(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid

Base Information

• Chemical Name: (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
• CAS No.: 327-97-9
• Deprecated CAS: 108657-60-9,12626-41-4,15076-00-3,16310-14-8,16431-25-7,16431-26-8
• Molecular Formula: C16H18O9
• Molecular Weight: 354.314
• Hs Code.: 29182900
• DSSTox Substance ID: DTXSID3024786
• Wikidata: Q27167119
• Metabolomics Workbench ID: 130655
• ChEMBL ID: CHEMBL3186431
• Mol file: 327-97-9.mol

Synonyms:NSC70861;NSC407296;(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid;Spectrum_001846;SpecPlus_000957;Prestwick0_000427;Prestwick1_000427;Spectrum2_001898;Spectrum3_001797;KBioSS_002357;DivK1c_007053;SPBio_001836;SPBio_002353;CHEMBL3186431;KBio1_001997;KBio2_002354;KBio2_004922;KBio2_007490;KBio3_002855;AKOS030228500;SMP1_000066;Q27167119;(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enoxy]-1,4,5-trihydroxy-1-cyclohexanecarboxylic acid

Chemical Property of (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid

Chemical Property:

• Appearance/Colour: white to slightly yellowish-beige powder
• Vapor Pressure: 1.38E-18mmHg at 25°C
• Melting Point: 210 °C (dec.)(lit.)
• Refractive Index: -37 ° (C=1, H2O)
• Boiling Point: 665 °C at 760 mmHg
• PKA: 3.91±0.50(Predicted)
• Flash Point: 245.5 °C
• PSA: 164.75000
• Density: 1.65 g/cm³
• LogP: -0.64590
• Storage Temp.: 0-6°C
• Solubility.: Soluble in ethanol and acetone.
• Water Solubility.: SOLUBLE IN HOT WATER
• 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:

1%-98% ^*data from raw suppliers

Chlorogenic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 68
• Safety Statements: 24/25

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=CC2=CC(=C(C=C2)O)O)O)O
• Chemical Composition and Properties: Chlorogenic acid (CGA) is a depside acid produced by caffeic acid and quinic acid. CGA is a phenylacrylate polyphenol compound synthesized in plants during aerobic respiration. It exists in various isomeric forms, including mono-caffeoyl quinic acid and dicaffeoyl quinic acid.
• Sources: Found in a wide range of plants, fruits, vegetables, and beverages, with coffee being a prominent source. Content varies among sources, with high levels in green coffee beans, prunes, apple, tomato, eggplant, carrot, tea, and herbal teas like jasmine and green tea.; In green coffee beans, 5-O-caffeoylquinic acid (5-CQA) is the most abundant form, comprising 50% of total CGA.
• Biological Activities: CGA exhibits various important biological activities, making it valuable in medicine, food, and other industries.; Known activities include antioxidant, anti-inflammatory, antibacterial, antiviral, hypoglycemic, lipid-lowering, anti cardiovascular, antimutagenic, anticancer, and immune regulation properties.
• Metabolism and Absorption: In rats, CGA is absorbed in the stomach and further hydrolyzed to caffeic acid and quinic acid in the intestine. After absorption, CGA is metabolized into glucuronic acid glycosides and sulfate metabolites. CGA's oral absorption rate is low, and it mainly exists as metabolites in plasma before excretion through the kidneys.
• Biotechnological Significance: Understanding CGA biosynthesis pathways and enhancing its content in medicinal plants and fungi through biotechnology is of great significance. With its diverse biological activities, CGA is considered internationally as a valuable bioactive substance with potential applications in various fields.
• General Description: Chlorogenic acid, a hydroxycinnamoyl quinate ester, plays a role in the storage of tropane alkaloids such as cocaine in *Erythroxylum coca* by forming physical complexes with these alkaloids, as demonstrated through spectroscopic analysis. Its biosynthesis involves a BAHD acyltransferase enzyme, and its accumulation correlates with tropane alkaloid levels, suggesting its function as a stabilizing or storage partner for these compounds in the plant.

Technology Process of (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid

There total 21 articles about (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic 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:

3,4-Dihydroxybenzoic acid

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

ortoquinone

caffeic acid

Refernces

The biosynthesis of hydroxycinnamoyl quinate esters and their role in the storage of cocaine in Erythroxylum coca

10.1016/j.phytochem.2012.09.009

The research aimed to determine if Erythroxylum coca, the plant from which cocaine is derived, uses hydroxycinnamoyl quinate esters to store tropane alkaloids like cocaine and cinnamoyl cocaine. The study established a correlation between the levels of these alkaloids and two hydroxycinnamoyl esters of quinic acid, chlorogenic acid, and 4-coumaroyl quinate. The researchers isolated and characterized the BAHD acyltransferase enzyme responsible for the final step in hydroxycinnamoyl quinate biosynthesis and found its gene expression to correlate with tropane alkaloid accumulation. They also observed and quantified the physical interaction between chlorogenic acid and cocaine in vitro using UV and NMR spectroscopic methods. The study concluded that hydroxycinnamoyl quinate esters likely serve as complexation partners for the storage of cocaine and other coca alkaloids in E. coca.

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