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+].[H][C@]12CCC(=CC1=CC[C@@]3([H])[C@@](C)(CCC[C@]23C)C([O-])=O)C(C)C
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 | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 |
|---|---|---|
| Abietane diterpenoids from the cones of Larix kaempferi and their inhibitory effects on Epstein-Barr virus activation. | 2001 Feb |
|
| Synthetic derivatives of abietic acid with radical scavenging activity. | 2001 Jun |
|
| Effects of ecabet sodium, an antiulcer drug, on gastric adaptive relaxation in isolated guinea-pig stomachs. | 2002 |
|
| Characterization of tdt genes for the degradation of tricyclic diterpenes by Pseudomonas diterpeniphila A19-6a. | 2002 Jan |
|
| Oak moss extracts in the diagnosis of fragrance contact allergy. | 2002 Mar |
|
| Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth. | 2004 Aug |
|
| Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. | 2004 Aug |
|
| Identification of diterpenes in canvas painting varnishes by gas chromatography-mass spectrometry with combined derivatisation. | 2004 Jan 23 |
|
| Anguilla anguilla L. genotoxic and liver biotransformation responses to abietic acid exposure. | 2004 Jun |
|
| A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds. | 2004 Nov |
|
| Medicinal herb use among asthmatic patients attending a specialty care facility in Trinidad. | 2005 Feb 15 |
|
| Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels. | 2005 Jun |
|
| Regio- and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina. | 2005 Sep |
|
| Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA. | 2006 Aug |
|
| Effect of aerobic sludge with increasing level of adaptation on abietic acid biodegradation. | 2006 Dec |
|
| Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid. | 2006 Jan |
|
| Antioxidant activity of a catechol derived from abietic acid. | 2006 Jan 25 |
|
| Reaction of abietic acid with maleic anhydride and fumaric acid and attempts to find the fundamental component of fortified rosin. | 2007 May 15 |
|
| Maleo- and fumaro-pimaric acids synthesized from Indonesian Pinus merkusii rosin and their sizing properties. | 2008 Aug 1 |
|
| Antiparasitic, nematicidal and antifouling constituents from Juniperus berries. | 2008 Dec |
|
| Fragrance material review on abietyl acetate. | 2008 Dec |
|
| Inhibitory effects of terpenoids on multidrug resistance-associated protein 2- and breast cancer resistance protein-mediated transport. | 2008 Jul |
|
| Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production. | 2008 Mar |
|
| Maleopimaric acid acetic acid solvate. | 2009 Jun 27 |
|
| Functional food targeting the regulation of obesity-induced inflammatory responses and pathologies. | 2010 |
|
| Tetrahydroabietic Acid, a Reduced Abietic Acid, Inhibits the Production of Inflammatory Mediators in RAW264.7 Macrophages Activated with Lipopolysaccharide. | 2010 Mar |
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
by
admin
on
Edited
Fri Dec 15 19:38:53 GMT 2023
by
admin
on
Fri Dec 15 19:38:53 GMT 2023
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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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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
