GRADE & PURITY Moligand™, ≥99%

Synonyms

Cinnamic acid, 3,4-dihydroxy-, 4-carboxy-2,4,6-trihydroxycyclohexyl ester | Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)- | 4-Caffeoylquinic acid | Quinic acid, 4-caffeoyl-, E- | AK

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Synonyms

Cinnamic acid, 3, 4-dihydroxy-, 4-carboxy-2, 4, 6-trihydroxycyclohexyl ester | Cyclohexanecarboxylic acid, 4-((3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1, 3, 5-trihydroxy-, (1alpha, 3R, 4alpha, 5R)- | 4-Caffeoylquinic acid | Quinic acid, 4-caffeoyl-, E- | AK

Specifications & Purity

Moligand™, ≥99%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥99%

Names and Identifiers

• Canonical Smiles: C1C(C(C(CC1(C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O
• IUPAC Name: (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid
• InChIKey: GYFFKZTYYAFCTR-AVXJPILUSA-N
• INCHI: 1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14?,16?/m1/s1
• Isomeric SMILES: C1[C@H](C([C@@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
• WGK Germany: 3
• Molecular Weight: 354.31
• Reaxy-Rn: 2177015
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2177015&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Cyclic alcohols and derivatives
          • Level6 Cyclitols and derivatives
            • Level7 Quinic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Cyclic alcohols and derivatives - Cyclitols and derivatives
• Direct Parent: Quinic acids and derivatives
• Alternative Parents: Coumaric acids and derivatives Cinnamic acid esters Styrenes Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Fatty acid esters Cyclohexanols Alpha hydroxy acids and derivatives Dicarboxylic acids and derivatives Tertiary alcohols Enoate esters Polyols Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Quinic acid - Cinnamic acid or derivatives - Coumaric acid or derivatives - Hydroxycinnamic acid or derivatives - Cinnamic acid ester - Catechol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Cyclohexanol - Fatty acid ester - Phenol - Fatty acyl - Hydroxy acid - Benzenoid - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Alpha-hydroxy acid - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Tertiary alcohol - Secondary alcohol - Carboxylic acid ester - Carboxylic acid - Carboxylic acid derivative - Polyol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: light sensitive
• Specific Rotation[α]: [α]/D -76.0±5.0°, c = 0.5 in H2O
• Melt Point(°C): 182-184°C
• Molecular Weight: 354.310 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 354.095 Da
• Monoisotopic Mass: 354.095 Da
• Topological Polar Surface Area: 165.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 520.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Dongsheng Hu, Xiaogang Liu, Yuyue Qin, Jiatong Yan, Rongmei Li, Qiliang Yang.  (2023)  The impact of different drying methods on the physical properties, bioactive components, antioxidant capacity, volatile components and industrial application of coffee peel.  Food Chemistry-X,      [PMID:37780243] [10.1016/j.fochx.2023.100807]

2. Yan Yu, Yan-Ping Liu, Jin-Fen Zheng, Xi-Jin Yang, Qi-Ju Shao, Dan Wang, Luo-Wei Wang, Fu-Zhen Li, Lan Yu, Rong-Xiang Chen.  (2025)  Comprehensive profiling of antioxidants in Zanthoxylum bungeanum leaves using two-dimensional liquid chromatography and regional comparisons.  INTERNATIONAL JOURNAL OF FOOD PROPERTIES,      [PMID:] [10.1080/10942912.2025.2479629]

3. Xue Bai, Yinuo Liu, Yuchen Cao, Zhouye Ma, Yue Chen, Shuai Guo.  (2024)  Exploring the potential of cryptochlorogenic acid as a dietary adjuvant for multi-target combined lung cancer treatment.  PHYTOMEDICINE,      [PMID:39053244] [10.1016/j.phymed.2024.155907]

4. Xu Han, Xiaqing Wu, Fanglin Liu, Huan Chen, Hongwei Hou.  (2024)  Inhibition of LPS-induced inflammatory response in RAW264.7 cells by natural Chlorogenic acid isomers involved with AKR1B1 inhibition.  BIOORGANIC & MEDICINAL CHEMISTRY,      [PMID:39396466] [10.1016/j.bmc.2024.117942]

5. Ming-Mai Bao, Ying-Chao Liu, Hao-Nan Xu, Jing Zhang, Yin-Long Guo.  (2025)  Energy-resolved in-source dissociation spectra by tunable pulsed arc plasma ionization for the differentiation of structural isomers.  CHINESE CHEMICAL LETTERS,      [PMID:] [10.1016/j.cclet.2025.112060]