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Details

Stereochemistry ABSOLUTE
Molecular Formula C7H12O6
Molecular Weight 192.1666
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Quinic Acid

SMILES

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

InChI

InChIKey=AAWZDTNXLSGCEK-WYWMIBKRSA-N
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

HIDE SMILES / InChI
Quinic acid is an acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, etc. For over 50 years, hippuric/quinic acids were believed to have no biological efficacy, but in 2009th these components were identified as major dietary components, and not simply originating from environmental pollution as previously had been thought. Quinic acid has been shown to possess radioprotection, anti-neuroinflammatory, and anti-oxidant activities. It also inhibits the TNF-α-stimulated induction of vascular cell adhesion molecule-1 (VCAM-1) by inhibiting the MAP kinase and NF-κB signaling pathways, which may explain the ability of QA to inhibit vascular inflammation such as atherosclerosis.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena.
1996 Dec 4
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.
1996 Jun 25
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.
1998 Jan
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
1999 Feb 11
Patents

Sample Use Guides

hippuric/quinic acids were identified as major dietary components, and not simply originating from environmental pollution as previously had been thought.
Route of Administration: Oral
Quinic acid (QA) inhibits the TNF-α-stimulated induction of vascular cell adhesion molecule-1 (VCAM-1) in VSMC by inhibiting the MAP kinase and NF-κB signaling pathways and the adhesion capacity of VSMC, which may explain the ability of QA to inhibit vascular inflammation such as atherosclerosis. Pre-incubation of MOVAS cells, the mouse vascular smooth muscle cell line for 2h with QA (0.1, 1 and 10 μg/mL) dose-dependently inhibits TNF-α-induced mRNA and protein expression of VCAM-1 and monocyte adhesion.
Name Type Language
Quinic Acid
INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
Quinic acid [WHO-DD]
Common Name English
QUINIC ACID [INCI]
Common Name English
QUINIC ACID [MI]
Common Name English
NSC-59258
Code English
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1α,3R,4α,5R)-
Systematic Name English
(-)-QUINIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Common Name English
D-(-)-Quinic acid
Common Name English
(1α,3R,4α,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
Systematic Name English
QUINIC ACID [USP-RS]
Common Name English
(-)-QUINIC ACID
Common Name English
1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid
Systematic Name English
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (-)-
Systematic Name English
Classification Tree Code System Code
DSLD 227 (Number of products:2)
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1594506
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-072-8
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
MERCK INDEX
m9445
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY Merck Index
CAS
77-95-2
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
CHEBI
17521
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
FDA UNII
058C04BGYI
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
CAS
562-73-2
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
SMS_ID
300000037939
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
DAILYMED
058C04BGYI
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID70998288
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
NSC
59258
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
WIKIPEDIA
QUINIC ACID
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY
RXCUI
1427232
Created by admin on Fri Dec 15 14:59:39 GMT 2023 , Edited by admin on Fri Dec 15 14:59:39 GMT 2023
PRIMARY RxNorm