Product Name

  • Name

    (E,E)-Farnesol

  • EINECS 225-004-1
  • CAS No. 106-28-5
  • Article Data64
  • CAS DataBase
  • Density 0.875 g/cm3
  • Solubility Miscible with alcohol. Immiscible with water.
  • Melting Point 61-63 °C
  • Formula C15H26O
  • Boiling Point 283.4 °C at 760 mmHg
  • Molecular Weight 222.371
  • Flash Point 112.5 °C
  • Transport Information
  • Appearance
  • Safety 24/25
  • Risk Codes 43
  • Molecular Structure Molecular Structure of 106-28-5 ((E,E)-Farnesol)
  • Hazard Symbols Xi
  • Synonyms 2,6,10-Dodecatrien-1-ol,3,7,11-trimethyl-(farnesol) (7CI);2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-,(E,E)- (8CI);(2E,6E)-Farnesol;(E)-b-Farnesol;2,6,10-Dodecatrien-1-ol,3,7,11-trimethyl-, (2E,6E)-;2,6-Di-trans-farnesol;2-trans,6-trans-Farnesol;3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol;Inhibitor A2;all-E-Farnesol;all-trans-Farnesol;trans,trans-Farnesol;trans-Farnesol;
  • PSA 20.23000
  • LogP 4.39790

Synthetic route

ethyl farnesoate
19954-66-6

ethyl farnesoate

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Inert atmosphere;95%
With lithium aluminium tetrahydride In diethyl ether at 20℃;90%
With lithium aluminium tetrahydride In diethyl ether88%
Stage #1: ethyl farnesoate With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at -5℃; for 1h;
Stage #2: With sodium hydroxide
farnesyl pyrophosphate
372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5

farnesyl pyrophosphate

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With water; alkaline phosphatase at 37℃; for 5h; Enzymatic reaction;
With calf intestine phosphatase; magnesium chloride In hexane at 30℃; for 2h; pH=7.5; Enzymatic reaction;
With calf intestinal phosphatase; water at 37℃; for 1h; pH=7.9; Enzymatic reaction;
(2E,6E)-farnesyl chloride
6784-45-8, 67023-85-2, 72132-86-6, 67023-84-1

(2E,6E)-farnesyl chloride

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide In methanol for 24h; Reflux;85%
(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol
40716-66-3

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
O=W(OR)4-ligand at 180 - 200℃;
Stage #1: (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol With vinyl acetate; Amano Lipase PS; C10H10NO6V In toluene at 50℃; for 168h; Enzymatic reaction;
Stage #2: With potassium carbonate In methanol at 0℃; for 2h; Overall yield = 67.7 %Chromat.; Optical yield = 78.947 %de; diastereoselective reaction;
(6E)-3,7,11-trimethyldodeca-2,6,10-trienal
72019-02-4

(6E)-3,7,11-trimethyldodeca-2,6,10-trienal

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; formic acid triethylamine complex; N-tosylethylenediamine In ethyl acetate at 20℃; for 20h; Inert atmosphere; Overall yield = 98 %;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In chlorobenzene at 130℃; for 72h; Reagent/catalyst;
(6E)-farnesyl acetate
226090-90-0

(6E)-farnesyl acetate

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With potassium carbonate In methanol at 0℃; for 2h; Overall yield = 86%; Overall yield = 1.45 mg;
With water; sodium hydroxide In methanol at 20℃; for 0.5h; Reagent/catalyst; Overall yield = 94 percent; Overall yield = 209 mg;
trans,trans-farnesyl diphenylurethane
76386-25-9

trans,trans-farnesyl diphenylurethane

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 6h; Heating;93%
isopentenylmagnesium bromide
97344-88-2

isopentenylmagnesium bromide

3,7-dimethyl-8-<(tetrahydro-2H-pyran-2-yl)oxy>-2E,6E-octadien-1-ol
95763-58-9

3,7-dimethyl-8-<(tetrahydro-2H-pyran-2-yl)oxy>-2E,6E-octadien-1-ol

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran for 12h;54%
(6E)-3,7,11-trimethyldodeca-2,6,10-trienal
72019-02-4

