Citronellol
β-Citronellol · BETA-CITRONELLOL · (S)-Citronellol · DL-CITRONELLOL · FEMA 2309 · CITRONELLOL 96 · 3,7-DIMETHYL-6-OCTEN-1-OL · Elenol

Identifikatoren & physikalische Daten
| CAS No. | 106-22-9 |
|---|---|
| Summenformel | C10H20O |
| Durchschnittliche Molmasse | 156,26 g/mol |
| Monoisotopische Masse | 156,15141526 g/mol |
| SMILES | CC(C)=CCCC(C)CCO |
| InChIKey | QMVPMAAFGQKVCJ-UHFFFAOYSA-N |
| PubChem CID | 8842 |
| ChEMBL | CHEMBL395827 |
| ChEBI | CHEBI:50462 |
| EC No. | 203-375-0 |
| DTXSID | DTXSID3026726 |
| Lokaler Name | Citronellol |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 112 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Kosmetika | Cosmetics ingredient -> BaseFlavorFragranceMoisturizing/HumectantOther (Specify)Masking |
| Duftstoffe | Fragrance substance (Citronellol) -> IFRA amendment 49Fragrance Ingredient (6-Octen-1-ol, 3,7-dimethyl-,(+/-)-) -> IFRA transparency ListFragrance Ingredient (dl-Citronellol) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 3.91 |
| Geruch | Fresh rosy odorRose odor |
| Geschmack | Bitter taste /d-Citronellol/sweet, peach-like flavor /l-citronellol/Taste characteristics at 20 ppm: floral, rose, sweet and green with fruity citrus nuances |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.8550 g/cu cm at 20 °C0.850-0.8600.857 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 11.1 mPa s (dynamic) at 20 °C5.33 mPa s (dynamic) at 40 °C |
| Color/Form | Colorless oily liquid |
| Löslichkeit | In water, 200 mg/L at 25 °CIn water, 307 mg/L at 25 °C300 mg/L at 20 °CSoluble in fixed oils, propylene glycolinsoluble in glycerinMiscible in ethanol and ether /(+)-citronellol/very soluble in ethanol and ether /(-)-citronellol/Insoluble in glycerolslightly soluble in watersoluble in most fixed oils, propylene glycolsoluble (in ethanol)Chloroform, Methanol (Sparingly) |
| Schmelzpunkt | 77-83 °C(lit.) |
| Siedepunkt | 225 °C(lit.) |
| Dampfdichte | 5.4 (vs air) |
| Dampfdruck | ~0.02 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.456(lit.) |
| FEMA | 2309 | DL-CITRONELLOL |
| Flammpunkt | 209 °F |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 15.13±0.10(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear almost colorless |
| Geruch | at 100.00 %. floral leather waxy rose bud citrus |
| Geruchsart | floral |
| Biologische Quelle | synthetic |
| Merck | 14,2330 |
| JECFA Number | 1219 |
| BRN | 1721507 |
| Henry-Konstante | 5.2×100 mol/(m3Pa) at 25℃, Martins et al. (2017) |
| Stabilität | Stable. Incompatible with oxidizing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3 |
| InChIKey | QMVPMAAFGQKVCJ-UHFFFAOYSA-N |
| SMILES | CC(CCO)CC\C=C(\C)C |
| LogP (Verteilungskoeffizient) | 3.41 at 25℃ |
| CAS Datenbank | 106-22-9(CAS DataBase Reference) |
| NIST chemische Informationen | 6-Octen-1-ol, 3,7-dimethyl-(106-22-9) |
| EPA chemische Informationen | Citronellol (106-22-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (95.7%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1657 reports by companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: 6-Octen-1-ol, 3,7-dimethyl-Regulation (EC) No 1831/2003 (amended)6-Octen-1-ol, 3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 6-Octen-1-ol, 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: 02-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14242Citronellol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 6-Octen-1-ol, 3,7-dimethyl-: Environment tier I assessment |
| Gefahrenübersicht | Causes degenerative changes to brain, dermatitis, changes in liver and kidney weights, and somnolence in acute oral studies of ratsCauses alteration of classical conditioning and abnormal liver function tests in 100-day inhalation studies of rats[RTECS] A moderate skin irritantCategory members and supporting chemicals demonstrate skin sensitization in humans and miceNo systemic toxicity in 112-day and 17-week oral studies of rats at the highest tested doses (approximately 500 mg/kg/day)Mortality, stomach lesions, and cytoplasmic vacuolization (lipidosis) of the liver, kidney, and myocardium in 13-week oral study of mice (LOAEL of 2,000 mg/kg/day)[EPA ChAMP: Terpenoid Primary Alcohols and Related Esters - 2009] Fragrance ingredient that is a recognized contact allergen in consumers[EC: SCCNFP] Generally regarded as safe (GRAS) by the FDA[ToxPlanet: EPA BRADs] Safe when used as a flavoring agent in food |
Anwendungen & Verwendung
Beschreibung
Citronellol is a kind of natural occurring acyclic monoterpenoid which can be found in citronella oils such as Cymbopogon nardus ((+)-citronellol) and rose oils and Pelargonium geraniums ((-)-citronellol). In addition to be extracted from natural oils, it can also be manufactured by the hydrogenation of geraniol or nerol. It is mainly used in perfumes and insects repellents as well as being used as a mite attractant. It should be noted that it is an excellent mosquito repellent at short distances. Combination with beta-cyclodextrin can make it has an average duration time of 1.5 hour against the mosquitoes. It can also be used for the manufacture of rose oxide. One of its most common applications is for adding floral and citrus notes to perfumes, soaps and cosmetics.
Occurrence
l-Citronellol has been found in the plants of the Rosaceae family; d- and dl-citronellol have been identified in Verbenaceae, Labiatae, Rutaceae, Geraniaceae and others; citronellol has been reported in about 70 essential oils and in the oil of Rosa bourbonia; the Bulgarian rose oil has been reported to contain more than 50% l-citronellol, whereas East African geranium contains more than 80% of the d-isomer; the natural product is always optically active. Reported found in guava fruit, orange, bilberry, blackcurrant, nutmeg, ginger, corn mint oil (Mentha arvensis L. var. piperascens), mustard, pennyroyal oil (Mentha pulegium L.), hop oil, tea, coriander seed, cardamom, beer, rum, and apple juice.
Verwenden
citronellol is a constituent of plant essential oils. Found abundantly in eucalyptus oil. It is used for masking odor or providing a fragrance component to a cosmetic product.
Herstellung & Synthese
synthetische
By reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967).