9-Octadecenoic Acid → 10-Nitrolinoleic acid

HRID 503668

Reaktionsgleichung

Reaktionsgleichung von HRID 503668
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].COC(=O)CCCCCCCC=CCCCCCCCC.C1([Se]Br)C=CC=CC=1.[N:50]([O-:52])=[O:51].[Na+].C(N1C2N=CNC=2C(=O)N(C)C1=O)C(C)C.B(F)(F)F>Cl[Hg]Cl.CC#N.O1CCCC1>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11]/[C:10](/[N+:50]([O-:52])=[O:51])=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19]

Komponenten

10

Edukt 6

HCID 9659-Octadecenoic AcidHCID 37583-Isobutyl-1-methylxanthineHCID 6356Boron trifluorideHCID 82029-Octadecenoic acid, methyl esterHCID 123446BromoselenobenzeneHCID 23668193Sodium Nitrite

Produkt 1

HCID 528225910-Nitrolinoleic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24085Mercuric ChlorideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Materials. 9-Octadecenoic acid (oleic acid) and its respective methyl ester, methyl-9-octadecenoate was purchased from Nu-Check Prep (Elysian, Minn.). LNO2 and [13C]LNO2 were synthesized as previously described (9,12); OA-NO2 and [13C]OA-NO2 were synthesized as described in below. Phenylselenium bromide, HgCl2, NaNO2, anhydrous tetrahydrofuran (THF), CH3CN, CDCl3, insulin, dexaniethasone and 3-isobutyl-1-methylxantliine were obtained from Sigma/Aldrich (St Louis, Mo.). Silica gel G and HF thin layer chromatography plates (250 and 2000 μm) were from Analtech (Newark, Del.). Methanolic BF3, horseradish peroxidase-linked goat anti-rabbit IgG and Coomasie Blue were from Pierce (Rockford, Ill.). Synthetic solvents were of HPLC grade or better from Fisher Scientific (Fairlawn, N.J.). Solvents used for extractions and mass spectrometric analyses were from Burdick and Jackson (Muskegon, Mich.). [13C]Oleic acid and [13C]linoleic acid were purchased from Cambridge Isotope Laboratories, Inc. (Andover, Mass.). Anti-PPARγ and anti-β-actin antibodies were from Santa Cruz (Santa Cruz, Calif.); anti-aP2 antibody was from Chemicon International Inc. (Temecula, Calif.).

Aufarbeitung

  1. extractionSolvents used for extractions and mass spectrometric analyses

Quellen und Nachweise

ORD-Eintrag
ord-2f682788ff6c4f1481c9bc10a13eaa08
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776916B2

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