N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl esterCAS: 615264-52-3
MF: C19H19NO4
MW: 325.36
An inhibitor of ACAT-1 and -2.

N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester (CAS 615264-52-3)

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Synonym: 4-Hydroxycinnamic acid (L-phenylalanine methyl ester) amide
Application: An inhibitor of ACAT-1 and -2
CAS Number: 615264-52-3
Purity: ≥98%
Molecular Weight: 325.36
Molecular Formula: C19H19NO4
* Refer to Certificate of Analysis for lot specific data (including water content).

N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester, inhibits human Acyl-Coenzyme A cyltransferase-1 and -2 (ACAT-1 and ACAT-2) equally (IC50 ~ 60 μM). ACAT-1 and ACAT-2 catalyze the formation of long chain fatty acyl-coenzyme A and cholesterol esters from cholesterol, and may play a role in the development of atherosclerosis. Additionally, at a concentration of 3μM, N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester, demonstrates ~28% inhibition of copper-mediated oxidation of low density lipoproteins.


References

1. Lee, R G., et al., 2000. Differential expression of ACAT1 and ACAT2 among cells within liver, intestine, kidney, and adrenal of nonhuman primates. Journal of lipid research. 41(12): 1991-2001. PMID: 11108732
2. Rudel, L L., et al., 2001. Acyl coenzyme A: cholesterol acyltransferase types 1 and 2: structure and function in atherosclerosis. Current opinion in lipidology. 12(2): 121-7. PMID: 11264983
3. Lee, Sangku., et al., 2004. Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA:cholesterol acyltransferase-1 and -2 activity, and decrease of HDL-particle size. Bioorganic & medicinal chemistry letters. 14(18): 4677-81. PMID: 15324887

Appearance :
Crystalline
Physical State :
Solid
Solubility :
Soluble in ethanol (~20 mg/ml), DMSO (~20 mg/ml), DMF (~20 mg/ml), DMSO: PBS (1: 5, pH 7.2) (~0.5 mg/ml), and water (0.5 mg/ml at 25.0° C).
Storage :
Store at -20° C
Melting Point :
215.26° C (Predicted)
Boiling Point :
~577.3° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.61 (Predicted)
IC50 :
ACAT-1: IC50 = ~60 µM (human); ACAT-2: IC50 = ~60 µM (human)
pK Values :
pKa: 9.74 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
10019206
MDL Number :
MFCD08062178
SMILES :
COC(=O)[[email protected]](CC1=CC=CC=C1)NC(=O)/C=C/C2=CC=C(C=C2)O

Download SDS (MSDS)

Certificate of Analysis

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Hi, I am looking for information in this page about how t dilute N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester : catalog: SC-221976A, I used PBS but look to me that is no well dissolved, there is a specific vehicle?

Asked by: Modesto
Thank you for your question. N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester (CAS 615264-52-3) sc-221976 is soluble in ethanol (~20 mg/ml), DMSO (~20 mg/ml), DMF (~20 mg/ml), DMSO: PBS (1: 5, pH 7.2) (~0.5 mg/ml), and water (0.5 mg/ml at 25.0° C). If there are issues with achieving the solubility values shown above, gentle heating and sonication may increase solubility.
Answered by: Tech Support Europe
Date published: 2019-07-11

What % of inhibition is expected using sc-221976A in vitro and vivo

Asked by: MROJAS
Thank you for your question. The only information we have for this chemical, N-[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-L-phenylalanine, methyl ester: sc-221976, is that it is an inhibitor of human ACAT-1 and ACAT-2 with an IC50 value of approximately 60 μM for both enzymes; also inhibits copper-mediated oxidation of LDL by about 28% at a concentration of 3 μM.
Answered by: Technical Support
Date published: 2017-09-01
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