U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H22O7
Molecular Weight 326.3417
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUGENYL GLUCOSIDE

SMILES

COC1=CC(CC=C)=CC=C1O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

InChI

InChIKey=VADSVXSGIFBZLI-IBEHDNSVSA-N
InChI=1S/C16H22O7/c1-3-4-9-5-6-10(11(7-9)21-2)22-16-15(20)14(19)13(18)12(8-17)23-16/h3,5-7,12-20H,1,4,8H2,2H3/t12-,13-,14+,15-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H22O7
Molecular Weight 326.3417
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27771920 | https://www.drugs.com/international/eugenol.html | https://www.ncbi.nlm.nih.gov/pubmed/1368038

Eugenyl glucoside is a product of eugenol glucosylation. Eugenol is the principal chemical component of clove oil, accounting for more than 90%, has been well known for its antioxidant, anti-proliferative, analgesic, local anesthetic, anti-inflammatory, antibacterial, and hair growing effects. Eugenol belongs to the class of essential oil that is generally recognized as safe (GRAS) by Food and Drug Administration. Eugenol is liable to sublimate and has a peculiar smell, its modification is needed for application as a component of hair restorers. Therefore, eugenyl glucoside is being produced by organic synthesis and commercially used as an additive in hair restorers since eugenyl glucoside is gradually degraded into eugenol by the indigeneous microorganisms of human skin and acts as a pro-drug of a hair restorer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.5 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
An effective way to biosynthesize α-glucosyl eugenol with a high yield by Xanthomonas maltophilia.
2012-06
Two new phenolic constituents of Humulus japonicus and their cytotoxicity test in vitro.
2007-11
Homonuclear long-range correlation spectra from HMBC experiments by covariance processing.
2007-07
Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme.
2006-09
Acetylated flavonoid glycosides potentiating NGF action from Scoparia dulcis.
2004-04
Selective alpha-glucosylation of eugenol by alpha-glucosyl transfer enzyme of Xanthomonas campestris WU-9701.
2003
Triterpenoids and other compounds from Salvia roborowskii Maxim.
2001-05
A new phenylpropanoid glucoside and other constituents of Oenanthe javanica.
1995-03
Biotransformation of isoeugenol and eugenol by cultured cells of Eucalyptus perriniana.
1992-03
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:49:37 GMT 2025
Edited
by admin
on Mon Mar 31 20:49:37 GMT 2025
Record UNII
TF6DX3Y0J8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EUGENYL GLUCOSIDE TH
Preferred Name English
EUGENYL GLUCOSIDE
INCI  
INCI  
Official Name English
GLUCOPYRANOSIDE, 4-ALLYL-2-METHOXYPHENYL, .BETA.-D-
Common Name English
EUGENYL O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 2-METHOXY-4-(2-PROPENYL)PHENYL
Common Name English
EUGENYL .BETA.-D-GLUCOPYRANOSIDEPHENYL
Common Name English
Code System Code Type Description
PUBCHEM
3084296
Created by admin on Mon Mar 31 20:49:37 GMT 2025 , Edited by admin on Mon Mar 31 20:49:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID201318555
Created by admin on Mon Mar 31 20:49:37 GMT 2025 , Edited by admin on Mon Mar 31 20:49:37 GMT 2025
PRIMARY
CAS
18604-50-7
Created by admin on Mon Mar 31 20:49:37 GMT 2025 , Edited by admin on Mon Mar 31 20:49:37 GMT 2025
PRIMARY
FDA UNII
TF6DX3Y0J8
Created by admin on Mon Mar 31 20:49:37 GMT 2025 , Edited by admin on Mon Mar 31 20:49:37 GMT 2025
PRIMARY