502-61-4

Basic information

• Product Name: FARNESENE
• Synonyms: FARNESENE;FARNESENE, TRANS-B-;FEMA 3839;(3E,6E)- alpha-Farnesene;(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene;(E;(E)-3, (E)-6-alpha-farnesene;(E,E)-alpha-farnesene
• CAS NO: 502-61-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 207-948-6
• Product Categories: Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 502-61-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 260 °C(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 0.844-0.8790 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00673mmHg at 25°C
• Refractive Index: n20/D 1.490-1.505(lit.)
• Storage Temp.: -20°C, Light sensitive
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: FARNESENE(CAS DataBase Reference)
• NIST Chemistry Reference: FARNESENE(502-61-4)
• EPA Substance Registry System: FARNESENE(502-61-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 502-61-4(Hazardous Substances Data)

Usage

Chemical Properties

Farnesene has a fruity, herbaceous odor.

Occurrence

Reported found in natural oils including angelica root oil (2,100 ppm), corn mint oil (<2,000 to 10,000 ppm), lemon peel oil (200 ppm), lime peel oil and peppermint oil (1,000 to 10,000 ppm) Also found in apple, chamomile, grapefruit juice, ginger, lemon juice, lime juice, mandarin peel, nutmeg, pear, grape, pepper, quince, rosemary, basil, sage, tea and thymus

Uses

α-Farnesene acts as an alarm pheromone in termites; also acts as a food attractants for the apple tree pest, the codling moth. α-Farnesene is also the chief compound contributing to the scent of gardenia, making up ~65% of the headspace constituents.

Definition

ChEBI: A farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.

Preparation

Isolation from natural coating of apples and oil of perilla.

Aroma threshold values

Aroma characteristics at 1.0%: dry woody, green leafy, herbal and vegetative with a foral nuance It has juniper berry and citrus nuances.

Taste threshold values

Taste characteristics at 10 to 20 ppm: woody juniper berry and woody, berry-like with nuances of ginger and tropical mango.

Synthesis Reference(s)

The Journal of Organic Chemistry, 34, p. 3789, 1969 DOI: 10.1021/jo01264a011

InChI:InChI=1/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

Synthetic route

(2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-3-methyl-2,5-dihydrothiophen 1,1-dioxide (94987-60-7) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
In xylene for 0.0833333h; Heating;	93%
In xylene Heating;	83%
With pyridine at 150℃; for 3h; Inert atmosphere;	80%
Multi-step reaction with 4 steps 1: 1.) H2O, NBS, 2.) K2CO3 / 1.) THF, 0 deg C, 1 h, 2.) MeOH 2: 73 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 3: 78.3 percent / xylene / 0.08 h / Heating 4: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme
Multi-step reaction with 4 steps 1: 1.) H2O, NBS, 2.) K2CO3 / 1.) THF, 0 deg C, 1 h, 2.) MeOH 2: 92 percent / xylene / 0.08 h / Heating 3: 42 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 4: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) → (E)-β-farnesene (18794-84-8) + (3Z,6E)-α-farnesene (26560-14-5) + (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With pyridine In dimethyl sulfoxide at 160℃; for 0.0833333h;	A 29% B 36% C 17%
With trichlorophosphate In dimethyl sulfoxide at 160℃; for 0.0833333h;	A 29% B 36% C 17%
With pyridine; trichlorophosphate In dimethyl sulfoxide at 160℃; for 0.0833333h;	A 29% B 36% C 17%
With pyridine; trichlorophosphate

(E)-β-farnesene (18794-84-8) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
rhodium(II) chloride In ethanol

(E)-β-farnesene (18794-84-8) → (E,E)-alpha-farnesene (502-61-4) + trans(C10)allofarnesene (26560-15-6)

Conditions	Yield
rhodium(II) chloride In ethanol

Farnesol (106-28-5) → (E)-β-farnesene (18794-84-8) + (E,E)-alpha-farnesene (502-61-4) + (Z)-γ-bisabolene (495-62-5, 5957-36-8, 13062-00-5, 53585-13-0, 90458-95-0) + β-bisabolene (4891-79-6)

Conditions	Yield
With potassium hydrogensulfate

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) → (E)-β-farnesene (18794-84-8) + (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With dimethyl sulfoxide Heating;

(3E,6E)-3,7,11-trimethyl-dodeca-3,6,10-triene-1,2-diol (57078-00-9) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
(i) PBr3, CuBr, Et2O, (ii) Zn; Multistep reaction;
(i) CuBr, PBr3, (ii) Zn; Multistep reaction;

phosphoric acid diphenyl ester (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester (63023-44-9) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
In diethyl ether

