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Key Documents

I6783

Sigma-Aldrich

Isopimaric Acid

≥98% (GC), powder

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About This Item

Fórmula empírica (notación de Hill):
C20H30O2
Número de CAS:
5835-26-7
Peso molecular:
302.45
MDL number:
MFCD04113116
UNSPSC Code:
12352106
PubChem Substance ID:
24724518
NACRES:
NA.77

assay

≥98% (GC)

form

powder

color

white

solubility

DMSO: 25 mg/mL

storage temp.

−20°C

SMILES string

[H][C@]12CC[C@@](C)(CC1=CC[C@@]3([H])[C@@](C)(CCC[C@]23C)C(O)=O)C=C

InChI

1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1

InChI key

MXYATHGRPJZBNA-KRFUXDQASA-N

General description

Isopimaric acid, a resin acid produced by conifer trees, is a tricyclic diterpene compound. High levels of isopimaric acid in the hepatocytes of the rainbow trout may impair calcium signalling machinery. Isopimaric acid is a potential big potassium (BK) channel opener.

Biochem/physiol Actions

Potent opener of large conductance calcium activated K+ (BK) channels.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H400

pcodes

P273

Hazard Classifications

Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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Enzyme cytochemical responses of mussels (Mytilus edulis) to resin acid constituents of pulp mill effluents.
G E Fâhraeus-Van Ree et al.
Bulletin of environmental contamination and toxicology, 63(4), 430-437 (1999-09-29)
The resin acids dehydroabietic acid and isopimaric acid release calcium from intracellular stores in rainbow trout hepatocytes.
Raabergh C, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 46(1), 55-65 (1999)
Neil C Henney et al.
American journal of physiology. Cell physiology, 297(6), C1397-C1408 (2009-09-25)
The pharmacology of the large-conductance K(+) (BK) channel in human osteoblasts is not well defined, and its role in bone is speculative. Here we assess BK channel properties in MG63 cells and primary human osteoblasts and determine whether pharmacological modulation
Eileen Smith et al.
Phytotherapy research : PTR, 19(6), 538-542 (2005-08-23)
The diterpene isopimaric acid was extracted from the immature cones of Pinus nigra (Arnold) using bioassay-guided fractionation of a crude hexane extract. Isopimaric acid was assayed against multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA). The minimum inhibitory concentrations (MIC) were
Dawn E Hall et al.
Plant physiology, 161(2), 600-616 (2013-02-02)
Diterpene resin acids (DRAs) are major components of pine (Pinus spp.) oleoresin. They play critical roles in conifer defense against insects and pathogens and as a renewable resource for industrial bioproducts. The core structures of DRAs are formed in secondary
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