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66990-30-5

66990-30-5 structure
66990-30-5 structure
  • Name: 10,12-TRICOSADIYNOIC ACID
  • Chemical Name: 10,12-Tricosadiynoic acid
  • CAS Number: 66990-30-5
  • Molecular Formula: C23H38O2
  • Molecular Weight: 346.547
  • Catalog: Chemical reagent Organic reagent fatty acid
  • Create Date: 2018-03-29 08:00:00
  • Modify Date: 2024-01-09 09:54:55
  • 10,12-Tricosadiynoic acid is a highly specific, selective, high affinity and orally active acyl-CoA oxidase-1 (ACOX1) inhibitor. 10,12-Tricosadiynoic acid can treat high fat diet- or obesity-induced metabolic diseases by improving mitochondrial lipid and ROS metabolism[1].

Name 10,12-Tricosadiynoic acid
Synonyms tricosa-10,12-diynoic acid
MFCD00041683
10,12-TRICOSADIYNOIC ACID
Description 10,12-Tricosadiynoic acid is a highly specific, selective, high affinity and orally active acyl-CoA oxidase-1 (ACOX1) inhibitor. 10,12-Tricosadiynoic acid can treat high fat diet- or obesity-induced metabolic diseases by improving mitochondrial lipid and ROS metabolism[1].
Related Catalog
Target

Acyl-CoA oxidase-1 (ACOX1)[1].

In Vitro 10,12-Tricosadiynoic acid-CoA rapidly inhibits ACOX1 activity in a time- and concentration-dependent manner. The activity of ACOX1 decreases by nearly 95% after 5 min of incubation with 10 eq of 10,12-Tricosadiynoic acid-CoA. ACOX1 activity is inhibited only if free 10,12-Tricosadiynoic Acid is activated as the CoA thioester, the substrate form. Inhibition of ACOX1 by 10,12-Tricosadiynoic acid-CoA is irreversible. And the kinetics parameters KI and kinact are calculated to be 680 nm and 3.18 min−1, respectively[1]. 10,12-Tricosadiynoic acid is the precursor of 10,12-Tricosadiynoic acid-CoA and is transformed into 10,12-Tricosadiynoic acid-CoA by peroxisomal very long chain acyl-CoA synthetase (VLACS) after entering into cells, and it inhibits ACOX1 in vivo[1].
In Vivo 10,12-Tricosadiynoic acid (100 μg/kg; oral gavage; daily; for 8 weeks; male Wistar rats) treatment increases hepatic mitochondrial fatty acid oxidation (FAO) via activation of the SIRT1-AMPK (adenosine 5′-monophosphate-activated protein kinase) pathway and proliferator activator receptor α and reduces hydrogen peroxide accumulation in high fat diet-fed rats, which significantly decreases hepatic lipid and ROS contents, reduces body weight gain, and decreases serum triglyceride and insulin levels[1]. Animal Model: Male Wistar rats (210-230 g) fed with high fat diet[1] Dosage: 100 μg/kg Administration: Oral gavage; daily; for 8 weeks Result: Reduced hydrogen peroxide accumulation in high fat diet-fed rats, which significantly decreased hepatic lipid and ROS contents, reduced body weight gain, and decreased serum triglyceride and insulin levels.
References

[1]. Zeng J, et al. Specific Inhibition of Acyl-CoA Oxidase-1 by an Acetylenic Acid Improves Hepatic Lipid and Reactive Oxygen Species (ROS) Metabolism in Rats Fed a High Fat Diet. J Biol Chem. 2017 Mar 3;292(9):3800-3809.

Density 0.9±0.1 g/cm3
Boiling Point 498.8±28.0 °C at 760 mmHg
Melting Point 56-60 °C
Molecular Formula C23H38O2
Molecular Weight 346.547
Flash Point 236.0±18.7 °C
Exact Mass 346.287170
PSA 37.30000
LogP 9.17
Vapour Pressure 0.0±2.7 mmHg at 25°C
Index of Refraction 1.487
Storage condition Refrigerator
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2916190090

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66990-30-5 structure

66990-30-5

Literature: Usov, O. M.; Tret'yakov, E. V.; Sveshnikova, L. L.; Shvartsberg, M. S. Russian Chemical Bulletin, 1995 , vol. 44, # 10 p. 1929 - 1932 Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995 , # 10 p. 2009 - 2012

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66990-30-5 structure

66990-30-5

Literature: Angewandte Chemie, , vol. 88, p. 805 - 806
HS Code 2916190090
Summary 2916190090 unsaturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%