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienal (31180-97-9) + Methylenetriphenylphosphorane (19493-09-5) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
In dimethyl sulfoxide at 40℃; for 3h;

3-buten-1-yne (689-97-4) + trimethylaluminum (75-24-1) + 1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); zirconocene dichloride 1.) 1,2-dichloroethane, xylene, room temperature, 12 h, 2.) THF, room temperature, 3 h; Yield given. Multistep reaction;

isopropyltriphenylphosphonium iodide (24470-78-8) + 4,8-dimethyldeca-4E,7E,9-trienal (28977-59-5) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With n-butyllithium 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min; Yield given. Multistep reaction;

(6E)-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol → (3Z,6E)-α-farnesene (26560-14-5) + (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Yield given. Yields of byproduct given;

(6E)-threo-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol → (3Z,6E)-α-farnesene (26560-14-5) + (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Yield given;

(6E)-erythro-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol → (3Z,6E)-α-farnesene (26560-14-5) + (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Yield given;

(+/-)-nerolidol (7212-44-4) → (E)-β-farnesene (18794-84-8) + (E,E)-alpha-farnesene (502-61-4) + (Z)-beta-Farnesene (28973-97-9) + (Z,Z)-α-farnesene (28973-99-1)

Conditions	Yield
With pyridine; trichlorophosphate 1) ice bath, 1 h; 2) rt, 12 h; Title compound not separated from byproducts;

farnesyl pyrophosphate (372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5) → (E)-β-farnesene (18794-84-8) + (E,E)-alpha-farnesene (502-61-4) + [E]-γ-bisabolene (53585-13-0) + γ-curcumene (451-55-8)

Conditions	Yield
With taxadiene synthase In phosphate buffer at 30℃; Product distribution; Enzymatic reaction;

Farnesol (106-28-5) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
With Dowex 50W-X4 cation exchange resin In hexane for 4h; Heating;
Multi-step reaction with 2 steps 1: KHSO4 2: RhCl2 / ethanol View Scheme
Multi-step reaction with 2 steps 1: KHSO4 2: RhCl2 / ethanol View Scheme
Multi-step reaction with 2 steps 1: (i) VO(acac)2, tBuO2H, benzene, (ii) Me3SiCl, hexamethyldisilazane, Py, (iii) diethylaluminium 2,2,6,6-tetramethyl-piperidide, (iv) KF, aq. MeOH 2: (i) PBr3, CuBr, Et2O, (ii) Zn View Scheme

trans-geranyl bromide (6138-90-5) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / BuLi / hexane; diethyl ether / 1.) 20 deg C, 15 min, 2.) -78 deg C, 30 min; r.t., 30 min 2: LDA / diethyl ether / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min; 25 deg C, 30 min 3: NaH / dimethylformamide View Scheme
Multi-step reaction with 3 steps 1: 72 percent / BuLi / hexane; diethyl ether / 1.) 20 deg C, 15 min, 2.) -78 deg C, 30 min; r.t., 30 min 2: LDA / diethyl ether / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min; 25 deg C, 30 min 3: NaH / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: 1.) BuLi 2: 83 percent / xylene / Heating View Scheme

1-(Diphenylphosphinyl)-4,8-dimethyl-3,7-nonadiene (170238-66-1) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: LDA / diethyl ether / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min; 25 deg C, 30 min 2: NaH / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: LDA / diethyl ether / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min; 25 deg C, 30 min 2: NaH / dimethylformamide View Scheme

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene (153580-68-8) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 42 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme

2-3'-methyl-6'-oxohexa-2'E-enyl-3-methyl-2,5-dihydrothiophene-1,1-dioxide (162189-12-0) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min 2: 93 percent / xylene / 0.08 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min 2: 1.) H2O, NBS, 2.) K2CO3 / 1.) THF, 0 deg C, 1 h, 2.) MeOH 3: 92 percent / xylene / 0.08 h / Heating 4: 42 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 5: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme
Multi-step reaction with 2 steps 1: 78.3 percent / xylene / 0.08 h / Heating 2: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme

2-Methyl-3-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-ylmethyl)-2-(4-methyl-pent-3-enyl)-oxirane (162189-10-8) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 2: 78.3 percent / xylene / 0.08 h / Heating 3: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme

2-3',7'-dimethyl-6',7'-epoxyocta-2'E-enyl-3-methyl-2,5-dihydrothiophene-1,1-dioxide → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / xylene / 0.08 h / Heating 2: 42 percent / periodic acid / tetrahydrofuran / 0.03 h / Ambient temperature 3: 1.) n-BuLi / 1.) THF, pentane, RT, 2.) THF, pentane, -78 deg C, 15 min View Scheme

