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Merck

O1008

Oleic acid

≥99% (GC)

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

Synonym(s):

9Z-Octadecenoic acid, cis-Oleic acid, cis-9-Octadecenoic acid, Elainic acid

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1 G

CLP 39,000

5 G

CLP 119,000

25 G

CLP 381,000

CLP 39,000


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About This Item

Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
282.46
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
204-007-1
Beilstein/REAXYS Number:
1726542
MDL number:

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Product Name

Oleic acid, ≥99% (GC)

InChI key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

InChI

1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

SMILES string

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

biological source

plant (Sunflower)

vapor pressure

1 mmHg ( 176 °C)

assay

≥99% (GC)

form

viscous liquid

color

colorless to very faintly yellow

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

solubility

H2O: insoluble (practically)
alcohol: soluble
benzene: soluble
chloroform: soluble
oil: soluble (fixed and volatile)

density

0.89 g/mL at 25 °C (lit.)

application(s)

life science and biopharma
lipidomics

functional group

oleic acid

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

−20°C

Quality Level

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1 of 4

This Item
W28150636452527728
biological source

plant (Sunflower)

biological source

-

biological source

plant

biological source

-

assay

≥99% (GC)

assay

-

assay

90%

assay

65.0-88.0% (GC)

functional group

oleic acid

functional group

-

functional group

oleic acid

functional group

carboxylic acid

solubility

H2O: insoluble (practically), benzene: soluble, oil: soluble (fixed and volatile), alcohol: soluble, chloroform: soluble

solubility

-

solubility

alcohol: soluble, benzene: soluble, chloroform: soluble, diethyl ether: soluble, water: insoluble

solubility

-

shipped in

ambient

shipped in

-

shipped in

ambient

shipped in

-

form

viscous liquid

form

liquid

form

liquid, semisolid, waxy solid

form

liquid

Application

Oleic acid has been used:
  • to study the effects of fatty acids on gastric cancer (GC)[1]
  • to induce lipid droplet formation in cell culture[2]
  • as an additive in the magnetorheological fluid preparation[3].
Oleic acid may be used in the preparation of 10-hydroxy octadecanoic acid and methyl ester of the 10-hydroxy octadecanoic acid.[4]

Biochem/physiol Actions

Oleic acid is known to improve immune function and health. Dietary supplement of this fatty acid contributes to the reduction in cholesterol levels, atherogenesis risk, blood pressure, and host versus graft response. Oleic acid has been proven to benefit autoimmune diseases by exhibiting anti-inflammatory action. It also ameliorates the condition of breast cancer.[5] Oleic acid produces physiological effects such as protein kinase C activation in hepatocytes, uncoupling oxidative phosphorylation, and 2,4-dinitrophenol−stimulated ATPase inhibition. This action can be reversed by adding serum albumin.

General description

Oleic acid (OA), a non-essential fatty acid, is classified as monounsaturated fatty acid (MUFA) richly present in olive oil.[5] Its quantitative removal from the mixtures of triglyceride and partial glycerides has been reported.[6] OA is widely used as a surfactant for the stabilization of magnetic nanoparticles. Monodisperse magnetite nanoparticles (7 and 19nm) coated with OA have been prepared.[7]

Other Notes

For additional information on our range of Biochemicals, please complete this form.

comparable product

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Description
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Storage Class

10 - Combustible liquids

wgk

WGK 1

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Certificates of Analysis (COA)

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Influence of graphite flakes on the strength of magnetorheological fluids at high temperature and its rheology
Thakur MK and Sarkar C
IEEE Transactions on Magnetics, 56(5) (2020)
Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)
THE STEREOSPECIFIC CONVERSION OF STEARIC ACID TO OLEIC ACID.
G J SCHROEPFER et al.
The Journal of biological chemistry, 240, 54-63 (1965-01-01)
CD36 mediates palmitate acid-induced metastasis of gastric cancer via AKT/GSK-3?/?-catenin pathway
Pan J, et al.
Journal of Experimental & Clinical Cancer Research, 38 (2019)
Kun Huang et al.
Journal of hepatology, 66(5), 962-977 (2016-12-17)
PARP1 is a key mediator of cellular stress responses and critical in multiple physiological and pathophysiological processes of cells. However, whether it is involved in the pathogenesis of non-alcoholic fatty liver disease (NAFLD) remains elusive. We analysed PARP1 activity in

Articles

How the unsaturated fatty acid, oleic acid and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Supplement cell culture systems with fatty acids for biomanufacturing heterologous proteins like monoclonal antibodies.

