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56-25-7

Basic Information
CAS No.: 56-25-7
Name: 4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-
Article Data: 12
Cas Database
Molecular Structure:
Molecular Structure of 56-25-7 (4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-)
Formula: C10H12O4
Molecular Weight: 196.203
Synonyms: 4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-, (3aa,4b,7b,7aa)-;7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicanhydride, 2,3-dimethyl- (8CI);Cantharidin (6CI,7CI);1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride;Cantharidine;Cantharone;Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione;Kantaridin;NSC 61805;
EINECS: 200-263-3
Density: 1.362 g/cm3
Melting Point: 215-217 °C(lit.)
Boiling Point: 326.869 °C at 760 mmHg
Flash Point: 146.137 °C
Solubility: 30mg/L(20 oC)
Appearance: white to light yellow crystal powder
Hazard Symbols: ToxicT, VeryT+
Risk Codes: 28-36/37/38-38-37-36-23/24/25
Safety: 53-45-36/37/39
Transport Information: UN 2811 6.1/PG 1
PSA: 52.60000
LogP: 0.64360
Synthetic route
75532-25-1

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

56-25-7

cantharidin

Conditions
ConditionsYield
Stage #1: furan; 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride With 1-butyl-3-methylimidazolium Tetrafluoroborate at 50℃; for 19h;
Stage #2: In ethyl acetate for 4h; Reagent/catalyst; Temperature; Reflux;
90%
75538-64-6

C10H10O4S

56-25-7

cantharidin

Conditions
ConditionsYield
With hydrogen In ethyl acetate under 760.051 Torr; Reflux;59%
With hydrogen In ethyl acetate at 50℃; under 1551.49 - 2585.81 Torr; for 20h;17%
With nickel In ethyl acetate Heating;
75532-25-1

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

A

80558-50-5

epi-catharidin

B

56-25-7

cantharidin

Conditions
ConditionsYield
nickel 1.) 7000 bar, 24 h, 2.) ethyl acetate, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
1,2t-dimethyl-3,6-dioxo-cyclohexane-1r,2c-dicarboxylic acid diethyl ester

1,2t-dimethyl-3,6-dioxo-cyclohexane-1r,2c-dicarboxylic acid diethyl ester

56-25-7

cantharidin

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol Behandeln des Reaktionsprodukts mit konz. Schwefelsaeure;
1-<(Ξ)-benzylidene>-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

1-<(Ξ)-benzylidene>-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

56-25-7

cantharidin

Conditions
ConditionsYield
With ozone; ethyl acetate at -40℃; Erhitzen des Reaktionsprodukts mit Essigsaeure und wss. Wasserstoffperoxid;
7647-01-0

hydrogenchloride

2-methoxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione

56-25-7

cantharidin

Conditions
ConditionsYield
at 150℃; im Rohr;

(+/-)-1-((Ξ)-benzylidene)-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

141-78-6

ethyl acetate

56-25-7

cantharidin

Conditions
ConditionsYield
at -40℃; Erhitzen des Reaktionsprodukts mit Essigsaeure und wss. Wasserstoffperoxid;
cantharidene

cantharidene

56-25-7

cantharidin

7647-01-0

hydrogenchloride

853200-58-5

2-hydroxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione

A

7803-49-8

hydroxylamine

B

56-25-7

cantharidin

Conditions
ConditionsYield
at 150℃; im Rohr;

(-)-2-bromo-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-8-carboxylic acid

A

56-25-7

cantharidin

B

dextrorotatory cantharic acid

dextrorotatory cantharic acid

C

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

Conditions
ConditionsYield
at 215 - 225℃;
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Chemistry

