ChemicalBook Product Catalog Analytical Chemistry food safety Fatty acid methyl ester OLEIC-1-13C ACID 99 ATOM % 13C

OLEIC-1-13C ACID 99 ATOM % 13C

Product NameOLEIC-1-13C ACID 99 ATOM % 13C
CAS82005-44-5
MFC18H34O2
MW283.47036
EINECS
MOL File82005-44-5.mol

Chemical Properties

Melting point	13.4 °C(lit.)
Boiling point	192-195 °C1.2 mm Hg(lit.)
Density	0.893 g/mL at 25 °C
refractive index	n20/D 1.4595(lit.)
Flash point	>230 °F(lit.)
storage temp.	-20°C
solubility	Ethanol: 1.5 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
form	Liquid
color	Colorless to light yellow
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-/i18+1
InChIKey	ZQPPMHVWECSIRJ-OLLJCFGNSA-N
SMILES	[H]\C(CCCCCCCC)=C(/[H])CCCCCCC[13C](O)=O
CAS Number Unlabeled	112-80-1

Safety Information

WGK Germany	3
Storage Class	10 - Combustible liquids

Usage And Synthesis

Description

Oleic acid-¹³C is intended for use as an internal standard for the quantification of oleic acid (Item Nos. 90260 | 24659) by GC- or LC-MS. Oleic acid is a monounsaturated fatty acid and a major component of membrane phospholipids that has been found in human plasma, cell membranes, and adipose tissue. It contributes approximately 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets. Oleic acid inhibits collagen-stimulated platelet aggregation by approximately 90% when used at a concentration of 10 μg/ml. It also inhibits fMLF-induced neutrophil aggregation and degranulation by 55 and 68%, respectively, when used at a concentration of 5 μM, similar to arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607). Oleic acid (60 μM) induces release of intracellular calcium in human platelets. In vivo, oleic acid increases TNF-α, IL-8, IL-6, and IL-1β production, neutrophil accumulation, and apoptotic and necrotic cell death in mouse lung and has been used to induce lung injury in a mouse model of acute respiratory distress syndrome (ARDS).

Uses

Labelled Oleic acid. Obtained by the hydrolysis of various animal and vegetable fats and oils.

References

[1] KLAUS W.J WAHLE Lesley I L P. Effects of isomeric cis and trans eighteen carbon monounsaturated fatty acids on porcine platelet function[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1996, 1301 1: Pages 141-149. DOI: 10.1016/0005-2760(96)00025-2
[2] C. GON?ALVES-DE ALBUQUERQUE. Acute Respiratory Distress Syndrome: Role of Oleic Acid-Triggered Lung Injury and Inflammation[J]. Mediators of Inflammation, 2015, 2015 1. DOI: 10.1155/2015/260465
[3] P.H. NACCACHE. Modulation of Rabbit Neutrophil Aggregation and Degranulation by Free Fatty Acids[J]. Journal of Leukocyte Biology, 1984, 36 3: 333-340. DOI: 10.1002/jlb.36.3.333
[4] ATHANASSIA SIAFAKA-KAPADAI Martin A J Donald J Hanahan. Oleic acid-induced Ca2+ mobilization in human platelets: is oleic acid an intracellular messenger?[J]. Journal of lipid mediators and cell signalling, 1997, 15 3: Pages 215-232. DOI: 10.1016/s0929-7855(96)00554-8

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