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

CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(O)=O)[C@H]2CC1

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

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 1447

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 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28389357	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Chemical composition of natural colophony from Pinus brutia and comparison with synthetic colophony.	2010-11	21213968
N-Morpholino-Δ-dihydro-abietamide.	2010-10-09	21588936
Methyl 7-oxo-12-propyl-amino-13-nitro-deisopropyl-dehydro-abietate.	2010-09-25	21587581
Skin sensitization, false positives and false negatives: experience with guinea pig assays.	2010-07	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).	2010-06-12	20540781
Tetrahydroabietic Acid, a Reduced Abietic Acid, Inhibits the Production of Inflammatory Mediators in RAW264.7 Macrophages Activated with Lipopolysaccharide.	2010-03	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.	2010-03	20044448
Synthesis and biological evaluation of dehydroabietic acid derivatives.	2010-02	19892441
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
A new abietic acid-type diterpene glucoside from the needles of Pinus densiflora.	2009-12	20162397
13-Ethoxy-carbonyl-16-(1-methyl-ethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid.	2009-07-22	21583637
Maleopimaric acid acetic acid solvate.	2009-06-27	21582965
Synthesis and biological evaluation of abietic acid derivatives.	2009-06	19217699
Cell transformation activities of abietic acid and dehydroabietic acid: safety assessment of possible contaminants in paper and paperboard for food contact use.	2009-04	19680931
Combined system of activated sludge and ozonation for the treatment of kraft E1 effluent.	2009-03	19440438
Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha.	2009-03	19101885
Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.	2008-12	19067375
Fragrance material review on abietyl acetate.	2008-12	18845214
Picosecond structural relaxation of abietic acid based amine end capped para-phenylenevinylene trimers in solution.	2008-10-24	18830995
Maleo- and fumaro-pimaric acids synthesized from Indonesian Pinus merkusii rosin and their sizing properties.	2008-08-01	18983029
SPE and HPLC/UV of resin acids in colophonium-containing products.	2008-08	18666177
Inhibitory effects of terpenoids on multidrug resistance-associated protein 2- and breast cancer resistance protein-mediated transport.	2008-07	18436619
Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.	2008-03	18392277
Methyl esterification of 15-hydroperoxyabietic acid does not affect the patch-test result in colophonium allergic patients.	2007-06	17577378
Reaction of abietic acid with maleic anhydride and fumaric acid and attempts to find the fundamental component of fortified rosin.	2007-05-15	19086503
Interaction forces between talc and pitch probed by atomic force microscopy.	2007-04-10	17352501
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	17306277
Discovery of anticonvulsant activity of abietic acid through application of linear discriminant analysis.	2007-03-15	17234417
Effect of aerobic sludge with increasing level of adaptation on abietic acid biodegradation.	2006-12	17219306
Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products.	2006-12	16904803
Natural products that reduce rotavirus infectivity identified by a cell-based moderate-throughput screening assay.	2006-09-01	16948846
Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA.	2006-08	16807212
Improved aerobic biodegradation of abietic acid in ECF bleached kraft mill effluent due to biomass adaptation.	2006-07-31	16386835
Strong overtones and combination bands in ultraviolet resonance Raman spectroscopy.	2006-05-01	16643007
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	16759406
Antioxidant activity of a catechol derived from abietic acid.	2006-01-25	16417289
Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid.	2006-01	16195419
Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens.	2006	16684230
Safety assessment of paper and board food packaging: chemical analysis and genotoxicity of possible contaminants in packaging.	2005-10	16227189
Regio- and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina.	2005-09	16215830
Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus.	2005-06	16114093
Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels.	2005-06	15883093
Effects of dehydroabietic acid and abietic acid on survival, reproduction, and growth of the crustacean Daphnia magna.	2005-05	15814313
Medicinal herb use among asthmatic patients attending a specialty care facility in Trinidad.	2005-02-15	15713232
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds of Scots pine (Pinus sylvestris) wood. Part I: lipophilic compounds.	2004-11	15477130
Evaluation of putative allelochemicals in rice root exudates for their role in the suppression of arrowhead root growth.	2004-08	15537166
Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates.	2004-08	15537165
Anguilla anguilla L. genotoxic and liver biotransformation responses to abietic acid exposure.	2004-06	15157574

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:16 GMT 2025`
Record UNII	V3DHX33184
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-25149

Preferred Name

English

ABIETIC ACID

Official Name

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

DIHYDROABIETIC ACID

Common Name

English

SYLVIC ACID

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 175.105