Synonym name: 2-Hydroxycymene; Cymophenol; p-Cymen-2-ol; 5-Isopropyl-o-cresol
Catalogue No.: BP0319
Cas No.: 499-75-2
Formula: C₁₀H₁₄O
Mol Weight: 150.221
Botanical Source: many essential oils. Esp. found in the Labiatae. Thyme oil (

HPLC of Carvacrol

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

Introduction/Overview

Carvacrol (CAS No.: 499-75-2) is a monoterpene natural compound widely found in various aromatic plants, especially abundant in thyme (Thymus vulgaris) and oregano (Origanum vulgare). As a natural compound with significant biological activity, aromacrephenol not only has good oral bioavailability but can also effectively cross the blood-brain barrier, demonstrating its potential application value in treating central nervous system diseases. In recent years, with advances in natural product pharmacology and molecular biology technologies, the multiple pharmacological activities and mechanisms of aromatic ketalin have been deeply analyzed, covering antioxidant, antibacterial, antifungal, cancer, anti-inflammatory, liver-protecting, antispasmodic, and vascular relaxation functions. Its role in cell cycle regulation and apoptosis induction, especially by downregulating key Notch signaling pathway molecules Notch-1 and Jagged-1, further reveals its antitumor potential. This paper aims to systematically review the chemical structure, origin, pharmacological activity, mechanism of action, druggability, and clinical application prospects of Cithovaleol, providing a theoretical basis and research direction for its development as a novel natural medicine.

Chemical structure and physicochemical properties

The chemical name of Citronol is 5-isopropyl-2-cresol, with a molecular formula of C_10H_14O and a molecular weight of 150.22. Its structure belongs to the monoterpene class, with a benzene ring at its core, containing a hydroxyl (-OH) and isopropyl side chain. This structure imparts strong hydrophobicity to spicylene oleole, with a LogP value of 3.48, indicating good lipid solubility and facilitating penetration of cell membranes and the blood-brain barrier. The topological pole surface area (TPSA) is 20.23 Ų, with only one hydrogen bond acceptor, further supporting its high permeability and oral absorption capacity. At room temperature, spicylene phenol is a colorless to pale yellow liquid with a distinctive aromatic odor. It is easily soluble in ethanol, ether, and other organic solvents, but has relatively poor water solubility. It has high chemical stability and is suitable for the development of various formulation forms.

Plant Origins and Extraction Methods

Aromacreamol is mainly found in essential oils of Lamiaceae plants, with thyme and oregano being particularly representative. Its content varies depending on plant species, geographical environment, harvest time, and extraction process. Traditional extraction methods mainly include distillation and solvent extraction methods. Steam distillation is the most commonly used industrial extraction technique and can effectively separate the aromatic nepotol components from plant essential oils. In recent years, the application of green technologies such as supercritical CO_2 extraction and microwave-assisted extraction has improved extraction efficiency and purity, while reducing the use of organic solvents, aligning with the modern trend of natural product extraction. After extraction, qualitative and quantitative analysis of viperol content and purity is usually performed using gas chromatography-mass spectrometry (GC-MS) technology.

Pharmacological activity research

Antioxidant activity

Olequin demonstrates remarkable free radical scavenging ability, inhibiting lipid peroxidation and protecting cells from oxidative stress damage. In vitro DPPH and ABTS radical scavenging experiments and cell models have confirmed their antioxidant effects, with related mechanisms involving regulation of endogenous antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GPx).

Antibacterial and antifungal activity

Aromacrephenol exhibits potent inhibitory effects on various Gram-positive and Gram-negative bacteria, targeting bacterial membrane structures and metabolic enzyme systems. Its targets include bacterial anti-apoptotic protein MCL1, immunomodulatory receptor TLR4, tyrosine phosphatase PTPN1, and others, which can disrupt bacterial membrane integrity and interfere with DNA replication and protein synthesis. It also has the ability to inhibit growth and biofilm formation against fungi such as Candida albicans, demonstrating broad-spectrum antimicrobial potential.

Anticancer activity

Aromacreaquin induces cell cycle arrest in various tumor cell lines, mainly stagnating in the G0/G1 phase, inhibiting cell proliferation. The mechanism involves downregulating key proteins in the Notch signaling pathway, Notch-1 and Jagged-1, blocking proliferation signal transmission in tumor cells and promoting apoptosis. Viperquin can also activate mitochondrial pathways, regulate the expression of Bcl-2 family proteins, and induce apoptosis. Additionally, viperol indirectly exerts anti-tumor effects by inhibiting tumor-related inflammatory factors and oxidative stress.

