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Details

Stereochemistry RACEMIC
Molecular Formula C16H16O4
Molecular Weight 272.2958
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VESTITOL, (±)-

SMILES

COC1=CC(O)=C(C=C1)C2COC3=C(C2)C=CC(O)=C3

InChI

InChIKey=XRVFNNUXNVWYTI-UHFFFAOYSA-N
InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3

HIDE SMILES / InChI

Molecular Formula C16H16O4
Molecular Weight 272.2958
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Vestitol is an isoflavonoid isolated from Brazilian red propolis with potential anti-inflammatory activity. Vestitol showed inhibitory activity on neutrophil migration induced by different inflammatory stimuli. Its activity is related to inhibition or decrease of the release of the chemokines CXCL1/KC and CXCL2/MIP-2 by resident macrophages, resulting in diminished rolling and adhesion of leukocytes in the mesenteric microcirculation. Vestitol, may have potential therapeutic application to modulate inflammation processes, such as those involved with periodontal diseases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Vestitol Isolated from Brazilian Red Propolis Inhibits Neutrophils Migration in the Inflammatory Process: Elucidation of the Mechanism of Action.
2016-04-22
[Chemical Constituents from Pueraria alopecuroides Ratten].
2015-07
Patents

Patents

Sample Use Guides

Mice were pre-treated with sc administration of vestitol (1, 3, or 10 mg/kg) 30 min prior to ip injection of LPS (300 ng/cavity). The mice were killed 6 h after the challenge (LPS) and cells from the peritoneal cavity were harvested. Pre-treatment with vestitol at 1, 3, or 10 mg/kg reduced LPS- or mBSA-induced neutrophil migration and the release of CXCL1/KC and CXCL2/MIP-2 in vivo.
Route of Administration: Other
Vestitol activity was evaluated in Neutrophil Chemotaxis assay. Neutrophils isolated from the bone marrow of mice were treated with Vestitol (3 or 10 mkM) for 60 min. There was a reduction on the chemotaxis of CXCL2/MIP-2 or LTB4-induced neutrophils after pre-treatment with the Vestitol.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:07:44 GMT 2025
Edited
by admin
on Mon Mar 31 22:07:44 GMT 2025
Record UNII
Z244UVZ669
Record Status Validated (UNII)
Record Version
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Name Type Language
VESTITOL, (±)-
Common Name English
(±)-VESTITOL
Preferred Name English
VESTITOL
Common Name English
2H-1-BENZOPYRAN-7-OL, 3,4-DIHYDRO-3-(2-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3,4-DIHYDRO-3-(2-HYDROXY-4-METHOXYPHENYL)-2H-1-BENZOPYRAN-7-OL
Systematic Name English
Code System Code Type Description
CAS
56701-24-7
Created by admin on Mon Mar 31 22:07:44 GMT 2025 , Edited by admin on Mon Mar 31 22:07:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID801178444
Created by admin on Mon Mar 31 22:07:44 GMT 2025 , Edited by admin on Mon Mar 31 22:07:44 GMT 2025
PRIMARY
FDA UNII
Z244UVZ669
Created by admin on Mon Mar 31 22:07:44 GMT 2025 , Edited by admin on Mon Mar 31 22:07:44 GMT 2025
PRIMARY
PUBCHEM
92503
Created by admin on Mon Mar 31 22:07:44 GMT 2025 , Edited by admin on Mon Mar 31 22:07:44 GMT 2025
PRIMARY