10, 12-Tricosadiynoic acid

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.

Product information

CAS Number: 66990-30-5

Molecular Weight: 346.55

Formula: C23H38O2

Chemical Name: tricosa-10,12-diynoic acid

Smiles: CCCCCCCCCCC#CC#CCCCCCCCCC(O)=O

InChiKey: DIEDVCMBPCRJFQ-UHFFFAOYSA-N

InChi: InChI=1S/C23H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25/h2-10,15-22H2,1H3,(H,24,25)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 100 mg/mL (288.56 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. 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. 10,12-Tricosadiynoic acid (500 nM) inhibits acyl-CoA oxidase-1 (ACOX1) activity. 10,12-Tricosadiynoic acid treatment abrogates the protective effect by Sirt5 siRNA.

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. 10,12-Tricosadiynoic acid (0 mg/kg, 37.5 mg/kg, 75 mg/kg, and 150 mg/kg diet) treatment does not affect weight gain, but significantly decreases peroxisomal β-oxidation in the liver, and increased body fat accumulation in Nile tilapia. The fish with impaired peroxisomal β-oxidation exhibited higher contents of serum lipid and peroxidation products, and alanine aminotransferase activity, and significantly lowered hepatic activities of superoxide dismutase and catalase.

Products are for research use only. Not for human use.