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P9417

Sigma-Aldrich

Palmitoleic acid

≥98.5% (GC), liquid

Synonym(s):

cis-9-Palmitoleic acid, cis-9-Hexadecenoic acid

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About This Item

Linear Formula:
CH3(CH2)5CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
254.41
Beilstein/REAXYS Number:
1725389
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

Macadamia integrifolia

assay

≥98.5% (GC)

form

liquid

refractive index

n20/D 1.457 (lit.)

bp

162 °C/0.6 mmHg (lit.)

mp

0.5 °C (lit.)

density

0.895 g/mL at 20 °C (lit.)

functional group

carboxylic acid
oleic acid

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCCC\C=C/CCCCCCCC(O)=O

InChI

1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

InChI key

SECPZKHBENQXJG-FPLPWBNLSA-N

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Application

Palmitoleic acid has been used:
  • to supplement Minimum Essential Media alpha (MEMα) to culture mouse spermatogonial stem cells (SSCs)
  • as a component of a defined serum-free medium for the long-term propagation of SSCs
  • in Dulbecco′s Modified Eagle Medium (DMEM) in the media for fatty acid treatment to assure a physiologic ratio between bound and unbound free fatty acid (FFA)

Biochem/physiol Actions

Palmitoleic acid is a 16-carbon, omega-7, monounsaturated fatty acid that is enriched in the triglycerides of human adipose tissue and in liver.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Yuko Akazawa et al.
Journal of hepatology, 52(4), 586-593 (2010-03-09)
Saturated free fatty acids induce hepatocyte lipoapoptosis. This lipotoxicity involves an endoplasmic reticulum stress response, activation of JNK, and altered expression and function of Bcl-2 proteins. The mono-unsaturated free fatty acid palmitoleate is an adipose-derived lipokine which suppresses free fatty
Geng Zong et al.
The American journal of clinical nutrition, 96(5), 970-976 (2012-09-28)
Palmitoleic acid has been shown to regulate adipokine expression and systemic metabolic homeostasis in animal studies. However, its association with human metabolic diseases remains controversial. We aimed to investigate associations of erythrocyte palmitoleic acid with adipokines, inflammatory markers, and metabolic
Dariush Mozaffarian et al.
The American journal of clinical nutrition, 97(4), 854-861 (2013-02-15)
Dairy consumption is linked to a lower risk of type 2 diabetes, but constituents responsible for this relation are not established. Emerging evidence suggests that trans-palmitoleate (trans 16:1n-7), a fatty acid in dairy and also partially hydrogenated oils, may be
Andressa Bolsoni-Lopes et al.
Lipids in health and disease, 13, 199-199 (2014-12-22)
Palmitoleic acid was previously shown to improve glucose homeostasis by reducing hepatic glucose production and by enhancing insulin-stimulated glucose uptake in skeletal muscle. Herein we tested the hypothesis that palmitoleic acid positively modulates glucose uptake and metabolism in adipocytes. For
Katherine E Pinnick et al.
Diabetes, 61(6), 1399-1403 (2012-04-12)
The expansion of lower-body adipose tissue (AT) is paradoxically associated with reduced cardiovascular disease and diabetes risk. We examined whether the beneficial metabolic properties of lower-body AT are related to the production and release of the insulin-sensitizing lipokine palmitoleate (16:1n-7).

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