NAV

Hydroxycitronellal

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

Identification

Generic Name
Hydroxycitronellal
DrugBank Accession Number
DB14187
Background

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.

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 172.2646
Monoisotopic: 172.146329884
Chemical Formula
C10H20O2
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
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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.

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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.

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Route of elimination

Not Available

Half-life

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

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 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) + 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
8SQ0VA4YUR
CAS number
107-75-5
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

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0031739
ChemSpider
7600
RxNav
1362893
ChEBI
53459
ChEMBL
CHEMBL3186027
Wikipedia
Hydroxycitronellal

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 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-MSsplash10-0a4i-9200000000-e8d34037dba31eb890cb
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9000000000-0b1976e02fea78c4c3f3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-06ei-9200000000-c7bb8f25b1ea9fc2f8da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-514e69a4a1faaf008da2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05o9-9000000000-6eccfbfc3ba6090983e0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-0900000000-ac4beba3e0b9a8572be4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9000000000-c8880e2daa2170f5185f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9100000000-85549f074e8a666aea74
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]-147.9537404
predicted
DarkChem Lite v0.1.0
[M-H]-136.84033
predicted
DeepCCS 1.0 (2019)
[M+H]+148.6316404
predicted
DarkChem Lite v0.1.0
[M+H]+140.51694
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.5687404
predicted
DarkChem Lite v0.1.0
[M+Na]+149.66917
predicted
DeepCCS 1.0 (2019)

Drug created at July 03, 2018 19:44 / Updated at June 12, 2020 16:53