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
As natural products continue to attract attention in drug development, Rosmarinus officinalis L., as a traditional herbal medicine, has increasingly in-depth research into the pharmacological effects of its active ingredients. 7-Ethoxyrosemary Ether (Rosmanol-7-ethyl ether, CAS No.: 111200-01-2), as one of the derivatives of rosemary phenols, 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 paper aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, and druggability evaluation of 7-ethoxyrosemarol, exploring its future clinical application prospects.
7-Ethoxyrosemaryol is a natural product derivative with a phenolic structure, molecular formula C_22H_30O_4, and molecular weight 374.4770. The structural features of this compound include a rosemary core backbone, with an ethoxy substituent attached to the 7-position carbon atom, giving it high lipid solubility in physical and chemical properties. Its LogP value is 4.5811, indicating strong lipophilicity that facilitates penetration of cell membranes and the blood-brain barrier (BBB), supported by its high BBB permeability parameters. The polar surface area (TPSA) is 75.9900, and moderate polarity helps bind molecules to biological targets. Low water solubility (0.0307 mg/mL) suggests limited solubility in the aqueous phase, possibly challenging drug formulation design. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, indicating that this compound does not show significant mutagenicity.
7-Ethoxyrosemaryl is mainly found in rosemary (Rosmarinus officinalis) and its related species. Rosemary, as an aromatic plant widely distributed in the Mediterranean region, contains abundant phenolic compounds and terpenes. This compound is typically obtained through the organic solvent extraction and subsequent separation and purification of rosemary. Common 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 CO_2 extraction and microwave-assisted extraction technologies have also been applied to improve extraction efficiency and purity. During extraction, attention must be paid to controlling temperature and pH conditions to prevent degradation and structural changes of 7-ethoxyrosemaryol.
7-Ethoxyrosemaryol exhibits significant antioxidant activity, scavenging free radicals and reducing cell damage caused by oxidative stress. In vitro studies have shown that this compound can effectively inhibit the scavenging reactions of free radicals such as DPPH and ABTS, demonstrating strong free radical capture capabilities. In cell models, 7-ethoxyrosemaryl can enhance the activity of intracellular antioxidant enzymes, reduce peroxide production, and protect cells from oxidative damage.
Oxidative stress is closely related to inflammatory responses. Previous studies have shown that 7-ethoxyrosemaryl indirectly inhibits the release of inflammatory mediators by regulating redox states, thereby alleviating inflammatory responses. In inflammation models, it can reduce the expression of pro-inflammatory cytokines such as TNF-α and IL-6, demonstrating potential anti-inflammatory effects.
Given its excellent blood-brain barrier permeability, the potential application of 7-ethoxyrosemary phenol in neurological diseases has attracted significant attention. Through antioxidant and anti-inflammatory mechanisms, it protects nerve cells from oxidative stress and inflammation-mediated damage, potentially providing protection against neurodegenerative diseases such as Alzheimer's and Parkinson's.
In addition to the above effects, preliminary studies suggest that 7-ethoxyrosemaryphenol may possess various biological activities such as antitumor and antibacterial properties, but related research is still in its early stages and requires further systematic validation.
The antioxidant effect of 7-ethoxyrosemariol is mainly achieved by activating the intracellular antioxidant defense system. Key targets include:
NFE2L2 (NRF2): As a core transcription factor in cellular antioxidant responses, NRF2 regulates the expression of various antioxidant enzymes. 7-Ethoxyrosemaryol can promote NRF2 nuclear translocation, enhancing its transcriptional activation of downstream antioxidant genes.
SOD1 and SOD2: Superoxide dismutases 1 and 2 are located in the cytoplasm and mitochondria respectively, catalyzing the disproportionation of superoxide anions and reducing the accumulation of reactive oxygen species (ROS). 7-Ethoxyrosemaryl can enhance SOD enzyme activity and enhance cellular antioxidant capacity.
CAT (Catalase): Catalyzes the breakdown of hydrogen peroxide into water and oxygen, preventing oxidative damage caused by hydrogen peroxide. This compound promotes CAT expression and activity, synergistically clearing ROS.
GPX1 (glutathione peroxidase 1): protects cell membrane lipids from oxidative damage by reducing hydrogen peroxide and organic peroxides. 7-Ethoxyrosemaryl can enhance GPX1 activity and maintain cellular redox homeostasis.
HMOX1 (Heme oxygenase 1): As a stress response protein, HMOX1 produces antioxidant products by breaking down hemoglobin. This compound promotes the expression of HMOX1 and exerts its protective effect on cells.
In summary, 7-ethoxyrosemaryol activates the NRF2 signaling pathway, regulates the expression and activity of various antioxidant enzymes, builds a multi-layered intracellular antioxidant defense network, and significantly reduces oxidative damage.
The druggability parameters of 7-ethoxyrosemary phenol indicate that it has certain potential for drug development. The molecular weight of 374.4770 meets the basic requirements of the Lipinski rule. Although the LogP value of 4.5811 is relatively high, it remains within an acceptable range, indicating good lipid solubility and membrane permeability. TPSA is 75.9900, suitable for oral absorption. Low water solubility may affect oral bioavailability, requiring improvement through formulation technology.
The high permeability of the blood-brain barrier gives it potential advantages in treating central nervous system diseases. hERG inhibitors are negative, reducing the risk of cardiotoxicity. The Ames test is non-mutagenic and relatively safe.
In terms of pharmacokinetics, current research is relatively limited. Preliminary in vivo experiments show that 7-ethoxyrosemariol is rapidly absorbed orally, has a moderate plasma half-life, and is widely distributed, especially at high concentrations in brain tissue. Metabolism mainly occurs through hepatic enzyme systems, and the metabolites still require further identification. The main excretion routes are bile and urine. In the future, systematic pharmacokinetics and toxicology studies are needed to clarify its in vivo behavior and safety.
7-Ethoxyrosemaryol, as a natural antioxidant, has broad clinical application potential. Its application is particularly prominent in diseases related to antioxidant damage, including neurodegenerative diseases, cardiovascular diseases, diabetes, and its complications. Moreover, thanks to its excellent blood-brain barrier penetration, the neuroprotective effects of 7-ethoxyrosemary phenol in central nervous system diseases are worth further exploration.
Future research directions should focus on:
Systematic pharmacological mechanism research: In-depth analysis of its molecular mechanisms on the NRF2 signaling pathway and its regulatory networks under different pathological states.
Pharmacokinetics and toxicology studies: Improving in vivo pharmacokinetic data to assess the safety and tolerability of long-term medication.
Formulation development: To address its poor water solubility, new drug delivery systems such as nanocarriers and solid dispersions are developed to improve bioavailability.
Preclinical and clinical research: Conduct animal models and clinical trials to verify therapeutic effects and safety, promoting their translation into clinical applications.
Multi-target combination therapy strategy: combining other drugs or natural products to create synergistic effects and enhance therapeutic outcomes.
7-Ethoxyrosemaryol, as an important derivative of rosemary phenols, demonstrates 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, possessing potential neuroprotective and anti-inflammatory effects. Its excellent druggability parameters and safety evaluation lay the foundation for future drug development. With further research, 7-ethoxyrosemaryol is expected to become a novel candidate drug for treating diseases related to antioxidant damage, providing an important example for the development of natural product drugs.
