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MedKoo Cat#: 581026 | Name: Melinamide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mechanism of the inhibition of cholesterol absorption by DL-melinamide: inhibition of cholesterol esterification.

Chemical Structure

Melinamide
Melinamide
CAS#14417-88-0

Theoretical Analysis

MedKoo Cat#: 581026

Name: Melinamide

CAS#: 14417-88-0

Chemical Formula: C26H41NO

Exact Mass: 383.3188

Molecular Weight: 383.62

Elemental Analysis: C, 81.41; H, 10.77; N, 3.65; O, 4.17

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Melinamide; AC 223; Melinamide [INN:JAN]; Melinamidum; Melinamidum [INN-Latin]; Melinamida.
IUPAC/Chemical Name
DL-a-Methylbenzyl linoleamide;N-(a-Methylbenzyl)linoleamide;N-(2-methylbenzyl)linoleamide;N-(α-Methylbenzyl)linoleamide;DL-N-(a-Methylbenzyl)linoleamide;N-(DL-a-Methylbenzyl) linoleamide;Linoleamide, N-(a-methylbenzyl)- (8CI);(9Z,12Z)-N-(1-Phenylethyl)-9,12-octadecadienamide
InChi Key
RWIUTHWKQHRQNP-NQLNTKRDSA-N
InChi Code
InChI=1S/C26H41NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23-26(28)27-24(2)25-21-18-17-19-22-25/h7-8,10-11,17-19,21-22,24H,3-6,9,12-16,20,23H2,1-2H3,(H,27,28)/b8-7-,11-10-
SMILES Code
CCCCC/C=C\C/C=C\CCCCCCCC(NC(C)C1=CC=CC=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 383.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Garmanchuk LV, Linchak OV, Denis EO, Nikulina VV, Dzhus OI, Khranovskaia NN, Nikolaenko TV, Babuta EN, Rybal'chenko VK. [Potential cytostatic effect of the maleimide derivative 1-(4-Cl-benzyl)-3-Cl-4-(CF3-phenylamino)-1-H-pyrrol-2,5-dione]. Eksp Klin Farmakol. 2013;76(8):39-42. Russian. PubMed PMID: 24228489. 2: Nakamura S, Kamiya S, Shirahase H, Kanda M, Yoshimi A, Tarumi T, Kurahashi K. Hypolipidemic and antioxidant activity of the novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor KY-455 in rabbits and hamsters. Arzneimittelforschung. 2004;54(2):102-8. PubMed PMID: 15038459. 3: Diczfalusy MA, Björkhem I, Einarsson C, Alexson SE. Formation of fatty acid ethyl esters in rat liver microsomes. Evidence for a key role for acyl-CoA: ethanol O-acyltransferase. Eur J Biochem. 1999 Jan;259(1-2):404-11. PubMed PMID: 9914520. 4: Aragane K, Kusunoki J, Kitamine T, Yamaura T, Ohnishi H. Effects of F-1394, an acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, on ACAT activity in HepG2 cells and on hepatic secretion of lipids in Triton WR-1339-induced hyperlipidemic rats: possible role of hepatic ACAT in very low density lipoprotein secretion. Jpn J Pharmacol. 1998 Mar;76(3):309-12. PubMed PMID: 9593225. 5: Kusunoki J, Aragane K, Kitamine T, Yamaura T, Ohnishi H. [Effect of F-1394, a potent and selective inhibitor of acyl-CoA:cholesterol acyltransferase (ACAT), on esterification of cholesterol and basolateral secretion of cholesteryl ester in Caco-2 cells]. Nihon Yakurigaku Zasshi. 1997 Dec;110(6):357-65. Japanese. PubMed PMID: 9503394. 6: Diczfalusy MA, Björkhem I, Einarsson K, Alexson SE. Acyl-coenzyme A:cholesterol O-acyltransferase is not identical to liver microsomal carboxylesterase. Arterioscler Thromb Vasc Biol. 1996 Apr;16(4):606-10. PubMed PMID: 8624784. 7: Kusunoki J, Aragane K, Kitamine T, Higashinakagawa S, Kase N, Yamaura T, Ohnishi H. Hypocholesterolemic action and prevention of cholesterol absorption via the gut by F-1394, a potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, in cholesterol diet-fed rats. Jpn J Pharmacol. 1995 Sep;69(1):53-60. PubMed PMID: 8847832. 8: Nagata Y, Yonemoto M, Iwasawa Y, Shimizu-Nagumo A, Hattori H, Sawazaki Y, Kamei T. N-[2-[N'-pentyl-(6,6-dimethyl-2,4-heptadiynyl)amino]ethyl]- (2-methyl-1-naphthylthio)acetamide (FY-087). A new acyl coenzyme a:cholesterol acyltransferase (ACAT) inhibitor of diet-induced atherosclerosis formation in mice. Biochem Pharmacol. 1995 Mar 1;49(5):643-51. PubMed PMID: 7887979. 9: Horie M, Iwasawa Y, Satoh T, Shimizu A, Nagata Y, Kamei T. Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells. Biochem Pharmacol. 1993 Jul 20;46(2):297-305. PubMed PMID: 8347152. 10: Krause BR, Anderson M, Bisgaier CL, Bocan T, Bousley R, DeHart P, Essenburg A, Hamelehle K, Homan R, Kieft K, et al. In vivo evidence that the lipid-regulating activity of the ACAT inhibitor CI-976 in rats is due to inhibition of both intestinal and liver ACAT. J Lipid Res. 1993 Feb;34(2):279-94. PubMed PMID: 8429262. 11: Suzuki H, Mori K, Yamada J, Suga T. Contribution of peroxisomal beta-oxidation system to the chain-shortening of N-(alpha-methylbenzyl)azelaamic acid in rat liver. Biochem Pharmacol. 1990 Jun 15;39(12):1975-81. PubMed PMID: 2353938. 12: Matsubara K, Matsuzawa Y, Jiao S, Kihara S, Takama T, Nakamura T, Tokunaga K, Kubo M, Tarui S. Cholesterol-lowering effect of N-(alpha-methylbenzyl)linoleamide (melinamide) in cholesterol-fed diabetic rats. Atherosclerosis. 1988 Aug;72(2-3):199-204. PubMed PMID: 3214468. 13: Seki K, Horie S, Watanabe T, Suga T. Influence of 5-tridecylpyrazole-3-carboxylic acid, a new hypolipidaemic agent, on cholesteryl ester formation in rabbit intestinal mucosa. J Pharm Pharmacol. 1988 Jul;40(7):473-7. PubMed PMID: 2904986. 14: Natori K, Okazaki Y, Nakajima T, Hirohashi T, Aono S. Mechanism of the inhibition of cholesterol absorption by DL-melinamide: inhibition of cholesterol esterification. Jpn J Pharmacol. 1986 Dec;42(4):517-23. PubMed PMID: 3807053. 15: Nakajima T, Natori K, Hirohashi T, Aono S. Inhibitory effect of melinamide on cholesterol solubility in mixed micellar solution of sodium taurocholate. Chem Pharm Bull (Tokyo). 1986 Oct;34(10):4273-9. PubMed PMID: 3829159. 16: Gomi H, Nakatsuka I, Yoshitake A. 14C-labelling of a hypocholesterolemic agents, N-(alpha-methylbenzyl) linoleamide. Radioisotopes. 1980 Sep;29(9):443-5. PubMed PMID: 7221023.