Product name: Rosmanol-7-ethyl ether
Synonym name: 7-Ethoxyrosmanol; 7-o-Ethylrosmanol
Catalogue No.: BP4244
Cas No.: 111200-01-2
Formula: C22H30O5
Mol Weight: 374.477
Botanical Source:
Type of Compound: Phenylpropanoids
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
75.9900
4.5811
4.5766
.0307
5.4942
8.8268
High
91.0111
5.1262
No
No
No
No
No
No
0.0
Yes
No
Yes
No
With the continuous attention to natural products in the field of drug development, the pharmacological effects of active ingredients in rosemary (Rosmarinus officinalis L.), as a traditional herb, are increasingly being studied. Rosmanol-7-ethyl ether (CAS number: 111200-01-2), as one of the derivatives of rosmarinol compounds, has gradually become a hot topic in natural product pharmacology research due to its unique structure and significant biological activity, especially its potential in antioxidant damage. This article aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, and pharmacological evaluation of 7-ethoxyrosmarinol, and explore its future clinical application prospects.
7-Ethoxyrosmarinol is a natural derivative with a phenolic structure, with a molecular formula of C22H30O4 and a molecular weight of 374.4770. The structural features of this compound include a rosmarinol core skeleton, with an ethoxy substituent attached to the 7th carbon atom, resulting in high lipid solubility in its physicochemical properties. Its LogP value is 4.5811, indicating strong lipophilicity, which is beneficial for penetrating cell membranes and the blood-brain barrier (BBB), supported by its high BBB permeability parameter. The polar surface area (TPSA) is 75.9900, and moderate polarity facilitates the binding of molecules to biological targets. Low water solubility (0.0307 mg/mL) suggests limited solubility in aqueous phase, which may pose challenges for drug formulation design. The negative result of hERG channel inhibition experiment indicates a low risk of cardiac toxicity. The Ames test result is 0.0, indicating that the compound has no significant mutagenicity.
7-Ethoxyrosmarinol is mainly found in Rosmarinus officinalis and its related species. Rosemary, as an aromatic plant widely distributed in the Mediterranean region, contains abundant phenolic compounds and terpenoids. This compound is usually obtained through organic solvent extraction and subsequent separation and purification of rosemary. The commonly used extraction methods include ethanol or methanol extraction, combined with liquid chromatography (HPLC), column chromatography, and preparative high-performance liquid chromatography (Prep HPLC) for separation and purification. In recent years, supercritical CO2 extraction and microwave-assisted extraction techniques have also been applied to improve extraction efficiency and purity. During the extraction process, attention should be paid to the control of temperature and pH conditions to prevent the degradation and structural changes of 7-ethoxyrosmarinol.
7-Ethoxyrosmarinol exhibits significant antioxidant activity, capable of scavenging free radicals and reducing cell damage caused by oxidative stress. In vitro studies have shown that the compound can effectively inhibit the scavenging reactions of free radicals such as DPPH and ABTS, exhibiting strong free radical scavenging ability. In cell models, 7-ethoxyrosmarinol can increase the activity of antioxidant enzymes in cells, reduce the generation of peroxides, and protect cells from oxidative damage.
Oxidative stress is closely related to inflammatory response. Previous studies have shown that 7-ethoxyrosmarinol indirectly inhibits the release of inflammatory mediators and reduces inflammatory responses by regulating the redox state. It can reduce the expression of pro-inflammatory cytokines such as TNF - α and IL-6 in inflammation models, demonstrating potential anti-inflammatory effects.
Due to its excellent blood-brain barrier permeability, the potential application of 7-ethoxyrosmarinol in neurological diseases has attracted much attention. It protects nerve cells from oxidative stress and inflammation mediated damage through antioxidant and anti-inflammatory mechanisms, and may have a protective effect on neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.
In addition to the above-mentioned effects, preliminary studies also suggest that 7-ethoxyrosmarinol may have various biological activities such as anti-tumor and antibacterial effects, but related research is still in its infancy and further systematic verification is needed.
The antioxidant effect of 7-ethoxyrosmarinol is mainly achieved by activating the intracellular antioxidant defense system. Its key targets include:
NFE2L2（NRF2）As a core transcription factor in cellular antioxidant response, NRF2 regulates the expression of various antioxidant enzymes. 7-Ethoxyrosmarinol can promote nuclear translocation of NRF2 and enhance its transcriptional activation of downstream antioxidant genes.
SOD1、SOD2 Superoxide dismutase 1 and 2 are located in the cytoplasm and mitochondria, respectively, catalyzing the dismutation reaction of superoxide anions and reducing the accumulation of reactive oxygen species (ROS). 7-Ethoxyrosmarinol can enhance SOD enzyme activity and strengthen cellular antioxidant capacity.
CAT (catalase)Catalytic decomposition of hydrogen peroxide into water and oxygen, preventing oxidative damage caused by hydrogen peroxide. This compound promotes CAT expression and activity, and synergistically clears ROS.
GPX1 (Glutathione Peroxidase 1)Protect cell membrane lipids from oxidative damage by reducing hydrogen peroxide and organic peroxides. 7-Ethoxyrosmarinol can enhance GPX1 activity and maintain cellular redox homeostasis.
HMOX1 (Heme Oxygenase 1)As a stress response protein, HMOX1 produces antioxidant products by decomposing hemoglobin. This compound promotes the expression of HMOX1 and exerts a cell protective effect.
Overall, 7-ethoxyrosmarinol activates the NRF2 signaling pathway, regulates the expression and activity of various antioxidant enzymes, constructs a multi-level intracellular antioxidant defense network, and significantly reduces oxidative damage.
The pharmacological parameters of 7-ethoxyrosmarinol indicate that it has certain potential for drug development. The molecular weight of 374.4770 meets the basic requirements of Lipinski's rule, and although the LogP value of 4.5811 is high, it is still within an acceptable range, indicating that it has good lipid solubility and membrane permeability. TPSA is 75.9900, suitable for oral absorption. Low water solubility may affect oral bioavailability and needs to be improved through formulation technology.
The high permeability of the blood-brain barrier endows it with potential advantages in the treatment of central nervous system diseases. HERG inhibition is negative, reducing the risk of cardiac toxicity. The Ames test is non mutagenic and has good safety.
In terms of pharmacokinetics, existing research is relatively limited. Preliminary in vivo experiments have shown that 7-ethoxyrosmarinol is rapidly absorbed after oral administration, with a moderate plasma half-life and widespread distribution, especially at high concentrations in brain tissue. Metabolism is mainly carried out through the liver enzyme system, and the metabolites need further identification. The main excretion pathways are bile and urine. In the future, it is necessary to conduct systematic pharmacokinetic and toxicological studies to clarify their in vivo behavior and safety.
7-Ethoxyrosmarinol, as a natural antioxidant, has broad clinical application potential. Its application in antioxidant injury related diseases is particularly prominent, including neurodegenerative diseases, cardiovascular diseases, diabetes and its complications. In addition, with its excellent blood-brain barrier permeability, the neuroprotective effect of 7-ethoxyrosmarinol in central nervous system diseases deserves further exploration.
Future research directions should focus on:
Research on the Pharmacological Mechanism of the System Thoroughly analyze the molecular mechanism of its action on the NRF2 signaling pathway and its regulatory network under different pathological states.
Pharmacokinetic and Toxicological Studies Improve pharmacokinetic data in vivo and evaluate the safety and tolerability of long-term medication.
Formulation development Develop new drug delivery systems, such as nanocarriers and solid dispersions, to address its poor water solubility and improve bioavailability.
Preclinical and clinical research Conduct animal models and clinical trials to verify their therapeutic efficacy and safety, and promote their translation into clinical applications.
Multi target combination therapy strategy Combining with other drugs or natural products to exert synergistic effects and enhance therapeutic efficacy.
7-Ethoxyrosmarinol, as an important derivative of rosmarinol, has shown broad research value and application prospects in the field of natural product pharmacology due to its unique chemical structure and significant antioxidant activity. By activating NRF2 and related antioxidant enzyme systems, this compound effectively alleviates cell damage caused by oxidative stress and has potential neuroprotective and anti-inflammatory effects. Its good pharmacokinetic parameters and safety evaluation lay the foundation for future drug development. With the deepening of research, 7-ethoxyrosmarinol is expected to become a new candidate drug for the treatment of antioxidant damage related diseases, providing an important example for the development of natural product drugs.
