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| CAS No.: | 4602-84-0 |
|---|---|
| Name: | Farnesol |
| Molecular Structure: | |
|
|
|
| Formula: | C15H26O |
| Molecular Weight: | 222.371 |
| Synonyms: | Farnesol(6CI);3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol;FCI 119a;Farnesyl alcohol;NSC 60597;Nikkosome; |
| EINECS: | 225-004-1 |
| Density: | 0.875 g/cm3 |
| Melting Point: | 25°C |
| Boiling Point: | 283.4 °C at 760 mmHg |
| Flash Point: | 112.5 °C |
| Solubility: | insoluble |
| Appearance: | colourless liquid with a floral odour |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 24/25-22 |
| Safety: | 24/25-22 |
| PSA: | 20.23000 |
| LogP: | 4.39790 |
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| Conditions | Yield |
|---|---|
| With N-chloro-succinimide In dichloromethane at 0 - 20℃; for 1.25h; | 98% |
- 10485-70-8
methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
- 4602-84-0
farnesol
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride | 85% |
- 20723-88-0
ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate
- 4602-84-0
farnesol
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride | 85% |
| Conditions | Yield |
|---|---|
| With perchloric acid; acetone at 15 - 20℃; for 24.25h; Product distribution / selectivity; | A 15.3% B 21.3% C 57.3% |
| With perchloric acid; trifluorormethanesulfonic acid; acetone In water at 15 - 20℃; for 8.16667h; Product distribution / selectivity; | A 1.8% B 52.7% C 16.2% |
| With perchloric acid; methanesulfonic acid; acetone In water at 15 - 20℃; for 24.1667h; Product distribution / selectivity; | A 1.9% B 51.7% C 16.2% |
- 19317-11-4
farnesal
- 4602-84-0
farnesol
| Conditions | Yield |
|---|---|
| With sodium amalgam; ethanol; acetic acid at 0℃; | |
| With potassium phosphate; recombinant rat brain aldo-keto reductase R1B10; NADP In methanol Kinetics; Enzymatic reaction; | |
| With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29); NADPH In aq. phosphate buffer; ethyl acetate at 37℃; for 0.5h; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction; |
- 7212-44-4
(+/-)-nerolidol
- 108-24-7
acetic anhydride
- 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate
A
- 125037-13-0
cis-α-farnesene
B
- 4602-84-0
farnesol
| Conditions | Yield |
|---|---|
| at 120 - 140℃; nachfolgendes Kochen des Reaktionsprodukts mit alkoh.Kalilauge im Wasserstoffstrom; dextrorotatory form of 2.6.10-trimethyl-dodecatrien-(2.6.11)-ol-(10); |
| Conditions | Yield |
|---|---|
| nachfolgendes Kochen des Reaktionsprodukts mit alkoh.Kalilauge im Wasserstoffstrom; inactive form of 2.6.10-trimethyl-dodecatrien-(2.6.11)-ol-(10); |
| Conditions | Yield |
|---|---|
| at 120 - 140℃; nachfolgenden Kochen des Reaktionprodukts mit alkoh.Kalilauge im Wasserstoffstrom; |
| Conditions | Yield |
|---|---|
| With sulfuric acid; copper (I) acetate; hydroquinone at 24℃; und folgendes Verseifen der erhaltenen Ester mit methylalkoh.KOH; |
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 190-195 deg C, 2 h; Yield given. Multistep reaction; |
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Chemistry
Molecular structure of Farnesol (CAS NO.4602-84-0) is:
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Product Name: Farnesol
CAS Registry Number: 4602-84-0
IUPAC Name: (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Molecular Weight: 222.36634 [g/mol]
Molecular Formula: C15H26O
XLogP3-AA: 4.8
H-Bond Donor: 1
H-Bond Acceptor: 1
EINECS: 225-004-1
Refractive index: n20/D 1.490(lit.)
Storage temp.: -20°C
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Surface Tension: 30.3 dyne/cm
Density: 0.875 g/cm3
Flash Point: 112.5 °C
Enthalpy of Vaporization: 60.62 kJ/mol
Boiling Point: 283.4 °C at 760 mmHg
Vapour Pressure: 0.00037 mmHg at 25°C
Product Categories: Biochemistry;Terpenes;Terpenes (Others)
History
Farnesol (CAS NO.4602-84-0) is from a flower extract with a long history of use in perfumery. The pure substance farnesol was named (ca. 1900-1905) from the type species Acacia farnesiana, the Farnese acacia, the flowers of which provided it commercially, as a floral essence. This particular acacia species in turn is named after Odoardo Cardinal Farnese (1573-1626) of the notable Italian Farnese family which (from 1550 though the 17th century) maintained some of the first private European botanical gardens in the Farnese gardens in Rome. The addition of the -ol ending results from it being chemically an alcohol.The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.
Uses
Farnesol (CAS NO.4602-84-0) is the building block of most (possibly all) acyclic sesquiterpenoids and is an important starting compound for organic synthesis. It is used in perfumery to emphasize the odors of sweet floral perfumes. It is especially used in lilac perfumes.It is a natural pesticide for mites and is a pheromone for several other insects.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 443mg/kg (443mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC | Therapie. Vol. 27, Pg. 893, 1972. |
| mouse | LD50 | oral | 7400mg/kg (7400mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC | Therapie. Vol. 27, Pg. 893, 1972. |
| rat | LD50 | oral | 6gm/kg (6000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC | Therapie. Vol. 27, Pg. 893, 1972. |
Safety Profile
Hazard Codes: 
Xi
Safety Statements: 24/25-22
R24/25:Toxic in contact with skin and if swallowed.
R22:Harmful if swallowed.
WGK Germany: 3
RTECS: JR4979000
F: 8
Hazard Note: Irritant
Specification
Farnesol , its cas register number is 4602-84-0. It also can be called 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl- ; 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol ; 3,7,11-Trimethyl-2,6,10-dodecatrienol ; Farnesyl alcohol .It is a colorless liquid with a delicate floral odor. It is a natural organic compound which is an acyclic sesquiterpene alcohol found as a colorless liquid. It is insoluble in water, but miscible with oils. It is the alcohol derivative of Farnesol Pyrophosphate. It is the building block of most (possibly all) acyclic sesquiterpenoids and is an important starting compound for organic synthesis.It is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam and tolu. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes.It is a natural pesticide for mites and is a pheromone for several other insects.