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1740-19-8,MFCD09839012
Catalog No.:AA001ZAH

1740-19-8 | 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aS,10aR)-

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1g
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5g
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25g
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001ZAH
Chemical Name:
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aS,10aR)-
CAS Number:
1740-19-8
Molecular Formula:
C20H28O2
Molecular Weight:
300.4351
MDL Number:
MFCD09839012
SMILES:
OC(=O)[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(C)C)C
NSC Number:
2952
Properties
Computed Properties
 
Complexity:
443  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
5.6  

Literature

Title: Antiprotozoal Activity of Triazole Derivatives of Dehydroabietic Acid and Oleanolic Acid.

Journal: Molecules (Basel, Switzerland) 20170301

Title: Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents.

Journal: Bioorganic & medicinal chemistry letters 20140101

Title: Variations in wood burning organic marker concentrations in the atmospheres of four European cities.

Journal: Journal of environmental monitoring : JEM 20120801

Title: Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay.

Journal: Fitoterapia 20120701

Title: Synthesis and antibacterial evaluation of New N-acylhydrazone derivatives from dehydroabietic acid.

Journal: Molecules (Basel, Switzerland) 20120420

Title: [Antioxidant constituents from Smilax riparia].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120301

Title: Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells.

Journal: Journal of biotechnology 20120120

Title: Evolution of diterpene metabolism: Sitka spruce CYP720B4 catalyzes multiple oxidations in resin acid biosynthesis of conifer defense against insects.

Journal: Plant physiology 20111201

Title: Induction of isoprenyl diphosphate synthases, plant hormones and defense signalling genes correlates with traumatic resin duct formation in Norway spruce (Picea abies).

Journal: Plant molecular biology 20111201

Title: A Case of Allergic Contact Dermatitis Due to DuoDERM Extrathin®.

Journal: Annals of dermatology 20111201

Title: Determination of resin acids during production of wood pellets--a comparison of HPLC/ESI-MS with the GC/FID MDHS 83/2 method.

Journal: Journal of environmental monitoring : JEM 20111001

Title: Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br.

Journal: Carbohydrate research 20110927

Title: [Diterpenoids from Chinese eaglewood].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110801

Title: Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini.

Journal: Archives of pharmacal research 20110601

Title: 2-Chloro-N-{5-[(4R,5R,10S)-dehydro-abiet-4-yl]-1,3,4-thia-diazol-2-yl}benzamide.

Journal: Acta crystallographica. Section E, Structure reports online 20110401

Title: Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.).

Journal: BMC plant biology 20110101

Title: Global transcriptome analysis of constitutive resistance to the white pine weevil in spruce.

Journal: Genome biology and evolution 20110101

Title: Dehydroabietic acid activates peroxisome proliferator-activated receptor-γ and stimulates insulin-dependent glucose uptake into 3T3-L1 adipocytes.

Journal: BioFactors (Oxford, England) 20110101

Title: Synthesis, Crystal Structure, and Spectra Properties of the Cadmium (II) Complex with Bis(N-allylbenzimidazol-2-ylmethyl)benzylamine.

Journal: Bioinorganic chemistry and applications 20110101

Title: Chemical and transcriptional responses of Norway spruce genotypes with different susceptibility to Heterobasidion spp. infection.

Journal: BMC plant biology 20110101

Title: Characterization by gas chromatography-mass spectrometry of diterpenoid resinous materials in Roman-age amphorae from northern Greece.

Journal: European journal of mass spectrometry (Chichester, England) 20110101

Title: Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives.

Journal: Bioorganic & medicinal chemistry 20101215

Title: (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.

Journal: Acta crystallographica. Section E, Structure reports online 20101201

Title: Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid.

Journal: European journal of medicinal chemistry 20101001

Title: Methyl 7-oxo-12-propyl-amino-13-nitro-deisopropyl-dehydro-abietate.

Journal: Acta crystallographica. Section E, Structure reports online 20101001

Title: Estrogenic and anti-estrogenic effects of wood extractives present in pulp and paper mill effluents on rainbow trout.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20100815

Title: Syntheses, characterization and fluorescent properties of two series of dehydroabietic acid C-ring derivatives.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100801

Title: Methyl 12-bromo-dehydro-abietate.

