SML1969
Linoleamide
≥98% (HPLC)
Synonym(s):
(9Z,12Z)-9,12-Octadecadienamide, Linoleic acid amide
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About This Item
Empirical Formula (Hill Notation):
C18H33NO
CAS Number:
Molecular Weight:
279.46
UNSPSC Code:
12352202
NACRES:
NA.77
MDL number:
Product Name
Linoleamide, ≥98% (HPLC)
InChI
1S/C18H33NO/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,(H2,19,20)/b7-6-,10-9-
SMILES string
NC(CCCCCCC/C=C\C/C=C\CCCCC)=O
InChI key
SFIHQZFZMWZOJV-HZJYTTRNSA-N
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
Quality Level
Biochem/physiol Actions
Linoleamide is an endogenous lipid, that stimulates sleep in cats, rats and humans.
Linoleamide is an endogenous primary fatty acid amide (PFAM) signaling lipid that modulates intracellular Ca2+ homeostasis. It has been shown to inhibit of SPCA2, a Golgi secretory pathway Ca(2+)-ATPase that transports ions of Ca2+ and Mn2+ and also to inhibit SPCA1a and the Ca2+-ATPase activity of three sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) pump isoforms. It is thought to be involved in a variety of biological activities including regulation of sleep.
Modulator of intracellular Ca2+ homeostasis; Inhibitor of SPCA2, a Golgi secretory pathway Ca(2+)-ATPase that transports ions of Ca2+ and Mn2+
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Jialin Chen et al.
The Journal of biological chemistry, 292(17), 6938-6951 (2017-03-08)
The Golgi/secretory pathway Ca
Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells
Huang J K, et al.
Life Sciences, 68(9), 997-1004 (2001)
Emma K Farrell et al.
Journal of lipid research, 53(2), 247-256 (2011-11-19)
Primary fatty acid amides (PFAM) are important signaling molecules in the mammalian nervous system, binding to many drug receptors and demonstrating control over sleep, locomotion, angiogenesis, and many other processes. Oleamide is the best-studied of the primary fatty acid amides
Sachiko Yamamoto et al.
Biochimica et biophysica acta, 1861(1 Pt A), 3399-3405 (2016-09-07)
SERCA maintains intracellular Ca2+ homeostasis by sequestering cytosolic Ca2+ into SR/ER stores. Two primary fatty acid amides (PFAAs), oleamide (18:19-cis) and linoleamide (18:29,12-cis), induce an increase in intracellular Ca2+ levels, which might be caused by their inhibition of SERCA. Three
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