FComEx: (-)-Quinic acid (PC000856)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:06 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000856

FoodDB Record

FDB001170

Chemical Information

Name

(-)-Quinic acid

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.

CAS Number

77-95-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-Quinate	biospider
(-)-Quinic acid	biospider
(1R,3R,4R,5R)-(-)-Tetrahydroxycyclohexanecarboxylic acid	biospider
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid	manual
Chinate	HMDB
Chinic acid	HMDB
D-(-)-Quinic acid	biospider
D-Quinic acid	biospider
Kinate	HMDB
Kinic acid	HMDB
L-Quinate	HMDB
L-Quinic acid	HMDB
N-(2-Phenylethyl)-acetamide	biospider
N-Acetylphenylethylamine	HMDB
N-Qcetylphenylethylamine	biospider
Quinate	HMDB
Quinic acid	manual

Chemical Formula

C7H12O6

IUPAC name

1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

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)

InChI Key

AAWZDTNXLSGCEK-UHFFFAOYSA-N

Isomeric SMILES

OC1CC(O)(CC(O)C1O)C(O)=O

Average Molecular Weight

192.1666

Monoisotopic Molecular Weight

192.063388116

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	1.19	RADZICKA,A & WOLFENDEN,R (1988)
Experimental Water Solubility	290 mg/mL at 9 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 162-163°	DFC

Foods of Origin