Journal: Acta crystallographica. Section E, Structure reports online 20100501

Title: The composition of the free fatty acids from Dendrolimus pini exuviae.

Journal: Journal of insect physiology 20100401

Title: Synthesis and biological evaluation of dehydroabietic acid derivatives.

Journal: European journal of medicinal chemistry 20100201

Title: Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr.

Journal: Bioorganic & medicinal chemistry 20100115

Title: Disproportionated rosin dehydroabietic acid in neoprene surgical gloves.

Journal: Dermatitis : contact, atopic, occupational, drug 20100101

Title: Functional food targeting the regulation of obesity-induced inflammatory responses and pathologies.

Journal: Mediators of inflammation 20100101

Title: 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).

Journal: BMC plant biology 20100101

Title: Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism.

Journal: PPAR research 20100101

Title: Anaerobic treatability and biogas production potential of selected in-mill streams.

Journal: Water science and technology : a journal of the International Association on Water Pollution Research 20100101

Title: (4R,5R,10S)-N-(4-Bromo-phen-yl)dehydro-abietamide.

Journal: Acta crystallographica. Section E, Structure reports online 20091201

Title: Dehydro-abietic acid.

Journal: Acta crystallographica. Section E, Structure reports online 20091001

Title: Evaluation of resin and fatty acid concentration levels by online sample enrichment followed by atmospheric pressure chemical ionization-mass spectrometry (APCI-MS).

Journal: Environmental science and pollution research international 20090501

Title: Cell transformation activities of abietic acid and dehydroabietic acid: safety assessment of possible contaminants in paper and paperboard for food contact use.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20090401

Title: Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro).

Journal: Evidence-based complementary and alternative medicine : eCAM 20090301

Title: Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha.

Journal: Planta medica 20090301

Title: Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior.

Journal: Carbohydrate research 20090105

Title: 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.

Journal: Organic letters 20090101

Title: Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice.

Journal: BioFactors (Oxford, England) 20090101

Title: Cancer chemopreventive activity of 'rosin' constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20081101

Title: Synthesis, structure analysis and cytotoxicity studies of novel unsymmetrically n,n'-substituted ureas from dehydroabietic Acid.

Journal: Chemical & pharmaceutical bulletin 20081101

Title: Effects of unsaturation on film structure and friction of fatty acids in a model base oil.

Journal: Journal of colloid and interface science 20081015

Title: Novel BK channel openers containing dehydroabietic acid skeleton: structure-activity relationship for peripheral substituents on ring C.

Journal: Bioorganic & medicinal chemistry letters 20081001

Title: SPE and HPLC/UV of resin acids in colophonium-containing products.

Journal: Journal of separation science 20080801

Title: Dehydroabietic acid, a phytochemical, acts as ligand for PPARs in macrophages and adipocytes to regulate inflammation.

Journal: Biochemical and biophysical research communications 20080502

Title: Exposure to wood dust, resin acids, and volatile organic compounds during production of wood pellets.

Journal: Journal of occupational and environmental hygiene 20080501

Title: 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.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20080401

Title: 13C and 1H NMR signal assignments of some new synthetic dehydroabietic acid derivatives.

Journal: Magnetic resonance in chemistry : MRC 20080401

Title: Tape-stripping as a method for measuring dermal exposure to resin acids during wood pellet production.

Journal: Journal of environmental monitoring : JEM 20080301

Title: Friction of fatty acids in nanometer-sized contacts of different adhesive strength.

Journal: Langmuir : the ACS journal of surfaces and colloids 20080219

Title: Effects of the wood extractives dehydroabietic acid and betulinol on reproductive physiology of zebrafish (Danio rerio)-a two-generation study.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20080218

Title: Solvent control of optical resolution of 2-amino-1-phenylethanol using dehydroabietic acid.

Journal: Organic & biomolecular chemistry 20080207

Title: Spasmolytic effect of constituents from Lepechinia caulescens on rat uterus.

Journal: Journal of ethnopharmacology 20080104

Title: The nature and fate of natural resins in the geosphere XIII: a probable pinaceous resin from the early Cretaceous (Barremian), Isle of Wight.

Journal: Geochemical transactions 20080101

Title: [Isolation and identification of diterpenoids from Pinus koraiensis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080101

Title: The green approaches for the synthesis of N-dehydroabietic alpha-aminophosphonates.

