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Carnosic Acid

Alias: Carnosic Acid; Salvin
Cat No.:V17591 Purity: ≥98%
Carnosic acid inhibits oxidative stress and inflammation, inhibits cell growth/proliferation, and has anti-bacterial effect.
Carnosic Acid
Carnosic Acid Chemical Structure CAS No.: 3650-09-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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50mg
100mg
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Product Description
Carnosic acid inhibits oxidative stress and inflammation, inhibits cell growth/proliferation, and has anti-bacterial effect.
Carnosic Acid (CAS 3650-09-7) is a naturally occurring phenolic abietane diterpenoid, primarily isolated from the herb *Rosmarinus officinalis* (rosemary). It is a potent antioxidant and has a variety of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties.
Biological Activity I Assay Protocols (From Reference)
Targets
Carnosic acid has multiple targets. It is a lipid absorption inhibitor and activates the Keap1/Nrf2 pathway via S-alkylation of targeted cysteines on Keap1. It also inhibits β-catenin-dependent transcription and destabilizes oncogenic β-catenin in colon cancer cells.
ln Vitro
Dried leaves of sage and rosemary have especially high amounts of carnosic acid, a neurogenic diterpene found deep inside the leaves of Lamiaceae plants. It has been demonstrated that carnosic acid inhibits oxidation and modulates inhibition. Based mostly on in vitro investigations, carbosic acid has been widely claimed to offer therapeutic promise in several cancer types. In the current experimental models of dementia, carnosic acid still has neuroprotective effects, mainly via activation of the antioxidant NRF2/ARE [1].
In vitro, Carnosic acid inhibits lipid peroxidation induced by NADH or NADPH oxidation. It scavenges peroxyl radicals and H2O2, reduces cytochrome C, and inhibits superoxide anion production. It also inhibits cell proliferation and induces apoptosis in various tumor cell lines.
ln Vivo
In vivo, Carnosic acid has been shown to protect neurons through activation of the Keap1/Nrf2 pathway. It inhibits cell growth and has anti-inflammatory and antibacterial effects. It is also an angiogenesis modulating agent.
Enzyme Assay
In vitro assays for Carnosic acid measure its antioxidant capacity. This includes its ability to scavenge free radicals (e.g., DPPH assay), inhibit lipid peroxidation, and reduce cytochrome C. Its activation of the Nrf2 pathway can be measured by assessing the expression of Nrf2 target genes.
Cell Assay
In vitro cell-based assays are performed in various cancer cell lines, such as colon cancer and medulloblastoma (MB) cells. The effects on cell proliferation, viability, and apoptosis are measured. The impact on signaling pathways, such as β-catenin, is also assessed via Western blotting.
Animal Protocol
In vivo activity is evaluated in animal models of disease. For example, its neuroprotective effects are studied in models of neurodegeneration. Its anticancer activity can be assessed in xenograft models, where tumor growth and angiogenesis are monitored.
ADME/Pharmacokinetics
The pharmacokinetic properties of Carnosic acid are not extensively detailed. As a natural product with oral activity, it is expected to be absorbed and distributed. However, its bioavailability may be limited due to poor solubility or rapid metabolism.
Toxicity/Toxicokinetics
Detailed toxicological data for Carnosic acid is not available in standard research literature. As a widely consumed dietary component from rosemary, it is generally recognized as safe (GRAS) at normal dietary levels. High doses may have pharmacological effects and potential toxicity.
References

[1]. Inhibitory effects of rosemary extracts, carnosic acid and rosmarinic acid on the growth of various human cancer cell lines. Plant Foods Hum Nutr. 2010 Jun;65(2):158-63.

Additional Infomation
Carnosic acid is an abietic diterpenoid compound with the structure abietic-8,11,13-triene, substituted with hydroxyl groups at positions 11 and 12 and a carboxyl group at position 20. It was isolated from rosemary (Rosmarinus officinalis) and sage (Salvia officinalis) and possesses anti-angiogenic, antitumor, antioxidant, and anti-HIV activities. It can be used as an antitumor agent, antioxidant, HIV protease inhibitor, angiogenesis regulator, apoptosis inducer, plant metabolite, anti-inflammatory agent, and food preservative. It is an abietic diterpenoid compound, a C3-cyclic compound, a catechol compound, and a monocarboxylic acid. It is the conjugate acid of Carnosic acid. Carnosic acid has been found in sage (Salvia officinalis), cumin (Cuminum cyminum), and other organisms with relevant data. See also: Rosemary (partial).
Carnosic acid is a major bioactive component of rosemary and is used as a natural food preservative due to its antioxidant properties. Its ability to activate the Nrf2 pathway makes it a promising lead compound for developing therapies for neurodegenerative diseases, cancer, and inflammatory conditions.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H28O4
Molecular Weight
332.43
Exact Mass
332.198
Elemental Analysis
C, 72.26; H, 8.49; O, 19.25
CAS #
3650-09-7
PubChem CID
65126
Appearance
White to light yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
506.4±50.0 °C at 760 mmHg
Melting Point
190 °C
Flash Point
274.2±26.6 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.576
LogP
4.93
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
24
Complexity
500
Defined Atom Stereocenter Count
2
SMILES
O([H])C([C@@]12C3=C(C(=C(C([H])(C([H])([H])[H])C([H])([H])[H])C([H])=C3C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H])O[H])O[H])=O
InChi Key
QRYRORQUOLYVBU-VBKZILBWSA-N
InChi Code
InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
Chemical Name
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
Synonyms
Carnosic Acid; Salvin
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.
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 : ~130 mg/mL (~391.06 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.08 mg/mL (6.26 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0082 mL 15.0408 mL 30.0815 mL
5 mM 0.6016 mL 3.0082 mL 6.0163 mL
10 mM 0.3008 mL 1.5041 mL 3.0082 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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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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