All Photos(1)
Synonym(s):
Sodium linolate, Sodium linoleate, cis-9,cis-12-Octadecadienoic acid sodium salt
Linear Formula:
C18H31O2Na
CAS Number:
Molecular Weight:
302.43
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
biological source
plant oil (safflower)
Quality Level
Assay
≥98% (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
For additional information on our range of Biochemicals, please complete this form.
Signal Word
Warning
Hazard Statements
Hazard Classifications
Skin Irrit. 2
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)
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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
Alketa Tarushi et al.
Journal of inorganic biochemistry, 170, 85-97 (2017-02-24)
From the reaction of ZnCl
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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