Journal: Natural product research 20080101

Title: Activity of dehydroabietic acid derivatives against wood contaminant fungi.

Journal: Journal of microbiological methods 20070901

Title: Dehydroabietic acid as a biomarker for exposure to colophony.

Journal: Occupational medicine (Oxford, England) 20070801

Title: Evaluation of the treatment efficiencies of paper mill whitewaters in terms of organic composition and toxicity.

Journal: Environmental pollution (Barking, Essex : 1987) 20070601

Title: Molecular detection and diversity of novel diterpenoid dioxygenase DitA1 genes from proteobacterial strains and soil samples.

Journal: Environmental microbiology 20070501

Title: [Characterization of the reaction products from pine gum catalytic disproportionation by gas chromatography/mass spectrometry].

Journal: Se pu = Chinese journal of chromatography 20070501

Title: Analysis of abietic acid and dehydroabietic acid in food samples by in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. A 20070330

Title: Fungal biotransformation products of dehydroabietic acid.

Journal: Journal of natural products 20070201

Title: Design, synthesis, and BK channel-opening activity of hexahydrodibenzazepinone derivatives.

Journal: Bioorganic & medicinal chemistry 20061201

Title: [Studies on diterpenes in needles of Pinus sylvestris].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061201

Title: Combined effects of pulp and paper effluent, dehydroabietic acid, and hypoxia on swimming performance, metabolism, and hematology of rainbow trout.

Journal: Ecotoxicology and environmental safety 20061101

Title: Efficient ortho-oxidation of phenol and synthesis of anti-MRSA and anti-VRE compound abietaquinone methide from dehydroabietic acid.

Journal: Chemical & pharmaceutical bulletin 20061001

Title: Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis.

Journal: Electrophoresis 20060901

Title: Characterization of DitA3, the [Fe3S4] ferredoxin of an aromatic ring-hydroxylating dioxygenase from a diterpenoid-degrading microorganism.

Journal: Biochimica et biophysica acta 20060901

Title: Migration of dehydroabietic and abietic acids from paper and paperboard food packaging into food-simulating solvents and Tenax TA.

Journal: Food additives and contaminants 20060801

Title: Improved aerobic biodegradation of abietic acid in ECF bleached kraft mill effluent due to biomass adaptation.

Journal: Journal of hazardous materials 20060731

Title: A biomimetic approach to the detection and identification of estrogen receptor agonists in surface waters using semipermeable membrane devices (SPMDs) and bioassay-directed chemical analysis.

Journal: Environmental science and pollution research international 20060701

Title: Fluorescence study of dehydroabietic acid-based bipolar arylamine-quinoxalines.

Journal: Journal of fluorescence 20060301

Title: Primary organic pollutants in New Zealand urban aerosol in winter during high PM10 episodes.

Journal: Environmental pollution (Barking, Essex : 1987) 20060101

Title: 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.

Journal: Geochemical transactions 20060101

Title: Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives.

Journal: Pharmacological research 20051101

Title: Safety assessment of paper and board food packaging: chemical analysis and genotoxicity of possible contaminants in packaging.

Journal: Food additives and contaminants 20051001

Title: Regio- and stereo-selective hydroxylation of abietic acid derivatives by Mucor circinelloides and Mortierella isabellina.

Journal: Biotechnology letters 20050901

Title: Oxidative stress and genotoxic responses to resin acids in Mediterranean mussels.

Journal: Ecotoxicology and environmental safety 20050601

Title: Direct exposure electron ionization mass spectrometry and gas chromatography/mass spectrometry techniques to study organic coatings on archaeological amphorae.

Journal: Journal of mass spectrometry : JMS 20050501

Title: Effects of dehydroabietic acid and abietic acid on survival, reproduction, and growth of the crustacean Daphnia magna.

Journal: Ecotoxicology and environmental safety 20050501

Title: [Studies on chemical constituents from pine cone of Pinus armandii].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050401

Title: Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101

Title: Dermal exposure to terpenic resin acids in Swedish carpentry workshops and sawmills.

Journal: The Annals of occupational hygiene 20040401

Title: Oxonitriles: multicomponent Grignard addition-alkylations.

