Structure Database (LMSD)

Common Name
Ricinenic acid
Systematic Name
9Z,11Z-octadecadienoic acid
Synonyms
  • cis-9, cis-11-octadecadienoic acid
  • C18:2n-7,9
LM ID
LMFA01030117
Formula
Exact Mass
Calculate m/z
280.24023
Sum Composition
Status
Curated


Classification

Biological Context

9(Z),11(Z)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in milk from cows and other animals.1,2 It is cytotoxic to Caco-2 human colon cancer cells (EC50 = 446.1 µM) and induces changes in the miRNA profile, including an upregulation hsa-miR-146a-5p and downregulation of hsa-miR-32-5p, which is involved in apoptosis.3 [Matreya, LLC. Catalog No. 1248]

This information has been provided by Cayman Chemical

References

2. Revilla, I., Escuredo, O., González-Martín, M.I., et al. Fatty acids and fat-soluble vitamins in ewe’s milk predicted by near infrared reflectance spectroscopy. Determination of seasonality. Food Chem. 214, 468-477 (2017).
3. Köpke, S., Buhrke, T., and Lampen, A. miRNA expression in human intestinal Caco-2 cells is comparably regulated by cis- and trans-fatty acids. Lipids 50(3), 227-239 (2015).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bos taurus (#9913)
Mammalia (#40674)
Milk from cows grazing on cool-season pastures provides an enhanced profile of bioactive fatty acids compared to those grazed on a monoculture of pearl millet,
Food Chem, 2017

String Representations

InChiKey (Click to copy)
JBYXPOFIGCOSSB-QRLRYFCNSA-N
InChi (Click to copy)
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7-,10-9-
SMILES (Click to copy)
C(/C=C\C=C/CCCCCC)CCCCCCC(=O)O

Other Databases

CHEBI ID
LIPIDBANK ID
DFA0156
PubChem CID
PlantFA ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 329.62
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.88
Molar Refractivity 86.99

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Created at
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Updated at
25th Apr 2022