(6E)-3,7,11-trimethyldodeca-2,6,10-trienal

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In chlorobenzene at 130℃; for 17.5h; Reagent/catalyst;
(2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene
61890-77-5

(2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With phosphomolybdic acid hydrate; silica gel In tetrahydrofuran at 20℃; for 0.25h;97%
trans geranyl acetone
3796-70-1

trans geranyl acetone

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaH / tetrahydrofuran / 2 h / 0 °C
1.2: 73 percent / tetrahydrofuran / 3 h / 0 - 20 °C
2.1: diisobutyl aluminum hydride / toluene / 1 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: NaH; 15-crown-6 / tetrahydrofuran / -30 °C
2: LiAlH4 / benzene / 55 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / t-AmOK / diethyl ether
2: 2) LAH / 2) ether, 0 degC, 2.5H
View Scheme
(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol
40716-66-3

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

acetic anhydride
108-24-7

acetic anhydride

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Stage #1: (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol; acetic anhydride With bis(acetylacetonato)dioxidomolybdenum(VI) In chloroform at 50℃; for 24h;
Stage #2: With potassium carbonate In methanol at 0℃; for 2h; Reagent/catalyst; Solvent; Temperature; Overall yield = 86 %; Overall yield = 362.5 mg;
...Expand
farnesal
19317-11-4

farnesal

A

(2Z,6Z)-farnesol
16106-95-9

(2Z,6Z)-farnesol

B

2E,6Z-farnesol
3879-60-5

2E,6Z-farnesol

C

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

D

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; formic acid triethylamine complex; N-tosylethylenediamine In ethyl acetate at 20℃; for 20h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Overall yield = 98 %;
...Expand
ethyl (2Z/E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate
33776-65-7

ethyl (2Z/E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In benzene at 55℃;
With diisobutylaluminium hydride In toluene at -78℃; for 1h;
formic acid
64-18-6

formic acid

(+/-)-nerolidol
7212-44-4

(+/-)-nerolidol

A

(2Z,6Z)-farnesol
16106-95-9

(2Z,6Z)-farnesol

B

2E,6Z-farnesol
3879-60-5

2E,6Z-farnesol

C

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

D

Farnesol
106-28-5

Farnesol

E

bisabolol
515-69-5, 23089-26-1, 23178-88-3, 25428-43-7, 72059-10-0, 72691-24-8, 76738-75-5, 78148-59-1, 123877-54-3

bisabolol

Conditions
ConditionsYield
Stage #1: formic acid; (+/-)-nerolidol In hexane at 10 - 15℃; for 21h;
Stage #2: With water; sodium hydroxide In methanol at 20 - 40℃; for 2.25h;
...Expand
formaldehyd
50-00-0

formaldehyd

trans geranyl acetone
3796-70-1

trans geranyl acetone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

A

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3790-71-4

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

B

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Stage #1: trans geranyl acetone; Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h;
Stage #2: With sec.-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #3: formaldehyd In tetrahydrofuran at 0 - 20℃;		A 29%
B n/a
...Expand
C18H27BrClF3O5S

C18H27BrClF3O5S

A

Farnesol
106-28-5

Farnesol

B

(R,2E,6E)-10-bromo-11-chloro-3,7,11-trimethyldodeca-2,6-dien-1-ol

(R,2E,6E)-10-bromo-11-chloro-3,7,11-trimethyldodeca-2,6-dien-1-ol

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;A n/a
B 62%
farnesol
4602-84-0

farnesol

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 4 h / 100 - 105 °C
2: 93 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating
View Scheme
formaldehyd
50-00-0

formaldehyd

(E)-6,10-dimethyl-5,9-undecadien-1-yne
22850-55-1

(E)-6,10-dimethyl-5,9-undecadien-1-yne

trimethylaluminum
75-24-1

trimethylaluminum

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With n-butyllithium; zirconocene dichloride Yield given. Multistep reaction;
...Expand
(2E,6E,10E)-3,7,11-trimethyl-5-p-tolylsulphonyldodeca-2,6,10-trien-1-ol
78284-80-7

