ABIETIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	( - )
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCC(=CC1=CC[C@@]3([H])[C@@](C)(CCC[C@]23C)C(O)=O)C(C)C

InChI

InChIKey=RSWGJHLUYNHPMX-ONCXSQPRSA-N

InChI=1S/C20H30O2/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)/t16-,17+,19+,20+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26621449 | https://www.ncbi.nlm.nih.gov/pubmed/28389357 | https://www.ncbi.nlm.nih.gov/pubmed/25496486

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

Targets

Primary Target	Pharmacology	Condition	Potency
PPAR alpha/gamma 2 Target ID: CHEMBL2111325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25496486	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26621449	Primary		Preclinical	Unknown Approved Use Unknown
Wounds 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28389357	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth.	2004 Aug	15537166
Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates.	2004 Aug	15537165
Anguilla anguilla L. genotoxic and liver biotransformation responses to abietic acid exposure.	2004 Jun	15157574
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.	2004 Nov	15477130
Medicinal herb use among asthmatic patients attending a specialty care facility in Trinidad.	2005 Feb 15	15713232
Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus.	2005 Jun	16114093
Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels.	2005 Jun	15883093
Effects of dehydroabietic acid and abietic acid on survival, reproduction, and growth of the crustacean Daphnia magna.	2005 May	15814313
Safety assessment of paper and board food packaging: chemical analysis and genotoxicity of possible contaminants in packaging.	2005 Oct	16227189
Regio- and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina.	2005 Sep	16215830
Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens.	2006	16684230
Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA.	2006 Aug	16807212
Effect of aerobic sludge with increasing level of adaptation on abietic acid biodegradation.	2006 Dec	17219306
Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products.	2006 Dec	16904803
Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid.	2006 Jan	16195419
Antioxidant activity of a catechol derived from abietic acid.	2006 Jan 25	16417289
Improved aerobic biodegradation of abietic acid in ECF bleached kraft mill effluent due to biomass adaptation.	2006 Jul 31	16386835
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 Mar 1	16759406
Strong overtones and combination bands in ultraviolet resonance Raman spectroscopy.	2006 May 1	16643007
Natural products that reduce rotavirus infectivity identified by a cell-based moderate-throughput screening assay.	2006 Sep 1	16948846
Interaction forces between talc and pitch probed by atomic force microscopy.	2007 Apr 10	17352501
Methyl esterification of 15-hydroperoxyabietic acid does not affect the patch-test result in colophonium allergic patients.	2007 Jun	17577378
Discovery of anticonvulsant activity of abietic acid through application of linear discriminant analysis.	2007 Mar 15	17234417
Analysis of abietic acid and dehydroabietic acid in food samples by in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry.	2007 Mar 30	17306277
Reaction of abietic acid with maleic anhydride and fumaric acid and attempts to find the fundamental component of fortified rosin.	2007 May 15	19086503
SPE and HPLC/UV of resin acids in colophonium-containing products.	2008 Aug	18666177
Maleo- and fumaro-pimaric acids synthesized from Indonesian Pinus merkusii rosin and their sizing properties.	2008 Aug 1	18983029
Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.	2008 Dec	19067375
Fragrance material review on abietyl acetate.	2008 Dec	18845214
Inhibitory effects of terpenoids on multidrug resistance-associated protein 2- and breast cancer resistance protein-mediated transport.	2008 Jul	18436619
Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.	2008 Mar	18392277
Picosecond structural relaxation of abietic acid based amine end capped para-phenylenevinylene trimers in solution.	2008 Oct 24	18830995
Cell transformation activities of abietic acid and dehydroabietic acid: safety assessment of possible contaminants in paper and paperboard for food contact use.	2009 Apr	19680931
A new abietic acid-type diterpene glucoside from the needles of Pinus densiflora.	2009 Dec	20162397
13-Ethoxy-carbonyl-16-(1-methyl-ethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid.	2009 Jul 22	21583637
Synthesis and biological evaluation of abietic acid derivatives.	2009 Jun	19217699
Maleopimaric acid acetic acid solvate.	2009 Jun 27	21582965
Combined system of activated sludge and ozonation for the treatment of kraft E1 effluent.	2009 Mar	19440438
Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha.	2009 Mar	19101885
Work-related respiratory symptoms and pulmonary function tests in northeast iranian (the city of Mashhad) carpenters.	2010	21120301
Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism.	2010	20613991
Functional food targeting the regulation of obesity-induced inflammatory responses and pathologies.	2010	20508825
Synthesis and biological evaluation of dehydroabietic acid derivatives.	2010 Feb	19892441
Skin sensitization, false positives and false negatives: experience with guinea pig assays.	2010 Jul	20583317
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 Jun 12	20540781
Tetrahydroabietic Acid, a Reduced Abietic Acid, Inhibits the Production of Inflammatory Mediators in RAW264.7 Macrophages Activated with Lipopolysaccharide.	2010 Mar	20216944
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 Mar	20044448
Chemical composition of natural colophony from Pinus brutia and comparison with synthetic colophony.	2010 Nov	21213968
N-Morpholino-Δ-dihydro-abietamide.	2010 Oct 9	21588936
Methyl 7-oxo-12-propyl-amino-13-nitro-deisopropyl-dehydro-abietate.	2010 Sep 25	21587581

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

Name

Type

Language

ABIETIC ACID

Official Name

English

NSC-25149

Code

English

13-ISOPROPYLPODOCARPA-7,13-DIEN-15-OIC ACID

Common Name

English

(1R,4AR,4BR,10AR)-1,2,3,4,4A,4B,5,6,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-1-PHENANTHRENECARBOXYLIC ACID

Common Name

English

ABIETIC ACID [MI]

Common Name

English

ABIETIC ACID [INCI]

Common Name

English

DIHYDROABIETIC ACID

Common Name

English

SYLVIC ACID

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 175.105