7-Hydroxycitronellal
Lilyl aldehyde · Cyclosia · 7-HYDROXYCITRONELLAL · LAURINE · OCTANAL, 7-HYDROXY-3,7-DIMETHYL · FEMA 2583 · CITRONELLAL HYDRATE · hydroxycitoronellal
Identifikatoren & physikalische Daten
| CAS No. | 107-75-5 |
|---|---|
| Summenformel | C10H20O2 |
| Durchschnittliche Molmasse | 172,26 g/mol |
| Monoisotopische Masse | 172,14632988 g/mol |
| SMILES | CC(CC=O)CCCC(C)(C)O |
| InChIKey | WPFVBOQKRVRMJB-UHFFFAOYSA-N |
| PubChem CID | 7888 |
| ChEMBL | CHEMBL3186027 |
| ChEBI | CHEBI:53459 |
| EC No. | 203-518-7 |
| DTXSID | DTXSID6042232 |
| Lokaler Name | 7-Hydroxycitronellal |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 130 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Kosmetika | Cosmetics ingredient -> BaseFlavorFragranceMoisturizing/HumectantOther (Specify)Masking |
| Duftstoffe | Fragrance Ingredient (Hydroxycitronellal) -> IFRA transparency List |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.918-0.9230.923 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | slightlyslightly soluble in watersoluble in alcohol, propylene glycol, and oilsinsoluble in glycerol1 ml in 1 ml 50% alcohol (in ethanol)Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)35g/L at 20℃ |
| Siedepunkt | 241.00 °C. @ 760.00 mm Hg241 °C94-96 °C (1 mm Hg)257 °C(lit.) |
| Brechungsindex | 1.447-1.450n20/D 1.448(lit.) |
| Physical Description | LiquidDry PowderCBI[Sigma-Aldrich MSDS]colourless liquid with sweet floral lily-like odour |
| Schmelzpunkt | 22-23 °C |
| Dampfdruck | 0.547Pa at 20℃ |
| FEMA | 2583 | HYDROXYCITRONELLAL |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Inert atmosphere,Store in freezer, under -20°C |
| pKa (Säurekonstante) | 15.31±0.29(Predicted) |
| Aggregatzustand | Liquid |
| Wichte | 0.93 |
| Farbe | Clear colorless |
| Geruch | at 100.00 %. floral lily sweet green waxy tropical melon |
| Geruchsart | floral |
| Biologische Quelle | synthetic |
| JECFA Number | 611 |
| Henry-Konstante | 9.4×102 mol/(m3Pa) at 25℃, Dupeux et al. (2022) |
| Stabilität | Air Sensitive |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C10H20O2/c1-9(6-8-11)5-4-7-10(2,3)12/h8-9,12H,4-7H2,1-3H3 |
| InChIKey | WPFVBOQKRVRMJB-UHFFFAOYSA-N |
| SMILES | [H]C(=O)CC(C)CCCC(C)(C)O |
| LogP (Verteilungskoeffizient) | 1.68 at 25℃ |
| CAS Datenbank | 107-75-5(CAS DataBase Reference) |
| NIST chemische Informationen | Hydroxycitronellal(107-75-5) |
| EPA chemische Informationen | Octanal, 7-hydroxy-3,7-dimethyl- (107-75-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2046) of reports.WarningH317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2046 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Octanal, 7-hydroxy-3,7-dimethyl-Hazard Traits - Fragrance AllergenOctanal, 7-hydroxy-3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octanal, 7-hydroxy-3,7-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12695Hydroxycitronellal: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Octanal, 7-hydroxy-3,7-dimethyl-: Human health tier II assessment |
| Gefahrenübersicht | A severe eye and moderate skin irritantCauses cutaneous sensitization in 3-day intermittent dermal studies of mice[RTECS] Fragrance ingredient that is a recognized contact allergen in consumers[EC: SCCNFP] Safe when used as a flavoring agent in food[JECFA] Contained in fragrance mix[Kanerva, p. 1803] An irritant[Sigma-Aldrich MSDS] See Citronellal. |
| Hazard Classes and Categories | Skin Sens. 1 (> 99.9%)Eye irritation - category 2ASerious eye damage/eye irritation - Category 2 |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Wassergefährdungsklasse (WGK) |
Anwendungen & Verwendung
Beschreibung
Hydroxycitronellal has an intense, sweet, floral, lily-type odor. It may be prepared by hydration of natural citronellal obtained from Java citronella or from Eucalyptus citriodora; P-pinene is converted to myrcene, which on hydration may yield either linalool or a mixture of geranoil and nerol; the latter mixture can be hydrogenated to citronellol and subsequently converted to citronellal and hydroxycitronellal; also by hydrogenation of 3,7-dimethyl- 7-hydroxy-2-octen-2-al over palladium carbon in ethyl acetate solution.
Occurrence
Reported found in pepper
Verwenden
Hydroxycitronellal is a fragrance for use in various perfumes, antiseptics, insecticides and household products; some perfumery uses (sweet pea Pois De Senteur; gardenia; cherry; melon; mint).
Herstellung & Synthese
synthetische
The most important synthetic routes to hydroxydihydrocitronellal are listed as follows. 1) Synthesis from citronellal: One of the oldest routes to hydroxydihydrocitronellal is the hydration of the citronellal bisulfite adduct (obtained at low temperature) with sulfuric acid, followed by decomposition with sodium carbonate. A more recent development is hydration of citronellal enamines or imines, followed by hydrolysis. 2) Synthesis from citronellol. Citronellol is hydrated to 3,7-dimethyloctane-1,7- diol, for example, by reaction with 60% sulfuric acid. The diol is dehydrogenated catalytically in the vapor phase at low pressure to give highly pure hydroxydihydrocitronellal in excellent yield.The process is carried out in the presence of, for example, a copper–zinc catalyst; at atmospheric pressure, noble metal catalysts can also be used. 3) Synthesis from 7-hydroxygeranyl/-neryl dialkylamine: The starting material can be obtained by treatment of myrcene with a dialkylamine in the presence of an alkali dialkylamide, followed by hydration with sulfuric acid. The 7-hydroxygeranyl/-neryl dialkylamine isomerizes to the corresponding 7-hydroxyaldehyde enamine in the presence of a palladium(II)- phosphine complex as catalyst. Hydrolysis of the enamine gives 7-hydroxydihydrocitronellal [151].