Hydroxycitronellal

Structural formula
Figure does not show the stereochemistry
General
Surname	Hydroxycitronellal
other names	7-hydroxy-3,7-dimethyloctanal 7-hydroxy-3,7-dimethyl-1-octanal 7-hydroxycitronellal HYDROXYCITRONELLAL ( INCI )
Molecular formula	C 10 H 20 O 2
Brief description	colorless liquid with a floral odor
External identifiers / databases
CAS number 107-75-5 34212-48-1 ( R shape) 34212-53-8 ( S shape) 123238-75-5 (± form) EC number 203-518-7 ECHA InfoCard 100.003.199 PubChem 7888 ChemSpider 7600 Wikidata Q25100775
properties
Molar mass	172.27 g mol −1
Physical state	liquid
density	0.92 g cm −3
boiling point	102-103 ° C (3 hPa) 241 ° C
Vapor pressure	<1 hPa (20 ° C)
solubility	poorly soluble in water soluble in ethanol, most fixed oils and propylene glycol practically insoluble in glycerine
Refractive index	1.448 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 317-319 P: 280-260-272-264-305 + 351 + 338-311-302 + 352-362-501
Toxicological data	> 5000 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Hydroxycitronellal is a chemical compound from the group of substituted aldehydes . It occurs in two stereoisomeric forms.

Occurrence

Hydroxycitronellal occurs naturally in pepper.

Extraction and presentation

Hydroxycitronellal may be made of citronellal by hydration of Citronellalbisulfit with sulfuric acid and subsequent hydrolysis with alkali are produced.

properties

Hydroxycitronellal is a flammable, hardly inflammable, colorless liquid with a flowery odor (like cyclamen , lilac and lily of the valley ) that is sparingly soluble in water. Hydroxycitronellal is very sensitive to alkalis and acids as well as to atmospheric oxygen; Forms acetals with alcohols , which are considerably more stable than the aldehyde , but do not have the fine fragrance.

use

Hydroxycitronellal is used as a fragrance in perfume, cosmetics, detergents and cleaning agents, and as a flavoring for food. It is only slightly resistant to soap.

safety instructions

Hydroxycitronellal is a type IV contact allergen .

Individual evidence

1. ↑ entry to Hydroxycitronellal in CosIng database of the European Commission, accessed on 19 June 2020th
2. ↑ ^{a b c d e f g h i j} Entry on hydroxycitronellal in the GESTIS substance database of the IFA , accessed on May 18, 2018(JavaScript required) .
3. ↑ ^{a b c d} George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 915 ( limited preview in Google Book search).
4. ↑ ^{a b} Data sheet Hydroxycitronellal, ≥95%, FCC, FG from Sigma-Aldrich , accessed on May 18, 2018 ( PDF ).
5. ↑ Ritsuko Ishino, J. u. Kumanotani: Synthesis of hydroxycitronellal. Hydration and subsequent hydrolysis of imines, enamines, or oxazolidines prepared from citronellal and amines. In: The Journal of Organic Chemistry. 39, 1974, p. 108, doi : 10.1021 / jo00915a028 .
6. ↑ ^{a b} Fred Winter: Handbook of the Entire Perfumery and Cosmetics . Springer-Verlag, 2013, ISBN 978-3-7091-2074-3 , pp. 49 ( limited preview in Google Book search).
7. ^ Fritz Ullmann, Wilhelm Foerst: Encyclopedia of Technical Chemistry, Volume 14 . Urban & Schwarzenberg, 1963, 1963, pp. 745 ( limited preview in Google Book search).
8. ↑ Allergen Hydroxycitronellal Allergie Allergologie: Allergen Hydroxycitronellal Allergie Allergologie , accessed on May 18, 2018
9. ↑ Internet offer : Food: Analysis of allergens in cosmetics 2009 - Internet offer , accessed on May 18, 2018
10. ↑ C. Svedman, M. Bruze, JD Johansen, KE Andersen, A. Goossens, PJ Frosch, JP Lepoittevin, S. Rastogi, IR White, T. Menné: Deodorants: an experimental provocation study with hydroxycitronellal. In: Contact Derm. 48, 2003, pp. 217-223, PMID 12786728 .
11. ↑ Human & Environmental Risk Assessment on ingredients of European household cleaning products: HYDROXYCITRONELLAL