3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) BuLi 2: 83 percent / xylene / Heating View Scheme

2-((Z)-3,7-dimethyl-octa-2,6-dienyl)-[1,3]dioxolane (31180-93-5) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: TsOH / acetone; H2O / 4 h / Ambient temperature 2: (i) NaH, diglyme, (ii) /BRN= 2238274/ 3: LiAlH4 / diethyl ether / 2 h / Ambient temperature 4: MnO2 / petroleum ether / 8 h 5: dimethylsulfoxide / 3 h / 40 °C View Scheme

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH 2: RhCl2 / ethanol View Scheme
Multi-step reaction with 2 steps 1: KOH 2: RhCl2 / ethanol View Scheme

(Z)-4,8-dimethylnona-3,7-dienal (76826-74-9) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) NaH, diglyme, (ii) /BRN= 2238274/ 2: LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: MnO2 / petroleum ether / 8 h 4: dimethylsulfoxide / 3 h / 40 °C View Scheme

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trien-1-ol (31180-96-8) → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: MnO2 / petroleum ether / 8 h 2: dimethylsulfoxide / 3 h / 40 °C View Scheme

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienoic acid ethyl ester → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether / 2 h / Ambient temperature 2: MnO2 / petroleum ether / 8 h 3: dimethylsulfoxide / 3 h / 40 °C View Scheme

[3t-((E)-4,8-dimethyl-nona-3,7-dienyl)-3c-methyl-oxiran-r-ylmethoxy]-trimethyl-silane → (E,E)-alpha-farnesene (502-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) diethylaluminium 2,2,6,6-tetramethyl-piperidide, benzene, (ii) KF, aq. MeOH 2: (i) CuBr, PBr3, (ii) Zn View Scheme

(E,E)-alpha-farnesene (502-61-4) + ethyl acetoacetate (141-97-9) → (4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate (51921-98-3)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine at 50℃; for 24h; Temperature; Large scale;	94%

(E,E)-alpha-farnesene (502-61-4) + acetoacetic acid methyl ester (105-45-3) → methyl (4E,8E)-2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine In ethanol at 70℃; for 15h; Large scale;	93%

formaldehyd (50-00-0) + 2-(2-naphthyl)pyridine (66318-88-5) + (E,E)-alpha-farnesene (502-61-4) → C31H37NO

Conditions	Yield
With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; acetic acid In 1,4-dioxane at 50℃; for 16h;	63%

(E,E)-alpha-farnesene (502-61-4) → 6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene + 10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene (153580-68-8) + 3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene + 3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature;	A 11% B 31% C 2% D 1%
With sodium acetate; 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 0 deg C, 15 min, 2.) 1 h; Further byproducts given;	A n/a B 20% C n/a D n/a

(E,E)-alpha-farnesene (502-61-4) → (-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol + (-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol (162250-46-6) + (-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol (162250-47-7)

Conditions	Yield
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) at 0℃; for 6h; Product distribution; with other phthalazines;	A 28% B 11% C 7%
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) at 0℃; for 6h;	A 28% B 11% C 7%

(E,E)-alpha-farnesene (502-61-4) → 3,4:10,11-bisepoxy-3,7,11-trimethyldodeca-1,6-diene + 3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

Conditions	Yield
With sodium acetate; 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 0 deg C, 15 min, 2.) 1 h;	A 9% B 19%

(E,E)-alpha-farnesene (502-61-4) → (+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol + (+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol (162250-48-8) + (+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol (168611-56-1)

Conditions	Yield
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) at 0℃; for 6h;	A 18% B 15% C 14%

(E,E)-alpha-farnesene (502-61-4) → (+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol + (+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol (162250-48-8) + (+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol (168611-56-1) + (+)-(3R,4R,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

Conditions	Yield
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yields of byproduct given;	A n/a B 15% C n/a D n/a
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yields of byproduct given;	A n/a B n/a C 14% D n/a
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(E,E)-alpha-farnesene (502-61-4) → (-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol + (-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol (162250-46-6) + (-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol (162250-47-7) + (-)-(3S,4S,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

Conditions	Yield
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yields of byproduct given;	A n/a B 11% C n/a D n/a
With osmium(VIII) oxide; (DHQ)2-PHAL; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yields of byproduct given;	A n/a B n/a C 7% D n/a
With osmium(VIII) oxide; (DHQ)2-PHAL; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(E,E)-alpha-farnesene (502-61-4) → 6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene + 10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene (153580-68-8) + 3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane for 1h;	A 5% B 7% C 9%

(E,E)-alpha-farnesene (502-61-4) → 6-Methyl-hept-5-en-2-on (110-93-0)

