HYDROXYCITRONELLAL

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H20O2
Molecular Weight	172.2646
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CCCC(C)(C)O)CC=O

InChI

InChIKey=WPFVBOQKRVRMJB-UHFFFAOYSA-N

InChI=1S/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ewg.org/skindeep/ingredient/703051/HYDROXYCITRONELLAL/ | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.515&SearchTerm=hydroxycitronellal | https://www.davidwolfe.com/10-year-old-girl-loses-hair-beauty-product/ | https://www.ncbi.nlm.nih.gov/pubmed/17936526 | https://www.ncbi.nlm.nih.gov/pubmed/14757700

Hydroxycitronellal is a perfume ingredient with a medium strength floral scent, reminiscent of lily and sweet tropical melon. It is produced synthetically from naturally occurring scent chemical citronellal. It is on the CFR - Code of Federal Regulations Title 21 list of synthetic flavoring substances and adjuvants. Hydroxycitronellal is banned in the European Union because of its toxic properties. Hydroxycitronellal is an allergen. Hydroxycitronellal has being shown to consistently modulate CCR5, CCL27, CCL2 and CCR7 in immature dendritic cells. Hydroxycitronellal is a TRPM8 agonist.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Transient receptor potential cation channel subfamily M member 8 18 Target ID: CHEMBL3108632 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14757700	Agonist 2752		19.6 mM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prespiration 2 Sources: https://www.drugs.com/otc/592325/esika-expression-antiperspirant-roll-on-deodorant.html	Inactive ingredient		Approved 8583	ESIKA EXPRESSION ANTIPERSPIRANT ROLL-ON DEODORANT Approved Use Reduces underarm perspiration

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP19A1 429 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 3.0	inconclusive [IC50 23.9185 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 4.0	inconclusive [IC50 37.9083 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 54.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 94.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 80.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 4.0	yes [IC50 37.9083 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 6.0	yes [IC50 79.1862 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 79 \| 82	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/7888#section=Biological-Test-Results Page: 95.0

PubMed

Title	Date	PubMed
Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay.	2015-06	25724174
Effect of a microemulsion system on hapten-peptide reactivity studies: examples of hydroxycitronellal and citral, fragrance skin sensitizers, with glutathione.	2010-09-20	20795681
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010-09	20491607
Polyvalent type IV sensitizations to multiple fragrances and a skin protection cream in a metal worker.	2009-06	19243479
Atopic dermatitis and allergic reactions to individual fragrance chemicals.	2009-02	19178409
Use of an ex vivo local lymph node assay to assess contact hypersensitivity potential.	2008-07	18830887
A smelling trip into the past: the influence of synthetic materials on the history of perfumery.	2008-06	18618400
ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1.	2008-03	19305786
Allergic and photoallergic contact dermatitis from ketoprofen: evaluation of cross-reactivities by a combination of photopatch testing and computerized conformational analysis.	2008	18991702
Chemicals with weak skin sensitizing properties can be identified using low-density microarrays on immature dendritic cells.	2007-11-01	17936526
Fragrance ingredient labelling in products on sale in the U.K.	2007-08	17573873
High-performance liquid chromatographic method for the simultaneous determination of 24 fragrance allergens to study scented products.	2007-07-27	17475438
Sensitization to 26 fragrances to be labelled according to current European regulation. Results of the IVDK and review of the literature.	2007-07	17577350
Phenotypic alterations and cytokine production in THP-1 cells in response to allergens.	2007-04	17118622
GC-MS quantification of suspected volatile allergens in fragrances. 2. Data treatment strategies and method performances.	2007-01-10	17199309
Evaluation of phototoxic properties of fragrances.	2007	17598033
Determination of fragrance allergens in cosmetics by size-exclusion chromatography followed by gas chromatography-mass spectrometry.	2006-11-03	16945383
CD8+ T cells are effector cells of contact dermatitis to common skin allergens in mice.	2006-04	16456532
[Contact allergy to fragrances].	2006	17340985
Correlations of patch test reactivity and the repeated open application test (ROAT)/provocative use test (PUT).	2004-11	15350669
Ethanol and diethyl phthalate: vehicle effects in the local lymph node assay.	2004-06-19	15204720
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.	2004-02	14757700
A stronger patch test elicitation reaction to the allergen hydroxycitronellal plus the irritant sodium lauryl sulfate.	2003-09	14678209
The fragrance hand immersion study - an experimental model simulating real-life exposure for allergic contact dermatitis on the hands.	2003-06	14531871
Deodorants: an experimental provocation study with hydroxycitronellal.	2003-04	12786728
Application of the risk assessment paradigm to the induction of allergic contact dermatitis.	2003-02	12662904
Multicentre study of fragrance allergy in Hungary. Immediate and late type reactions.	2002-06	12190620
Sensitization methodology and primary prevention of the research institute for fragrance materials.	2002	12145447
Fragrance chemicals in domestic and occupational products.	2001-10	11683833
Characterization of T cell responses to fragrances.	2001-05-01	11312644
In vitro primary sensitization of hapten-specific T cells by cultured human epidermal Langerhans cells--a screening predictive assay for contact sensitizers.	1996-05	8735869

Patents

Sample Use Guides

In Vivo Use Guide

Deodorants containing hydroxycitronellal in the concentration range of 0.032-0.32% used twice daily on healthy skin in individuals hypersensitive to hydroxycitronellal can elicit axillary dermatitis in a few weeks.

Route of Administration: Topical

In Vitro Use Guide

PHA-induced mitogenesis assays revealed that Hydroxycitronellal could be applied to PBMC in final concentrations of 0.1 to 100 ug/ml

Name

Type

Language

HYDROXYCITRONELLAL

Official Name

English

FEMA NO. 2583

Preferred Name

English

CITRONELLAL HYDRATE

Systematic Name

English

NSC-406740

Code

English

HYDROXYCITRONELLAL [FHFI]

Common Name

English

HYDROXYCITRONELLAL [FCC]

Common Name

English

HYDROXY CITRONELLAL

Systematic Name

English

MUGUETTINE PRINCIPLE

Common Name

English

7-HYDROXYCITRONELLAL

Common Name

English

1-OCTANAL, 3,7-DIMETHYL-7-HYDROXY-

Systematic Name

English

3,7-DIMETHYL-7-HYDROXY-OCTANAL

Systematic Name

English

OCTANAL, 7-HYDROXY-3,7-DIMETHYL-

Systematic Name

English

7-HYDROXY-3,7-DIMETHYLOCTANAL

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515