(2E,6E,10E)-3,7,11-trimethyl-5-p-tolylsulphonyldodeca-2,6,10-trien-1-ol

A

Farnesol
106-28-5

Farnesol

B

(3Z,6E)-3,7,11-trimethyldodeca-3,6,11-trien-1-ol
78284-81-8

(3Z,6E)-3,7,11-trimethyldodeca-3,6,11-trien-1-ol

C

(3Z,7E)-3,7,11-trimethyldodeca-3,7,11-trien-1-ol
78284-82-9

(3Z,7E)-3,7,11-trimethyldodeca-3,7,11-trien-1-ol

Conditions
ConditionsYield
With lithium; ethylamine In diethyl ether at -78℃; for 2.5h;A 27%
B n/a
C n/a
With lithium; ethylamine In diethyl ether at -78℃; for 2.5h; Yields of byproduct given;
...Expand
Farnesal
502-67-0

Farnesal

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With manganese; water; 2,4,6-collidine hydrochloride In tetrahydrofuran at 20℃; chemoselective reaction;69%
With human aldo-keto reductase 1A1; NADPH at 25℃; pH=7.4; Kinetics; Reagent/catalyst; aq. phosphate buffer;
With sodium tetrahydroborate In methanol at 20℃; for 0.5h;
ethyl (2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate
64759-51-9

ethyl (2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -70℃; for 1h; Inert atmosphere;
farnesyl pyrophosphate
104715-19-7

farnesyl pyrophosphate

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
With 2-amino-6-mercapto-7-methylpurine ribonucleoside; purine nucleoside phosphorylase; YisP from Bacillus subtilis; magnesium chloride In aq. buffer pH=7.5; Enzymatic reaction;
1-((tert-butyldiphenylsilyl)oxy)-3-methyl-2-butene
188263-82-3

1-((tert-butyldiphenylsilyl)oxy)-3-methyl-2-butene

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 37 percent / SeO2, salicylic acid, t-BuOOH, H2O / CH2Cl2 / 20 h / Ambient temperature
2: 1.) MsCl, Et3N, 2.) LiBr / 1.) CH2Cl2, -40 deg C, 1 h, 2.) THF, 0 deg C, 2 h
3: 1.) BaI2*H2O, biphenyl radical, 3.) TBAF / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h, 3.) THF, 0 deg C, 1 h; room temperature, 3 h
View Scheme
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 82 percent / Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
2: 37 percent / SeO2, salicylic acid, t-BuOOH, H2O / CH2Cl2 / 20 h / Ambient temperature
3: 1.) MsCl, Et3N, 2.) LiBr / 1.) CH2Cl2, -40 deg C, 1 h, 2.) THF, 0 deg C, 2 h
4: 1.) BaI2*H2O, biphenyl radical, 3.) TBAF / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h, 3.) THF, 0 deg C, 1 h; room temperature, 3 h
View Scheme
Geraniol
106-24-1

Geraniol

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
3: Cu(acac)2 / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: phosphorus tribromide; pyridine / diethyl ether / -10 °C
2: potassium carbonate / acetone / 5 h / Reflux
3: potassium hydroxide / methanol / Reflux
4: sodium hydride / tetrahydrofuran; mineral oil / 20 °C
5: lithium aluminium tetrahydride / diethyl ether / 20 °C
View Scheme
trans geranyl acetone
3796-70-1

trans geranyl acetone

methoxy-ethynyl magnesium bromide

methoxy-ethynyl magnesium bromide

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / NaH / benzene
2: 88 percent / LiAlH4 / diethyl ether
View Scheme
pseudoionone
141-10-6

pseudoionone

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HEH, silica gel / benzene / 20 h / Heating; dark
2: 65 percent / NaH / benzene
3: 88 percent / LiAlH4 / diethyl ether
View Scheme
8-hydroxygeranyl acetate
37905-03-6

