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Sigma-Aldrich

Acide oléique

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

≥99% (GC)

Synonyme(s) :

Acide 9Z-octadécénoïque, acide cis-oléique, Acide cis-9-octadécènoïque, Acide élaïnique

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1 G
69.90 CHF
5 G
224.00 CHF
25 G
773.00 CHF

69.90 CHF


Date d'expédition estimée le02 avril 2025


Devis pour commande en gros

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1 G
69.90 CHF
5 G
224.00 CHF
25 G
773.00 CHF

About This Item

Formule linéaire :
CH3(CH2)7CH=CH(CH2)7COOH
Numéro CAS:
Poids moléculaire :
282.46
Beilstein:
1726542
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
Nomenclature NACRES :
NA.25

69.90 CHF


Date d'expédition estimée le02 avril 2025


Devis pour commande en gros

Source biologique

plant (Sunflower)

Niveau de qualité

Pression de vapeur

1 mmHg ( 176 °C)

Essai

≥99% (GC)

Forme

viscous liquid

Couleur

colorless to very faintly yellow

Indice de réfraction

n20/D 1.459 (lit.)

pb

194-195 °C/1.2 mmHg (lit.)

Pf

13-14 °C (lit.)

Solubilité

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

Densité

0.89 g/mL at 25 °C (lit.)

Application(s)

life science and biopharma
lipidomics

Groupe fonctionnel

oleic acid

Type de lipide

unsaturated FAs

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

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

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-

Clé InChI

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

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Catégories apparentées

Description générale

L'acide oléique (AO), un acide gras non essentiel présent en grande quantité dans l'huile d'olive, appartient à la catégorie des acides gras mono-insaturés (AGMI ou MUFA).[1] Son élimination quantitative de mélanges de triglycérides et de glycérides partiels a été signalée.[2] L'AO est très utilisé comme tensioactif pour stabiliser les nanoparticules magnétiques. Des nanoparticules monodispersées de magnétite (de 7 et 19 nm) revêtues d'AO ont été préparées.[3]

Application

L'acide oléique a été utilisé :
  • pour étudier les effets d'acides gras sur le cancer gastrique[4].
  • pour induire la formation de gouttelettes lipidiques en culture cellulaire[5].
  • comme additif dans la préparation d'un fluide magnétorhéologique[6].
L'acide oléique peut servir à préparer de l'acide 10-hydroxyoctadécanoïque et l'ester méthylique de l'acide 10-hydroxyoctadécanoïque.[7]

Actions biochimiques/physiologiques

L'acide oléique est connu pour renforcer les fonctions immunitaires et la santé en général. Une supplémentation du régime alimentaire avec cet acide gras contribue à réduire le taux de cholestérol, le risque d'athérogenèse, la pression artérielle et la réponse de l'hôte par rapport aux greffons. Il a été montré que l'acide oléique est bénéfique pour les maladies auto-immunes car il présente une action anti-inflammatoire. Il améliore également l'état des cancers du sein.[1] L'acide oléique produit des effets physiologiques tels que l'activation de la protéine kinase C dans les hépatocytes, le découplage de la phosphorylation oxydative et l'inhibition de l'ATPase stimulée par le 2,4−dinitrophénol. Il est possible d'inverser cette action par ajout d'albumine sérique.

Autres remarques

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Produit(s) apparenté(s)

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Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 1

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Certificats d'analyse (COA)

Lot/Batch Number

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Pan J, et al.
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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)
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)
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
Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)

Articles

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

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.

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

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Questions

1–10 of 13 Questions  
  1. 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?

  2. 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?

  3. 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

      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. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

1–10 of 13 Questions  

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