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

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 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
Reactivity of Trametes laccases with fatty and resin acids.	2001 Apr	11341313
Occupational allergic contact dermatitis caused by wood dusts.	2001 Apr	11260236
Abietane diterpenoids from the cones of Larix kaempferi and their inhibitory effects on Epstein-Barr virus activation.	2001 Feb	11270723
Anti-inflammatory activity of abietic acid, a diterpene isolated from Pimenta racemosa var. grissea.	2001 Jun	11428663
Juvenile sea bass liver biotransformation induction and erythrocytic genotoxic responses to resin acids.	2002 Jul	12297086
Oak moss extracts in the diagnosis of fragrance contact allergy.	2002 Mar	12000325
Catechols from abietic acid synthesis and evaluation as bioactive compounds.	2003 Apr 17	12659748
Abietic acid activates peroxisome proliferator-activated receptor-gamma (PPARgamma) in RAW264.7 macrophages and 3T3-L1 adipocytes to regulate gene expression involved in inflammation and lipid metabolism.	2003 Aug 28	12935909
A rapid screening assay for inhibitors of 11beta-hydroxysteroid dehydrogenases (11beta-HSD): flavanone selectively inhibits 11beta-HSD1 reductase activity.	2003 Dec 30	14654249
Respiratory symptoms and occupational exposures in New Zealand plywood mill workers.	2003 Jun	12765869
Terpenoids as major precursors of dissolved organic matter in landfill leachates, surface water, and groundwater.	2003 Jun 1	12831012
Tepidimonas aquatica sp. nov., a new slightly thermophilic beta-proteobacterium isolated from a hot water tank.	2003 Sep	14529180
Dermal exposure to terpenic resin acids in Swedish carpentry workshops and sawmills.	2004 Apr	15059803
Contact dermatitis and other skin conditions in instrumental musicians.	2004 Apr 16	15090069
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. plasma cortisol, lactate and glucose responses to abietic acid, dehydroabietic acid and retene.	2004 Jan	14592577
Identification of diterpenes in canvas painting varnishes by gas chromatography-mass spectrometry with combined derivatisation.	2004 Jan 23	14753721
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
Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA.	2006 Aug	16807212
Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid.	2006 Jan	16195419
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
Interaction forces between talc and pitch probed by atomic force microscopy.	2007 Apr 10	17352501
SPE and HPLC/UV of resin acids in colophonium-containing products.	2008 Aug	18666177
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
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
Maleopimaric acid acetic acid solvate.	2009 Jun 27	21582965
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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:17:58 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:58 GMT 2023`
Record UNII	V3DHX33184
Record Status	`Validated (UNII)`
Record Version

Download

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