Record Information |
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Version | 1.0 |
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Created at | 2006-05-22 15:12:30 UTC |
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Updated at | 2024-04-19 09:28:02 UTC |
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NP-MRD ID | NP0001192 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Quinic acid |
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Description | Quinic acid, also known as quinate, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives 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. Quinic acid is a sugar acid. It is also a cyclitol, or cyclic polyol. More specifically, quinic acid is a crystalline acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, peaches, pears, plums, vegetables, etc. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee. |
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Structure | O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 |
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Synonyms | Value | Source |
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Chinic acid | ChEBI | D-Quinic acid | ChEBI | Kinic acid | ChEBI | (-)-Quinic acid | Kegg | Chinate | Generator | D-Quinate | Generator | Kinate | Generator | (-)-Quinate | Generator | Quinate | Generator | (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid | HMDB | (1Α,3R,4α,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid | HMDB | 1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid | HMDB | 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid | HMDB | D-(-)-Quinic acid | HMDB | Hexahydro-1,3,4,5-tetrahydroxybenzoic acid | HMDB | Quinic acid | ChEBI |
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Chemical Formula | C7H12O6 |
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Average Mass | 192.1666 Da |
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Monoisotopic Mass | 192.06339 Da |
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IUPAC Name | (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid |
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Traditional Name | (-)-quinic acid |
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CAS Registry Number | 77-95-2 |
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SMILES | OC1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O |
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InChI Identifier | InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4?,5-,7+/m1/s1 |
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InChI Key | AAWZDTNXLSGCEK-RKGSPJAZSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives 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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Quinic acids and derivatives |
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Alternative Parents | |
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Substituents | - Quinic acid
- Cyclohexanol
- Hydroxy acid
- Alpha-hydroxy acid
- Tertiary alcohol
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 162.5 °C | Not Available | Boiling Point | 438.42 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | Water Solubility | 290 mg/mL at 9 °C | Not Available | LogP | 1.19 | Radzicka, A, Wolfenden, R. (1988) Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solution. Biochemistry 27, 5, 1664-1670. |
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Predicted Properties | |
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General References | - Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
- Akesson C, Lindgren H, Pero RW, Leanderson T, Ivars F: Quinic acid is a biologically active component of the Uncaria tomentosa extract C-Med 100. Int Immunopharmacol. 2005 Jan;5(1):219-29. [PubMed:15589483 ]
- Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
- Hyskova V, Belonoznikova K, Doricova V, Kavan D, Gillarova S, Henke S, Synkova H, Ryslava H, Cerovska N: Effects of heat treatment on metabolism of tobacco plants infected with Potato virus Y. Plant Biol (Stuttg). 2021 May;23 Suppl 1:131-141. doi: 10.1111/plb.13234. Epub 2021 Feb 4. [PubMed:33417742 ]
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