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Methyl carnosate

Cat No.:V39053 Purity: ≥98%
Methyl camosate is a diterpene extracted from sage or rosemary that has potent antioxidant and anti-bacterial effect.
Methyl carnosate
Methyl carnosate Chemical Structure CAS No.: 82684-06-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Methyl camosate is a diterpene extracted from sage or rosemary that has potent antioxidant and anti-bacterial effect.
Methyl carnosate is a methyl ester derivative of carnosic acid, a naturally occurring phenolic diterpene abundantly found in the leaves of rosemary (Rosmarinus officinalis) and sage (Salvia officinalis). This bioactive compound exhibits a diverse range of pharmacological properties, including potent antioxidant, anti-inflammatory, and antimicrobial activities. Methyl carnosate has attracted significant interest in nutraceutical and pharmaceutical research as a potential therapeutic agent for managing oxidative stress-related disorders and infectious diseases.
Biological Activity I Assay Protocols (From Reference)
Targets
Methyl carnosate does not have a single defined molecular target, but rather exerts its biological effects through multiple mechanisms. As an antioxidant, it directly scavenges free radicals and reactive oxygen species (ROS). Its anti-inflammatory activity is mediated through the inhibition of pro-inflammatory signaling pathways including NF-kappaB and the suppression of inflammatory mediators such as COX-2 and nitric oxide. The antimicrobial action of Methyl carnosate involves disruption of bacterial cell membranes, particularly against Gram-positive pathogens.
ln Vitro
In relation to Bacillus cereus, methyl carnosate exhibits antibacterial action [2].
In vitro studies have confirmed the antibacterial activity of Methyl carnosate against various pathogenic bacteria, particularly against Bacillus cereus. The compound demonstrates dose-dependent growth inhibition in bacterial cultures, likely through disruption of cell membrane integrity and interference with cellular metabolism. Its antioxidant capacity has been confirmed in cell-free chemical assays such as DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, ABTS cation decolorization, and ferric reducing antioxidant power (FRAP) tests. These assays collectively demonstrate the ability of Methyl carnosate to neutralize various types of free radicals.
ln Vivo
The in vivo efficacy of Methyl carnosate has been documented in preclinical animal models of inflammation and oxidative stress. Oral or intraperitoneal administration of the diterpene has been shown to reduce markers of systemic inflammation, including the production of pro-inflammatory cytokines such as TNF-alpha and IL-6. In models of chemically induced oxidative injury, Methyl carnosate treatment leads to the restoration of endogenous antioxidant enzyme activities (e.g., superoxide dismutase, catalase, glutathione peroxidase) and a reduction in lipid peroxidation end-products such as malondialdehyde.
Enzyme Assay
For in vitro antioxidant assays, the DPPH radical scavenging activity of Methyl carnosate is assessed by mixing 100 microL of various concentrations of the test compound (dissolved in methanol or ethanol) with 100 microL of a 0.1 mM DPPH solution in a 96-well plate. The mixture is incubated for 30 minutes at room temperature in the dark. Absorbance is measured at 517 nm using a microplate reader. The percentage of radical scavenging activity is calculated relative to a control (DPPH solution without compound). Ascorbic acid or Trolox is used as a positive control. The IC50 value is determined from a dose-response curve.
Cell Assay
For antibacterial susceptibility testing, the minimum inhibitory concentration (MIC) of Methyl carnosate is determined using the broth microdilution method according to CLSI guidelines. Bacterial strains (e.g., Bacillus cereus, Staphylococcus aureus) are cultured overnight in Mueller-Hinton broth. A 96-well plate is prepared with serial two-fold dilutions of Methyl carnosate (typically 0.5-512 microg/mL). Each well is then inoculated with approximately 5×10⁵ CFU/mL of the test bacterium. After incubation at 37degC for 18-20 hours, the MIC is read as the lowest concentration of compound that visibly inhibits bacterial growth. The MBC (minimum bactericidal concentration) is determined by subculturing wells with no visible growth onto agar plates.
Animal Protocol
The in vivo anti-inflammatory activity of Methyl carnosate can be evaluated using the carrageenan-induced mouse paw edema model. Male ICR mice (20-25 g) are fasted overnight. Methyl carnosate (25, 50, or 100 mg/kg) is administered orally one hour before subplantar injection of 50 microL of 1% λ-carrageenan solution into the right hind paw. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 hours after carrageenan challenge. The percentage inhibition of edema is calculated by comparing the paw volume of treated groups to the vehicle control group. Indomethacin (10 mg/kg) is used as a positive control. At the end of the experiment, inflammatory tissues may be collected for analysis of cytokine levels and myeloperoxidase activity.
ADME/Pharmacokinetics
As a natural product diterpene, Methyl carnosate is expected to have moderate oral bioavailability and reasonable metabolic stability. The methyl ester group may be subject to hydrolysis by esterases in the gastrointestinal tract, liver, and plasma, potentially converting the compound back to its parent molecule, carnosic acid. Both Methyl carnosate and carnosic acid are lipophilic compounds that can efficiently cross cell membranes. Detailed pharmacokinetic parameters such as half-life, maximum plasma concentration, area under the curve, and volume of distribution have not been fully characterized.
Toxicity/Toxicokinetics
Methyl carnosate has demonstrated a favorable safety profile in preliminary studies, typical of naturally occurring dietary polyphenolic compounds. No significant acute toxicity has been reported at doses commonly used for in vitro and in vivo research. The compound is generally recognized as safe when consumed as part of rosemary or sage extracts in food products. As a research chemical, formal Good Laboratory Practice (GLP) toxicology studies have not been conducted. High doses in animal studies may cause mild gastrointestinal disturbances, but no severe organ toxicity has been documented.
References

