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 2678		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 8429	ESIKA EXPRESSION ANTIPERSPIRANT ROLL-ON DEODORANT Approved Use Reduces underarm perspiration

PubMed

Title	Date	PubMed
In vitro primary sensitization of hapten-specific T cells by cultured human epidermal Langerhans cells--a screening predictive assay for contact sensitizers.	1996 May	8735869
Deodorants: an experimental provocation study with hydroxycitronellal.	2003 Apr	12786728
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.	2004 Feb	14757700
Evaluation of phototoxic properties of fragrances.	2007	17598033
Phenotypic alterations and cytokine production in THP-1 cells in response to allergens.	2007 Apr	17118622
Sensitization to 26 fragrances to be labelled according to current European regulation. Results of the IVDK and review of the literature.	2007 Jul	17577350
Allergic and photoallergic contact dermatitis from ketoprofen: evaluation of cross-reactivities by a combination of photopatch testing and computerized conformational analysis.	2008	18991702
A smelling trip into the past: the influence of synthetic materials on the history of perfumery.	2008 Jun	18618400
Atopic dermatitis and allergic reactions to individual fragrance chemicals.	2009 Feb	19178409
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010 Sep	20491607
Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay.	2015 Jun	25724174

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

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

HYDROXYCITRONELLAL [INCI]

Common Name

English

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

Systematic Name

English

FEMA NO. 2583

Code

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