8-hydroxygeranyl acetate

Farnesol
106-28-5

Farnesol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: PBr3 / diethyl ether / 0.33 h / -25 °C
2: BuLi, N,N'-dimethyl-N,N'-propyleneurea / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h; 2.) -50 deg C, 1 h
3: KOH / diethyl ether; methanol / 1 h / Ambient temperature
4: Na, dibenzo<18>crown-6 / liquid ammonia; tetrahydrofuran / 0.03 h
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / 6 h / 50 °C
2: sodium hydroxide / water; ethanol / 5 h / 20 °C
3: copper(l) iodide / tetrahydrofuran / 12 h
View Scheme
dimethylallyl diphosphate
358-72-5

dimethylallyl diphosphate

isopentenyl diphosphate
358-71-4

isopentenyl diphosphate

A

Farnesol
106-28-5

Farnesol

B

Geranylgeraniol
24034-73-9

Geranylgeraniol

Conditions
ConditionsYield
Stage #1: dimethylallyl diphosphate; isopentyl pyrophosphate With DL-dithiothreitol; ammonium chloride; magnesium chloride at 37℃; for 1h; pH=8.5; Enzymatic reaction;
Stage #2: In isopropyl alcohol at 37℃; for 12h; Enzymatic reaction;
...Expand
Farnesol
106-28-5

Farnesol

Farnesal
502-67-0

Farnesal

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -63℃; for 0.5h;100%
With dipyridinium dichromate In dichloromethane at 0 - 25℃; for 24h;100%
With Dess-Martin periodane In dichloromethane at 20℃; Inert atmosphere;99%
Farnesol
106-28-5

Farnesol

farnesyl bromide
24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7

farnesyl bromide

Conditions
ConditionsYield
With pyridine; phosphorus tribromide In diethyl ether at 5℃; for 3h; Darkness;100%
With phosphorus tribromide In diethyl ether at 0℃; for 1h;99%
With phosphorus tribromide In pyridine99%
Farnesol
106-28-5

Farnesol

(2E,6E)-farnesyl chloride
6784-45-8, 67023-85-2, 72132-86-6, 67023-84-1

(2E,6E)-farnesyl chloride

Conditions
ConditionsYield
Stage #1: Farnesol With 2,4,6-trimethyl-pyridine; methanesulfonyl chloride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: With lithium chloride In N,N-dimethyl-formamide at 0℃; for 3h;		100%
With N-chloro-succinimide; dimethylsulfide99.1%
With phosphorus trichloride In diethyl ether at -5 - 20℃; for 1.75h;97%
Farnesol
106-28-5

Farnesol

acetic anhydride
108-24-7

acetic anhydride

(2E,6E)-farnesyl acetate
4128-17-0

(2E,6E)-farnesyl acetate

Conditions
ConditionsYield
With dmap In pyridine for 0.5h; Ambient temperature;100%
In pyridine for 3h;99%
In pyridine for 1h; Ambient temperature;99.5%
Farnesol
106-28-5

Farnesol

1-hydroxy-3,7,11-trimethyl-6,10-dodecadiene
37519-97-4

1-hydroxy-3,7,11-trimethyl-6,10-dodecadiene

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen In ethyl acetate for 0.666667h;100%
With hydrogen; {RhCl(PPh3)2}2 In tetrahydrofuran Ambient temperature;36%
With 5% active carbon-supported ruthenium; hydrogen In methanol at 120℃; under 30402 Torr; for 16h; Autoclave; stereoselective reaction;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Farnesol
106-28-5

Farnesol

3-oxo-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyloxy)propanoic acid

3-oxo-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyloxy)propanoic acid

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;100%
In toluene Heating;85%
Farnesol
106-28-5

Farnesol

trityl chloride
76-83-5

trityl chloride

((((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)methanetriyl)tribenzene

((((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)methanetriyl)tribenzene

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 23℃; for 32h;100%
Farnesol
106-28-5

Farnesol

3,7,11-trimethyldodecyl alcohol
6750-34-1

3,7,11-trimethyldodecyl alcohol

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethyl acetate99%
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 2068.65 Torr; for 5.5h;95%
With hydrogen; palladium on activated charcoal In ethanol for 21h;93%
Farnesol
106-28-5

Farnesol

2-acetoxy-ethanesulfinyl chloride
106730-50-1

2-acetoxy-ethanesulfinyl chloride

Acetic acid 2-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxysulfinyl)-ethyl ester
125417-10-9

Acetic acid 2-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxysulfinyl)-ethyl ester

