| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:51 UTC |
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| Update date | 2019-11-26 02:56:03 UTC |
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| Primary ID | FDB001170 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (-)-Quinic acid |
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| Description | Occurs in coffee beans and many other plant sources. Food acidulant with good taste characteristics, use limited by cost
Quinic acid is an organic acid which is found in cinchona bark and elsewhere in plants. 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 and Shikimic acid are key intermediates in the biosynthesis of aromatic compounds in living systems. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.; Quinic acid, C7H12O6 is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.; This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A new medicament for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market recently. |
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| CAS Number | 77-95-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C7H12O6 |
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| IUPAC name | 1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid |
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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) |
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| InChI Key | AAWZDTNXLSGCEK-UHFFFAOYSA-N |
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| Isomeric SMILES | OC1CC(O)(CC(O)C1O)C(O)=O |
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| Average Molecular Weight | 192.1666 |
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| Monoisotopic Molecular Weight | 192.063388116 |
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| Classification |
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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 | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 43.75%; H 6.29%; O 49.95% | DFC |
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| Melting Point | Mp 162-163° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 290 mg/mL at 9 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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| Experimental logP | 1.19 | RADZICKA,A & WOLFENDEN,R (1988) |
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| Experimental pKa | pKa 3.58 (25°) | DFC |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]26D -42.1 (H2O) | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | (-)-Quinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-9600000000-5fad8732698ac44de438 | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002g-0900000000-59471dc3f2bf86989e30 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004j-0900000000-d0b09550df3fa08a1420 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-5900000000-ab505f7c0b75a85ee3cd | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-0900000000-fe8d862acce93dd7eb84 | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-3900000000-f7e8be1495cce9a344ae | 2017-06-28 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05bb-9700000000-e16830e0be835671623b | 2017-06-28 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 16498843 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C06746 |
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| Pubchem Compound ID | 6508 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 17521 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03072 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HBH46-E:BVJ24-C |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | (-)-QUINIC-ACID|QUINIC-ACID|QUINIC-ACIC |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00001201 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Quinic acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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