Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H29O2.Na |
| Molecular Weight | 324.4328 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C([O-])=O)[C@H]2CC1
InChI
InChIKey=ITCAUAYQCALGGV-XTICBAGASA-M
InChI=1S/C20H30O2.Na/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;/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22);/q;+1/p-1/t16-,17+,19+,20+;/m0./s1
| Molecular Formula | C20H29O2 |
| Molecular Weight | 301.4431 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Abietic acid (AA), a diterpene produced by conifer species, such as grand fir and lodgepole pine, has been reported to have anti-inflammatory and immunomodulatory effects and can be used as a wound-healing agent. Its treatment elevates cell migration and tube formation in human umbilical vein vascular endothelial cells by the activation of ERK and p38 MAPKs. In addition was shown, that abietic acid could be used as an antimetastatic agent or as an adjuvant for anticancer therapy. AA acts as a PPARα/γ dual activator to inhibit age-related inflammation by suppressing NF-κB and the MAPK/AP-1 pathway and can be a useful agent for improving skin photoaging.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chemical composition of natural colophony from Pinus brutia and comparison with synthetic colophony. | 2010-11 |
|
| N-Morpholino-Δ-dihydro-abietamide. | 2010-10-09 |
|
| Methyl 7-oxo-12-propyl-amino-13-nitro-deisopropyl-dehydro-abietate. | 2010-09-25 |
|
| Skin sensitization, false positives and false negatives: experience with guinea pig assays. | 2010-07 |
|
| Laser microdissection of conifer stem tissues: isolation and analysis of high quality RNA, terpene synthase enzyme activity and terpenoid metabolites from resin ducts and cambial zone tissue of white spruce (Picea glauca). | 2010-06-12 |
|
| Tetrahydroabietic Acid, a Reduced Abietic Acid, Inhibits the Production of Inflammatory Mediators in RAW264.7 Macrophages Activated with Lipopolysaccharide. | 2010-03 |
|
| Identification and functional characterization of monofunctional ent-copalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms. | 2010-03 |
|
| Synthesis and biological evaluation of dehydroabietic acid derivatives. | 2010-02 |
|
| Work-related respiratory symptoms and pulmonary function tests in northeast iranian (the city of Mashhad) carpenters. | 2010 |
|
| Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism. | 2010 |
|
| Functional food targeting the regulation of obesity-induced inflammatory responses and pathologies. | 2010 |
|
| A new abietic acid-type diterpene glucoside from the needles of Pinus densiflora. | 2009-12 |
|
| 13-Ethoxy-carbonyl-16-(1-methyl-ethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid. | 2009-07-22 |
|
| Maleopimaric acid acetic acid solvate. | 2009-06-27 |
|
| Synthesis and biological evaluation of abietic acid derivatives. | 2009-06 |
|
| Cell transformation activities of abietic acid and dehydroabietic acid: safety assessment of possible contaminants in paper and paperboard for food contact use. | 2009-04 |
|
| Combined system of activated sludge and ozonation for the treatment of kraft E1 effluent. | 2009-03 |
|
| Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha. | 2009-03 |
|
| Antiparasitic, nematicidal and antifouling constituents from Juniperus berries. | 2008-12 |
|
| Fragrance material review on abietyl acetate. | 2008-12 |
|
| Picosecond structural relaxation of abietic acid based amine end capped para-phenylenevinylene trimers in solution. | 2008-10-24 |
|
| Maleo- and fumaro-pimaric acids synthesized from Indonesian Pinus merkusii rosin and their sizing properties. | 2008-08-01 |
|
| SPE and HPLC/UV of resin acids in colophonium-containing products. | 2008-08 |
|
| Inhibitory effects of terpenoids on multidrug resistance-associated protein 2- and breast cancer resistance protein-mediated transport. | 2008-07 |
|
| Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production. | 2008-03 |
|
| Methyl esterification of 15-hydroperoxyabietic acid does not affect the patch-test result in colophonium allergic patients. | 2007-06 |
|
| Reaction of abietic acid with maleic anhydride and fumaric acid and attempts to find the fundamental component of fortified rosin. | 2007-05-15 |
|
| Interaction forces between talc and pitch probed by atomic force microscopy. | 2007-04-10 |
|
| Analysis of abietic acid and dehydroabietic acid in food samples by in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry. | 2007-03-30 |
|
| Discovery of anticonvulsant activity of abietic acid through application of linear discriminant analysis. | 2007-03-15 |
|
| Effect of aerobic sludge with increasing level of adaptation on abietic acid biodegradation. | 2006-12 |
|
| Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. | 2006-12 |
|
| Natural products that reduce rotavirus infectivity identified by a cell-based moderate-throughput screening assay. | 2006-09-01 |
|
| Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA. | 2006-08 |
|
| Improved aerobic biodegradation of abietic acid in ECF bleached kraft mill effluent due to biomass adaptation. | 2006-07-31 |
|
| Strong overtones and combination bands in ultraviolet resonance Raman spectroscopy. | 2006-05-01 |
|
| The nature and fate of natural resins in the geosphere. XII. Investigation of C-ring aromatic diterpenoids in Raritan amber by pyrolysis-GC-matrix isolation FTIR-MS. | 2006-03-01 |
|
| Antioxidant activity of a catechol derived from abietic acid. | 2006-01-25 |
|
| Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid. | 2006-01 |
|
| Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens. | 2006 |
|
| Safety assessment of paper and board food packaging: chemical analysis and genotoxicity of possible contaminants in packaging. | 2005-10 |
|
| Regio- and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina. | 2005-09 |
|
| Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus. | 2005-06 |
|
| Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels. | 2005-06 |
|
| Effects of dehydroabietic acid and abietic acid on survival, reproduction, and growth of the crustacean Daphnia magna. | 2005-05 |
|
| Medicinal herb use among asthmatic patients attending a specialty care facility in Trinidad. | 2005-02-15 |
|
| A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds. | 2004-11 |
|
| Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth. | 2004-08 |
|
| Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. | 2004-08 |
|
| Anguilla anguilla L. genotoxic and liver biotransformation responses to abietic acid exposure. | 2004-06 |
Patents
Sample Use Guides
B16F10-Bearing mice: Abietic Ac (10 and 20 mg/kg of body weight, daily) suspended in olive oil via oral gavage.
Route of Administration:
Oral
Inhibitory effects of abietic acid (AA) on the migration, invasion, motility, and activity of MMPs and u-PA of A2058 human melanoma cells were studied. A2058 cells were treated with AA (concentration range: 10, 20, 30, 40 and 50 uM) for 24 h. it was shown, that AA inhibited A2058 cell migration, invasion, and motility. AA clearly inhibited the secretion of MMP-2, MMP-9, and u-PA. These results indicated that AA might exhibit anti-invasive properties against a broad spectrum of melanoma cells
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
0E9Y24M11F
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
