Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H28O2 |
| Molecular Weight | 300.4351 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C1=CC=C2C(CC[C@H]3[C@@](C)(CCC[C@]23C)C(O)=O)=C1
InChI
InChIKey=NFWKVWVWBFBAOV-MISYRCLQSA-N
InChI=1S/C20H28O2/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/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1
| Molecular Formula | C20H28O2 |
| Molecular Weight | 300.4351 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24959678
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24959678
Dehydroabietic acid (DHA or DAA), a diterpene, is obtained from Commiphora oppbalsamum. DHA has potential as treatment for obesity and metabolic syndrome, obese diabetic KK-Ay mice treated with DHA showed decreased plasma glucose, insulin, and triglyceride levels. It has been reported that DHA inhibits the production of proinfammatory mediators such as TNF-α in macrophages and adipocytes and causes endothelium-dependent relaxation of pulmonary artery via PI3K/Akt-eNOS signaling pathway. Also was shown, that DHA could reverse several cell responses stimulated by TNF-α, including the activation of FOXO1 and the TGF-β1/Smad3 signaling pathway. Thus, DAA could be useful in improving the diabetic wound healing.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A small molecule directly inhibits the p53 transactivation domain from binding to replication protein A. | 2013-02-01 |
|
| Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives. | 2010-12-15 |
|
| (1R,4aS,10aR)-1,4a-Dimethyl-N-[(morpholin-4-yl)carbothio-yl]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carboxamide. | 2010-11-06 |
|
| Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid. | 2010-10 |
|
| Methyl 7-oxo-12-propyl-amino-13-nitro-deisopropyl-dehydro-abietate. | 2010-09-25 |
|
| Estrogenic and anti-estrogenic effects of wood extractives present in pulp and paper mill effluents on rainbow trout. | 2010-08-15 |
|
| Syntheses, characterization and fluorescent properties of two series of dehydroabietic acid C-ring derivatives. | 2010-08 |
|
| 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 |
|
| Disproportionated rosin dehydroabietic acid in neoprene surgical gloves. | 2010-05-22 |
|
| Methyl 12-bromo-dehydro-abietate. | 2010-04-28 |
|
| The composition of the free fatty acids from Dendrolimus pini exuviae. | 2010-04 |
|
| Synthesis and biological evaluation of dehydroabietic acid derivatives. | 2010-02 |
|
| Anaerobic treatability and biogas production potential of selected in-mill streams. | 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 |
|
| (4R,5R,10S)-N-(4-Bromo-phen-yl)dehydro-abietamide. | 2009-11-28 |
|
| Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice. | 2009-09-16 |
|
| Dehydro-abietic acid. | 2009-09-09 |
|
| Evaluation of resin and fatty acid concentration levels by online sample enrichment followed by atmospheric pressure chemical ionization-mass spectrometry (APCI-MS). | 2009-05 |
|
| Cell transformation activities of abietic acid and dehydroabietic acid: safety assessment of possible contaminants in paper and paperboard for food contact use. | 2009-04 |
|
| Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha. | 2009-03 |
|
| Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro). | 2009-03 |
|
| Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior. | 2009-01-05 |
|
| Highly enantioselective synthesis of gamma-nitro heteroaromatic ketones in a doubly stereocontrolled manner catalyzed by bifunctional thiourea catalysts based on dehydroabietic amine: a doubly stereocontrolled approach to pyrrolidine carboxylic acids. | 2009-01-01 |
|
| Synthesis, structure analysis and cytotoxicity studies of novel unsymmetrically n,n'-substituted ureas from dehydroabietic Acid. | 2008-11 |
|
| Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test. | 2008-11 |
|
| Effects of unsaturation on film structure and friction of fatty acids in a model base oil. | 2008-10-15 |
|
| Novel BK channel openers containing dehydroabietic acid skeleton: structure-activity relationship for peripheral substituents on ring C. | 2008-10-01 |
|
| SPE and HPLC/UV of resin acids in colophonium-containing products. | 2008-08 |
|
| Dehydroabietic acid, a phytochemical, acts as ligand for PPARs in macrophages and adipocytes to regulate inflammation. | 2008-05-02 |
|
| Exposure to wood dust, resin acids, and volatile organic compounds during production of wood pellets. | 2008-05 |
|
| 13C and 1H NMR signal assignments of some new synthetic dehydroabietic acid derivatives. | 2008-04 |
|
| The use of primary hepatocytes from brown trout (Salmo trutta lacustris) and the fish cell lines RTH-149 and ZF-L for in vitro screening of (anti)estrogenic activity of wood extractives. | 2008-04 |
|
| Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production. | 2008-03 |
|
| Friction of fatty acids in nanometer-sized contacts of different adhesive strength. | 2008-02-19 |
|
| Effects of the wood extractives dehydroabietic acid and betulinol on reproductive physiology of zebrafish (Danio rerio)-a two-generation study. | 2008-02-18 |
|
| Solvent control of optical resolution of 2-amino-1-phenylethanol using dehydroabietic acid. | 2008-02-07 |
|
| The nature and fate of natural resins in the geosphere XIII: a probable pinaceous resin from the early Cretaceous (Barremian), Isle of Wight. | 2008-01-29 |
|
| Spasmolytic effect of constituents from Lepechinia caulescens on rat uterus. | 2008-01-04 |
|
| [Isolation and identification of diterpenoids from Pinus koraiensis]. | 2008-01 |
|
| The green approaches for the synthesis of N-dehydroabietic alpha-aminophosphonates. | 2008 |
|
| Activity of dehydroabietic acid derivatives against wood contaminant fungi. | 2007-09 |
|
| Dehydroabietic acid as a biomarker for exposure to colophony. | 2007-08 |
|
| Evaluation of the treatment efficiencies of paper mill whitewaters in terms of organic composition and toxicity. | 2007-06 |
|
| [Characterization of the reaction products from pine gum catalytic disproportionation by gas chromatography/mass spectrometry]. | 2007-05 |
|
| Molecular detection and diversity of novel diterpenoid dioxygenase DitA1 genes from proteobacterial strains and soil samples. | 2007-05 |
|
| 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 |
|
| Fungal biotransformation products of dehydroabietic acid. | 2007-02 |
|
| [Studies on diterpenes in needles of Pinus sylvestris]. | 2006-12 |
|
| Efficient ortho-oxidation of phenol and synthesis of anti-MRSA and anti-VRE compound abietaquinone methide from dehydroabietic acid. | 2006-10 |
Sample Use Guides
The back (2*8 cm2) of each mouse was shaved with surgical clippers and treated topically with DMBA (100 mg, 390 nmol) in acetone as an initiation treatment. For group 1(positive control group), 1 week after the initiation with DMBA, papilloma formation was promoted twice weekly by the application of TPA (1 mg, 1.7nmol) in acetone on the skin. Groups III received a topical application of test samples, dehydroabietic acid (4), (85nmol) in acetone 1h before the promotion treatment. The percentage of papilloma bearers and the average number of papillomas per mouse were observed weekly for 20 weeks. Dehydroabietic acid exhibited high activity in the in vivo anti-tumor-promoting test.
Route of Administration:
Topical
Microtiter plates containing 2.5 mkL per well of 2-fold serial dilutions of each antimicrobial agent were inoculated with 100 mkL of bacterial suspension to yield the appropriate density ((1-5) * 10-5 CFU/mL). The plates were incubated for 18 h at 35 °C in ambient air. The MIC was defined as the lowest concentration of a compound that completely inhibited the growth of the organism
| Substance Class |
Chemical
Created
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| Record UNII |
0S5XP6S3AU
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| Record Status |
Validated (UNII)
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