Agaric acid

Base Information

• Chemical Name: Agaric acid
• CAS No.: 666-99-9
• Molecular Formula: C22H40 O7
• Molecular Weight: 416.555
• European Community (EC) Number: 211-566-5
• NSC Number: 65690,60429
• UNII: 2XE342S7L6
• DSSTox Substance ID: DTXSID2046705
• Nikkaji Number: J85J
• Wikipedia: Agaric_acid
• Wikidata: Q27255762
• NCI Thesaurus Code: C83523
• Metabolomics Workbench ID: 105052
• ChEMBL ID: CHEMBL78764
• Mol file: 666-99-9.mol

Synonyms:(+-)-agaricic acid;2-hydroxy-1,2,3-nonadecanetricarboxylic acid;agaric acid;agaricic acid;agaricin;alpha-cetyl citric acid;N-hexadecylcitric acid

Chemical Property of Agaric acid

Chemical Property:

• Vapor Pressure: 1.67E-12mmHg at 25°C
• Melting Point: 142° (dec)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 509.3°C at 760 mmHg
• PKA: 2.93±0.36(Predicted)
• Flash Point: 275.9°C
• PSA: 132.13000
• Density: 1.115g/cm³
• LogP: 4.84900
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 20
• Exact Mass: 416.27740361
• Heavy Atom Count: 29
• Complexity: 478

Purity/Quality:

98%,99%, ^*data from raw suppliers

AgaricinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCC(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Uses: antiperspirant Agaric Acid has been used as antiperspirant. Agaric acid (Agaricic acid), an inducer of mitochondrial permeability transition (MPT), is used to study the MPT process at the level of the ADP and ATP exchange via the adenine nucleotide carrier/translocase.

Technology Process of Agaric acid

There total 4 articles about Agaric acid 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:

2-hydroxy-nonadecane-1,2,3-tricarboxylic acid triethyl ester (42065-60-1,52438-47-8) → (2S,3S)-2-hydroxy-nonadecane-1,2,3-tricarboxylic acid (666-99-9) + acetic acid (64-19-7,77671-22-8) + stearic acid (57-11-4)

Guidance literature:

Reference yield:

2-hydroxy-nonadecane-1,2,3-tricarboxylic acid trimethyl ester (116632-15-6) → (2S,3S)-2-hydroxy-nonadecane-1,2,3-tricarboxylic acid (666-99-9) + acetic acid (64-19-7,77671-22-8) + stearic acid (57-11-4)

Guidance literature:

Reference yield:

→ Agaric acid (666-99-9,116819-92-2)

Guidance literature:

Versuche zur Darst., 2.Mitt.;

DOI:10.1002/ardp.19673000410

upstream raw materials:

2-hydroxy-nonadecane-1,2,3-tricarboxylic acid trimethyl ester

2-hydroxy-nonadecane-1,2,3-tricarboxylic acid triethyl ester

Downstream raw materials:

nonadecan-2-one

3-hexadecyl-4-methylmaleic anhydride

acetic acid

stearic acid

Refernces

• 1、 Graf,Liu. "Experiments on the synthesis of agaricic acid. 2. On the accumulation of alpha-bromstearic acid ethyl ester on oxalacetic acid diethylester". . p. 348 - 353. Retrieved 2007/10/05.