Articles:
(3aa,4b,7b,7aa)-hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione
Notes:
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.
| CAS Number: | 56-25-7 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 200-263-3 | |
| FDA UNII: | IGL471WQ8P | |
| Nikkaji Web: | J1.376E | |
| Beilstein Number: | 0085302 | |
| MDL: | MFCD00134968 | |
| XlogP3-AA: | 0.60 (est) | |
| Molecular Weight: | 196.20244000 | |
| Formula: | C10 H12 O4 | |
| BioActivity Summary: | listing | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
Physical Properties:
| Appearance: | brown to black powder (est) |
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Melting Point: | 218.00 °C. @ 760.00 mm Hg |
| Boiling Point: | 326.87 °C. @ 760.00 mm Hg (est) |
| Flash Point: | 295.00 °F. TCC ( 146.10 °C. ) (est) |
| logP (o/w): | -0.409 (est) |
| Soluble in: | |
| water, 4138 mg/L @ 25 °C (est) | |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Cantharidin 98% |
| ExtraSynthese |
| For experimental / research use only. |
| Cantharidin |
| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Cantharidin ≥98% |
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Cantharidin |
Safety Information:
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
|
oral-cat LDLo 310 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. oral-dog LDLo 50 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. oral-frog LDLo 7273 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. oral-human LDLo 428 ug/kg "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 646, 1969. intraperitoneal-mammal (species unspecified) LD50 1710 ug/kg "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher,Peop. Rep. China, 1994Vol. -, Pg. 183, 1994. oral-mammal (species unspecified) LDLo 75 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. unreported-mammal (species unspecified) LDLo 50 mg/kg Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 20, Pg. 135, 1989. intraperitoneal-mouse LD50 1 mg/kg Journal of Agricultural and Food Chemistry. Vol. 35, Pg. 823, 1987. oral-rabbit LDLo 20 mg/kg CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Toxicon. Vol. 23, Pg. 36, 1985. | |
| Dermal Toxicity: | |
|
subcutaneous-chicken LDLo 75 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. subcutaneous-rabbit LDLo 1 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | natural substances and extractives | ||
| Recommendation for cantharidin usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for cantharidin flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| EPI System: | View |
| ClinicalTrials.gov: | search |
| Chemical Carcinogenesis Research Information System: | Search |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA Substance Registry Services (TSCA): | 56-25-7 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 5944 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| Chemidplus: | 0000056257 |
| EPA/NOAA CAMEO: | hazardous materials |
| RTECS: | RN8575000 for cas# 56-25-7 |
References:
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5944 |
| Pubchem (sid): | 134972601 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C16778 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2932.90.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
| Formulations/Preparations: •it is available as cantharidin collodion (cantharone), cantharidin (0.7%) in a film-forming vehicle containing acetone, ethocel, flexible collodion, ether (35%) and alcohol (11%). •cantharone (seres). liquid containing cantharidin 0.7% in a vehicle containing ether 35%, acetone, ethocel, and flexible collodion in 7.5 ml containers. | |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| found in nature |
Synonyms:
| cantharides camphor | |
| cantharidine | |
| cantharone | |
| (1R,2S,3R,6S)-1,2- | dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride |
| (1S,3S,4R,7R)-2,6- | dimethyl-4,10-dioxa-tricyclo[5.2.1.0-2,6]decane-3,5-dione |
| (1R,2S,6R,7S)-2,6- | dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione |
| (1R,7S)-2,6- | dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione |
| (1S,2R,6S,7R)-2,6- | dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione |
| (2S,7S,1R,6R)-2,6- | dimethyl-4,10-dioxatricyclo[5.2.1.0<2,6>]decane-3,5-dione |
| (3aR,4S,7R,7aS)-3a,7a- | dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione |
| 4,7- | epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)- |
| 4,7- | epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel- |
| (3aa,4b,7b,7aa)- | hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione |
| kantaridin | |
| kantharidin |