Magnetic nanoparticles have attracted tremendous attention due to their novel properties and their potential applications in magnetic recording, magnetic energy storage and biomedicine.

DISCOVER Bioactive Small Molecules for Neuroscience

Protocols

Strat-M® synthetic membrane mimics the human skin for In-vitro permeation testing (IVPT) of topical and transdermal formulations

Questions

1–10 of 13 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. Can be used in mice?

    1 answer
    1. This product is not tested for use in research animals such as mice. But there certainly is precedence for its use by researchers in a mouse model:
      1. https://pubmed.ncbi.nlm.nih.gov/32663612/
      See Table 1.
      2. https://pubmed.ncbi.nlm.nih.gov/37380774/
      See Methods section.

      Helpful?

  3. How to store the product after opening the amplue?

    1 answer
    1. The stability of this product in solution has not been determined. However, cell culture supplements containing Oleic acid, available as sterile solutions, are stored at 2-8°C and assigned a shelf life of 1 year. See the table below:

      Helpful?

  4. 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

      Helpful?

  5. What solvent is used to resuspend oleic acid in this product?

    1 answer
    1. This product is a neat or pure liquid that has not been diluted. The recommended solvents are ethanol, methanol, chloroform, and benzene. This information is listed in the 'PROPERTIES' section of the product page.

      Helpful?

  6. What sort of packaging for the vial do you offer ?

    1 answer
    1. The packaging varies according to the quanitity. The 1G package is in a 5 mL clear glass, flat bottom, sealed ampule. The 5G package is in a 10 mL clear glass, flat bottom, sealed ampule. The 25G package is in a 50 mL clear glass, flat bottom, sealed ampule.

      Helpful?

  7. Hello, would OA be soluble in DMSO? Also, after diluting in solvent, how long can it be stored in -20?

    1 answer
    1. Oleic acid is completely miscible with Dimethyl sulfoxide (DMSO) in all proportions. It is generally not recommended to store solutions of unsaturated fatty acids such as oleic acid, due to oxidation. But if the solution is stored under an inert gas (e.g., nitrogen gas or argon gas), that would extend the stability of the solution.

      The exact amount of time that the solution is stable is undetermined. Evidence for instability of the solution would be a change in color (colorless to yellow, or yellow to dark yellow, or dark yellow to brown).

      Helpful?

  8. How to sterilize pure oleic acid?

    1 answer
    1. This product can be sterilized by autoclaving. When diluted in medium or buffer to a working concentration, solutions can be filter-sterilized.

      Helpful?

  9. hello, i would like to know please the concentration of oeic acid in this solution and in what solution we can dissolve it else than chloroform for exemple can we dissolve it in the water and heat (70°C) or in the BSA directly thank you

    1 answer
    1. The solubility information is listed on the product detail page under the "Properties" section as follows:
      H2O: insoluble (practically)
      alcohol: soluble
      benzene: soluble
      chloroform: soluble
      oil: soluble (fixed and volatile)

      The concentration for this product will be lot specific as purity changes with each batch. The concentration of this material can be calculated by the equation density x 1000, x purity percent divided by the molecular weight. For example, lot 0000216415 on the sample certificate of analysis will have a concentration of about 3.12 M

      Helpful?

  10. In what solvents can Product O1008, Oleic acid, be dissolved or diluted?

    1 answer
    1. Per the chemicals encyclopedia published by the Royal Society of Chemistry, 12th ed., Entry# 6965, oleic acid is soluble in alcohol, benzene, chloroform, ether, fixed and volatile oils, but is practically insoluble in water.

      Helpful?

1–10 of 13 Questions  

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