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C1530

Sigma-Aldrich

Cyclopiazonic acid

from Penicillium cyclopium, ≥98% (HPLC), powder, sarcoplasmic reticulum Ca²⁺-pump inhibitor

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Synonym(s):
CPA
Empirical Formula (Hill Notation):
C20H20N2O3
CAS Number:
Molecular Weight:
336.38
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

product name

Cyclopiazonic acid from Penicillium cyclopium, ≥98% (HPLC), powder

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: soluble
chloroform: soluble

storage temp.

−20°C

SMILES string

CN1C(=O)C(=C(\C)O)\C(=O)C2C(Cc3cccc4[nH]cc2c34)C1(C)C

InChI

1S/C20H22N2O3/c1-10(23)15-18(24)17-12-9-21-14-7-5-6-11(16(12)14)8-13(17)20(2,3)22(4)19(15)25/h5-7,9,13,17,21,23H,8H2,1-4H3/b15-10-

InChI key

WJCPGKDPOYBOOJ-GDNBJRDFSA-N

General description

Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species.

Application

Cyclopiazonic acid from Penicillium cyclopium has been used:
  • as a standard in aflatoxin detection and quantification by thin layer chromatography (TLC)
  • as a component in Ca2+-free DMEM/10% fetal bovine serum (FBS)
  • as a reversible inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) to examine the role of luminal calcium in endoplasmic recticulum (ER)-to-Golgi trafficking
  • as an endoplasmic reticulum Ca2+-ATPase blocker, to treat neurons and also to study the role of the endoplasmic reticulum (ER) in releasing and sustaining Ca2+ during Ca2+-induced Ca2+ release (CICR) to inhibit SERCA

Biochem/physiol Actions

Inhibits the sarcoplasmic reticulum Ca2+-pump.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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