Loganic acid

Base Information

• Chemical Name: Loganic acid
• CAS No.: 22255-40-9
• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.361
• European Community (EC) Number: 244-875-9
• UNII: UX3J3KK2UG
• DSSTox Substance ID: DTXSID80944913
• Nikkaji Number: J15.893C
• Wikipedia: Loganic_acid
• Wikidata: Q19597767
• Metabolomics Workbench ID: 52009
• ChEMBL ID: CHEMBL1081585
• Mol file: 22255-40-9.mol

Synonyms:8-epiloganic acid;loganic acid

Chemical Property of Loganic acid

Chemical Property:

• Vapor Pressure: 1.97E-19mmHg at 25°C
• Refractive Index: 1.633
• Boiling Point: 646.257 °C at 760 mmHg
• PKA: 4.55±0.70(Predicted)
• Flash Point: 235.557 °C
• PSA: 166.14000
• Density: 1.6 g/cm³
• LogP: -2.23920
• Storage Temp.: ?20°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 376.13694696
• Heavy Atom Count: 26
• Complexity: 565

Purity/Quality:

99.5% ^*data from raw suppliers

Loganic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• Description: Loganic acid is an iridoid glycoside that has been found in C. mas and has diverse biological activities, including antidiabetic, antiadipogenic, anti-atherosclerotic, and anti-inflammatory properties. Loganic acid (1 μM) stimulates glucagon-like peptide-1 (GLP-1) secretion by NCI H716 human enteroendocrine colorectal cancer cells. It inhibits dexamethasone-, 3-isobutyl-1-methylxanthine-, and insulin-induced differentiation of mouse 3T3-L1 fibroblasts into adipocytes when used at a concentration of 10 μg/ml. Loganic acid (20 mg/kg per day) decreases the plasma atherogenic index, a ratio of triglyceride to HDL cholesterol, and the cardiac risk ratio, a ratio of total cholesterol to HDL cholesterol, in a rabbit model of atherosclerosis induced by a cholesterol-rich diet. It also decreases IL-6, TNF-α, and oxidized LDL (oxLDL) plasma levels in the same model.

Technology Process of Loganic acid

There total 11 articles about Loganic 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:

(1S,4aS,6S,7R,7aS)-7-Methyl-6-[(E)-(3-phenyl-acryloyl)oxy]-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid (79636-20-7) → (E)-3-phenylacrylic acid (140-10-3) + loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With sodium hydroxide; Ambient temperature;

Reference yield:

methanol (67-56-1) + 2'-(2'',3''-dihydroxybenzoyl)loganic acid → methyl-2,3-dihydroxybenzoate (2411-83-8) + loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With sodium hydroxide; at 30 ℃; for 3h;

DOI:10.1007/s10600-016-1728-y

Reference yield:

bis-desoxy-dihydro-monotropein (22487-36-1) → loganic acid (82509-41-9,22255-40-9)

Guidance literature:

With NADPH; 7-deoxyloganin 7-hydroxylase; In water; at 30 ℃; for 0.166667h; pH=7.5;

DOI:10.1016/S0031-9422(01)00181-9

upstream raw materials:

Ligustrinoside

loganin

(1S,4aS,6S,7R,7aS)-7-Methyl-6-[(E)-(3-phenyl-acryloyl)oxy]-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid

bis-desoxy-dihydro-monotropein

Downstream raw materials:

loganin

alyxialactone

4-epi-Alyxialactone

2',3',4',6',7-penta-O-acetylloganin

Refernces

• 1、 Wu, Min,Wu, Ping,Liu, Meifang,Xie, Haihui,Jiang, Yueming,Wei, Xiaoyi. "Iridoids from Gentiana loureirii". . p. 746 - 750. Retrieved 2009.
• 2、 Misra, Anju P.,Mathad, Vijayavitthal T.,Raj, Kanwal,Bhaduri, Amiya P.,Tiwari, Rashmi,Srivastava, Anuradha,Mehrotra. "Modified iridoid glycosides as anti-implantation agents: Inhibition of cell adhesion as an approach for developing pregnancy interceptive agents". . p. 2763 - 2772. Retrieved 2007/10/03.