(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid

Cantharidin Struktur
56-25-7
CAS-Nr.
56-25-7
Bezeichnung:
(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid
Englisch Name:
Cantharidin
Synonyma:
Cantharidine;Cantharone;cantharides;(1r,2s,3r,6s)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride;Canthari;7aalpha)-t;Antharidin;Kantaridin;CANTHARIDIN;Kantharidin
CBNumber:
CB0710248
Summenformel:
C10H12O4
Molgewicht:
196.2
MOL-Datei:
56-25-7.mol

(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid Eigenschaften

Schmelzpunkt:
215-217 °C (lit.)
Siedepunkt:
253.08°C (rough estimate)
Dichte
1.0357 (rough estimate)
Brechungsindex
1.4699 (estimate)
storage temp. 
2-8°C
Löslichkeit
Soluble in DMSO (25 mg/ml warm), acetone (8 mg/ml), ethanol (8 mg/ml warm), chloroform (1:65), ether (1:560), and ethyl acetate (1:150).
Aggregatzustand
solution
Farbe
white
Biologische Quelle
insect
Wasserlöslichkeit
30mg/L(20 ºC)
Merck 
14,1752
Stabilität:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 weeks.
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-
InChIKey
DHZBEENLJMYSHQ-XCVPVQRUSA-N
SMILES
C[C@]12C3CCC(O3)[C@@]1(C)C(=O)OC2=O
LogP
-0.409 (est)
CAS Datenbank
56-25-7(CAS DataBase Reference)
NIST chemische Informationen
Cantharidin(56-25-7)
IARC
3 (Vol. 10, Sup 7) 1987
EPA chemische Informationen
Cantharidin (56-25-7)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T+,T
R-Sätze: 28-36/37/38-38-37-36-23/24/25
S-Sätze: 53-45-36/37/39
RIDADR  UN 2811 6.1/PG 1
WGK Germany  3
RTECS-Nr. RN8575000
TSCA  TSCA listed
HazardClass  6.1(a)
PackingGroup  I
HS Code  29329990
Speicherklasse 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard Classifications Acute Tox. 2 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Giftige Stoffe Daten 56-25-7(Hazardous Substances Data)
Bildanzeige (GHS) Skull and Crossbones (GHS06)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H300 Lebensgefahr bei Verschlucken. Akute Toxizität oral Kategorie 2 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H331 Giftig bei Einatmen. Akute Toxizität inhalativ Kategorie 3 Achtung P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P271 Nur im Freien oder in gut belüfteten Räumen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P332+P313 Bei Hautreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P337+P313 Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R28:Sehr giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R38:Reizt die Haut.
R37:Reizt die Atmungsorgane.
R36:Reizt die Augen.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

S-Sätze Betriebsanweisung:

S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

Chemische Eigenschaften

Cantharidin is a brown to black powder.

Verwenden

Cantharidin is a natural toxin produced by blister beetles that moderately inhibits protein phosphatases 1 (PP1) (IC50 = 1.7 μM) and PP2A (IC50 = 0.2 μM) and only weakly inhibits the activity of PP2B (IC50 = 1 mM). It has been shown to stimulate cell cycle progression and induce premature mitosis, used topically (0.7%) as an anti-wart treatment, and has been shown to be active in cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and various other cancer cell lines.

Definition

ChEBI: A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.

Indications

Cantharidin, from the beetle Cantharis vesicatoria, causes intraepidermal vesiculation and is used in the treatment of warts and other benign cutaneous lesions. Cantharidin is extremely toxic if taken internally; it should not be prescribed for at-home use.
Cantharidin (Cantharone), a mitochondrial poison derived from the blister beetle Cantharis vesicatoria, leads to changes in cell membranes, epidermal cell dyshesion, acantholysis, and blister formation and is also useful. Cantharidin can be compounded with salicylic acid and podophyllin resin; occlusion for only 2 hours is needed with this combination. Thick hyperkeratotic lesions should be pared down before painting. The lesion should then be painted with cantharidin, allowed to dry, and covered with Blenderm or other nonporous occlusive tape; 40% salicylic acid plaster may be used to achieve greater activity. The tape is left on for 24 hours or until the area begins to hurt. A blister, often hemorrhagic, will form, break, crust, and fall off in 7 to 14 days; at this time, the lesion is pared down, and any wart remnants are retreated. Because the effect of cantharidin is entirely intraepidermal, no scarring ensues. Ring-like or "donut configuration" recurrences may be seen occasionally after treatment with cantharidin or, at times, following liquid nitrogen therapy. Owing to this agent’s toxicity, application by a physician is recommended. Verrusol, which contains 30% salicylic acid, 5% podophyllin, and 1% cantharidin, may be used in the same manner.

Allgemeine Beschreibung

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.

Reaktivität anzeigen

Organic anhydrides, such as Cantharidin, are incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Hazard

Extremely toxic; questionable carcinogen; powerful irritant to all cells and tissues; deadly poi- son; respiratory failure; death.

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.