Journal: Angewandte Chemie (International ed. in English) 20040220

Title: Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid.

Journal: Bioorganic & medicinal chemistry 20040102

Title: Anguilla anguilla L. plasma cortisol, lactate and glucose responses to abietic acid, dehydroabietic acid and retene.

Journal: Environment international 20040101

Title: Dehydroabietic acid derivatives as a novel scaffold for large-conductance calcium-activated K+ channel openers.

Journal: Bioorganic & medicinal chemistry letters 20031117

Title: Tepidimonas aquatica sp. nov., a new slightly thermophilic beta-proteobacterium isolated from a hot water tank.

Journal: Systematic and applied microbiology 20030901

Title: Characterization of surface n-alkanes and fatty acids of the epiphytic lichen Xanthoria parietina, its photobiont a green alga Trebouxia sp., and its mycobiont, from the Jerusalem hills.

Journal: European journal of biochemistry 20030501

Title: Antibacterial diterpenes from Calceolaria pinifolia.

Journal: Journal of natural products 20030201

Title: Dehydroabietic acid, a major component of wood industry effluents, interferes with cellular energetics in rainbow trout hepatocytes.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20030110

Title: Selected resin acids in effluent and receiving waters derived from a bleached and unbleached kraft pulp and paper mill.

Journal: Environmental toxicology and chemistry 20030101

Title: Potential antitumor-promoting diterpenes from the cones of Pinus luchuensis.

Journal: Journal of natural products 20021201

Title: Biotransformation, genotoxic, and histopathological effects of environmental contaminants in European eel (Anguilla anguilla L.).

Journal: Ecotoxicology and environmental safety 20021101

Title: Biomarker responses and resin acids in fish chronically exposed to effluents from a total chlorine-free pulp mill during regular production.

Journal: Ecotoxicology and environmental safety 20021001

Title: Juvenile sea bass liver biotransformation and erythrocytic genotoxic responses to pulp mill contaminants.

Journal: Ecotoxicology and environmental safety 20020901

Title: Structural effects on the bioactivity of dehydroabietic acid derivatives.

Journal: Planta medica 20020801

Title: Juvenile sea bass liver biotransformation induction and erythrocytic genotoxic responses to resin acids.

Journal: Ecotoxicology and environmental safety 20020701

Title: Bioaugmentation with the resin acid-degrading bacterium Zoogloea resiniphila DhA-35 to counteract pH stress in an aerated lagoon treating pulp and paper mill effluent.

Journal: Water research 20020601

Title: Fate of resin acids in pulp mill secondary treatment systems.

Journal: Water research 20020601

Title: Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry.

Journal: Journal of environmental monitoring : JEM 20020401

Title: Oak moss extracts in the diagnosis of fragrance contact allergy.

Journal: Contact dermatitis 20020301

Title: Lipids as indicators of eutrophication in marine coastal sediments.

Journal: Journal of microbiological methods 20020201

Title: Characterization of tdt genes for the degradation of tricyclic diterpenes by Pseudomonas diterpeniphila A19-6a.

Journal: Canadian journal of microbiology 20020101

Title: Identification of a possible biomarker for colophony exposure.

Journal: Occupational medicine (Oxford, England) 20011201

Title: Photoinduced toxicity of retene to Daphnia magna under enhanced UV-B radiation.

Journal: Chemosphere 20011101

Title: Detecting organic tracers from biomass burning in the atmosphere.

Journal: Marine pollution bulletin 20011001

Title: Synthetic derivatives of abietic acid with radical scavenging activity.

Journal: Journal of natural products 20010601

Title: Reactivity of Trametes laccases with fatty and resin acids.

Journal: Applied microbiology and biotechnology 20010401

Title: Bioaugmentation with resin-acid-degrading bacteria enhances resin acid removal in sequencing batch reactors treating pulp mill effluents.

Journal: Water research 20010301

Title: Copper resinate: preparation, characterisation and study of degradation.

Journal: Annali di chimica 20010101

Title: Fonseca T, et al. Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid. Bioorg Med Chem. 2004 Jan 2;12(1):103-12.

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Tags:1740-19-8 Molecular Formula|1740-19-8 MDL|1740-19-8 SMILES|1740-19-8 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aS,10aR)-