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P9417

Sigma-Aldrich

Palmitoleic acid

Palmitoleic acid
1 of 1 reviewers received a sample product or took part in a promotion

≥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
Beilstein:
1725389
EC Number:
206-765-9
MDL number:
MFCD00004437
UNSPSC Code:
12352211
PubChem Substance ID:
24899035
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

Macadamia integrifolia

Quality Level

300

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

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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Certificates of Analysis (COA)

Lot/Batch Number
0000418196
0000418195
0000418194
0000418194
0000418195

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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
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
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
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
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Can you specify the molar concentration of this product? Does the different amounts have different molar concentration?

    1 answer

    1. The concentration of this product can be determined using the lot specific purity reported in the Certificate of Analysis, the density, and the compound molecular weight. This product has a density of 0.895 g/mL and a molecular weight of 254.41 g/mol. Based on the specifications on the Certificate of Analysis, the minimum purity is 98.5%, thus the molarity will vary slightly from lot to lot. The molarity can range from 3.46M (98.5%) to 3.52M (100%).

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Reviews

1 of 1 reviewers received a sample product or took part in a promotion

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    • Review 1
    • Votes 0
    5 out of 5 stars.

    Palmitoleic acid

    exactly what we ordered, quality was what we needed

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