Dehydroabietic acidCAS# 1740-19-8 |
- (+)-Dehydroabietic acid
Catalog No.:BCX1531
CAS No.:1231-75-0
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1740-19-8 | SDF | Download SDF |
| PubChem ID | 94391 | Appearance | Powder |
| Formula | C20H28O2 | M.Wt | 300.4 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid | ||
| SMILES | CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)O)C | ||
| Standard InChIKey | NFWKVWVWBFBAOV-MISYRCLQSA-N | ||
| Standard InChI | InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Dehydroabietic acid , a major poison to fishes in pulp and paper mill effluents, which could be useful in improving the diabetic wound healing, it can reverse several cell responses stimulated by TNF-α, including the activation of FOXO1 and the TGF-β1/Smad3 signaling pathway. Dehydroabietic acid derivatives displays antisecretory and antipepsin effect, have gastroprotective activity in the HCl/EtOH-induced gastric lesions in mice as well as for cytotoxicity in human lung fibroblasts (MRC-5) and human epithelial gastric (AGS) cells. |
| Targets | TNF-α | TGF-β/Smad | Caspase | Bcl-2/Bax | ROS | FOXO1 |
| In vivo | Dehydroabietic acid reverses TNF-α-induced the activation of FOXO1 and suppression of TGF-β1/Smad signaling in human adult dermal fibroblasts.[Pubmed: 25674226]Int J Clin Exp Pathol. 2014 Dec 1;7(12):8616-26.Wound healing impairment is a well-documented phenomenon in clinical and experimental diabetes, and in diabetic wound healing impaired fibroblast has been linked to increased levels of tumor necrosis factor-α (TNF-α).
Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives.[Pubmed: 16125407 ]Pharmacol Res. 2005 Nov;52(5):429-37.Dehydroabietic acid derivatives have been reported to display antisecretory and antipepsin effect in animal models. Some 19 Dehydroabietic acid diterpenes were prepared and assessed for gastroprotective activity in the HCl/EtOH-induced gastric lesions in mice as well as for cytotoxicity in human lung fibroblasts (MRC-5) and human epithelial gastric (AGS) cells.
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| Cell Research | Dehydroabietic acid derivative QC2 induces oncosis in hepatocellular carcinoma cells.[Pubmed: 25110686]Biomed Res Int. 2014;2014:682197.Rosin, the traditional Chinese medicine, is reported to be able to inhibit skin cancer cell lines. In this report, we investigate the inhibitory effect against HCC cells of QC2, the derivative of rosin's main components Dehydroabietic acid.
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| Animal Research | Toxicological effects of dehydroabietic acid (DHAA) on the trout, Salmo gairdneri Richardson, in fresh water.[Reference: WebLink]Water Res., 1983, 17(1):81-9.
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Dehydroabietic acid Dilution Calculator
Dehydroabietic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.3289 mL | 16.6445 mL | 33.2889 mL | 66.5779 mL | 83.2224 mL |
| 5 mM | 0.6658 mL | 3.3289 mL | 6.6578 mL | 13.3156 mL | 16.6445 mL |
| 10 mM | 0.3329 mL | 1.6644 mL | 3.3289 mL | 6.6578 mL | 8.3222 mL |
| 50 mM | 0.0666 mL | 0.3329 mL | 0.6658 mL | 1.3316 mL | 1.6644 mL |
| 100 mM | 0.0333 mL | 0.1664 mL | 0.3329 mL | 0.6658 mL | 0.8322 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Laboratory study on OH-initiated degradation kinetics of dehydroabietic acid.[Pubmed:25824374]
Phys Chem Chem Phys. 2015 Apr 28;17(16):10953-62.
Dehydroabietic acid (DHAA) is a specific organic tracer for the pyrolysis of conifer resin. To understand its atmospheric stability, the degradation behavior of particulate DHAA in the presence of hydroxyl radicals (OH) was investigated under different environmental conditions using a stainless steel reactor with volume of 30 cm(3), in the dark. At 25 degrees C and 40% relative humidity (RH), the second-order rate constant (k2) of pure DHAA with OH was measured to be 5.72 +/- 0.87 x 10(-12) cm(3) molecule(-1) s(-1). The influence of temperature, RH and mixing state on the degradation kinetics of DHAA were also investigated. At 40% RH, k2 of pure DHAA increases with increasing temperature and follows the Arrhenius equation k2 = (8.9 +/- 1.9) x 10(-10) exp[-(1508.2 +/- 64.2)/T], while RH does not have significant impact on k2 at 25 degrees C. At 25 degrees C and 40% RH, compared with pure DHAA, the corresponding k2 for DHAA mixed with (NH4)2SO4 decreased to 4.58 +/- 0.95 x 10(-12) cm(3) molecule(-1) s(-1), while the value was 3.30 +/- 0.79 x 10(-12) cm(3) molecule(-1) s(-1) when mixed with soot. The atmospheric lifetime of DHAA varied from 2.3 +/- 0.2 to 4.4 +/- 0.8 days under different environmental conditions. This study indicates that degradation of DHAA by OH radicals is appreciable, and a significant error in source apportionment should be introduced if the contribution of degradation to DHAA concentration is not considered during air mass aging.
Dehydroabietic acid derivative QC2 induces oncosis in hepatocellular carcinoma cells.[Pubmed:25110686]
Biomed Res Int. 2014;2014:682197.
AIM: Rosin, the traditional Chinese medicine, is reported to be able to inhibit skin cancer cell lines. In this report, we investigate the inhibitory effect against HCC cells of QC2, the derivative of rosin's main components Dehydroabietic acid. METHODS: MTT assay was used to determine the cytotoxicity of QC2. Morphological changes were observed by time-lapse microscopy and transmission electron microscopy and the cytoskeleton changes were observed by laser-scanning confocal microscopy. Cytomembrane integrity and organelles damage were confirmed by detection of the reactive oxygen (ROS), lactate dehydrogenase (LDH), and mitochondrial membrane potential (Deltapsim). The underlying mechanism was manifested by Western blotting. The oncotic cell death was further confirmed by detection of oncosis related protein calpain. RESULTS: Swelling cell type and destroyed cytoskeleton were observed in QC2-treated HCC cells. Organelle damage was visualized by transmission electron microscopy. The detection of ROS accumulation, increased LDH release, and decreased ATP and Deltapsim confirmed the cell death. The oncotic related protein calpain was found to increase time-dependently in QC2-treated HCC cells, while its inhibitor PD150606 attenuated the cytotoxicity. CONCLUSIONS: Dehydroabietic acid derivative QC2 activated oncosis related protein calpain to induce the damage of cytomembrane and organelles which finally lead to oncosis in HCC cells.
Dehydroabietic acid reverses TNF-alpha-induced the activation of FOXO1 and suppression of TGF-beta1/Smad signaling in human adult dermal fibroblasts.[Pubmed:25674226]
Int J Clin Exp Pathol. 2014 Dec 1;7(12):8616-26. eCollection 2014.
Wound healing impairment is a well-documented phenomenon in clinical and experimental diabetes, and in diabetic wound healing impaired fibroblast has been linked to increased levels of tumor necrosis factor-alpha (TNF-alpha). A number of signaling pathways including TNF-alpha/forkhead box O1 (FOXO1) and transforming growth factor-beta1 (TGF-beta1)/Smads in fibroblasts appear to play a cardinal role in diabetic wound healing. Dehydroabietic acid (DAA) is obtained from Commiphora oppbalsamum and inhibits the production of TNF-alpha in macrophages and adipocytes, decreases the level of TNF-alpha in obese diabetic KK-Ay mice, but its effect on diabetic wound healing is unknown. This study was to investigate the effect of DAA on TNF-alpha-stimulated human adult dermal fibroblasts. On the one hand, TNF-alpha significantly decreased the fibroblast proliferation and the expression of PCNA, Ki67 and cyclin D1, increased the fibroblast apoptosis, caspase-8/3 activity, expressions of cleaved caspase-8 and caspase-3, decreased the Bcl-2/Bax ratio and increased activation of the pro-apoptotic transcription factor FOXO1. All the above-mentioned cell responses were remarkably reversed by DAA. On the other hand, TNF-alpha also inhibited TGF-beta1-induced the Smad3 signaling pathway what is closely related to the fibroblast migration and the differentiation of myofibroblasts. However, DAA significantly promoted the migration and increased the expression of alpha-smooth muscle actin and fibronectin under the stimulus of a combination of TNF-alpha and TGF-beta1. In conclusion, DAA could reverse several cell responses stimulated by TNF-alpha, including the activation of FOXO1 and the TGF-beta1/Smad3 signaling pathway. These results suggested that DAA could be useful in improving the diabetic wound healing.
Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives.[Pubmed:16125407]
Pharmacol Res. 2005 Nov;52(5):429-37.
Dehydroabietic acid derivatives have been reported to display antisecretory and antipepsin effect in animal models. Some 19 Dehydroabietic acid diterpenes were prepared and assessed for gastroprotective activity in the HCl/EtOH-induced gastric lesions in mice as well as for cytotoxicity in human lung fibroblasts (MRC-5) and human epithelial gastric (AGS) cells. At a single oral dose of 100 mg kg(-1), highest gastroprotective effect was provided by dehydroabietanol, its corresponding aldehyde, Dehydroabietic acid (DHA) and its methyl ester, N-(m-nitrophenyl)-, N-(o-chlorophenyl)- and N-(p-iodophenyl)abieta-8,11,13-trien-18-amide (compounds 12-14), N-2-aminothiazolyl- and N-benzylabieta-8,11,13-trien-18-amide (compounds 18-19) being as active as lansoprazole at 20 mg kg(-1) and reducing the lesion index by at least 75%. In the compound series including the alcohol, ester, aldehyde, acid and methyl ester at C-18 (compounds 1-9), highest activity was related with the presence of an alcohol, aldehyde, acid or methyl ester at C-18, the activity being strongly reduced after esterification. The cytotoxicity of the compounds 1-9 towards AGS cells and fibroblasts was higher than the values for the amides 10-19. In the compounds 10-19, the best gastroprotective effect was observed for the aromatic amides 12-14 (75-85% inhibition of gastric lesions) bearing a nitro or halogen function in the N-benzoyl moiety. Lowest cytotoxicity was found for the amides, with IC(50) values >1000 microM for fibroblasts and from 200 up to >1000 microM for AGS cells, respectively. The N-2-aminothiazolyl- and N-benzylamide derivatives were also very active as gastroprotectors with higher cytotoxicity against AGS cells.
