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Palmitelaidic acid

Names

[ CAS No. ]:
10030-73-6

[ Name ]:
Palmitelaidic acid

[Synonym ]:
Palmitelaidic acid
trans-9-Hexadecenoic acid
(9E)-9-Hexadecenoic acid
(E)-Palmitoleic acid
trans-9-palmitoleic acid
trans-palmitoleic acid
trans-Hexadec-9-enoic acid
9-trans-Hexadecenoic acid
(9E)-hexadec-9-enoic acid
9-Hexadecenoic acid, (9E)-
9-Hexadecenoic acid, (E)-
cis-9hexadecenoic acid

Biological Activity

[Description]:

Palmitelaidic acid is the trans isomer of palmitoleic acid. Palmitoleic acid is one of the most abundant fatty acids in serum and tissue.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Glucokinase
Natural Products >> Acids and Aldehydes
Research Areas >> Metabolic Disease

[Target]

AMPK

PPARα

Glucokinase


[In Vitro]

The monounsaturated fatty acid palmitoleate (palmitoleic acid) is one of the most abundant fatty acids in serum and tissues, particularly adipose tissue and liver. Its endogenous production by stearoyl-CoA desaturase 1 gives rise to its cis isoform, cis-palmitoleate. Palmitoleic acid has been correlated with multiple cardiometabolic risk factors, including high blood pressure, total cholesterol, TGs, apoA-I, apoB, and endothelial dysfunction[1].

[In Vivo]

Palmitoleic acid promotes a faster uptake of glucose in the body, associated with higher insulin concentration. Palmitoleic acid increases the phosphorylation of AMPK, up-regulates glucokinase and down-regulates SREBP-1. Regarding AMPK downstream, palmitoleic acid increases the production of FGF-21 and stimulates the expression of PPARα[2]. Palmitoleic acid reduces body weight increase, ameliorates the development of hyperglycemia and hypertriglyceridemia, and improves insulin sensitivity. Furthermore, palmitoleic acid down-regulates mRNA expressions of proinflammatory adipocytokine genes (TNFα and resistin) in white adipose tissue and lipogenic genes (SREBP-1, FAS, and SCD-1) in liver[3].

[Animal admin]

Mice: Male C57BL/6J wild type and PPARα-KO mice are fed a high-fat diet or a standard diet for 12 weeks. In the last two weeks, the HF-fed mice are treated daily with oleic acid (300 mg/kg of body weight) or palmitoleic acid (00 mg/kg of body weight) by oral gavage. After 12 weeks, the mice are fasted for 6 h, injected with insulin or PBS vehicle. Blood and liver samples are collected and stored for the further analysis of RNA and protein expression[2].

[References]

[1]. Frigolet ME, et al. The Role of the Novel Lipokine Palmitoleic Acid in Health and Disease.

[2]. de Souza CO, et al. Palmitoleic Acid Improves Metabolic Functions in Fatty Liver by PPARα-Dependent AMPK Activation. J Cell Physiol. 2016 Dec 7. doi: 10.1002/jcp.25715.

[3]. Yang ZH, et al. Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes. Lipids Health Dis. 2011 Jul 21;10:120.


[Related Small Molecules]

Dorsomorphin dihydrochloride | Acadesine (AICAR) | GW9662 | Retinoic acid | Elafibranor | GW501516 | A-769662 | Troglitazone | T0070907 | Pemafibrate | CDDO-Im | Wy-14643 | GW0742 | GW1929 | Phenformin (hydrochloride)

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
363.6±0.0 °C at 760 mmHg

[ Molecular Formula ]:
C16H30O2

[ Molecular Weight ]:
254.408

[ Flash Point ]:
239.2±14.4 °C

[ Exact Mass ]:
254.224579

[ PSA ]:
37.30000

[ LogP ]:
6.64

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.466

[ Storage condition ]:
-20°C

Precursor & DownStream

Precursor

DownStream

Related Compounds