HYDROXYTOLUIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O3
Molecular Weight	152.1473
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(O)C(=CC=C1)C(O)=O

InChI

InChIKey=WHSXTWFYRGOBGO-UHFFFAOYSA-N

InChI=1S/C8H8O3/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4,9H,1H3,(H,10,11)

HIDE SMILES / InChI

Molecular Formula	C8H8O3
Molecular Weight	152.1473
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0002390 | https://www.ncbi.nlm.nih.gov/pubmed/13618547 | https://www.ncbi.nlm.nih.gov/pubmed/4932011

Hydroxytoluic acid is a long-acting derivative of salicylate with antilipidemic properties. It shows fibrinolytic activity in human plasma by activating the fibrinolytic system and has been shown to lower plasma free fatty acid, cholesterol levels, and to raise metabolic oxygen consumption.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12183910	Primary		Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4932011	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.	2001 Jan 11	11429881
[Anti-inflammatory activity of (o-cresotinate) copper and zinc aquacomplexes].	2002 Jul	12183910
Synthesis and characterisation of tungsten(VI) oxo-salicylate complexes for use in the chemical vapour deposition of self-cleaning films.	2005 Apr 7	15782266
Construction and evaluation of nagR-nagAa::lux fusion strains in biosensing for salicylic acid derivatives.	2005 Mar	15767693
Enhanced skin permeation of salicylate by ion-pair formation in non-aqueous vehicle and further enhancement by ethanol and l-menthol.	2006 Apr	16595949
Mechanisms influencing the vasoactive effects of lidocaine in human skin.	2007 Feb	17223807
Gene expression-based screening for inhibitors of PDGFR signaling.	2008	18312689
Photophysical properties of lanthanide hybrids covalently bonded to functionalized MCM-41 by modified aromatic carboxylic acids.	2009 Mar	18649125

Patents

Sample Use Guides

In Vivo Use Guide

Diabetic geriatric patients received 900 mg Hydroxytoluic acid orally as a single dose or as a daily dose of up to 2.7g/day for 3 months. For patients receiving a single dose a 50 g glucose tolerance test was performed 2 hours after dosing, for longitudinal patients the glucose tolerance test was performed monthly or every two months. After a single 900 mg dose, plasma insulin levels showed considerable increases, plasma free fatty acid fell 2 hours after dosing with hydroxytoluic acid. Daily dosing of 1.8 g/day hydroxytoluic acid as the sole treatment allowed patients to control their diabetes but was not significantly different from controls. When added to the existing drug regimen patients receiving hydroxy toluic acid showed a smoothing of control of blood sugar with decreased needs of insulin or sulphonylurea.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:19:52 GMT 2023` Edited by `admin` on `Fri Dec 15 16:19:52 GMT 2023`
Record UNII	ZH3HEY032H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

HYDROXYTOLUIC ACID

Official Name

English

Hydroxytoluic acid [WHO-DD]

Common Name

English

2-HYDROXY-3-METHYLBENZOIC ACID

Systematic Name

English

O-CRESOTIC ACID [MI]

Common Name

English

CRESOTIC ACID, O-

Common Name

English

hydroxytoluic acid [INN]

Common Name

English

3-MS

Code

English

3 MS

Code

English

NSC-17561

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29703