pathways, and indirectly regulate cell apoptosis and inflammatory responses.
• PTPN1 (protein tyrosine phosphatase 1B): As a negative regulator of insulin signaling, inhibition of PTPN1 helps improve insulin sensitivity and reduce cardiovascular risk associated with metabolic syndrome.
• ESR2 (estrogen receptor β): α-tocopherol may act as anti-inflammatory and antioxidant agents by modulating ESR2-mediated signaling pathways, protecting the cardiovascular system.
• APEX1 (DNA repair enzyme): By regulating APEX1, α-tocopherol participates in intracellular oxidative damage repair, improving cell survival rates.
• AKR1B1 (aldose reductase): Inhibiting AKR1B1 helps alleviate diabetic complications and indirectly protects cardiovascular health.
• SELP (Selectin P): α-tocopherol reduces SELP expression, decreasing platelet adhesion to endothelial cells, and preventing thrombosis.
• NFE2L2 (nuclear factor red blood cell 2-related factor 2): activates the NFE2L2 signaling pathway, enhancing cellular antioxidant defenses.
• SHBG (sex hormone-binding globulin): regulates SHBG levels, affects hormone balance and cardiovascular metabolism.
• TOP1 (Topoisomerase I): Participates in DNA topological regulation and maintains gene stability.
• HIF1A (hypoxia-inducing factor 1α): regulates cellular adaptation to hypoxic environments, promotes angiogenesis and metabolic regulation.

Through these targets, α-tocopherol not only exerts direct antioxidant and anti-inflammatory effects but also regulates cellular signaling networks, improves cardiovascular function, and slows disease progression.

Druggability evaluation and pharmacokinetics

The druggability parameters of α-tocopherol indicate good safety and a long in vivo half-life. Its high lipid solubility (LogP=10) facilitates cell membrane penetration and distribution in lipid environments, but may also limit its water solubility and oral bioavailability. Its low polarity and low number of hydrogen bond receptors (2) help cross the blood-brain barrier, suggesting its potential application in central nervous system diseases.

Pharmacokinetic studies show that α-tocopherol is mainly metabolized in the liver body, with a half-life of about 48 hours, providing a relatively long duration and making it suitable for daily supplementation. Toxicological evaluation showed low acute toxicity (LD50 about 2000 mg/kg), no significant hepatotoxicity or cardiotoxicity (hERG inhibitor negative), and no mutagenic risk (Ames test negative), indicating high safety.

However, the high lipid solubility of α-tocopherol also presents challenges in formulation development, such as solubility limitations and unstable bioavailability, which require optimization through modern drug delivery systems like nanocarriers and liposomes.

Prospects and outlooks for clinical applications

α-tocopherol, as a natural antioxidant and multifunctional pharmacologically active molecule, has broad application prospects in clinical nutritional supplementation and disease prevention. Its protective effect in cardiovascular diseases is particularly outstanding, as it can regulate oxidative stress, inflammatory responses, and hemorheology through multiple targets, reducing the risk of atherosclerosis and thrombosis.

In addition, the potential of α-tocopherol in immunomodulatory, antiviral, and neuroprotective fields is gradually being recognized. In the future, combining precision medicine with molecular targeting strategies, α-tocopherol is expected to be developed as a multi-target therapeutic drug, especially for applications in metabolic syndrome, neurodegenerative diseases, and chronic inflammatory diseases.

However, current clinical studies still face controversies regarding dosage, route of administration, and long-term safety, requiring further large-scale, multicenter clinical trials to clarify the best treatment regimens and indications. Moreover, innovations in formulation technology will help improve bioavailability and therapeutic outcomes.

Conclusion

As the most active natural isomer in the vitamin E family, α-tocopherol demonstrates rich pharmacological activity and good safety due to its unique chemical structure and excellent antioxidant properties. Its multi-target mechanism provides new ideas for the prevention and treatment of cardiovascular diseases and related chronic diseases. In the future, with continuous advances in extraction technology and drug delivery systems, as well as deeper analysis of its molecular mechanisms, α-tocopherol is expected to play a greater role in clinical treatment and health promotion, becoming an important model for pharmacological research and application of natural products.