Neochlorogenic acid

Base Information

• Chemical Name: Neochlorogenic acid
• CAS No.: 906-33-2
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.314
• Hs Code.: 29182900
• European Community (EC) Number: 212-997-1
• UNII: O4601UER1Z
• ChEMBL ID: CHEMBL249450
• DSSTox Substance ID: DTXSID301347903
• Metabolomics Workbench ID: 50481
• Nikkaji Number: J443.985F,J1.453.978F
• Wikidata: Q6992128
• Wikipedia: Neochlorogenic_acid
• Mol file: 906-33-2.mol

Synonyms:5'-O-caffeoylquinic acid;5-O-caffeoylquinic acid;neochlorogenic acid

Chemical Property of Neochlorogenic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.38E-18mmHg at 25°C
• Melting Point: 204-206 °C (decomp)
• Refractive Index: 1.69
• Boiling Point: 665 °C at 760 mmHg
• PKA: 3.90±0.50(Predicted)
• Flash Point: 245.5 °C
• PSA: 164.75000
• Density: 1.65 g/cm³
• LogP: -0.64590
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Heated, Sonicated), Methanol (Slightly, Heat
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 354.09508215
• Heavy Atom Count: 25
• Complexity: 534

Purity/Quality:

99%min ^*data from raw suppliers

Neochlorogenic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
• Uses: (E)-Neochlorogenic Acid is an antioxidant compound used in the treatment of oxidative stress and related afflictions.

Technology Process of Neochlorogenic acid

There total 18 articles about Neochlorogenic 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: 69.0%

4-methoxybenzyl (2'S,3'S)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-5-O-(3,4-di-O-methoxymethylcaffeoyl)quinate → neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8)

Guidance literature:

With pentamethylbenzene,; boron trichloride; In dichloromethane; at -40 - 0 ℃; for 3h; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.tet.2014.08.064

Reference yield: 23.0%

methyl (2'S,3'S)-5-O-(3'',4''-di-O-acetylcaffeoyl)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate → neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 45 ℃; for 4h;

DOI:10.1016/j.tetlet.2005.07.146

Reference yield:

neochlorogenic acid (342811-68-1) → chlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8) + 4-O-caffeoylquinic acid

Guidance literature:

In water; at 100 ℃; for 0.5h; pH=8;

DOI:10.1021/jf071942r

upstream raw materials:

neochlorogenic acid

3-caffeoylquinic acid

(E)-3,4-di-O-acetylcaffeoyl chloride

(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Downstream raw materials:

3-O-caffeoylquinic acid methyl ester

3,4-Dihydroxybenzoic acid

(E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoic acid

(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Refernces

• 1、 Regos, Ionela,Urbanella, Andrea,Treutter, Dieter. "Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)". body text. p. 5843 - 5852. Retrieved 2010/06/17.
• 2、 Toyama-Kato, Yuki,Kondo, Tadao,Yoshida, Kumi. "Synthesis of designed acylquinic acid derivatives involved in blue color development of hydrangea and their co-pigmentation effect". . p. 239 - 254. Retrieved 2008/03/12.