Capsiate

Base Information

• Chemical Name: Capsiate
• CAS No.: 205687-01-0
• Molecular Formula: C18H26O4
• Molecular Weight: 306.402
• UNII: PX8I7HG5I3
• DSSTox Substance ID: DTXSID20174575
• Nikkaji Number: J1.827.634H,J969.320C
• Wikidata: Q27286800
• Metabolomics Workbench ID: 46681
• Mol file: 205687-01-0.mol

Synonyms:capsiate;dihydrocapsiate;nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl ester

Chemical Property of Capsiate

Chemical Property:

• Boiling Point: 421.3±40.0 °C(Predicted)
• PKA: 9.51±0.20(Predicted)
• PSA: 55.76000
• Density: 1.053
• LogP: 4.21660
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 306.18310931
• Heavy Atom Count: 22
• Complexity: 338

Purity/Quality:

98%Min ^*data from raw suppliers

Capsiate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C=CCCCCC(=O)OCC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CC(C)/C=C/CCCCC(=O)OCC1=CC(=C(C=C1)O)OC
• Recent NIPH Clinical Trials: Effects of capsiate intake and intake cessation on human brown adipose tissue density
• Uses: Capsiate is a capsinoid compound which are non-pungent capsaicin analogs that can promote metabolic health and exercise tolerance.

Technology Process of Capsiate

There total 9 articles about Capsiate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.6%

trans-8-methyl-6-nonenoic acid (59320-77-3) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) → capsiate (205687-01-0)

Guidance literature:

Novozym 435; at 50 ℃; for 16h; Polyacrylate

Reference yield: 79.42%

4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate (1073340-78-9) → capsiate (205687-01-0)

Guidance literature:

With hydrogenchloride; water; In ethanol; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jf9035029

Reference yield:

8-methylnonanoic acid methyl ester (5129-54-4) + methyl isononanoate (5129-53-3) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) + methyl (E)-8-methyl-6-nonenoate (112375-54-9) → Dihydrocapsiate + capsiate (205687-01-0) + Nordihydrocapsiate

Guidance literature:

novozyme 435; at 25 ℃; for 45h;

upstream raw materials:

trans-8-methyl-6-nonenoic acid

4-hydroxymethyl-2-methoxyphenol

8-methylnonanoic acid methyl ester

methyl isononanoate

Refernces

• 1、 Barbero, Gerardo F.,Molinillo, Jose M. G.,Varela, Rosa M.,Palma, Miguel,MacIas, Francisco A.,Barroso, Carmelo G.. "Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids". experimental part. p. 3342 - 3349. Retrieved 2011/07/30.
• 2、 -. "PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION". Page/Page column 40-41. . Retrieved 2008/06/13.