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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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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
I Kononenko et al.
Environmental science and pollution research international, 24(3), 2160-2165 (2016-07-29)
The chemical composition of sandarac resin was investigated qualitatively and quantitatively by gas chromatography-mass spectrometry (GC-MS). Six compounds with labdane and pimarane skeletons were identified in the resin. The obtained mass spectra were interpreted and the mass spectrometric behaviour of
Sohag N Saleh et al.
The Journal of pharmacology and experimental therapeutics, 321(3), 1075-1084 (2007-03-10)
Because chloride (Cl(-)) channel blockers such as niflumic acid enhance large-conductance Ca(2+)-activated potassium channels (BK(Ca)), the aim of this study was to determine whether there is a reciprocal modification of Ca(2+)-activated chloride Cl(-) currents (I(ClCa)) by two selective activators of
Suresh Awale et al.
Chemical & pharmaceutical bulletin, 51(3), 268-275 (2003-03-04)
From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O-deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K
Molecular basis of pimarane compounds as novel activators of large-conductance Ca2+-activated K+ channel alpha-subunit.
Imaizumi Y, et al.
Molecular Pharmacology, 62(4), 836-846 (2002)
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