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145-73-3

145-73-3 structure
145-73-3 structure
  • Name: Endothall
  • Chemical Name: endothal
  • CAS Number: 145-73-3
  • Molecular Formula: C8H10O5
  • Molecular Weight: 186.16200
  • Catalog: Signaling Pathways Metabolic Enzyme/Protease Phosphatase
  • Create Date: 2018-05-30 08:00:00
  • Modify Date: 2025-08-20 10:33:21
  • Endothall (Endothal) is a protein phosphatase 2A (PP2A) inhibitor with IC50s of 90 nM and 5 µM for PP2A and PP1, respectively. Endothall can be used as an herbicide. Endothall also is useful in cancer chemotherapy[1].
Name endothal
Synonyms aquatholplus
7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicacid
Aquathol
Hydout
7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
ENDOTHAL
ACCELERATE
MFCD00137362
Niagrathal
Hydrothol
Hydrothal
EINECS 205-660-5
(1Ξ,2Ξ,3Ξ,4Ξ)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
ENDOTHALL
Emdothal
Description Endothall (Endothal) is a protein phosphatase 2A (PP2A) inhibitor with IC50s of 90 nM and 5 µM for PP2A and PP1, respectively. Endothall can be used as an herbicide. Endothall also is useful in cancer chemotherapy[1].
Related Catalog
In Vitro Endothall, an organic acid, is the least toxic structural analogue of Cantharidin that still inhibits PP2A[2]. Endothall inhibits preferentially hepatocellular carcinoma (HCC) growth and these new rat hepatocellular carcinoma lines may be useful for further biochemical and pharmacological studies on PP2A inhibitors, and for testing new forms of treatment of hepatic cell carcinomas. The HR-2, HR-3, HR-4, and Zajdela hepatocellular carcinomas are most sensitive to Endothall (IC50 of 1.7, 1.2, 0.9, and 1.7 µg/mL), whereas newborn rat hepatocytes growing exponentially in primary culture (IC50=6.2 µg/mL), rat DHD/K12 colon carcinoma cells (IC50=3.6 µg/mL), or human HT-29 colon carcinoma cells (IC50=4.9 µg/mL) were less sensitive[2]. Endothall inhibits the growth of HCC lines in culture more than that of normal hepatocytes or colon carcinomas, inducing mitotic arrest, followed by cell death. Endothall causes dose- and time-dependent cytostasis specifically in G2/M[2]. Endothall (3 µg/mL) inhibits the cell cycle at G2/M and subsequent apoptotic cell death[2].
In Vivo Endothall exhibits acute LD50 of 14 mg/kg in mice[2].
References

[1]. Janetti R Signorelli, et al. Protein phosphatases decrease their activity during capacitation: a new requirement for this event. PLoS One. 2013 Dec 2;8(12):e81286.

[2]. J P Thièry, et al. Hepatocellular carcinoma cell lines from diethylnitrosamine phenobarbital-treated rats. Characterization and sensitivity to endothall, a protein serine/threonine phosphatase-2A inhibitor. Hepatology. 1999 May;29(5):1406-17.
Density 1.431
Boiling Point 350ºC(e)
Melting Point 144ºC
Molecular Formula C8H10O5
Molecular Weight 186.16200
Flash Point 190.5ºC
Exact Mass 186.05300
PSA 83.83000
Vapour Pressure 2.88E-09mmHg at 25°C
Index of Refraction 1.568

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RN7875000
CHEMICAL NAME :
7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic acid
CAS REGISTRY NUMBER :
145-73-3
LAST UPDATED :
199701
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C8-H10-O5
MOLECULAR WEIGHT :
186.18
WISWESSER LINE NOTATION :
T55 A AOTJ CVQ DVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
571 uL/kg
TOXIC EFFECTS :
Cardiac - other changes Kidney, Ureter, Bladder - urine volume decreased Nutritional and Gross Metabolic - metabolic acidosis
REFERENCE :
AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983- Volume(issue)/page/year: 6,509,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCOC** Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. (Topeka, KS) Volume(issue)/page/year: -,471,1966
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 7,299,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14 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 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989
Hazard Codes T
Risk Phrases 21-25-36/37/38
Safety Phrases S45;S36/S37/S39
RIDADR UN 2811 6.1/PG 2
WGK Germany 1
RTECS RN7875000
Packaging Group II
Hazard Class 6.1(a)
HS Code 2932190013
5629-08-3 structure

5629-08-3

~%

145-73-3 structure

145-73-3

Literature: Zeitschrift fuer Chemie (Stuttgart, Germany), , vol. 24, # 11 p. 405 - 406
81486-09-1 structure

81486-09-1

~%

145-73-3 structure

145-73-3

Literature: Zeitschrift fuer Chemie (Stuttgart, Germany), , vol. 24, # 11 p. 405 - 406
3215-51-8 structure

3215-51-8

~%

145-73-3 structure

145-73-3

Literature: Justus Liebigs Annalen der Chemie, , vol. 535, p. 113,120 Journal fuer Praktische Chemie (Leipzig), , vol. <2> 156, p. 285,305
4505-29-7 structure

4505-29-7

~%

145-73-3 structure

145-73-3

Literature: Justus Liebigs Annalen der Chemie, , vol. 535, p. 113,120
1829-60-3 structure

1829-60-3

~%

145-73-3 structure

145-73-3

Literature: Journal fuer Praktische Chemie (Leipzig), , vol. <2> 156, p. 285,305
HS Code 2932190013
Summary 2932190013 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%
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