(±)-Norcantharidin

Names

[ Name ]:
(±)-Norcantharidin

[Synonym ]:
(1R,2S,6R,7S)-4,10-Dioxatricyclo[5.2.1.0]decane-3,5-dione
norcantharadin
(3aR,4S,7R,7aS)-hexahydro-4,7-epoxy-2-benzofuran-1,3-dione
4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
exo-3,6-Epoxyhexahydrophthalic Anhydride
exo-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic Anhydride
MFCD00213361
Isocantharidin
demethyl cantharidin
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (4R,7S)-
7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylc acid anhydride
7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid anhydride
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-
(1R,7S)-4,10-Dioxatricyclo[5.2.1.0]decane-3,5-dione
endothallanhydride
Norcantharidin
exo,exo-4,10-dioxatricyclo[5.2.1.02.6]decane-3,5-dione
Exo-7-oxabicyclo(2.2.1)h
(4R,7S)-hexahydro-4,7-epoxy-2-benzofuran-1,3-dione

Biological Activity

[Description]:

(±)-Norcantharidin ((±)-NCTD) is a compound possessing anti-angiogenetic activity with potential use in anti-cancertherapy. (±)-Norcantharidin could prevent tumorigenesis by inhibiting cell proliferation, inducing apoptosis and the cell cycle arrest, and anti-angiogenic effects[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

(±)-Norcantharidin ((±)-NCTD) inhibits HMC cell proliferation, induces apoptosis, and affects the cell cycle[1].

[References]

[1]. Ye K, et al. Effect of norcantharidin on the proliferation, apoptosis, and cell cycle of human mesangialcells. Ren Fail. 2017 Nov;39(1):458-464.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
362.5±35.0 °C at 760 mmHg

[ Melting Point ]:
114-116ºC

[ Molecular Formula ]:
C₈H₈O₄

[ Molecular Weight ]:
168.147

[ Flash Point ]:
167.0±26.0 °C

[ Exact Mass ]:
168.042252

[ PSA ]:
52.60000

[ LogP ]:
-0.85

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.550

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RN8400000

CHEMICAL NAME :: 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, exo-

CAS REGISTRY NUMBER :: 29745-04-8

BEILSTEIN REFERENCE NO. :: 0084287

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H8-O4

MOLECULAR WEIGHT :: 168.16

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 35,823,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RN8400000

[ HS Code ]:
2932999099

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Two triterpenoid glycosides from the roots of Camellia oleifera and their cytotoxic activity.

J. Asian Nat. Prod. Res. 17 , 800-7, (2015)

Two new triterpenoid saponins, oleiferoside N and oleiferoside O, were isolated from the EtOH extract from the roots of Camellia oleifera C. Abel. Their structures were elucidated as 16α-acetoxy-21β,2...

Cantharidin represses invasion of pancreatic cancer cells through accelerated degradation of MMP2 mRNA.

Sci. Rep. 5 , 11836, (2015)

Cantharidin is an active constituent of mylabris, a traditional Chinese medicine, and is a potent and selective inhibitor of protein phosphatase 2A (PP2A) that plays an important role in cell cycle co...

A novel cantharidin analogN-Benzylcantharidinamide reduces the expression of MMP-9 and invasive potentials of Hep3B via inhibiting cytosolic translocation of HuR

Biochem. Biophys. Res. Commun. 447(2) , 371-7, (2014)

Graphical abstract

Related Compounds

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