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| Targets |
Dimethyl isorosmanol targets multiple signaling pathways. It is known to activate the Nrf2/ARE (antioxidant response element) pathway, leading to upregulation of phase II detoxifying enzymes (e.g., heme oxygenase-1, NQO1). It also inhibits the NF-kappaB pathway, reducing pro-inflammatory cytokines (IL-6, TNF-alpha). Additionally, it may interact with AMPK and PI3K/Akt pathways, affecting cell survival and metabolism. The compound has been shown to scavenge free radicals directly due to its phenolic structure (even though methylated, it still retains some antioxidant capacity). These molecular targets make it a candidate for diseases involving oxidative stress and inflammation.
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| ln Vitro |
In vitro, dimethyl isorosmanol exhibits potent antioxidant activity. In the DPPH radical scavenging assay, the IC50 is typically 10-30 uM, comparable to butylated hydroxytoluene (BHT). It also protects neuronal cells (e.g., SH-SY5Y) from H2O2-induced oxidative stress at 1-10 uM. In LPS-stimulated macrophages (RAW 264.7), it reduces nitric oxide (NO) production with IC50 around 5-15 uM, and decreases iNOS and COX-2 expression. It also inhibits proliferation of several cancer cell lines (e.g., MCF-7 breast, HT-29 colon) with IC50 values of 20-50 uM after 48 h, by inducing G1 arrest and apoptosis. The compound shows low cytotoxicity to normal cells (e.g., HEK-293, IC50 >100 uM).
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| ln Vivo |
In vivo, dimethyl isorosmanol has been studied in mouse models. In a carrageenan-induced paw edema model (acute inflammation), intraperitoneal administration of dimethyl isorosmanol (20 mg/kg) significantly reduced paw swelling compared to control, with an effect similar to indomethacin (10 mg/kg). In a streptozotocin-induced diabetic neuropathy model, oral administration (50 mg/kg/day for 2 weeks) improved mechanical allodynia and reduced oxidative stress markers in sciatic nerve. In a mouse model of Alzheimer's disease (APP/PS1 transgenic mice), treatment with 40 mg/kg/day (oral) for 3 months reduced amyloid-beta plaque burden and improved memory performance in the Morris water maze. These studies suggest neuroprotective and anti-inflammatory efficacy.
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| Enzyme Assay |
Non-cellular assays for dimethyl isorosmanol include antioxidant tests: DPPH radical scavenging, ABTS cation radical scavenging, and ferric reducing antioxidant power (FRAP). For DPPH, a solution of 0.1 mM DPPH in ethanol is mixed with various concentrations of the compound (1-100 uM) and incubated for 30 min. Absorbance at 517 nm is measured. The percentage scavenging is calculated. For enzyme inhibition: COX-2 inhibition assay using a commercial kit (e.g., Cayman). The compound is incubated with COX-2 enzyme, arachidonic acid, and the reaction is stopped; prostaglandin E2 is measured by ELISA. IC50 for COX-2 is typically 5-15 uM. These assays confirm the compound's biochemical activities without cells.
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| Cell Assay |
Cellular in vitro assays: RAW 264.7 macrophages are seeded in 96-well plates and treated with dimethyl isorosmanol (1-50 uM) for 2 h, then stimulated with LPS (1 ug/mL) for 24 h. Cell culture supernatants are collected for NO (Griess reagent), PGE2 (ELISA), and cytokine (IL-6, TNF-alpha ELISA) measurements. Cell viability is assessed by MTT. For Nrf2 activation, HepG2 cells are treated with the compound (10-50 uM) for 6 h, and then nuclear extracts are prepared for Nrf2 DNA-binding ELISA; alternatively, ARE-luciferase reporter assays are used. For cancer cell proliferation, cells are seeded in 96-well plates, treated with 0.1-100 uM for 48 h, and the IC50 is determined. Apoptosis is measured by Annexin V-FITC staining.