Conditions	Yield
With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide In dichloromethane for 2h;	6%

(E,E)-alpha-farnesene (502-61-4) + acetic anhydride (108-24-7) → [(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] acetate (40266-29-3)

Conditions	Yield
With manganese triacetate In acetic acid for 1.5h; Heating;	4%

(E,E)-alpha-farnesene (502-61-4) → 2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol (17909-91-0)

Conditions	Yield
With selenium(IV) oxide In ethanol at 80℃; for 0.333333h; Product distribution; other oxidizers (photooxidizers) and products;	3%
With selenium(IV) oxide In ethanol at 80℃; for 0.333333h;	3%

(E,E)-alpha-farnesene (502-61-4) → 2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol (17909-91-0) + 3,7,11-trimethyldodeca-1,3,6,10-tetraen-8-ol

Conditions	Yield
With selenium(IV) oxide; 4-methylmorpholine N-oxide In methanol; dichloromethane for 6h; Heating;	A 1% B 1%

(E,E)-alpha-farnesene (502-61-4) → (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene (3899-18-1)

Conditions	Yield
(i) (irradiation), (ii) Na, EtOH; Multistep reaction;

(E,E)-alpha-farnesene (502-61-4) → (3Z,6E)-α-farnesene (26560-14-5)

Conditions	Yield
In benzene Irradiation;

(E,E)-alpha-farnesene (502-61-4) → 3,7,11-trimethyldodeca-1,3(E),5(E),10-tetraen-7-ol (67832-25-1, 340013-36-7)

Conditions	Yield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;

(E,E)-alpha-farnesene (502-61-4) → (E)-3,11-dimethyl-7-methylene-dodeca-1,3,10-trien-6-ol (30220-29-2)

Conditions	Yield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;

(E,E)-alpha-farnesene (502-61-4) → 3,7-dimethyl-11-methylenedodeca-1,3,6-trien-10-ol (30220-28-1)

Conditions	Yield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;

(E,E)-alpha-farnesene (502-61-4) → 3,7,11-trimethyldodeca-1,3,6,9-tetraen-11-ol (30220-27-0)

Conditions	Yield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;

Upstream product

• 3790-78-1 cis-nerolidol 
• 40716-66-3 (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 
• 63023-44-9 phosphoric acid diphenyl ester (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester 
• 94987-60-7 (2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-3-methyl-2,5-dihydrothiophen 1,1-dioxide 
• 689-97-4 3-buten-1-yne 
• 75-24-1 trimethylaluminum 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 31180-97-9 (2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienal 
• 19493-09-5 Methylenetriphenylphosphorane 
• 106-28-5 Farnesol 
• 18794-84-8 (E)-β-farnesene 
• 20536-36-1 neryl chloride 
• 372-97-4 farnesyl pyrophosphate 
• 4128-17-0 (2E,6E)-farnesyl acetate 

Downstream Products

• 26560-14-5 (3Z,6E)-α-farnesene 
• 1150-17-0 (E)-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-en-2-one 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 127-47-9 Retinol acetate 
• 68-26-8 RETINOL 
• 39668-33-2 (+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-nonatetraene-(1.3.5.8) 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 111-01-3 2,6,10,15,19,23-hexamethyltetracosane 
• 626-96-0 4-oxopentanal 
• 67-64-1 acetone 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 3891-98-3 2,6,10-trimethyldodecane 

Relevant articles and documents

PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL

An in-situ method for making a conjugated diene from an allyl alcohol comprising the conversion of the allyl alcohol to an allyl carbonate, allyl ester or allyl formate with concomitant or subsequent conversion of the allyl carbonate, allyl ester or allyl formate to the conjugated diene; the products obtained by said method, and the uses of said products.

Templating effects in aristolochene synthase catalysis: Elimination versus cyclisation

Analysis of the products generated by mutants of aristolochene synthase from P. roqueforti (PR-AS) revealed the prominent structural role played by the aliphatic residue Leu 108 in maintaining the productive conformation of farnesyl diphosphate to ensure C1-C10 (σ-bond) ring-closure and hence (+)-aristolochene production.

Sesquiterpenes produced by truncated taxadiene synthase

Soluble, highly active N-terminal truncated taxadiene synthase catalyzes the formation of an isomeric mixture of taxadienes from geranylgeranyl diphosphate. Farnesyl diphosphate was also found to be a good substrate, producing four sesquiterpenes which were characterized. The dual activities of taxadiene synthase and product inhibition caused by sesquiterpene metabolites make it imperative that active GGDP synthase be present in order for multi-enzyme systems to follow the taxol pathway in vitro. (C) 2000 Published by Elsevier Science Ltd.