CYCLOPIAZONIC ACID

Base Information

• Chemical Name: CYCLOPIAZONIC ACID
• CAS No.: 18172-33-3
• Molecular Formula: C₂₀H₂₀N₂O₃
• Molecular Weight: 336.39
• Hs Code.: 29337900
• Mol file: 18172-33-3.mol

Synonyms:9H-Pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one,10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aa,11ab,11ba)- (8CI); Cyclopiazonic acid; NSC 117181; a-Cyclopiazonic acid

Chemical Property of CYCLOPIAZONIC ACID

Chemical Property:

• Melting Point: 245-246℃
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 598.6°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 315.8°C
• PSA: 73.40000
• Density: 1.42g/cm³
• LogP: 2.76580
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• Water Solubility.: Soluble in DMSO (100 mM), ethanol (5 mM), DMF (~20 mg/ml), and 1:1 DMSO:PBS(pH 7.2) (0.5 mg/ml). Insoluble in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclopiazonic Acid, ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Cyclopiazonic acid is a mycotoxin that has been found in Penicillium and Aspergillus and an inhibitor of sarcoplasmic/endoplasmic reticulum Ca2+-ATPase (SERCA; IC50 = 0.6 μM). In vivo, cyclopiazonic acid (11-14 mg/kg) induces ptosis, hypothermia, tremor, and cachexia, as well as induces lethality (LD50 = 13 mg/kg), in rats. It induces tachycardia and sedation in rabbits when administered at a dose of 10 mg/kg.
• Uses: Cyclopiazonic acid is a tremorigenic indole produced by several species of Aspergillus and Penicillium. Cyclopiazonic acid is a highly specific inhibitor of calcium ATPase of sarcoplasmic reticulum, altering calcium homeostasis and ATP-dependent calcium transport and resulting in the release of intracellular stored Ca2+ without increasing IP3. The use of Cyclopiazonic acid on Langendorff-perfused murine hearts displayed anti-arrhythmic effects. Also, administration of cyclopiazonic acid on rat soleus muscle showed a decrease in hormone sensitive lipase activity and triacylglycerol hydrolysis. It is also used as an inhibitor of endoplasmic reticulum Ca2+-ATPase. 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 traffickingas 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

Technology Process of CYCLOPIAZONIC ACID

There total 1 articles about CYCLOPIAZONIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ cyclopiazonic acid (18172-33-3,18172-38-8)

Guidance literature:

Cyclopiazonsaeure-Cu(II)-salz, HCl, CHCl3;

DOI:10.1016/0040-4020(68)88113-X

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