[1]. Antioxidant Constituents in Sage (Salvia officinalis). J. Agric. Food Chem. 1994, 42, 005-609 005.

[2]. Methyl carnosate, an antibacterial diterpene isolated from Salvia officinalis leaves. Nat Prod Commun. 2013 Apr;8(4):429-30.

Additional Infomation
It has been reported that plants of the genera Salvia officinalis, Salvia, and Salvia lanigera contain methyl salvia esters, and relevant data are available for reference.
Methyl carnosate (CAS# 82684-06-8) is a research-grade natural product isolate that serves as an analytical standard for quality control of rosemary and sage extracts in the food and nutraceutical industries. It is not an approved pharmaceutical drug. Its molecular weight is 346.46 with molecular formula C21H30O4. The compound exhibits notable antioxidant, anti-inflammatory, and antimicrobial properties, making it of interest for pharmacological and nutraceutical research. Other names for this compound include methyl camosate. The compound is typically stored at -20degC as a powder and is soluble in organic solvents such as DMSO and ethanol.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H30O4
Molecular Weight
346.461
Exact Mass
346.214
CAS #
82684-06-8
PubChem CID
11336941
Appearance
Light green to green solid powder
LogP
5.2
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
25
Complexity
514
Defined Atom Stereocenter Count
2
SMILES
COC(=O)[C@]12CCCC(C)(C)C1CCC3=C2C(=C(O)C(=C3)C(C)C)O
InChi Key
IIJLVJMZYPZQLW-YCRPNKLZSA-N
InChi Code
InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(24)25-5)16(13)18(23)17(14)22/h11-12,15,22-23H,6-10H2,1-5H3/t15-,21+/m0/s1
Chemical Name
methyl (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~288.63 mM)
Ethanol : ~50 mg/mL (~144.32 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.22 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8863 mL 14.4317 mL 28.8634 mL
5 mM 0.5773 mL 2.8863 mL 5.7727 mL
10 mM 0.2886 mL 1.4432 mL 2.8863 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.
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