2-Tetradecyl-2-oxiranecarboxylic acid methyl ester

Modify Date: 2024-01-30 20:33:14

2-Tetradecyl-2-oxiranecarboxylic acid methyl ester Structure
2-Tetradecyl-2-oxiranecarboxylic acid methyl ester structure
Common Name 2-Tetradecyl-2-oxiranecarboxylic acid methyl ester
CAS Number 69207-52-9 Molecular Weight 298.46100
Density 0.944g/cm3 Boiling Point 361.4ºC at 760 mmHg
Molecular Formula C18H34O3 Melting Point 44-46 ºC
MSDS N/A Flash Point 150.9ºC

 Use of 2-Tetradecyl-2-oxiranecarboxylic acid methyl ester


McN3716 is a carnitine palmitoyltransferase I (CPT-1) inhibitor.

 Names

Name Methyl palmoxirate
Synonym More Synonyms

  Biological Activity

Description McN3716 is a carnitine palmitoyltransferase I (CPT-1) inhibitor.
Related Catalog
Target

Carnitine palmitoyltransferase I (CPT-1)[1]

In Vivo Inhibition of brain mitochondrial β-oxidation by McN3716 (Methyl palmoxirate, MEP) significantly reduces the levels of all measured HETE and epoxytrienoic acids (EET), nonenzymatic auto-oxidative metabolites of ARA, by 23% to 44% and 32% to 50% compared with vehicle-injected rats, respectively, except for 15-HETE which was unaffected. There is a significant 34% reduction in the level of 6-keto-PGF1α, a byproduct of PGI2 (prostacyclin) in McN3716-treated rats. Similarly, the brain level of hydroxyeicosapentaenoic acids, nonenzymatic auto-oxidative metabolites of EPA, is reduced by 35% to 76% upon McN3716 treatment relative to vehicle[1].
Animal Admin Rats[1] Male Sprague Dawley rats are used. The rats receive ad libitum access to standard chow and water. At 15 weeks of age, six rats were subjected to either high-energy, head-focused microwave irradiation or CO2 asphyxiation. A separate group of 11 rats were implanted with a tail vein catheter (intravenous catheter 24 gauge/0.75 inch) and received either an intravenous injection of vehicle or 10 mg/kg of McN3716. Fifteen minutes after injection, rats were rapidly euthanized by high-energy, head-focused microwave irradiation (13.5 kW for 1.6 seconds) to avert ischemia for accurate quantification of in vivo basal levels of nonenzymatic auto-oxidative PUFA metabolites and enzymatically derived metabolites. Previously, we reported that this method reduced β-oxidation of fatty acid by 23% to 74%. McN3716 (Methyl palmoxirate, MEP) readily crosses the blood–brain barrier with a plasma half-life of 0.6 minute in the rat. The brain was excised and stored at -80°C for lipidomics profiling.
References

[1]. Chen CT, et al. Inhibiting mitochondrial β-oxidation selectively reduces levels of nonenzymatic oxidative polyunsaturated fatty acid metabolites in the brain. J Cereb Blood Flow Metab. 2014 Mar;34(3):376-9.

 Chemical & Physical Properties

Density 0.944g/cm3
Boiling Point 361.4ºC at 760 mmHg
Melting Point 44-46 ºC
Molecular Formula C18H34O3
Molecular Weight 298.46100
Flash Point 150.9ºC
Exact Mass 298.25100
PSA 38.83000
LogP 5.01960
Index of Refraction 1.46
Storage condition 2-8℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RR0425000
CHEMICAL NAME :
2-Oxiranecarboxylic acid, 2-tetradecyl-, methyl ester
CAS REGISTRY NUMBER :
69207-52-9
LAST UPDATED :
198910
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C18-H34-O3
MOLECULAR WEIGHT :
298.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
145 mg/kg
SEX/DURATION :
female 15-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 35,47A,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
29 mg/kg
SEX/DURATION :
female 15-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 35,47A,1987

 Synonyms

methyl 2-tetradecyloxirane-2-carboxylate
2-Tetradecyloxiranecarboxylic acid methyl ester
methyl 2-tetradecylglycidate
MCN-3716
Methyl parmoxirate
methyl 2-tetradecyloxiranecarboxylate
2-Tetradecyloxirane-2-carboxylic acid methyl ester
ethyl palmoxirate
2-Tetradecyl-2-oxiranecarboxylic acid methyl ester
McN3716