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P9417

Sigma-Aldrich

Palmitoleic acid

≥98.5% (GC), liquid

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Synonym(s):
cis-9-Palmitoleic acid, cis-9-Hexadecenoic acid
Linear Formula:
CH3(CH2)5CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
254.41
Beilstein:
1725389
EC Number:
MDL number:
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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1 of 4

This Item
P9667V0384L1376
Palmitoleic acid ≥98.5% (GC), liquid

Sigma-Aldrich

P9417

Palmitoleic acid

Methyl palmitoleate ≥99% (capillary GC), liquid

Sigma-Aldrich

P9667

Methyl palmitoleate

cis-Vaccenic acid ≥97% (capillary GC), oil

Sigma-Aldrich

V0384

cis-Vaccenic acid

Linoleic acid ≥99%

Sigma-Aldrich

L1376

Linoleic acid

assay

≥98.5% (GC)

assay

≥99% (capillary GC)

assay

≥97% (capillary GC)

assay

≥99%

form

liquid

form

liquid

form

oil

form

liquid

refractive index

n20/D 1.457 (lit.)

refractive index

n20/D 1.451 (lit.)

refractive index

n20/D 1.459 (lit.)

refractive index

n20/D 1.466 (lit.)

bp

162 °C/0.6 mmHg (lit.)

bp

180-183 °C/1 mmHg (lit.)

bp

150 °C/0.03 mmHg (lit.)

bp

229-230 °C/16 mmHg (lit.)

mp

0.5 °C (lit.)

mp

−0.5-0.5 °C (lit.)

mp

14-15 °C (lit.)

mp

−5 °C (lit.)

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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).
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

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