ChemFOnt: Showing chemical card for 1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid (CFc000157473)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:44:09 UTC

Chemfont ID

CFc000157473

Molecule Identification

Common Name

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

Definition

Quinic acid, also known as quinate or chinate, 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. It is also a cyclitol, a cyclic polyol. Quinic acid is a sugar acid. Quinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 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 is implicated in the perceived acidity of coffee. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Quinate	Generator
(1R,3R,4S)-1,3,4,5-Tetrahydroxycyclohexane-1-carboxylate	HMDB
(-)-Quinate	HMDB
(-)-Quinic acid	HMDB
Chinate	HMDB
Chinic acid	HMDB
D-Quinic acid	HMDB
Kinate	HMDB
Kinic acid	HMDB
L-Quinate	HMDB
L-Quinic acid	HMDB

Chemical Formula

C₇H₁₂O₆

Average Molecular Weight

192.1666

Monoisotopic Molecular Weight

192.063388116

IUPAC Name

(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

Traditional Name

(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

CAS Registry Number

77-95-2

SMILES

OC1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O

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

InChI Key

AAWZDTNXLSGCEK-RKGSPJAZSA-N

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

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	765 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.7	ChemAxon
logS	0.6	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.71 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon