Farnesol
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl- · 3,7,11-TRIMETHYL-2,6,10-DODECATRIEN-1-OL · FEMA 2478 · Polyprenol · Farnesol 95% · Farnesyl alcohol · LINALOOL, DL-(SG) · LINALOOL, (-)-(SG)
Identifikatoren & physikalische Daten
| CAS No. | 4602-84-0 |
|---|---|
| Summenformel | C15H26O |
| Durchschnittliche Molmasse | 222,37 g/mol |
| Monoisotopische Masse | 222,19836545 g/mol |
| SMILES | CC(C)=CCCC(C)=CCCC(C)=CCO |
| InChIKey | CRDAMVZIKSXKFV-UHFFFAOYSA-N |
| PubChem CID | 3327 |
| ChEMBL | CHEMBL4464165 |
| DTXSID | DTXSID3032389 |
| Lokaler Name | Farnesol |
Chemische & physikalische Eigenschaften
| XLogP | 4,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 265 |
| Schmelzpunkt | 25°C |
| Siedepunkt | 149 °C4 mm Hg(lit.) |
| Dichte | 0.886 g/mL at 20 °C(lit.) |
| Dampfdruck | 13Pa at 20℃ |
| FEMA | 2478 | FARNESOL |
| Brechungsindex | n20/D 1.490(lit.) |
| Flammpunkt | 205 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO:100.0(Max Conc. mg/mL)449.7(Max Conc. mM)Not miscible or difficult to mix in water. |
| pKa (Säurekonstante) | 14.69±0.10(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to faint yellow |
| Geruch | at 100.00 %. mild fresh sweet linden floral angelica |
| Geruchsart | floral |
| Biologische Quelle | synthetic |
| Merck | 14,3937 |
| JECFA Number | 1230 |
| BRN | 1763926 |
| Henry-Konstante | 3.9×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGDEODORANT |
| InChI | 1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+ |
| InChIKey | CRDAMVZIKSXKFV-YFVJMOTDSA-N |
| SMILES | C/C(CC/C=C(C)/CCC=C(C)C)=C\CO |
| LogP (Verteilungskoeffizient) | 4.72 at 22.3℃ |
| CAS Datenbank | 4602-84-0(CAS DataBase Reference) |
| NIST chemische Informationen | 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-(4602-84-0) |
| EPA chemische Informationen | Farnesol (4602-84-0) |
Sicherheit & Vorschriften
| F | 8 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3082 9 / PGIII |
| Zollcode | 29052200 |
| RTECS-Nr. | JR4979000 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 24/25-22 |
| Gefahrenklasse | 9Aquatic Acute 1Aquatic Chronic 1Skin Irrit. 2Skin Sens. 1 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 4602-84-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Farnesol has a characteristic flowery odor.
Occurrence
The presence of this terpene alcohol in nature has been reported in more than 30 essential oils; the levels are generally low (0.5 to 1.0%) with the exception of cabreuva, which contains up to 2 5% farensol, and the distillate from fowers of Oxystigma buccholtzii Harms which contains up to 18% farnesol Among the essential oils containing farnesol are lemongrass, Ceylon citronella, cananga, ambrette seeds, ylang-ylang, Acacia farnesiana, Peru balsam, palmarosa, tuberose, and others Reported found in apricot, citrus peel oils, grapefruit juice, strawberry jam, ginger, clove bud, hop oil, cardamom, ginger, thyme, beer, whiskey, basil, papaya, anise seed, German chamomile and Cympogon citratus oils
Verwenden
farnesol is described as a substance of high biological potential, capable of acting in the skin as a true bioactivator. A biological precursor and fatty alcohol, farnesol is one component of vitamin K. It is said to help smooth wrinkles, normalize sebum secretion, and increase the skin’s elasticity, tissue tension, and moisture-binding capability. It is able to penetrate the epidermis. In humans, farnesol is found in the skin and is involved in sterol biosynthesis. It is also used for its deodorant, odor-masking, and skin-soothing properties. In clinical studies, farnesol has demonstrated anti-microbial activity, though it is unclear if this remains the case once incorporated into a cosmetic formulation. It is widely present in vegetables and found in many essential oils (for example, acacia, lilac, lily of the valley, rose, orange blossom, oak moss, and sandalwood).
Herstellung & Synthese
synthetische
One method uses cabreuva as the starting material (Swiss Patent 261,120-Givaudan and Co ), while a second method starts from ambrette seeds (German Patent 149, 603-Haarmann and Reimer).