Brandgefahr

When heated to decomposition Cantharidin emits acrid smoke and irritating fumes.

Biologische Aktivität

Natural toxin inhibitor of protein phosphatases 1 and 2A (K i values are 1.1 and 0.19 μ M respectively); similar to okadaic acid (9,10-Deepithio-9,10-didehydroacanthifolicin ). Displays > 500-fold selectivity over PP2B.

mögliche Exposition

Formerly used as a counterirritant and vesicant. Also used for the removal of benign epithelial growths, e.g., warts. Used as an experimental antitumor agent. The active ingredient in “Spanish fly,” a reputed aphrodisia

Versand/Shipping

Cantharidin is not specifically listed in the DOT Performance-Oriented Packaging Standards with respect to labeling requirements or restrictions on shipping quantities.

Waste disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


(1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 246)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hangzhou ICH Biofarm Co., Ltd
+86-0571-28186870; +undefined8613073685410
sales@ichemie.com China 1002 58
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806
sales@capot.com China 29626 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21533 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29766 58
Chengdu Biopurify Phytochemicals Ltd.
+86-28-82633860; +86-18080483897
sales@biopurify.com China 4616 58
Xi'an Kono chem co., Ltd.,
029-86107037 13289246953
info@konochemical.com China 1168 58
Lotusland Life Sciences
+8615821988213
info@longyupharma.com China 2411 58
CONIER CHEM AND PHARMA LIMITED

sales@conier.com China 49906 58
SIMAGCHEM CORP
+86-5922680277 +86-13806087780
sale@simagchem.com China 17339 58
Hefei Hangang Pharmaceutical Technology Co., Ltd.
+8618062405514
ada@ipurechemical.com China 10224 58

56-25-7((1R, 2S 3R, 6S)-1,2-Dimethyl-3,6-epoxycyclohexan-1,2-dicarbon-säureanhydrid)Verwandte Suche:


  • CANTHARIDIN
  • dimethyl-3,6-epoxyperhydrophthalic anhydride
  • HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZO-FURAN-1,3-DIONE
  • 4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3a-alpha,4-beta
  • 4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3aalpha,4beta,7
  • 4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3aalpha,4beta,7be
  • 7aalpha)-bet
  • 7aalpha)-t
  • 7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3a.alpha.,4.beta.,7.beta.,7a.alpha.)-4
  • 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-
  • cantharides
  • Cantharides camphor
  • 4,7-EPOXYISOBENZOFURAN-1,3-DIONE,HEXAHYDRO-3A,7A-DIMETHYL-, (3A,4,7,7A)-
  • (3A-ALPHA,4B,7B,7A-ALPHA)-HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZOFURAN-1,3-DIONE
  • (3AA,4B,7B,7AA)-HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZOFURAN-1,3-DIONE
  • 3a,7a-Dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione
  • 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran
  • Hexahydro-3α,7α-dimethyl-4β,7β-epoxyisobenzofuran-1,3-dione
  • 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-
  • CANTHARIDIN(RG)
  • 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
  • CANTHARIDIN \ INHIBITOR OF PHOSPHATASES
  • CANTHARIDIN:4,7-EPOXYISOBENZOFURAN-1,3-DIONE,HEXAHYDRO-3A,7A- DIMETHYL-, (3A,4,7,7A)-,
  • Cantharidin ,98%
  • 3a,4,5,6,7,7a-Hexahydro-3aα,7aα-dimethyl-4β,7β-epoxyisobenzofuran-1,3-dione
  • 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran Cantharidine
  • Canthari
  • (3aα,4β,7β,7aα)-Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione
  • Cantharidic acid anhydride
  • Ban cantharidin
  • Cantharidin Dimethyl-3,6-epoxyperhydrophthalic anhydride
  • Lactone of cantharidic acid
  • Antharidin
  • ,7-beta,7a-alpha)
  • 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride
  • 1,2-dimethyl-3,6-epoxyperhydrophthalicanhydride
  • 2,3-Dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride
  • 2,3-dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylicanhydride
  • 2,3-dimethyl-7-oxabicyclo(2.2.1)heptane-3-dicarboxylicanhydride
  • 2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylicacidanhydride
  • 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-
  • 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aalpha,4beta,7beta,7aalpha)-
  • cantharidescamphor
  • Cantharone
  • exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride
  • exo-1,2-cis-dimethyl-3,6-epoxyhexahydrophthalicanhydride
  • Hexahydro-3,7-dimethyl-4,7-epoxyisobenzofura
  • hexahydro-3aalpha,7aalpha-dimethyl-4beta,7beta-epoxyisobenzofuran-1,3-dione
  • Kantaridin
  • Kantharidin
  • (3aR,4S,7R,7aS)-3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione
  • Cantharidin, 98%, from Lytta vesicatoria
  • Cantharidin Ready Made Solution
  • rel-(3aR,4S,7R,7aS)-Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione
  • Cantharidin USP/EP/BP
  • Cantharidin (6CI, 7CI)
  • Cantharidin(P)
  • Cantharidin-RM
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