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C7632

Sigma-Aldrich

Cantharidin

Synonym(s):

3a,7a-Dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione, 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran, Cantharidine, Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione

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About This Item

Empirical Formula (Hill Notation):
C10H12O4
CAS Number:
56-25-7
Molecular Weight:
196.20
EC Number:
200-263-3
MDL number:
MFCD00134968
UNSPSC Code:
12352200
PubChem Substance ID:
24278334
NACRES:
NA.77

Quality Level

200

color

white

mp

215-217 °C (lit.)
215-218 °C

solubility

DMSO: soluble
ethanol: soluble

SMILES string

C[C@]12C3CCC(O3)[C@@]1(C)C(=O)OC2=O

InChI

1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-

InChI key

DHZBEENLJMYSHQ-XCVPVQRUSA-N

Gene Information

human ... PPP2CA(5515) , PPP2CB(5516) , PPP2CBP(5517) , PPP2R1A(5518) , PPP2R1B(5519) , PPP2R2A(5520) , PPP2R2B(5521) , PPP2R2C(5522) , PPP2R3A(5523) , PPP2R5A(5525)

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General description

Cantharidin is a poisonous vesicant, which is produced by blister bees. It is used to treat piles, ulcers, venomous worms and tuberculous scrofuloderma. It is used as an aphrodisiac, abortifacient and a veterinary medicine diuretic.

Application

Cantharidin has been used to inhibit protein phosphatase 2 (PP2A).

Biochem/physiol Actions

Inhibitor of protein phosphatase 2A.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300,H315,H319,H335

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Calyculin A, Discodermia calyx Calyculin A, CAS 101932-71-2, is a cell-permeable inhibitor of protein phosphatase 2A (IC₅₀ = 0.5-1 nM) and protein phosphatase 1 (PP1; IC₅₀ = 2 nM).

Sigma-Aldrich

208851

Calyculin A, Discodermia calyx

Famotidine

Sigma-Aldrich

F6889

Famotidine

Ali Thaqi et al.
European journal of medicinal chemistry, 45(5), 1717-1723 (2010-02-16)
Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer
Hong-Chang Li et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 43(5), 1829-1840 (2017-10-20)
Cantharidin, a type of terpenoid secreted by the blister beetle Mylabris phalerata (Pallas), has attracted great attention in cancer therapy because of its potential anti-cancer activities. Here, we report the effects on apoptosis and autophagy in human triple-negative breast cancer
Heat Oscillations Driven by the Embryonic Cell Cycle Reveal the Energetic Costs of Signaling
Rodenfels J, et al.
Developmental Cell (2019)
Chie-Hong Wang et al.
International journal of molecular sciences, 23(23) (2022-12-12)
Myeloid zinc finger 1 (MZF1), also known as zinc finger protein 42, is a zinc finger transcription factor, belonging to the Krüppel-like family that has been implicated in several types of malignancies, including glioblastoma multiforme (GBM). MZF1 is reportedly an
Cécile Segonzac et al.
The EMBO journal, 33(18), 2069-2079 (2014-08-03)
Recognition of pathogen-associated molecular patterns (PAMPs) by surface-localized pattern-recognition receptors (PRRs) activates plant innate immunity, mainly through activation of numerous protein kinases. Appropriate induction of immune responses must be tightly regulated, as many of the kinases involved have an intrinsic
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ReadyShield® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

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