Ethacrynic acid

Modify Date: 2025-08-20 12:51:32

Ethacrynic acid Structure
Ethacrynic acid structure
 Common Name Ethacrynic acid
CAS Number 58-54-8 Molecular Weight 303.13800
Density 1.35g/cm3 Boiling Point 480ºC at 760mmHg
Molecular Formula C13H12Cl2O4 Melting Point 125 °C
MSDS Chinese USA Flash Point 244.1ºC
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ethacrynic acid


Ethacrynic acid is a diuretic. Ethacrynic acid is an inhibitor of glutathione S-transferases (GSTs). Ethacrynic acid is a potent inhibitor of NF-kB-signaling pathway, and also modulates leukotriene formation. Ethacrynic acid also inhibits L-type voltage-dependent and store-operated calcium channel, leading to relaxation of airway smooth muscle (ASM) cells. Ethacrynic acid has anti-inflammatory properties that reduces the retinoid-induced ear edema in mice[1][2][3][4].

 Names

Name etacrynic acid
Synonym More Synonyms

 Ethacrynic acid Biological Activity

Description Ethacrynic acid is a diuretic. Ethacrynic acid is an inhibitor of glutathione S-transferases (GSTs). Ethacrynic acid is a potent inhibitor of NF-kB-signaling pathway, and also modulates leukotriene formation. Ethacrynic acid also inhibits L-type voltage-dependent and store-operated calcium channel, leading to relaxation of airway smooth muscle (ASM) cells. Ethacrynic acid has anti-inflammatory properties that reduces the retinoid-induced ear edema in mice[1][2][3][4].
Related Catalog
References

[1]. Li XQ, et al. Metabolism of Strained Rings: Glutathione S-transferase-Catalyzed Formation of a Glutathione-Conjugated Spiro-azetidine without Prior Bioactivation. Drug Metab Dispos. 2019 Nov;47(11):1247-1256.

[2]. Harada T, et al. Ethacrynic acid decreases expression of proinflammatory intestinal wall cytokines and ameliorates gastrointestinal stasis in murine postoperative ileus. Clinics (Sao Paulo). 2018 Oct 18;73:e332.

[3]. Zhao XX, et al. Ethacrynic acid inhibits airway smooth muscle contraction in mice. Sheng Li Xue Bao. 2019 Dec 25;71(6):863-873.

[4]. Byun HJ, et al. Ethacrynic Acid Inhibits Sphingosylphosphorylcholine-Induced Keratin 8 Phosphorylation and Reorganization via Transglutaminase-2 Inhibition. Biomol Ther (Seoul). 2013 Sep 30;21(5):338-42.

 Chemical & Physical Properties

Density 1.35g/cm3
Boiling Point 480ºC at 760mmHg
Melting Point 125 °C
Molecular Formula C13H12Cl2O4
Molecular Weight 303.13800
Flash Point 244.1ºC
Exact Mass 302.01100
PSA 63.60000
LogP 3.60570
InChIKey AVOLMBLBETYQHX-UHFFFAOYSA-N
SMILES C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
Storage condition -20?C Freezer

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AG6600000
CHEMICAL NAME :
Acetic acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-
CAS REGISTRY NUMBER :
58-54-8
LAST UPDATED :
199612
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C13-H12-Cl2-O4
MOLECULAR WEIGHT :
303.15
WISWESSER LINE NOTATION :
QV1OR BG CG DVY2&U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
4 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - change in acuity
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 117,715,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - change in acuity Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 117,715,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
3 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - tinnitus
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 117,715,1966
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 21,775,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
43 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 21,775,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
189 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
176 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 23,438,1964
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0016635
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
449 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
78300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
469 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
14800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3792 No. of Facilities: 150 (estimated) No. of Industries: 2 No. of Occupations: 11 No. of Employees: 14149 (estimated) No. of Female Employees: 10194 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302 + H312 + H332-H315-H319-H335
Precautionary Statements P261-P280-P301 + P312 + P330-P305 + P351 + P338
Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22;R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS AG6600000

 Synthetic Route

Formaldehyde structure

Formaldehyde

CAS#:50-00-0

Acetic acid, [2,3-dichloro-4-(1-oxobutyl)phenoxy]-, ethyl ester structure

Acetic acid, [2...

CAS#:2977-51-7

~%

Ethacrynic acid Structure

Ethacrynic acid

CAS#:58-54-8

Literature: Molecules, , vol. 14, # 1 p. 19 - 35
2,3-dichloro-4-(2-methylenebutyryl)-phenol structure

2,3-dichloro-4-...

CAS#:4115-00-8

~%

Ethacrynic acid Structure

Ethacrynic acid

CAS#:58-54-8

Literature: US4952724 A1, ;
1-(2,3-dichloro-4-hydroxyphenyl)butan-1-one structure

1-(2,3-dichloro...

CAS#:2350-46-1

~%

Ethacrynic acid Structure

Ethacrynic acid

CAS#:58-54-8

Literature: Comptes Rendus Chimie, , vol. 16, # 7 p. 660 - 664
2,3-Dichlorophenol structure

2,3-Dichlorophenol

CAS#:576-24-9

~%

Ethacrynic acid Structure

Ethacrynic acid

CAS#:58-54-8

Literature: Comptes Rendus Chimie, , vol. 16, # 7 p. 660 - 664

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 Synonyms

MFCD00056693
Ethacrynic Acid
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
EINECS 200-384-1
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