Citronellsäure
3,7-DIMETHYL-6-OCTENOIC ACID · FEMA 3142 · 6-Octenoic acid, 3,7-dimethyl- · Citronellate · RHODINIC ACID · CITRONELLIC ACID · TIMTEC-BB SBB006596 · Citronellic acid 98%
Identifikatoren & physikalische Daten
| CAS No. | 502-47-6 |
|---|---|
| Summenformel | C10H18O2 |
| Durchschnittliche Molmasse | 170,25 g/mol |
| Monoisotopische Masse | 170,13067982 g/mol |
| SMILES | CC(C)=CCCC(C)CC(=O)O |
| InChIKey | GJWSUKYXUMVMGX-UHFFFAOYSA-N |
| PubChem CID | 10402 |
| ChEMBL | CHEMBL2288023 |
| ChEBI | CHEBI:80507 |
| EC No. | 207-939-7 |
| DTXSID | DTXSID1047106 |
| Lokaler Name | Citronellsäure |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 167 |
| Stoffklassen | Other Classes -> Organic Acids |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102] |
| Duftstoffe | Fragrance Ingredient (3,7-Dimethyl-6-octenoic acid) -> IFRA transparency List |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.920-0.926 (20 °C)0.923 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | slightlyInsoluble in glycerol, watersoluble in most fixed oils, propylene glycolsoluble (in ethanol)Almost insoluble in water, soluble in tslcohol and oils.Insoluble in water. |
| Siedepunkt | 121.00 to 122.00 °C. @ 1.00 mm Hg121-122 °C (1 mm Hg)121-122 °C1 mm Hg(lit.) |
| Schmelzpunkt | 257 °C |
| Brechungsindex | 1.455-1.462n20/D 1.454(lit.) |
| Physical Description | Liquid[Sigma-Aldrich MSDS]SolidColourless liquidsmokey, whisky aroma |
| Collision Cross Section | 148.8 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID1047106] |
| FEMA | 3142 | 3,7-DIMETHYL-6-OCTENOIC ACID |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Storage temp. 2-8°C |
| pKa (Säurekonstante) | 4.78±0.10(Predicted) |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Light yellow |
| Geruch | Faint, fresh-green, somewhat grassy odor |
| Geruchsart | green |
| Biologische Quelle | synthetic |
| JECFA Number | 1221 |
| Kosmetik-Inhaltsstoffe Funktionen | ANTI-SEBORRHEICANTIMICROBIALFRAGRANCE |
| InChI | 1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12) |
| InChIKey | GJWSUKYXUMVMGX-UHFFFAOYSA-N |
| SMILES | CC(CC\C=C(\C)C)CC(O)=O |
| LogP (Verteilungskoeffizient) | 3.35 |
| CAS Datenbank | 502-47-6(CAS DataBase Reference) |
| EPA chemische Informationen | 6-Octenoic acid, 3,7-dimethyl- (502-47-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH311 (> 99.9%): Toxic in contact with skin [Danger Acute toxicity, dermal]P262, P264, P270, P280, P302+P352, P316, P321, P361+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1635 reports by companies from 6 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 6-Octenoic acid, 3,7-dimethyl-Regulation (EC) No 1831/2003 (amended)6-Octenoic acid, 3,7-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A moderate skin irritant[RTECS] Safe when used as a flavoring agent in food[JECFA] A skin irritantToxic by skin absorption[Sigma-Aldrich MSDS] See Citronellol. |
| Hazard Classes and Categories | Acute Tox. 3 (> 99.9%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2810 6.1/PG 3 |
| Zollcode | 29161995 |
| RTECS-Nr. | RH3230000 |
| R-Sätze (R) | 21-38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalSkin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Occurrence
The d-form is reportedly a constituent of Java citronella, geranium, Borosma pulchellum, Xanthoxylum piperitum, bitter-orange leaves, lemongrass, Calytrix virgata and Calytrix tetragona leaves; the l-form has been reportedly identified in cypress oil (Callitirs glauca R. Br.), Callitirs intratropica, in the oil of Chamaecyparis obtusa and of Thujopsis dolabrata; the d,l-form is isolated from camphor oil. Also reported found in mandarin peel oil, swangi (Citrus hystrix D.C.), peppermint oil and black tea.
Verwenden
Citronellic acid was used in synthesis of stereoisomers of 3,11- dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one.
Herstellung & Synthese
synthetische
By oxidation of citronellal; also by the conversion of pulegone.