Anti-inflammatory and liver-protective effects

Aromatic nephelin alleviates inflammatory responses by inhibiting inflammatory mediators such as TNF-α, IL-6, and NF-κB signaling pathways. Its hepatoprotective effect is reflected in reducing liver enzyme levels, alleviating histopathological damage, and providing antioxidant protection in models of liver injury. Related studies have shown that vipercol can regulate the antioxidant defense system within liver cells and inhibit the process of liver fibrosis.

Antispasmodic and vasorelaxing effects

Viperquinol has a smooth muscle relaxing effect and can alleviate spasmodic diseases by regulating calcium channels and NO (nitric oxide) signaling pathways. Its vasodilatory effect helps improve microcirculation, lower blood pressure, and demonstrates cardiovascular protective potential.

Mechanism of action and molecular targets

The multi-target mechanism of viperol is the basis of its broad pharmacological activity. For bacterial infections, vibraquin works by regulating the following key proteins:

• MCL1: An anti-apoptotic protein, viperol promotes bacterial cell death by regulating its expression.
• TLR4: Immune receptor, aromacreaquin regulates its signaling transduction, enhancing host immune responses.
• PTPN1: Protein tyrosine phosphatase, involved in signal transduction; aromacrephenol affects bacterial metabolism by inhibiting its activity.
• APEX1 :D NA repair enzyme, and aromacrephenol interfere with bacterial DNA repair mechanisms.
• SERPINE1. PRKCA, GYRA, GYPB, FTSZ, FABI: involved in bacterial growth, metabolism, and cell wall synthesis, and aromacreta phenol inhibits bacterial proliferation through multi-target action.

In tumor cells, viperol mainly blocks cell cycle progression and induces apoptosis by downregulating key molecules in the Notch signaling pathway, Notch-1 and Jagged-1. Additionally, viperol regulates Bcl-2 family proteins and mitochondrial membrane potentials, activating intracellular apoptosis signaling pathways.

Druggability evaluation and pharmacokinetics

The molecular weight of spicylene is 150.22, which complies with the Lipinski rule, with a LogP of 3.48, demonstrating good lipid solubility and cell membrane permeability. TPSA is only 20.23 Ų, indicating its high blood-brain barrier penetration capacity, making it suitable for drug development for central nervous system diseases. It has 1 hydrogen bond receptor, further supporting good oral absorption.

Toxicological evaluation showed that the LD50 of Viperquinol is about 980 mg/kg, with low toxicity, no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition. The Ames test result was negative, indicating no risk of mutagenicity. These safety data lay the foundation for its clinical application.

Pharmacokinetic studies have shown that spicy ketaphenol is rapidly absorbed orally, has a moderate plasma half-life, and can effectively distribute in brain tissue, demonstrating good in vivo stability and bioavailability. Its metabolism mainly occurs through the hepatic enzyme system, and the metabolites are safe.

Prospects and outlooks for clinical applications

As a versatile natural product, viperoneol has broad clinical application potential. Its antibacterial and antifungal properties make it an ideal choice for natural preservatives and food additives, especially advantageous in combating resistant strains. Its anticancer activity offers potential applications in adjuvant tumor therapy, especially in combination chemotherapy or targeted therapy, where synergistic effects are achieved. Its anti-inflammatory, liver-protecting, and vasodilatory effects offer new approaches for the treatment of chronic inflammatory diseases, liver diseases, and cardiovascular diseases.

Future research should focus on preclinical in vivo pharmacodynamics and safety evaluation of viperoneol, optimizing its formulation and delivery routes to enhance bioavailability and targeting. At the same time, based on its multi-target mechanism of action and combined with modern molecular targeting technologies, its derivatives or compound formulations are being developed to expand its clinical indications. The application of viperoneol in neurological diseases is also worth further exploration, especially its ability to cross the blood-brain barrier and provide opportunities for drug development for neurodegenerative diseases.

Conclusion

As a natural monoterpenol with a wide source, simple structure, and rich bioactivity, it exhibits multiple pharmacological activities and good druggability. Its multiple mechanisms of action—antibacterial, anticancer, anti-inflammation, and neuroprotection—provide a solid foundation for its development as a novel natural medicine. In the future, through in-depth mechanistic research, pharmacokinetic optimization, and clinical translation, aromatic ketamine is expected to become an important player in the development of natural product drugs, promoting the application and advancement of natural products in modern medicine.