Oleyl Anilide

Cayman Chemical Item Number 10006529

Oleic Acid Anilide; OA (CAS 5429-85-6)

Oleyl Anilide (CAS 5429-85-6)

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Description

AcylCoA:cholesterol acyltransferase (ACAT) is an intracellular cholesteryl ester synthase tied closely to the absorption of dietary cholesterol.1 Oleyl analide (OA) is a weak inhibitor of ACAT with an IC50 of 26 µM.2 OA and the related glyceride dioleoyl phenylamino propane 1,2-diol have been linked to a syndrome of eosinophilia, excessive T-cell activation, and elevated interleukin-4 (IL-4), soluble IL-2R, and IL-5. The clinical consequences are an acute pulmonary inflammatory reaction followed by chronic neuropathy, myalgia, and autoimmune connective tissue disease, generally referred to as toxic oil syndrome (TOS). Aniline-denatured cooking oil is a source of OA associated with TOS.3

1 Suckling, K.E., and Stange, E.F. Role of acyl-CoA: Cholesterol acyltransferase in cellular cholesterol metabolism. J Lipid Res 26 647-671 (1985).

2 Roth, B.D., Blankley, C.J., Hoefle, M.L., et al. Inhibitors of acyl-CoA: Cholesterol acyltransferase. 1. Identification and structure-activity relationship of a novel series of fatty acid anilide hypocholesterolemic agents. J Med Chem 35 1609-1617 (1992).

3 Gelpi, E., de la Paz, M.P., Terracini, B., et al. The spanish toxic oil syndrome 20 years after its onset: A multidisciplinary review of scientific knowledge. Environ Health Perspect 110(5) 457-464 (2002).

Synonyms
  • Oleic Acid Anilide
  • OA
Formal Name N-​phenyl-​9Z-​octadecenamide
CAS Number 5429-85-6
Molecular Formula C24H39NO
Formula Weight 357.6
Formulation A crystalline solid
Purity ≥95%
λmax 243 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCC/C=C\CCCCCCCC(=O)​Nc1ccccc1
InCHI Code
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​1S/C24H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-24(26)​25-23-20-17-16-18-21-23/h9-10,16-18,20-21H,2-8,11-15,19,22H2,1H3,(H,25,26)​/b10-9-
InCHI Key
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YPUOCYKJOLQYQS-KTKRTIGZSA-N

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Oleyl Anilide is available in the following screening library:

Size Price Quantity Subtotal
5 mg $14.00 $0.00
10 mg $27.00 $0.00
50 mg $112.00 $0.00
100 mg $196.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-16. Prices are subject to change without notice.

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