CANTHARIDINE

CANTHARIDINE
PRODUCT IDENTIFICATION
CAS NO.	56-25-7
EINECS NO.	200-263-3
FORMULA	C₁₀H₁₂O₄
MOL WT.	196.20
H.S. CODE	2918.99.5000
TOXICITY	Oral-Human LDLO - 0.428 mg/kg
SYNONYMS	exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride;
Cantharidine; 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride; 2,3-Dimethyl-7-oxabicyclo(2.2.1) heptane-2,3-dicarboxylic anhydride; Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione; (3a-alpha,4-beta,7-beta,7a-alpha)- Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione; 2,3-Dimethyl- 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride; CAN (Alkaloid); Cantharides camphor; Cantharidin; Cantharone; Hexahydro-3aalpha,7aalpha-dimethyl-4beta,7 beta-epoxy isobenzofuran-1,3-dione; Kantaridin; Kantharidin; (1R,2S,3R,6S)-1,2-Dimethyl-3,6-epoxycyclohexane -1,2-dicarboxylic anhydride; 2,3-ADimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride;
SMILES	C1([C@@]2([C@@]([C@@H]3CC[C@@H]2O3)(C(=O)O1)C)C)=O
CLASSIFICATION	Acid anhydride, Monoterpene, Phosphatase inhibitor
EXTRA NOTES	Overall Carcinogenic Evaluation: Group 3. Inhibitor of protein phosphatase 2A. A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.
PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE	white powder
MELTING POINT	`215 - 218 C`
BOILING POINT
SPECIFIC GRAVITY	1.41
SOLUBILITY IN WATER	30 mg/l
pH
VAPOR DENSITY
AUTOIGNITION
log P	1.22 (Octanol-water)
OH RATE CONSTANT	1.68E-11 (cm3/molecule-sec at 25 C Atmospheric)
NFPA RATINGS	Health: 3; Flammability: ; Reactivity:
REFRACTIVE INDEX
FLASH POINT
STABILITY	Stable under ordinary conditions
EXTERNAL LINKS & GENERAL DESCRIPTION
Wikipedia Linking - Cantharidin Google Scholar Search Drug Information Portal (U.S. National Library of Medicine) - Cantharidine PubChem Compound Summary - Cantharidine http://www.ebi.ac.uk/chebi/ - Cantharidin KEGG (Kyoto Encyclopedia of Genes and Genomes) - Cantharidin http://www.faidherbe.org/ The cantharidin was first isolated by Robiquet, a French chemist in 1810. It has an important role in the ecology of different kinds of insects that use or produce it as a defense ability to preserve their eggs from predators. In the ancient world, the dried spanish flies had the reputation of aphrodisiac virtues. In fact, these supposed properties are not attested neither in theory nor in experimentation. The cantharidin seems to be a dangerous substance with the same toxicity as the most violent poisonus like strychnin. Journal of Chinese Pharmaceutical Sciences Improved synthesis and structure identification of L-histidine norcantharimide, a potent PP2A inhibitor was reported. Condensation between norcantharidin and L-histidine in 95% EtOH at reflux temperature affords L-histidine norcantharimide in 97.0% yield which is much higher compared with literature, and more importantly, the configuration is retained. The chemical structure of the compound was re-elucidated through IR, FAB-MS, 1H NMR, 13C NMR and 2D NMR (1H, 13C-COSY and HMBC), the fundamental physical data, including optical data being also firstly reported. Preliminary cytotoxicity evaluation showed that the target compound was probably more potent than norcantharidin against a panel of human cancer cell lines. Design and synthesis of amino acid (nor) cantharimides would provide a convenient and rational structure modification of (nor) cantharidin and open new avenues to explore new promising candidates.
SALES SPECIFICATION
APPEARANCE	white powder
ASSAY	98.0% min (GC)
MELTING POINT	`215 -218 C`
TRANSPORTATION
PACKING
HAZARD CLASS	6.1 (Packing Group I)
UN NO.	2811
SAFETY INFORMATION
Hazard Overview	OSHA Hazards: Target Organ Effect, Highly toxic by ingestion, Irritant. Target Organs: Kidney, Cardiovascular system.
GHS
SIGNAL WORD	Danger
PICTOGRAMS
HAZARD STATEMENTS	H300 Fatal if swallowed. H315 Causes skin irritation. H319 Causes serious eye irritation. H335 May cause respiratory irritation.
PRECAUTIONARY STATEMENTS	P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray. P264 Wash hands thoroughly after handling. P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/ physician. P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
EC DIRECTIVES
HAZARD CODES	T+ Very Toxic
RISK PHRASES	28 Very Toxic if swallowed 36/37/38 Irritating to eyes, respiratory system and skin
SAFETY PHRASES	45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 53 Avoid exposure - obtain special instruction before use
PRICE INFORMATION