Product Name: Cantharidin
Synonyms: (2R,6S)-2,6-Dimethyl-4,10-dioxatricyclo[5.2.1.0~2,6~]decan-3,5-dion ; (2R,6S)-2,6-Dimethyl-4,10-dioxatricyclo[5.2.1.0~2,6~]decane-3,5-dione ; (2R,6S)-2,6-Diméthyl-4,10-dioxatricyclo[5.2.1.0~2,6~]décane-3,5-dione ; (3aR,7aS)-3a,7a-Dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione
Molecular Structure of Cantharidin (CAS NO.56-25-7) :
Molecular Formula of Cantharidin (CAS NO.56-25-7) : C10H12O4
Molecular Weight of Cantharidin (CAS NO.56-25-7) : 196.20
CAS NO: 56-25-7
EINECS: 200-263-3
Product Categories: chiral
Mol File: 56-25-7.mol
Merck : 13,1757
Index of Refraction: 1.547
Surface Tension: 49.2 dyne/cm
Density: 1.362 g/cm3
Flash Point: 146.2 °C
Enthalpy of Vaporization: 56.91 kJ/mol
Boiling Point: 326.9 °C at 760 mmHg
Vapour Pressure: 0.00021 mmHg at 25°C
Melting point 215-217 ºC
Appearance:white to light yellow crystal powder

History

Cantharidin was first isolated by Pierre Robiquet in 1810. It is an odorless and colorless solid at room temperature. It is secreted by the male blister beetle and given to the female during the mating. Afterwards the female beetle will cover its eggs with it as a defense against predators. The complete mechanism of the biosynthesis is currently unknown. If cantharidin is ingested, it severely irritates the urinary tract as it is excreted, causing swelling of the genitalia. This can cause a harmful condition known as priapism in men, where an erection lasts more than about four hours.

Uses

1. Cantharidin (CAS NO.56-25-7) is used in biochemical research, clinically as antineoplastic agents, mainly for primary liver cancer, It is often used in conjunction with other antineoplastic agents.
2. Cantharidin (CAS NO.56-25-7) is used as hydroxycanthayridimide intermediates.

Production

Raw materials Magnesium stearate -->MAGNESIUM TRISILICATE-->Oils, animal, mixed with vegetable oil Me esters, sulfurized -->Pioneer Blue Natural Rubber Latex Gloves, Size 9
 Cantharidin (CAS NO.56-25-7) can be extracted from the insect cantharis body,also can be chemically synthesized.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 310mg/kg (310mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
chicken LDLo subcutaneous 75mg/kg (75mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
dog LDLo oral 50mg/kg (50mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
frog LDLo oral 7273mg/kg (7273mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
human LDLo oral 428ug/kg (0.428mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 646, 1969.
mammal (species unspecified) LD50 intraperitoneal 1710ug/kg (1.71mg/kg)   "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher,Peop. Rep. China, 1994Vol. -, Pg. 183, 1994.
mammal (species unspecified) LDLo oral 75mg/kg (75mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
mammal (species unspecified) LDLo unreported 50mg/kg (50mg/kg)   Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 20, Pg. 135, 1989.
mouse LD50 intraperitoneal 1mg/kg (1mg/kg)   Journal of Agricultural and Food Chemistry. Vol. 35, Pg. 823, 1987.
pigeon LDLo oral 32mg/kg (32mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LDLo oral 20mg/kg (20mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Toxicon. Vol. 23, Pg. 36, 1985.
rabbit LDLo subcutaneous 1mg/kg (1mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.

Safety Profile

Hazard Codes VeryT+T
Risk Statements 28-36/37/38-23/24/25
 R28:Very toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements 53-45-36/37/39
S53:Avoid exposure - obtain special instructions before use. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR UN 2811 6.1/PG 1
WGK Germany 3
RTECS RN8575000
HazardClass 6.1(a)
PackingGroup I

Specification

1.General Description: Brown to black powder or plates or scales. Formerly used as a counterirritant and vesicant. Used for the removal of warts. Used as an experimental anti tumor agent. Active ingredient in spanish fly, a reputed aphrodisiac.
2.Reactivity Profile: Organic anhydrides, such as Cantharidin, are incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
3.Health Hazard :Cantharidin is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste of less than 7 drops for a 70 kg (150 lb.) person. It is very toxic by absorption through skin.
4.Fire Hazard: When heated to decomposition Cantharidin emits acrid smoke and irritating fumes.