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L8134

Sigma-Aldrich

Acide linoléique sodium salt

≥98% (GC)

Synonyme(s) :

Acide cis-9,cis-12-octadécadiénoïque, sel sodique

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About This Item

Formule linéaire :
C18H31O2Na
Numéro CAS:
Poids moléculaire :
302.43
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Source biologique

plant oil (safflower)

Niveau de qualité

Pureté

≥98% (GC)

Forme

powder

Technique(s)

activity assay: suitable

Couleur

white

Pf

230 °C (446 °F)

Solubilité

methanol: 50 mg/mL, clear, yellow

Application(s)

general analytical
life science and biopharma

Groupe fonctionnel

carboxylic acid

Type de lipide

omega FAs

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

[Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O

InChI

1S/C18H32O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20);/q;+1/p-1/b7-6-,10-9-;

Clé InChI

WYPBVHPKMJYUEO-NBTZWHCOSA-M

Description générale

Linoleic acid, an essential omega-6 polyunsaturated fatty acid (PUFA), serves as a precursor to arachidonic acid (AA), necessary for synthesizing prostaglandins and other eicosanoids. Being an essential fatty acid, linoleic acid must be acquired through diet as the body cannot produce it. Deficiencies in linoleic acid are linked to health issues such as impaired wound healing, growth retardation, and dermatitis. Arachidonate 15 Lipoxygenase (15-LO) metabolizes linoleic acid in both plants and animals, forming 9- and 13-hydroxyoctadecadienoic acid (HODE). This versatile molecule finds applications in biochemical, metabolomics, and lipidomics research, enabling investigations into various metabolic pathways and providing insights into lipid functions in living organisms.

Application

Linoleic acid sodium salt has been used:
  • in the β-carotene-linoleic acid assay
  • as a component in basal medium to treat peripheral blood mononuclear cells (PBMCs)
  • in Dulbecco′s modified Eagle′s medium (DMEM)/F-12 HEPES (4-(2-hydroxyethyl) piperazine-1-ethanesulfonic acid) to incubate human trophoblast-derived choriocarcinoma cells (BeWo) and study its effects on adherens junctions (AJ) marker level, cell layer permeability, and intracellular lipid accumulation

Actions biochimiques/physiologiques

Linoleic acid, as a component of acylglycosyl ceramides, plays a physiological role in maintaining the water permeability barrier of the skin. The deficiency of linoleic acid may cause poor growth or development, scaly dermatitis, and an impaired immune response in infants. It is used in cosmetic and personal care products. Linoleic acid is mainly used as emollients or moisturizers for skin, nails, and hair.

Caractéristiques et avantages

  • High-quality molecule suitable for mulitple research applications
  • Commonly employed in Metabolomics and Biochemical studies

Autres remarques

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

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

T Sakamoto et al.
Applied and environmental microbiology, 64(7), 2361-2366 (1998-07-02)
Laboratory conditions have been identified that cause the rapid death of cultures of cyanobacteria producing urease. Once the death phase had initiated in the stationary growth phase, cells were rapidly bleached of all pigmentation. Null mutations in the ureC gene
Hila Seti et al.
Archives of physiology and biochemistry, 115(3), 127-136 (2009-06-02)
The insulin-like growth factor (IGF) system plays a critical role in normal growth and development as well as in malignant states. Most of the biological activities of the IGFs are mediated by the IGF-IR, which is over-expressed in most tumours
E P Kilsdonk et al.
Journal of lipid research, 33(9), 1373-1382 (1992-09-01)
Human endothelial cells (EA.hy 926 line) were loaded with cationized low density lipoprotein (LDL) and subsequently incubated with fatty acid/bovine serum albumin complexes. The fatty acids were palmitic, oleic, linoleic, arachidonic, and eicosapentaenoic acids. The preincubations resulted in extensively modified
Allison Dilzer et al.
Critical reviews in food science and nutrition, 52(6), 488-513 (2012-03-29)
Conjugated linoleic acid (CLA) has drawn significant attention in the last two decades for its variety of biologically beneficial effects. CLA reduces body fat, cardiovascular diseases and cancer, and modulates immune and inflammatory responses as well as improves bone mass.
Moran Cohen-Berkman et al.
eLife, 9 (2020-03-28)
How lifespan and the rate of aging are set is a key problem in biology. Small RNAs are conserved molecules that impact diverse biological processes through the control of gene expression. However, in contrast to miRNAs, the role of endo-siRNAs

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