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8-(2-Octyl-1-cyclopropen-1-yl)octanoic acid

Names

[ CAS No. ]:
738-87-4

[ Name ]:
8-(2-Octyl-1-cyclopropen-1-yl)octanoic acid

[Synonym ]:
1-Cyclopropene-1-octanoic acid, 2-octyl-
Sterculia-Saeure
Sterculinic acid
Poly-saeure: <C19H34O2>x
9,10-methylene-9-octadecenoic acid
8-(2-octylcyclopropen-1-yl)octanoic acid
8-(2-Octyl-1-cyclopropen-1-yl)octanoic acid
Sterculinsaeure
Sterculic-saeure

Biological Activity

[Description]:

Sterculic acid is a stearoyl-CoA desaturase-1 (SCD1) inhibitor. Sterculic acid specifically inhibits the delta-9 desaturase (Δ9D) activity with an IC50 value of 0.9 μM[1].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Stearoyl-CoA Desaturase (SCD)
Research Areas >> Inflammation/Immunology

[Target]

delta-9 desaturase:0.9 μM (IC50)


[In Vitro]

Sterculic acid (SA) is a cyclopropene fatty acid originally found in the seeds of the plant Sterculia foetida with numerous biological activities[2]. Sterculic acid is able to reduce adrenomedullin expression (AP, RP, APS, IML, in preparation)[2]. Sterculic acid is also able to mediate anti-inflammatory and protective effects[2]. Sterculic acid has a potent luteolytic effect in ovines by inhibition in the synthesis of progesterone, which causes luteal regression[2].

[In Vivo]

Sterculic acid has been proposed as a potential tool for the treatment of metabolic syndrome (MS) since it inhibits the activity of the stearoyl-CoA desaturase-1 (SCD1) in vivo[3].

[References]

[1]. Lei Zhang, et al. A multiplexed cell assay in HepG2 cells for the identification of delta-5, delta-6, and delta-9 desaturase and elongase inhibitors. J Biomol Screen. 2010 Feb;15(2):169-76.

[2]. Rafael Peláez, et al. Sterculic Acid: The Mechanisms of Action beyond Stearoyl-CoA Desaturase Inhibition and Therapeutic Opportunities in Human Diseases. Cells. 2020 Jan 7;9(1):140.

[3]. Abril Ramírez-Higuera, et al. Preventive Action of Sterculic Oil on Metabolic Syndrome Development on a Fructose-Induced Rat Model. J Med Food. 2020 Mar;23(3):305-311.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
418.7±24.0 °C at 760 mmHg

[ Molecular Formula ]:
C19H34O2

[ Molecular Weight ]:
294.472

[ Flash Point ]:
315.4±18.0 °C

[ Exact Mass ]:
294.255890

[ PSA ]:
37.30000

[ LogP ]:
7.72

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.487

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds