ChemicalBook > CAS DataBase List > Isochlorogenic acid C

Isochlorogenic acid C

Product Name: Isochlorogenic acid C
CAS No.: 57378-72-0
Chemical Name: Isochlorogenic acid C
Synonyms: 4,5-Dicaffeoylquinic acid;3,4-O-Dicaffeoylquinic acid;Isochlorogenic acid C;Isochlorogenic acid C(4,5');3,4-Dicaffeoylquinic acid-RM;4,5-Dicaffeoylquinic acid, >99%;Isochlorogenic acid C USP/EP/BP;Isochlorogenic acid C in Methanol;4,5-Dicaffeoylquinic acid, 10 mM in DMSO;3,4-Dicaffeoylquinic acid|||Isochlorogenic acid C
CBNumber: CB42201548
Molecular Formula: C25H24O12
Formula Weight: 516.45
MOL File: 57378-72-0.mol

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Isochlorogenic acid C Property

Boiling point:: 810.8±65.0 °C(Predicted)
Density: 1?+-.0.1 g/cm3(Predicted)
storage temp.: Inert atmosphere,Store in freezer, under -20°C
solubility: DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml; DMSO: 5 mg/ml
form: A solid
pka: 3.70±0.50(Predicted)
color: White to off-white
InChIKey: UFCLZKMFXSILNL-GCBRTHAASA-N
SMILES: [C@@]1(O)(C(O)=O)C[C@@H](O)[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)C1

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SMB00221
Product name: 4,5-Di-O-caffeoylquinic acid
Purity: ≥85% (LC/MS-ELSD)
Packaging: 1mg
Price: $487
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHL80425
Product name: 3,4-Dicaffeoylquinic acid
Purity: phyproof? Reference Substance
Packaging: 10mg
Price: $481
Updated: 2025/07/31

Cayman Chemical

Product number: 27892
Product name: 4,5-Dicaffeoylquinic Acid
Packaging: 25mg
Price: $667
Updated: 2024/03/01

Cayman Chemical

Product number: 27892
Product name: 4,5-Dicaffeoylquinic Acid
Packaging: 50mg
Price: $1175
Updated: 2024/03/01

Cayman Chemical

Product number: 27892
Product name: 4,5-Dicaffeoylquinic Acid
Packaging: 5mg
Price: $158
Updated: 2024/03/01

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Isochlorogenic acid C Chemical Properties,Usage,Production

Description

4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties. It inhibits HIV-1 integrase 3'' end processing, 3’ end joining, and disintegration with IC₅₀ values of 0.13, 0.24, and 0.3 μg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC₅₀ value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC₅₀ = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF; ) and cytochalasin B (; IC₅₀ = 1.49 μM). It decreases prostaglandin E₂ (PGE₂; ) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 μg/ml but increases it when used at 200 μg/ml and increases production of TNF-α at concentrations ranging from 5 to 200 μg/ml. It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 μM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.

Uses

4,5-Dicaffeoylquinic Acid is a selective inhibitor of human immunodeficiency virus type 1 integrase.

Definition

ChEBI: 4,5-di-O-caffeoylquinic acid is a quinic acid.

in vivo

4,5-Dicaffeoylquinic acid enhances the expression of GLUT2, GK, and PDX-1 protein, and effectively alleviate glycaemia and insulin resistance and enhance insulin sensitivity in type 2 diabetic mice^[1].

References

[1] A. K. BOGAEVSKII M. I B L I Dranik. The hydroxycinnamic acids of Galium fagetorum and G. pseudomollugo[J]. Chemistry of Natural Compounds, 1970, 6 6: 761-762. DOI: 10.1007/bf00565353
[2] YU-LI CHEN. Ilex kaushue and Its Bioactive Component 3,5-Dicaffeoylquinic Acid Protected Mice from Lipopolysaccharide-Induced Acute Lung Injury[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep34243
[3] M. D. SANTOS. Effects of Caffeoylquinic Acid Derivatives and C-Flavonoid from Lychnophora ericoides on in vitro Inflammatory Mediator Production[J]. Natural Product Communications, 2010, 35 1. DOI: 10.1177/1934578x1000500512
[4] JI HOON HA Soo N P. Mechanism underlying inhibitory effect of six dicaffeoylquinic acid isomers on melanogenesis and the computational molecular modeling studies[J]. Bioorganic & Medicinal Chemistry, 2018, 26 14: Pages 4201-4208. DOI: 10.1016/j.bmc.2018.07.014

Isochlorogenic acid C Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Isochlorogenic acid C manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Isochlorogenic acid C 57378-72-0
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-11-27

57378-72-0, Isochlorogenic acid CRelated Search:

Isochlorogenic acid C BAVACHININ A epiberberine Isochlorogenic Acid B glaucocalyxin A Taxifolin Isochlorogenic acid A Isoastilbin Fluorescein isothiocyanate Isocitric acid trisodium salt (E,E)-3,5-Di-O-caffeoylquinic acid CAFTARIC ACID Cryptochlorogenic acid Chlorogenic acid CYNARIN 1,3,5-Tricaffeoylquinic acid 1-Caffeoylquinic acid 2,3,4,5-Tetracaffeoyl-D-Glucaric acid

Isochlorogenic acid C

(1R)-1,3β-Dihydroxy-4α,5α-bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-1β-cyclohexanecarboxylic acid

(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid

1β,5α-Dihydroxy-3β,4β-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid

3,4-O-Dicaffeoylquinic acid

Isochlorogenic acid C(4,5')

4,5-Dicaffeoylquinic acid

4,5-Dicaffeoylquinic acid, >99%

Cyclohexanecarboxylic acid, 3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-, (1R,3R,4S,5R)-

(1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylic acid

(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylicaci

Isochlorogenic acid C USP/EP/BP

3,4-Dicaffeoylquinic acid|||Isochlorogenic acid C

3,4-Dicaffeoylquinic acid-RM

Isochlorogenic acid C in Methanol

4,5-Dicaffeoylquinic acid, 10 mM in DMSO

57378-72-0