Conditions | Yield |
---|---|
With N-chloro-succinimide In dichloromethane at 0 - 20℃; for 1.25h; | 98% |
methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
farnesol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 85% |
ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate
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% |
farnesal
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; |
(+/-)-nerolidol
acetic anhydride
methylammonium carbonate
A
cis-α-farnesene
B
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); |
(+/-)-nerolidol
acetic anhydride
A
cis-α-farnesene
B
farnesol
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; |
farnesol
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid | |
With formic acid |
Conditions | Yield |
---|---|
at 120 - 140℃; nachfolgenden Kochen des Reaktionprodukts mit alkoh.Kalilauge im Wasserstoffstrom; |
farnesol
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide at -15℃; Schuetteln des erhaltenen Farnesylbromids mit Kaliumacetat in wasserfreiem Aceton und Verseifen des Farnesylacetats mit siedender methylalkoh.KOH; |
Conditions | Yield |
---|---|
at 0℃; |
(+/-)-nerolidol
sulfuric acid
acetic acid
A
cis-α-farnesene
B
farnesol
Conditions | Yield |
---|---|
inactive form of 2.6.10-trimethyl-dodecatrien-(2.6.11)-ol-(10); |
Conditions | Yield |
---|---|
inactive form of 2.6.10-trimethyl-dodecatrien-(2.6.11)-ol-(10); |
(E)-2-Methanesulfinyl-3,7,11-trimethyl-dodeca-6,10-dienoic acid ethyl ester
farnesol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / calcium carbonate / toluene / 7 h / Heating 2: 85 percent / LiAl-hydride View Scheme |
(E)-3,7,11-Trimethyl-dodeca-6,10-dienoic acid methyl ester
farnesol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: 1. sodium methaperiodate 2. reflux, toluene, 20 h, CaCO3 3: 85 percent / LiAlH4 View Scheme |
farnesol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1. sodium methaperiodate 2. reflux, toluene, 20 h, CaCO3 2: 85 percent / LiAlH4 View Scheme |
3,7,11-trimethyl-6,10-dodecadien-1-yn-3-ol
farnesol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium; diethyl ether / 0 °C 2: 120 - 140 °C / nachfolgenden Kochen des Reaktionprodukts mit alkoh.Kalilauge im Wasserstoffstrom View Scheme |
Conditions | Yield |
---|---|
With perchloric acid; methanesulfonic acid In water; acetone at 10 - 15℃; for 24.5h; Product distribution / selectivity; | |
With phosphotungstic acid In acetone at 30℃; for 3h; Catalytic behavior; Solvent; Green chemistry; Overall yield = 55 %Chromat.; |
Conditions | Yield |
---|---|
With perchloric acid; methanesulfonic acid In water; acetone at 15 - 20℃; for 24.67h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With methanol; sodium hydroxide; water at 20 - 40℃; for 2.25h; Product distribution / selectivity; |
farnesyl benzoate
farnesol
Conditions | Yield |
---|---|
With methanol; potassium hydroxide at 20℃; Reflux; |
farnesyl pyrophosphate
farnesol
Conditions | Yield |
---|---|
With Mycobacterium tuberculosis N-terminal His-tagged Rv3376 enzyme; water Enzymatic reaction; |
farnesol
farnesal
Conditions | Yield |
---|---|
With dipyridinium dichromate In dichloromethane at 0 - 25℃; for 24h; | 100% |
With pyridinium chlorochromate In hexane at 25℃; for 2h; Oxidation; | 87% |
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; toluene-4-sulfonic acid In dichloromethane 1) 0 deg C, 1 h, 2) r.t., 1 h; | 86% |
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In tetrahydrofuran | 100% |
With toluene-4-sulfonic acid at 25℃; |
farnesol
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -50℃; Molecular sieve; Inert atmosphere; enantioselective reaction; | 100% |
With bis(acetylacetonate)dioxotungsten(VI); C96H142N2O4; sodium chloride In dichloromethane at 20℃; for 3h; | 88% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium methanolate at 110 - 120℃; for 18.4333h; Inert atmosphere; | 99.3% |
Conditions | Yield |
---|---|
With platinum/carbon xerogel catalyst; hydrogen In ethanol at 20℃; for 12h; Inert atmosphere; | 99% |
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; | 97% |
With hydrogen; palladium 10% on activated carbon In ethanol for 36h; | 93% |
Conditions | Yield |
---|---|
With N-chloro-succinimide; dimethylsulfide In dichloromethane at 0 - 20℃; for 2.5h; | 98% |
With N-chloro-succinimide; dimethylsulfide In dichloromethane at 0 - 20℃; for 2.83h; | 98% |
With N,N-dimethyl-formamide; phosphorus trichloride In tetrahydrofuran at 20℃; for 0.5h; |
farnesol
tert-butylchlorodiphenylsilane
