| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 5mg | |||
| 50mg | |||
| Other Sizes |
Purity: ≥98%
| Targets |
The primary targets of dextropimaric acid include the transcription factors NF-κB and AP-1, which regulate the expression of matrix metalloproteinase-9 (MMP-9). The compound also shares structural and functional similarities with isopimaric acid, a known opener of large conductance calcium-activated potassium (BK) channels.
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|---|---|
| ln Vitro |
Dextropimaric acid inhibits TNF-α-induced MMP-9 production in human aortic smooth muscle cells (HASMCs). It reduces MMP-9 mRNA expression, protein levels, and promoter activity through down-regulation of NF-κB and AP-1 transcriptional activity. The compound demonstrates anti-inflammatory activity and shares properties with abietic acid, which possesses antiproliferative, antibacterial, and anti-obesity activities.
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| ln Vivo |
In vivo activity data for dextropimaric acid is limited in the published literature. Based on its mechanism of inhibiting TNF-α-induced MMP-9 production and modulating NF-κB/AP-1 signaling, the compound is expected to exhibit anti-inflammatory effects in vivo. Related resin acids such as abietic acid have demonstrated in vivo anti-obesity and antibacterial activities.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for dextropimaric acid typically measure its effects on MMP-9 promoter activity and transcription factor activation. HASMCs are treated with TNF-α in the presence or absence of the compound, and NF-κB and AP-1 DNA-binding activity is assessed using electrophoretic mobility shift assays (EMSA) or luciferase reporter gene assays. MMP-9 promoter activity is measured using promoter-reporter constructs transfected into cells.
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| Cell Assay |
In vitro cell-based assays evaluate the anti-inflammatory activity of dextropimaric acid in human aortic smooth muscle cells (HASMCs). Cells are stimulated with TNF-α to induce MMP-9 expression, and the compound's ability to inhibit this response is assessed by measuring MMP-9 mRNA levels via qPCR, protein levels via ELISA or Western blot, and promoter activity via luciferase reporter assays.
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| Animal Protocol |
In vivo animal study protocols for dextropimaric acid are not extensively documented in the published literature. Based on the compound's mechanism as an inhibitor of TNF-α-induced inflammatory responses, potential in vivo models could include rodent models of inflammation where TNF-α plays a pathogenic role. These studies would assess endpoints such as tissue MMP-9 levels, inflammatory markers, and histological changes.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for dextropimaric acid is not extensively reported. As a naturally occurring diterpene resin acid with molecular weight approximately 302.45 g/mol, it is a lipophilic compound that may exhibit properties similar to other resin acids. Its absorption, distribution, metabolism, and excretion profile would need to be characterized in dedicated pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Toxicity data for dextropimaric acid is limited in the published literature. As a naturally occurring compound, its safety profile has not been comprehensively evaluated in standard toxicology studies. Related resin acids have been used in various applications, but comprehensive toxicological data is not publicly available.
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| References |
: HARRIS GC, SANDERSON TF. Resin acids; the position of the ring double bond in dextropimaric acid and the structure of isodextropimaric acid. J Am Chem Soc. 1948 Jun;70(6):2081-5. PubMed PMID: 18863802.
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| Additional Infomation |
(+)-Pimaric acid is a diterpenoid compound. It has been reported to exist in European fir, black pine, and other organisms with relevant data.
Dextropimaric acid (pimaric acid) is a naturally occurring diterpene resin acid found in pine species. It inhibits TNF-α-induced MMP-9 production through down-regulation of NF-κB and AP-1 pathways. The compound shares structural features with isopimaric acid (a BK channel opener) and abietic acid (which has antiproliferative, antibacterial, and anti-obesity properties). It is used as a research tool for studying inflammation and MMP-9 regulation. |
| Molecular Formula |
C20H30O2
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|---|---|
| Molecular Weight |
302.5
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| Exact Mass |
302.224
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| CAS # |
471-74-9
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| Related CAS # |
127-27-5
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| PubChem CID |
220338
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
413.2±45.0 °C at 760 mmHg
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| Melting Point |
217-219°
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| Flash Point |
198.7±23.4 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.538
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| LogP |
6.6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
22
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| Complexity |
534
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@@]1(CC[C@H]2C(=C1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C)C=C
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| InChi Key |
MHVJRKBZMUDEEV-APQLOABGSA-N
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| InChi Code |
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1
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| Chemical Name |
(1R,4aR,4bS,7S,10aR)-7-Ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
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| Synonyms |
D-Pimaric acid NSC-2956 NSC 2956 NSC2956Dextropimaric acid Pimaric acid D Pimaric acid
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 : ~100 mg/mL (~330.63 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (8.27 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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: ≥ 2.5 mg/mL (8.27 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3058 mL | 16.5289 mL | 33.0579 mL | |
| 5 mM | 0.6612 mL | 3.3058 mL | 6.6116 mL | |
| 10 mM | 0.3306 mL | 1.6529 mL | 3.3058 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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