Cinnamyl alcohol

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

Identification

Generic Name
Cinnamyl alcohol
DrugBank Accession Number
DB14186
Background

Cinnamyl alcohol is a naturally occurring compound that is found within cinnamon. Due to the low levels found in cinnamon, cinnamyl alcohol is usually supplied as Cinnamaldehyde within commercial products.

Cinnamyl alcohol has been shown to be a skin sensitizer, with a NOEL (No Effect Level) of ~4% 1. Sensitivity to cinnamyl alcohol may be identified with a clinical patch test.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 134.1751
Monoisotopic: 134.073164942
Chemical Formula
C9H10O
Synonyms
  • (2E)-3-phenylprop-2-en-1-ol
  • (E)-cinnamyl alcohol
  • Cinnamyl alcohol
  • Styrylcarbinol

Pharmacology

Indication

Cinnamyl alcohol 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.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Cinnamyl alcohol is 66% absorbed through the skin and shown to be rapidly absorbed from the gut 1.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

In general, esters containing an aromatic ring system are expected to be hydrolyzed in vivo. Cinnamyl alcohol is hydrolyzed to Cinnamaldehyde 1.

Hover over products below to view reaction partners

Route of elimination

Cinnamyl alcohol is metabolized and excreted primarily in the urine and, to a minor extent, in the feces 1. After oral or intraperitoneal administration to rats and mice, 76–77% of the dose of cinnamyl alcohol was recovered in the urine and feces within 24 h 1.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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

Products
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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
T.R.U.E. Test Thin-Layer Rapid Use Patch TestCinnamyl alcohol (63 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) + 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) + Isoeugenol (17 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)PatchCutaneousSmartPractice Denmark ApS2012-03-01Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
SS8YOP444F
CAS number
4407-36-7
InChI Key
OOCCDEMITAIZTP-QPJJXVBHSA-N
InChI
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
IUPAC Name
(2E)-3-phenylprop-2-en-1-ol
SMILES
OC\C=C\C1=CC=CC=C1

References

General References
  1. Belsito D, Bickers D, Bruze M, Calow P, Greim H, Hanifin JM, Rogers AE, Saurat JH, Sipes IG, Tagami H: A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients. Food Chem Toxicol. 2007;45 Suppl 1:S1-23. doi: 10.1016/j.fct.2007.09.087. Epub 2007 Sep 18. [Article]
Human Metabolome Database
HMDB0029698
KEGG Compound
C02394
ChemSpider
21105870
BindingDB
50310446
RxNav
1362889
ChEBI
33227
ChEMBL
CHEMBL324794
ZINC
ZINC000001529427
Wikipedia
Cinnamyl_alcohol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.34 mg/mLALOGPS
logP1.93ALOGPS
logP1.82ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.19 m3·mol-1ChemAxon
Polarizability15.41 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-05qc-9700000000-718fd9691cbd38d42c60
GC-MS Spectrum - EI-BGC-MSsplash10-001l-6900000000-44b04269b7d35e886fb9
GC-MS Spectrum - EI-BGC-MSsplash10-002f-9400000000-da49ee491f3478b8fa96
GC-MS Spectrum - EI-BGC-MSsplash10-0036-9400000000-540e90374e70aac0f48b
GC-MS Spectrum - EI-BGC-MSsplash10-014i-0931100000-d1566613e817621550ba
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1910000000-f620d5e707e1170fdbb6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on July 03, 2018 17:55 / Updated on June 12, 2020 16:53