Conditions
ConditionsYield
With pyridine at -20℃; for 0.583333h;99%
With pyridine97%
Farnesol
106-28-5

Farnesol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene
61890-77-5

(2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;99%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;99%
With dmap; triethylamine In dichloromethane for 6h; Ambient temperature;95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
Farnesol
106-28-5

Farnesol

ethyl isocyanate
109-90-0

ethyl isocyanate

ethyl 2E,6E-farnesyl carbamate

ethyl 2E,6E-farnesyl carbamate

Conditions
ConditionsYield
With pyridine; dmap for 3h; Ambient temperature;99%
Farnesol
106-28-5

Farnesol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(2E,6E)-1-((tert-butyldiphenylsilyl)oxy)-3,7,11-trimethyl-2,6,10-dodecatriene
151409-23-3

(2E,6E)-1-((tert-butyldiphenylsilyl)oxy)-3,7,11-trimethyl-2,6,10-dodecatriene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;99%
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide99%
With 1H-imidazole In dichloromethane at 0℃; for 1h;
Farnesol
106-28-5

Farnesol

ethyl vinyl ether
109-92-2

ethyl vinyl ether

(2E,6E)-1-(1-ethoxyethoxy)-3,7,11-trimethyldodeca-2,6,10-triene
1298063-48-5

(2E,6E)-1-(1-ethoxyethoxy)-3,7,11-trimethyldodeca-2,6,10-triene

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 2h; Inert atmosphere;99%
Farnesol
106-28-5

Farnesol

(-)-α-cuprenene

(-)-α-cuprenene

Conditions
ConditionsYield
With sesquiterpene synthases Cop6 from Coprinus cinereus In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;98.2%
Farnesol
106-28-5

Farnesol

A

N,N,2-trimethylpropionamide
21678-37-5

N,N,2-trimethylpropionamide

B

2(E),6(E)-farnesyl iodide
89111-65-9

2(E),6(E)-farnesyl iodide

Conditions
ConditionsYield
With 1-iodo-N,N,2-trimethylprop-1-en-1-amine In dichloromethane 1.) 0 deg C; 2.) rt., 3h;A n/a
B 98%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

Farnesol
106-28-5

Farnesol

2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)tetrahydro-2H-pyran
79577-53-0, 110990-63-1, 120732-61-8, 120732-65-2, 67858-93-9

2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; Addition;98%
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 1h;98%
With toluene-4-sulfonic acid98%
Farnesol
106-28-5

Farnesol

acetyl chloride
75-36-5

acetyl chloride

(2E,6E)-farnesyl acetate
4128-17-0

(2E,6E)-farnesyl acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 23h; Inert atmosphere;98%
With dmap; triethylamine at 0℃; for 3h;93%
Farnesol
106-28-5

Farnesol

((2S,3S)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl)methanol
147127-72-8

((2S,3S)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl)methanol

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve In dichloromethane at -34℃;97%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In decane; dichloromethane; acetonitrile at -40℃; for 10h; Sharpless Asymmetric Epoxidation; Inert atmosphere; Molecular sieve; Cooling with ice;95%
With diethyl (2R,3R)-tartrate87%
Farnesol
106-28-5

Farnesol

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Farnesal
502-67-0

Farnesal

Conditions
ConditionsYield
With hydrogenchloride; aluminum isopropoxide In n-heptane; cyclohexane; water; acetone97%
With hydrogenchloride; aluminum isopropoxide In hexane; benzene93%
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

Farnesol
106-28-5

Farnesol

2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)tetrahydro-2H-pyran
79577-53-0, 110990-63-1, 120732-61-8, 120732-65-2, 67858-93-9

2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 3h;97%
Farnesol
106-28-5

Farnesol

(3S)-(6E)-2,3-dihydrofarnesol
20576-54-9, 34083-92-6, 37519-97-4, 51411-24-6, 69686-26-6, 69743-81-3, 76190-00-6, 113889-56-8, 27745-36-4