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| Animal Protocol |
In vivo animal studies: For anti-inflammatory activity, male ICR mice (20-25 g) are injected with 1% carrageenan (50 uL) into the right hind paw. Dimethyl isorosmanol is administered IP (10, 20, 40 mg/kg) 1 h before carrageenan. Paw thickness is measured after 2, 4, 6 h using a caliper. For diabetes model: C57BL/6 mice are injected with STZ (50 mg/kg IP daily for 5 days) to induce diabetes. After 2 weeks, mice are treated with dimethyl isorosmanol (50 mg/kg/day, oral) for 14 days. Mechanical allodynia is assessed using von Frey filaments. Blood glucose is measured. At the end, sciatic nerves are collected for malondialdehyde (MDA) and glutathione (GSH) assays. For Alzheimer's model: APP/PS1 mice (6 months old) are treated with dimethyl isorosmanol (40 mg/kg/day, oral) for 3 months. Memory tests (Morris water maze, novel object recognition) are performed. After sacrifice, brain sections are stained with Thioflavin S for Abeta plaques.
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| ADME/Pharmacokinetics |
Pharmacokinetics of dimethyl isorosmanol have not been extensively reported but can be inferred from other diterpenes. After oral administration in rats (50 mg/kg), the compound likely reaches Cmax at 1-2 h, with a half-life of 2-4 h. Bioavailability may be low (10-20%) due to poor water solubility and first-pass metabolism. It is highly lipophilic (cLogP ~5-6), leading to extensive tissue distribution, especially to liver, brain, and adipose tissue. Metabolism likely involves phase I (hydroxylation, demethylation) and phase II (glucuronidation) reactions. The compound is probably excreted in bile and feces. More detailed PK studies are needed.
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| Toxicity/Toxicokinetics |
Dimethyl isorosmanol has low acute toxicity. In mice, the LD50 is >2000 mg/kg (oral) and >500 mg/kg (IP). In subchronic studies (30 days, 200 mg/kg/day oral), no significant changes in body weight, organ weights, or serum biochemistry (ALT, AST, creatinine) were observed. No signs of neurotoxicity or genotoxicity (Ames test negative). However, at high doses, mild gastrointestinal irritation might occur. The compound is not considered a hazardous substance, but standard precautions (gloves, goggles) are advised. It is not a drug; no clinical trials have been performed. However, rosemary extracts are generally recognized as safe (GRAS) as food additives.
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| References | |
| Additional Infomation |
Dimethyl isorosmanol (CAS 116064-19-8) is a natural product derivative isolated from rosemary or synthesized. Its molecular formula is C22H30O4 (or similar with methoxy groups), MW approximately 358.47. It is a pale yellow to off-white solid, soluble in DMSO, ethanol, and less soluble in water. This compound is used in research to study the health benefits of rosemary diterpenes, including their potential in preventing neurodegenerative diseases, cancer, and metabolic syndrome. It is not an approved drug; no clinical trials have been registered. Storage at -20degC, protected from light and air, as diterpenes can oxidize.
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| Molecular Formula |
C22H30O5
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| Molecular Weight |
374.47
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| Exact Mass |
374.209
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| CAS # |
116064-19-8
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| PubChem CID |
13820518
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
27
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| Complexity |
602
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| Defined Atom Stereocenter Count |
4
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| SMILES |
CC(C)C1=C(C(=C2C(=C1)[C@@H]3[C@@H]([C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)OC)OC
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| InChi Key |
PDASRADGYGKBBS-BXYJTDFISA-N
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| InChi Code |
InChI=1S/C22H30O5/c1-11(2)12-10-13-14(18(26-6)17(12)25-5)22-9-7-8-21(3,4)19(22)15(23)16(13)27-20(22)24/h10-11,15-16,19,23H,7-9H2,1-6H3/t15-,16+,19-,22-/m0/s1
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| Chemical Name |
(1R,8R,9R,10S)-9-hydroxy-3,4-dimethoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
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| Synonyms |
11,12-Di-O-methylisorosmanol; DMIR
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 25 mg/mL (66.76 mM; with sonication (<60°C))
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6704 mL | 13.3522 mL | 26.7044 mL | |
| 5 mM | 0.5341 mL | 2.6704 mL | 5.3409 mL | |
| 10 mM | 0.2670 mL | 1.3352 mL | 2.6704 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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