Hydroxycitronellal

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

Identification

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Name
Hydroxycitronellal
Accession Number
DB14187
Type
Small Molecule
Groups
Approved, Experimental
Description

Hydroxycitronellal is a synthetic fragrance that is widely used in many cosmetics and hygiene products such as deodorants, soaps, antiseptics, and other household items. It has the smell of lilac, lily, and lily of the valley 1. Hydroxycitronellal has also been shown to be a dermatologic irritant and allergen, and as a result commercially available products are restricted by the International Fragrance Association (IFRA) to contain only 0.1-3.6%.

Sensitivity to hydroxycitronellal may be identified with a clinical patch test.

Structure
Thumb
Synonyms
  • 3,7-dimethyl-7-hydroxyoctan-1-al
  • 3,7-Dimethyl-7-hydroxyoctanal
  • 7-hydroxy-3,7-dimethyloctanal
  • 7-hydroxycitronellal
  • Citronellal hydrate
  • Cyclalia
  • Cyclosia
  • Fixol
  • hydroxy citronellal
  • Laurine
  • Lilyl aldehyde
  • Muguet synthetic
  • Muguettine principle
  • Oxydihydrocitronellal
  • Phixia
External IDs
AI3-05823
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
T.R.U.E. Test Thin-Layer Rapid Use Patch TestHydroxycitronellal (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) + 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) + 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) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (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)KitCutaneousSmartPractice Denmark ApS2012-03-01Not applicableUs
Categories
UNII
8SQ0VA4YUR
CAS number
107-75-5
Weight
Average: 172.2646
Monoisotopic: 172.146329884
Chemical Formula
C10H20O2
InChI Key
WPFVBOQKRVRMJB-UHFFFAOYSA-N
InChI
InChI=1S/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3
IUPAC Name
7-hydroxy-3,7-dimethyloctanal
SMILES
[H]C(=O)CC(C)CCCC(C)(C)O

Pharmacology

Indication

Hydroxycitronellal 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.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution

Tmax was found to be 2.70 ± 1.36 2

Protein binding
Not Available
Metabolism

Studies in rabbits have shown that hydroxycitronellal is converted to two primary metabolites: reduction to the alcohol 7-hydroxycitronellol and oxidation to the carboxylic acid 7-hydroxycitronellylic acid 2. On average, about 50% of hydroxycitronellal is excreted as 7-hydroxycitronellylic acid which is therefore regarded as the major metabolite 2.

Route of elimination
Not Available
Half life

The mean elimination half-life has been found to be 3.3 h 1.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
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

References

General References
  1. Stoeckelhuber M, Krnac D, Pluym N, Scherer M, Peschel O, Leibold E, Scherer G: Human metabolism and excretion kinetics of the fragrance 7-hydroxycitronellal after a single oral or dermal dosage. Int J Hyg Environ Health. 2018 Mar;221(2):239-245. doi: 10.1016/j.ijheh.2017.10.015. Epub 2017 Oct 28. [PubMed:29108680]
  2. Ishida T, Toyota M, Asakawa Y: Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Xenobiotica. 1989 Aug;19(8):843-55. [PubMed:2815827]
External Links
Human Metabolome Database
HMDB0031739
ChemSpider
7600
ChEBI
53459
ChEMBL
CHEMBL3186027
Wikipedia
Hydroxycitronellal

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.639 mg/mLALOGPS
logP2.5ALOGPS
logP1.64ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)18.21ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.28 m3·mol-1ChemAxon
Polarizability20.69 Å3ChemAxon
Number of Rings0ChemAxon
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9000000000-0b1976e02fea78c4c3f3
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

Taxonomy

Classification
Not classified

Drug created on July 03, 2018 13:44 / Updated on November 02, 2019 03:21