(3S)-(6E)-2,3-dihydrofarnesol

Conditions
ConditionsYield
With diacetato[(R)-(+)-2,2-bis(di-p-tolylphosphono)-1,1′−binaphthyl]ruthenium(II); hydrogen In methanol at 20℃; under 26252.6 Torr; for 5h; High pressure; Autoclave; enantioselective reaction;96%
With hydrogen; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; ((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro( In methanol under 72402.6 Torr; for 24h; Hydrogenation;95%
With Ru2Cl4-((R)-2,2'-bis[di(p-tolyl)phosphino]-1,1'-binaphthyl)2N(ethyl)3; hydrogen In methanol at 20℃; under 30402 Torr; for 16h; Autoclave; stereoselective reaction;82%
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol
307-30-2

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol

Farnesol
106-28-5

Farnesol

(2E,6E)-3,7,11-Trimethyl-1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octyloxy)-dodeca-2,6,10-triene

(2E,6E)-3,7,11-Trimethyl-1-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-octyloxy)-dodeca-2,6,10-triene

Conditions
ConditionsYield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene for 2h; Ambient temperature;95%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

Farnesol
106-28-5

Farnesol

(E)-cinnamic acid (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester
128638-94-8

(E)-cinnamic acid (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester

Conditions
ConditionsYield
Stage #1: Farnesol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;		95%
Farnesol
106-28-5

Farnesol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

(2E,6E)-farnesyl triisopropylsilyl ether
1026784-62-2

(2E,6E)-farnesyl triisopropylsilyl ether

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 60h;94%
Farnesol
106-28-5

Farnesol

(S)-(-)-germacrene A
28028-64-0, 28387-44-2, 69460-21-5, 69460-22-6, 69609-31-0, 69609-33-2, 69686-13-1, 69686-14-2, 75023-40-4, 83509-17-5

(S)-(-)-germacrene A

Conditions
ConditionsYield
With germacrene A synthase from Nostoc sp. PCC7120 (NS1) In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;93.5%
Farnesol
106-28-5

Farnesol

(2R,3R)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl-methanol
85505-95-9

(2R,3R)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl-methanol

Conditions
ConditionsYield
With titanium(IV) isopropylate; D-(-)-diisopropyl tartrate In dichloromethane; tert-butyl alcohol at -45℃; Molecular sieve; Inert atmosphere;93%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate in the presence of molecular sieves;92%
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate In dichloromethane at -50 - -45℃; for 1h;84%
phthalimide
136918-14-4

phthalimide

Farnesol
106-28-5

Farnesol

N-farnesylphtalimide
123022-37-7

N-farnesylphtalimide

Conditions
ConditionsYield
With Zn(N3)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 4h; Ambient temperature;93%
Mitsunobu reaction;

(E,E)-Farnesol Chemical Properties

The Molecular Structure of (E,E)-Farnesol (CAS NO.106-28-5):

IUPAC Name:  2,6,10-Dodecatrien-1-ol,3,7,11-trimethyl-, (2E,6E)-
Molecular Formula: C15H26O
Molecular Weight: 222.366340 g/mol 
Index of Refraction: 1.485
Molar Refractivity: 72.77 cm3
Molar Volume: 253.8 cm3
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
XLogP3-AA: 4.8
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 7
Exact Mass: 222.198365
MonoIsotopic Mass: 222.198365
Topological Polar Surface Area: 20.2
Heavy Atom Count: 16 
Canonical SMILES: CC(=CCCC(=CCCC(=CCO)C)C)C
Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CO)/C)/C)C
InChI: 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
EINECS: 225-004-1
Classification Code: TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]

(E,E)-Farnesol Uses

 (E,E)-Farnesol (CAS NO.106-28-5) can be widely used as perfuming agent in cosmetics. It can also be used as food flavor.

(E,E)-Farnesol Safety Profile

Safety Statements: 24/25 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: JR4979000
F: 8

(E,E)-Farnesol Specification

 (E,E)-Farnesol (CAS NO.106-28-5) is also named as 2,6-Di-trans-farnesol ; 2-trans,6-trans-Farnesol ; Inhibitor A2 ; all-trans-Farnesol ; trans-Farnesol ; 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)- ; 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)- . (E,E)-Farnesol (CAS NO.106-28-5) is colorless oily liquid.

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