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Merck

C7632

Cantharidin

protein phosphatase 2 A (PPA2) inhibitor

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
NACRES:
NA.77
PubChem Substance ID:
24278334
UNSPSC Code:
12352200
EC Number:
200-263-3
MDL number:
MFCD00134968
Quality level:
200

Key Documents

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Product Name

Cantharidin,

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

SMILES string

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

color

white

mp

215-217 °C (lit.), 215-218 °C

solubility

DMSO: soluble, ethanol: soluble

Quality Level

200

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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Related Categories

Application

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

Biochem/physiol Actions

Inhibitor of protein phosphatase 2A.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP3226
BCCM7986
BCCL3516
BCCK0647
BCCJ4895

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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
T I Baskin et al.
Plant physiology, 113(2), 493-502 (1997-02-01)
To investigate molecular mechanisms controlling plant morphogenesis, we examined the morphology of primary roots of Arabidopsis thaliana and the organization of cortical microtubules in response to inhibitors of serine/threonine protein phosphatases and kinases. We found that cantharidin, an inhibitor of
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
Timothy A Hill et al.
Bioorganic & medicinal chemistry, 15(18), 6126-6134 (2007-07-04)
A range of amines was reacted with norcantharidin (2) to provide the corresponding norcantharimides (9-43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (20) which was amenable to epoxidation (mCPBA, 22) and subsequent ring opening (MeOH/H(+); 23) or alternatively
Elena Lissina et al.
PLoS genetics, 7(10), e1002332-e1002332 (2011-10-27)
Using small molecule probes to understand gene function is an attractive approach that allows functional characterization of genes that are dispensable in standard laboratory conditions and provides insight into the mode of action of these compounds. Using chemogenomic assays we
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