NAV

Isoeugenol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Isoeugenol
DrugBank Accession Number
DB14188
Background

Isoeugenol is a commonly used fragrance added to many commercially available products, and occurs naturally in the essential oils of plants such as ylang-ylang. It is also a significant dermatologic sensitizer and allergen, and as a result has been restricted to 200 p.p.m. since 1998 according to guidelines issued by the fragrance industry 1. Allergic reactivity to Isoeugenol may be identified with a patch test.

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 164.204
Monoisotopic: 164.083729626
Chemical Formula
C10H12O2
Synonyms
  • 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
  • 2-methoxy-4-(prop-1-en-1-yl)phenol
  • 2-Methoxy-4-propenylphenol
  • 3-Methoxy-4-hydroxypropenylbenzene
  • 4-Propenylguaiacol
  • Propenylguaiacol
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Pharmacology

Indication

Isoeugenol is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
T.R.U.E. Test Thin-Layer Rapid Use Patch TestIsoeugenol (17 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h)KitCutaneousSmartPractice Denmark ApS2012-03-01Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
5M0MWY797U
CAS number
97-54-1
InChI Key
BJIOGJUNALELMI-UHFFFAOYSA-N
InChI
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3
IUPAC Name
2-methoxy-4-(prop-1-en-1-yl)phenol
SMILES
COC1=CC(C=CC)=CC=C1O

References

Synthesis Reference

Immoos JE Jr: A novel synthesis of isoeugenol, [ring-(U)-(14)C]. J Labelled Comp Radiopharm. 2015 Sep-Oct;58(11-12):419-24. doi: 10.1002/jlcr.3329. Epub 2015 Aug 26. [PubMed:26306463]

General References
  1. Rastogi SC, Johansen JD: Significant exposures to isoeugenol derivatives in perfumes. Contact Dermatitis. 2008 May;58(5):278-81. doi: 10.1111/j.1600-0536.2007.01283.x. [Article]
  2. Immoos JE Jr: A novel synthesis of isoeugenol, [ring-(U)-(14)C]. J Labelled Comp Radiopharm. 2015 Sep-Oct;58(11-12):419-24. doi: 10.1002/jlcr.3329. Epub 2015 Aug 26. [Article]
KEGG Compound
C10469
ChemSpider
7061
RxNav
1363706
ChEBI
18224
ChEMBL
CHEMBL2135887
Wikipedia
Isoeugenol

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitCutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
logP2.79ALOGPS
logP2.64Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area29.46 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity49.86 m3·mol-1Chemaxon
Polarizability18.25 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-275bc28afe0374ec7ecc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-74f8b2c7a6696a7ebc4b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-5900000000-654656a5e96622269cab
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-023a-0900000000-c97ea4be6ebce71e17d2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-9700000000-a400dce84856478d45e1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-0bd829222e06834b2728
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-144.1249102
predicted
DarkChem Lite v0.1.0
[M-H]-144.8766102
predicted
DarkChem Lite v0.1.0
[M-H]-144.4188102
predicted
DarkChem Lite v0.1.0
[M-H]-134.22235
predicted
DeepCCS 1.0 (2019)
[M+H]+145.0087102
predicted
DarkChem Lite v0.1.0
[M+H]+146.0114102
predicted
DarkChem Lite v0.1.0
[M+H]+144.9109102
predicted
DarkChem Lite v0.1.0
[M+H]+136.82883
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.6707102
predicted
DarkChem Lite v0.1.0
[M+Na]+144.8258102
predicted
DarkChem Lite v0.1.0
[M+Na]+145.89911
predicted
DeepCCS 1.0 (2019)

Drug created at July 03, 2018 20:12 / Updated at June 12, 2020 16:53