(2E,6E)-1-((tert-butyldiphenylsilyl)oxy)-3,7,11-trimethyl-2,6,10-dodecatriene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: farnesol With lithium hexamethyldisilazane at 0 - 20℃; Inert atmosphere; Stage #2: With methanol Inert atmosphere; | 97% |
With dodecacarbonyl-triangulo-triruthenium; 4,5-bis((diisopropylphosphanyl)methyl)acridine; ammonia In tert-Amyl alcohol at 170℃; for 21h; Temperature; Inert atmosphere; Schlenk technique; Autoclave; |
Conditions | Yield |
---|---|
With oxygen; copper In acetonitrile for 4h; Reagent/catalyst; Temperature; Reflux; | 95% |
With tert.-butylhydroperoxide; oxygen In decane; toluene at 80℃; under 750.075 Torr; | 87% |
Conditions | Yield |
---|---|
Stage #1: farnesol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; | 92% |
farnesol
farnesyl bromide
Conditions | Yield |
---|---|
With phosphorus tribromide; triethylamine In toluene at -5℃; for 2h; Product distribution / selectivity; | 91% |
With methanesulfonyl chloride; triethylamine; lithium bromide In tetrahydrofuran at -45 - 0℃; for 1.91667h; Inert atmosphere; | 86% |
With pyridine; phosphorus tribromide at -5℃; |
Conditions | Yield |
---|---|
With benzotriazole*CrO3 In acetone for 5h; Heating; | 91% |
Multi-step reaction with 2 steps 1: Cr2O3-H2SO4 / das Edukt ist natuerlich vorkommendes Farnesol 2: AgNO3; aqueous alcoholic NaOH View Scheme | |
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / -78 - 20 °C / Inert atmosphere 2: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; N,N'-diethylurea; (2S)-methyl 2-(4,8-di-tert-butyl-2,10-dimethoxydibenzo[d,f][1,3,2]dioxaphosphepin-6-ylamino)benzylethanoate In toluene at 80℃; for 20h; regioselective reaction; | 90% |
With {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; N,N'-diethylurea; (2S)-methyl 2-(4,8-di-tert-butyl-2,10-dimethoxydibenzo[d,f][1,3,2]dioxaphosphepin-6-ylamino)benzylethanoate In toluene at 80℃; for 20h; regioselective reaction; | 57% |
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 3h; | 90% |
Stage #1: farnesol With manganese(II) iodide; naphthalene; lithium In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: benzoyl chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With triphenylphosphine; trifluoroacetic acid; palladium dichloride In toluene at 120℃; under 30003 Torr; for 24h; Inert atmosphere; Autoclave; | 88% |
farnesol
10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid
farnesyl idebenone carboxylate
Conditions | Yield |
---|---|
novozyme 435 at 50℃; Product distribution / selectivity; Enzymatic reaction; Inert atmosphere; | 87% |
farnesol
Conditions | Yield |
---|---|
In toluene at 50℃; for 1.5h; | 87% |
Conditions | Yield |
---|---|
With pyridine; trichloroacetonitrile at 80℃; for 0.25h; Microwave irradiation; | 86% |
farnesol
Conditions | Yield |
---|---|
Stage #1: farnesol; triethylammonium (2S,3R,4S,5S,6S)-3,4,5-tris-(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl phosphonate With pyridine; pivaloyl chloride at -15℃; for 1.5h; Stage #2: With iodine at 20℃; for 1h; | 83% |
farnesol
ethylene glycol
2-methyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-1,3-dioxolane
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In benzene at 90℃; for 8h; Inert atmosphere; Dean-Stark; | 82.6% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 95℃; under 450.045 - 525.053 Torr; for 6h; | 81% |
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 4h; | 81% |
Conditions | Yield |
---|---|
With perchloric acid | 80% |
farnesol
O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate
C29H44O10
Conditions | Yield |
---|---|
With gold(I) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; stereoselective reaction; | 80% |
farnesol
Conditions | Yield |
---|---|
Stage #1: farnesol With dihydrogen peroxide; bis(2,4-pentanedionato)dioxomolybdenum(VI) In acetonitrile at 20 - 50℃; Stage #2: With diphenyl sulfide regioselective reaction; | 79% |
farnesol
(2Z,6E)-10-Chloro-3,7,11-trimethyl-dodeca-2,6,11-trien-1-ol
Conditions | Yield |
---|---|
With hypochloric acid In dichloromethane | 78% |
Conditions | Yield |
---|---|
Stage #1: farnesol With manganese(II) iodide; naphthalene; lithium In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: acetic anhydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 77% |
Molecular structure of Farnesol (CAS NO.4602-84-0) is:
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)
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.
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.
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. |
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
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.
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