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I6783

Sigma-Aldrich

Isopimaric Acid

≥98% (GC), powder

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About This Item

Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
5835-26-7
Molecular Weight:
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

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Ammanamanchi S R Anjaneyulu et al.
Journal of Asian natural products research, 4(1), 53-61 (2002-05-07)
Chemical examination of the ethyl acetate extract of the roots of Rhizophora mucronata collected from Mangalore Coast resulted in the isolation of three more new diterpenoids, rhizophorins C-E (1-3) in addition to the two, rhizophorin A, (6R,11S,13S)-6,11,13-trihydroxy-2,3-seco-14-labden-2,8-olid-3-oic acid, and rhizophorin
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