ChemicalBook >> CAS DataBase List >>CYCLOPIAZONIC ACID
CYCLOPIAZONIC ACID
- CAS No.
- 18172-33-3
- Chemical Name:
- CYCLOPIAZONIC ACID
- Synonyms
- CPA;CYCLOPIAZONIC ACID;gamma-linolenoyl-CoA;PENICILLIUM CYCLOPIUM;Cyclopiazonic acid,98%;ALPHA CYCLOPIAZONIC ACID;Cyclopiazonic acid (CPA);Penicillium cyclopiumPCR;CYCLOPIAZONICACID,BIOTECHGRADE;Penicillium cyclopium Westling
- CBNumber:
- CB9207176
- Molecular Formula:
- C20H20N2O3
- Molecular Weight:
- 336.38
- MDL Number:
- MFCD00167445
- MOL File:
- 18172-33-3.mol
- MSDS File:
- SDS
Last updated:2023-09-04 15:51:00
| Melting point | 245-246°C |
|---|---|
| Boiling point | 472.86°C (rough estimate) |
| Density | 1.2171 (rough estimate) |
| refractive index | 1.5700 (estimate) |
| storage temp. | -20°C |
| solubility | DMSO: soluble |
| form | powder |
| pka | 4.50±1.00(Predicted) |
| color | white to off-white |
| 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. |
| FDA UNII | X9TLY4580Z |
| EPA Substance Registry System | Cyclopiazonic acid (18172-33-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300 | |||||||||
| Precautionary statements | P264-P301+P310 | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 25 | |||||||||
| Safety Statements | 36/37/39-45 | |||||||||
| RIDADR | UN 2811 6.1/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UY8587000 | |||||||||
| HazardClass | 6.1(a) | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29337900 | |||||||||
| Toxicity | chicken,LD50,oral,12mg/kg (12mg/kg),Poultry Science. Vol. 65(Suppl, | |||||||||
| NFPA 704 |
|
CYCLOPIAZONIC ACID price More Price(20)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | C1530 | Cyclopiazonic acid from Penicillium cyclopium ≥98% (HPLC), powder | 18172-33-3 | 5mg | $118 | 2024-03-01 | Buy |
| Sigma-Aldrich | 239805 | Cyclopiazonic Acid, A cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca | 18172-33-3 | 5mg | $96.4 | 2023-01-07 | Buy |
| Alfa Aesar | J61594 | Cyclopiazonic acid, 98% | 18172-33-3 | 10mg | $185.65 | 2024-03-01 | Buy |
| Alfa Aesar | J61594 | Cyclopiazonic acid, 98% | 18172-33-3 | 50mg | $698.65 | 2024-03-01 | Buy |
| Cayman Chemical | 11326 | Cyclopiazonic Acid ≥95% | 18172-33-3 | 1mg | $25 | 2024-03-01 | Buy |
CYCLOPIAZONIC ACID Chemical Properties,Uses,Production
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.
Chemical Properties
off-white powder or crystals
Uses
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
Uses
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.
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.
General Description
Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species.
Biological Activity
Cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca 2+ -ATPase.
Biochem/physiol Actions
Inhibits the sarcoplasmic reticulum Ca2+-pump.
storage
-20°C
CYCLOPIAZONIC ACID Preparation Products And Raw materials
Raw materials
Preparation Products
Global( 97)Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| BOC Sciences | +16314854226 | inquiry@bocsci.com | United States | 19743 | 58 |
| Wuhan Topule Biopharmaceutical Co., Ltd | +8618327326525 | masar@topule.com | China | 8474 | 58 |
| Shanghai Acmec Biochemical Technology Co., Ltd. | +undefined18621343501 | product@acmec-e.com | China | 33349 | 58 |
| Aladdin Scientific | +1-833-552-7181 | sales@aladdinsci.com | United States | 57511 | 58 |
| J & K SCIENTIFIC LTD. | 010-82848833 400-666-7788 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 821-50328103-801 18930552037 | 3bsc@sina.com | China | 15848 | 69 |
| Ascent Scientific | 4401179829988 | customerservice@ascentscientific.co.uk | United Kingdom | 279 | 60 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4428 | 55 |
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1of4
-Cyclopiazonic acid / CPA
Cyclopiazonic acid from Penicillium grisefulvum
Cyclopiazonic acid (CPA)
Cyclopiazonic acid, FroM PenicilliuM griseofulvuM
(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
(6a-alpha,11a,11b-alpha)--10-acetyl-7-dimethyl-11-hydroxy-
9h-pyrrolo(1’,2’:2,3)isoindolo(4,5,6-cd)indol-9-one,2,6,6a,7,11a,11b-hexahydro
(6AA, 10Z, 11AB, 11BA)-6A,7,11A,11B-TETRAHYDRO-10-(1-HYDROXYETHYLIDENE)-7,7- DIMETHYL-6H-PYRROLO [1',2':2,3]ISOINDOLO [4,5,6-CD]INDOLE-9,11 (2H,10H)-DIONE
(6AR,11AS,11BR)-REL-10-ACETYL-2,6,6A,7,11A,11B-HEXAHYDRO-7,7-DIMETHYL-9H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-9-ONE
ALPHA CYCLOPIAZONIC ACID
CPA
CYCLOPIAZONIC ACID
CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM
CYCLOPIAZONIC ACID FROM PENICILLIUMCYCLO PIUM MINIM
9H-Pyrrolo1,2:2,3isoindolo4,5,6-cdindol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-rel-
CYCLOPIAZONICACID,BIOTECHGRADE
[5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-(2-octadeca-6,9,12-trienoylsulfanylethylcarbamoyl)ethylcarbamoyl]propoxy]phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid
gamma-linolenoyl-CoA
Cyclopiazonic acid from Penicillium cyclopium
PENICILLIUM CYCLOPIUM
10-Acetyl-2,6,6aβ,7,11aα,11bβ-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Cyclopiazonic acid,98%
Cyclopiazonic acid, 98%, from Penicillium griseofulvum
Cyclopiazonic Acid, Penicillium cyclopium - CAS 18172-33-3 - Calbiochem
Cyclopiazonic Acid, 98.0+ % (HPLC)
Penicillium cyclopium Westling
Penicillium cyclopiumPCR
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-, (6aR,11aS,11bR)-
18172-33-3
181172-33-3
C20H20N2O3
C39H64N7O17P3S
Intracellular Calcium Regulators
Intracellular Calcium Signaling
Cell Biology
Cell Signaling and Neuroscience
BioChemical
antibiotic
Signalling
Calcium signaling