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Key Documents

L8134

Sigma-Aldrich

Linoleic acid sodium salt

≥97% (GC)

Synonym(s):

Sodium linolate, Sodium linoleate, cis-9,cis-12-Octadecadienoic acid sodium salt

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About This Item

Linear Formula:
C18H31O2Na
CAS Number:
Molecular Weight:
302.43
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

plant oil (safflower)

Assay

≥97% (GC)

form

powder

technique(s)

activity assay: suitable

color

white

mp

230 °C (446 °F)

solubility

methanol: 50 mg/mL, clear, yellow

application(s)

general analytical
life science and biopharma

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

[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-;

InChI key

WYPBVHPKMJYUEO-NBTZWHCOSA-M

General description

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

Biochem/physiol Actions

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.

Features and Benefits

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

Other Notes

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Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ling Zhang et al.
Frontiers in nutrition, 9, 849684-849684 (2022-05-03)
Maternal overnutrition can affect fetal growth and development, thus increasing susceptibility to obesity and diabetes in later life of the offspring. Placenta is the central organ connecting the developing fetus with the maternal environment. It is indicated placental fatty acid
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
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
Miriam E van Gent et al.
Antibiotics (Basel, Switzerland), 11(5) (2022-05-29)
Recently, using a deep learning approach, the novel antibiotic halicin was discovered. We compared the antibacterial activities of two novel bactericidal antimicrobial agents, i.e., the synthetic antibacterial and antibiofilm peptide (SAAP)-148 with this antibiotic halicin. Results revealed that SAAP-148 was

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