Skip to Content
Merck
All Photos(2)

Key Documents

P9417

Sigma-Aldrich

Palmitoleic acid

≥98.5% (GC), liquid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
CH3(CH2)5CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
254.41
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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).
Andreas Koeberle et al.
The Journal of biological chemistry, 287(32), 27244-27254 (2012-06-16)
Controversial correlations between biological activity and concentration of the novel lipokine palmitoleate (9Z-hexadecenoate, 16:1) might depend on the formation of an active 16:1 metabolite. For its identification, we analyzed the glycerophospholipid composition of mouse Swiss 3T3 fibroblasts in response to
Tahira Fatima et al.
PloS one, 7(4), e34099-e34099 (2012-05-05)
Sea buckthorn (Hippophae rhamnoides L.) is a hardy, fruit-producing plant known historically for its medicinal and nutraceutical properties. The most recognized product of sea buckthorn is its fruit oil, composed of seed oil that is rich in essential fatty acids
Claudia Y Janda et al.
Science (New York, N.Y.), 337(6090), 59-64 (2012-06-02)
Wnts are lipid-modified morphogens that play critical roles in development principally through engagement of Frizzled receptors. The 3.25 angstrom structure of Xenopus Wnt8 (XWnt8) in complex with mouse Frizzled-8 (Fz8) cysteine-rich domain (CRD) reveals an unusual two-domain Wnt structure, not
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

Articles

Lipid Induced Insulin Resistance

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service