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Dehydroabietic acid

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-D1008

  • Specification : 98%

  • CAS number : 1740-19-8

  • Formula : C20H28O2

  • Molecular Weight : 300.44

  • PUBCHEM ID : 94391

  • Volume : 20mg

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Catalogue Number

BF-D1008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

300.44

Appearance

White crystalline powder

Botanical Source

barks of Pinus yunnanensis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)O)C

Synonyms

dehydroabietic acid/abietic acid, dehydro-/1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid/(+)-Dehydroabietic aci/1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aS,10aR)-/Abieta-8(14),9(11),12-trien-18-oic acid/Abieta-8,11,13-trien-18-oic acid,Dehydroabietate

IUPAC Name

(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

Applications

Dehydroabietic acid possesses antiviral activity[1]

Density

1.1±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

202.5±20.3 °C

Boiling Point

425.1±34.0 °C at 760 mmHg

Melting Point

174-176ºC

InChl

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

InChl Key

NFWKVWVWBFBAOV-MISYRCLQSA-N

WGK Germany

RID/ADR

HS Code Reference

2942000000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1740-19-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31591296

Abstract

A high-throughput quantitative Nuclear Magnetic Resonance 1H-NMR method was developed and applied to screen the quantity of the diterpenic resin acids in the heartwood of black pine, due to the renewed scientific interest in their medicinal properties and use in various diseases treatment. The 260 samples were taken from Pinus nigra clones, selected from four provenances of the Peloponnese (Greece), participating in a 35-year-old clonal seed orchard. Total resin acids per dry heartwood weight (dhw) varied greatly, ranging from 30.05 to 424.70 mg/gdhw (average 219.98 mg/gdhw). Abietic was the predominant acid (76.77 mg/gdhw), followed by palustric acid (47.94 mg/gdhw), neoabietic acid (39.34 mg/gdhw), and pimaric acid (22.54 mg/gdhw). Dehydroabietic acid was at moderate levels (11.69 mg/gdhw), while levopimaric, isopimaric, and sandaracopimaric acids were in lower concentrations. The resin acid fraction accounted for 72.33% of the total acetone extractives. Stilbenes were presented in significant quantities (19.70%). The resin acid content was composed mainly of the abietane type resin acids (83.56%). Peloponnesian Pinus nigra heartwood was found to be the richest source of resin acids identified to date and is considered the best natural source for the production of such bioactive extracts. The results indicate a high potential for effective selection and advanced breeding of pharmaceutical and high economic value bioactive substances from Pinus nigra clones.

KEYWORDS

Pinus nigra; diterpenes; high-throughput screening; provenances; quantitative nuclear magnetic resonance; resin acids

Title

High-Throughput 1H-Nuclear Magnetic Resonance-Based Screening for the Identification and Quantification of Heartwood Diterpenic Acids in Four Black Pine (Pinus nigra Arn.) Marginal Provenances in Greece.

Author

Ioannidis K1,2, Melliou E3, Magiatis P4.

Publish date

2019 Oct 7

PMID

31472409

Abstract

In this work, amphiphilic surfactant was obtained using dehydroabietic acid from pine rosin and then pre-adsorbed with acid-pretreated bamboo residues (AP-BR) to block the residual lignin adsorption site, which is expected to improve its enzymatic digestibility. Results from cryogenic-transmission electron microscopy (Cryo-TEM) indicated amphiphilic surfactant with PEG with polymerization degree of 34 (D-34) aggregated to form worm-like micelles, which improved enzymatic hydrolysis yield of AP-BR from 24.3% to 71.9% by pre-adsorbing with 0.8 g/L. Amphiphilic surfactants pre-adsorbed on AP-BR could reduce hydrophobicity of AP-BR, adsorption affinity and adsorption capacity of lignin for cellulase from 0.51 L/g to 0.48-0.32 L/g, from 2.9 mL/mg to 1.8-1.4 mL/mg, and from 122.3 mg/g to 101.9-21.4 mg/g, respectively. These changed properties showed compelling positive contributions (R2 > 0.9) for free enzymes in the supernatants and sequently for final enzymatic hydrolysis yield, which was caused by blocking non-productively hydrophobic adsorption between lignin and cellulase.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

Acid pretreatment; Amphiphilic surfactant; Bamboo; Enzymatic hydrolysis; Lignin adsorption site

Title

Improving enzymatic hydrolysis of acid-pretreated bamboo residues using amphiphilic surfactant derived from dehydroabietic acid.

Author

Lin W1, Chen D2, Yong Q1, Huang C3, Huang S4.

Publish date

2019 Dec

PMID

31448648

Abstract

In this paper, a series of novel 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid bearing different N-(piperazin-1-yl)alkyl side chains were designed, synthesised and evaluated for their in vitro anticancer activities against three human hepatocarcinoma cell lines (SMMC-7721, HepG2 and Hep3B). Among them, compound 10g exhibited the most potent activity against three cancer cell lines with IC50 values of 1.39 ± 0.13, 0.51 ± 0.09 and 0.73 ± 0.08 µM, respectively. In the kinase inhibition assay, compound 10g could significantly inhibit MEK1 kinase activity with IC50 of 0.11 ± 0.02 µM, which was confirmed by western blot analysis and molecular docking study. In addition, compound 10g could elevate the intracellular ROS levels, decrease mitochondrial membrane potential, destroy the cell membrane integrity, and finally lead to the oncosis and apoptosis of HepG2 cells. Therefore, compound 10g could be a potent MEK inhibitor and a promising anticancer agent worthy of further investigations.

KEYWORDS

Dehydroabietic acid; MEK inhibitor; anticancer activity; apoptosis; oncosis

Title

Synthesis and biological evaluation of novel N-(piperazin-1-yl)alkyl-1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential MEK inhibitors.

Author

Chen H1, Qiao C1, Miao TT1, Li AL1, Wang WY1, Gu W1.

Publish date

2019 Dec