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Merck

P9417

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:
373-49-9
Molecular Weight:
254.41
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
24899035
EC Number:
206-765-9
Beilstein/REAXYS Number:
1725389
MDL number:
MFCD00004437

Key Documents

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Product Name

Palmitoleic acid, ≥98.5% (GC), liquid

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

SMILES string

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

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

Quality Level

300

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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
GHS07

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL3536
SLCK4898
SLCJ9685
SLCJ7552
SLCJ3499

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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
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
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).
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