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
Structure for Cinnamyl alcohol (DB14186)
- 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.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
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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.
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interactions in your softwareTenofovir alafenamide The serum concentration of Tenofovir alafenamide can be increased when it is combined with Cinnamyl alcohol. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image T.R.U.E. Test Thin-Layer Rapid Use Patch Test Cinnamyl 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) Kit Cutaneous SmartPractice Denmark ApS 2012-03-01 Not applicable US 
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
- 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]
- External Links
- Human Metabolome Database
- HMDB0029698
- KEGG Compound
- C02394
- ChemSpider
- 21105870
- BindingDB
- 50310446
- 1362889
- ChEBI
- 33227
- ChEMBL
- CHEMBL324794
- ZINC
- ZINC000001529427
- Wikipedia
- Cinnamyl_alcohol
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Cutaneous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.34 mg/mL ALOGPS logP 1.93 ALOGPS logP 1.82 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 15.62 Chemaxon pKa (Strongest Basic) -2.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 43.19 m3·mol-1 Chemaxon Polarizability 15.41 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Drug created at July 03, 2018 17:55 / Updated at June 12, 2020 16:53