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502-61-4

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502-61-4 Usage

Description

Farnesene, also known as α-farnesene, is a naturally occurring organic compound with a chemical structure of 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7, and 11 respectively. It is characterized by its fruity, herbaceous odor and is found in various natural oils and plants.

Uses

Used in Pheromone Production:
Farnesene is used as an alarm pheromone in termites, playing a crucial role in their communication and defense mechanisms.
Used in Pest Attraction:
It acts as a food attractant for the codling moth, an apple tree pest, making it useful in pest control strategies.
Used in Fragrance Industry:
Farnesene is used as a key compound in the scent of gardenia, contributing to approximately 65% of the headspace constituents. Its aroma characteristics include dry woody, green leafy, herbal, and vegetative notes with a floral nuance, as well as juniper berry and citrus nuances.
Used in Flavor Industry:
Farnesene is used to impart woody juniper berry and woody, berry-like taste characteristics with nuances of ginger and tropical mango in the flavor industry, with taste threshold values ranging from 10 to 20 ppm.
Used in Natural Oils:
Farnesene is found in various natural oils, including angelica root oil, corn mint oil, lemon peel oil, lime peel oil, and peppermint oil, contributing to their unique scents and flavors.
Used in Food Industry:
Farnesene is found in various fruits and spices such as apple, chamomile, grapefruit juice, ginger, lemon juice, lime juice, mandarin peel, nutmeg, pear, grape, pepper, quince, rosemary, basil, sage, tea, and thymus, enhancing their flavors and aromas.

Preparation

Isolation from natural coating of apples and oil of perilla.

Synthesis Reference(s)

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

Check Digit Verification of cas no

The CAS Registry Mumber 502-61-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 502-61:
(5*5)+(4*0)+(3*2)+(2*6)+(1*1)=44
44 % 10 = 4
So 502-61-4 is a valid CAS Registry Number.
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+

502-61-4Synthetic route

(2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-3-methyl-2,5-dihydrothiophen 1,1-dioxide
94987-60-7

(2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-3-methyl-2,5-dihydrothiophen 1,1-dioxide

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

A

(E)-β-farnesene
18794-84-8

(E)-β-farnesene

B

(3Z,6E)-α-farnesene
26560-14-5

(3Z,6E)-α-farnesene

C

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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)-β-farnesene

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
rhodium(II) chloride In ethanol
(E)-β-farnesene
18794-84-8

(E)-β-farnesene

A

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

B

trans(C10)allofarnesene
26560-15-6

trans(C10)allofarnesene

Conditions
ConditionsYield
rhodium(II) chloride In ethanol
Farnesol
106-28-5

Farnesol

A

(E)-β-farnesene
18794-84-8

(E)-β-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

D

β-bisabolene
4891-79-6

β-bisabolene

Conditions
ConditionsYield
With potassium hydrogensulfate
(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

(E)-β-farnesene
18794-84-8

(E)-β-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
With dimethyl sulfoxide Heating;
(3E,6E)-3,7,11-trimethyl-dodeca-3,6,10-triene-1,2-diol
57078-00-9

(3E,6E)-3,7,11-trimethyl-dodeca-3,6,10-triene-1,2-diol

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
(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

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

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
In diethyl ether
(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienal
31180-97-9

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienal

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
In dimethyl sulfoxide at 40℃; for 3h;
3-buten-1-yne
689-97-4

3-buten-1-yne

trimethylaluminum
75-24-1

trimethylaluminum

1-chloro-3,7-dimethylocta-2,6-diene
5389-87-7

1-chloro-3,7-dimethylocta-2,6-diene

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

isopropyltriphenylphosphonium iodide

4,8-dimethyldeca-4E,7E,9-trienal
28977-59-5

4,8-dimethyldeca-4E,7E,9-trienal

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(6E)-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol

A

(3Z,6E)-α-farnesene
26560-14-5

(3Z,6E)-α-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(6E)-threo-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol

A

(3Z,6E)-α-farnesene
26560-14-5

(3Z,6E)-α-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide Yield given;
(6E)-erythro-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol

(6E)-erythro-3,7,11-Trimethyl-4-(diphenylphosphinyl)dodecatrien-3-ol

A

(3Z,6E)-α-farnesene
26560-14-5

(3Z,6E)-α-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide Yield given;
(+/-)-nerolidol
7212-44-4

(+/-)-nerolidol

A

(E)-β-farnesene
18794-84-8

(E)-β-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

C

(Z)-beta-Farnesene
28973-97-9

(Z)-beta-Farnesene

D

(Z,Z)-α-farnesene
28973-99-1

(Z,Z)-α-farnesene

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

A

(E)-β-farnesene
18794-84-8

(E)-β-farnesene

B

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

C

[E]-γ-bisabolene
53585-13-0

[E]-γ-bisabolene

D

γ-curcumene
451-55-8

γ-curcumene

Conditions
ConditionsYield
With taxadiene synthase In phosphate buffer at 30℃; Product distribution; Enzymatic reaction;
Farnesol
106-28-5

Farnesol

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

trans-geranyl bromide

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

1-(Diphenylphosphinyl)-4,8-dimethyl-3,7-nonadiene

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

2-3'-methyl-6'-oxohexa-2'E-enyl-3-methyl-2,5-dihydrothiophene-1,1-dioxide

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

2-Methyl-3-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ6-thiophen-2-ylmethyl)-2-(4-methyl-pent-3-enyl)-oxirane

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

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

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

3-methyl-2,5-dihydrothiophen-1,1-dioxide

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

2-((Z)-3,7-dimethyl-octa-2,6-dienyl)-[1,3]dioxolane

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(Z)-4,8-dimethylnona-3,7-dienal

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trien-1-ol

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(2Ξ,5Z)-2,6,10-trimethyl-undeca-2,5,9-trienoic acid ethyl ester

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

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

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

(4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate
51921-98-3

(4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine at 50℃; for 24h; Temperature; Large scale;94%
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl (4E,8E)-2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate

methyl (4E,8E)-2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine In ethanol at 70℃; for 15h; Large scale;93%
formaldehyd
50-00-0

formaldehyd

2-(2-naphthyl)pyridine
66318-88-5

2-(2-naphthyl)pyridine

(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

C31H37NO

C31H37NO

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene

6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene

B

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene
153580-68-8

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene

C

3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene

3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene

D

3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

(-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

(-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

B

(-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol
162250-46-6

(-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol

C

(-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol
162250-47-7

(-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

3,4:10,11-bisepoxy-3,7,11-trimethyldodeca-1,6-diene

3,4:10,11-bisepoxy-3,7,11-trimethyldodeca-1,6-diene

B

3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

3,4;10,11-diepoxy-3,7,11-trimethyldodeca-1,3E-diene

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

(+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

(+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

B

(+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol
162250-48-8

(+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol

C

(+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol
168611-56-1

(+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

(+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

(+)-(3E,6R,7R)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

B

(+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol
162250-48-8

(+)-(3E,6E,10R)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol

C

(+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol
168611-56-1

(+)-(3E,6R,7R,10R)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-tetraol

D

(+)-(3R,4R,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

(+)-(3R,4R,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

(-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

(-)-(3E,6S,7S)-3,7,11-trimethyldodeca-1,3,10-triene-6,7-diol

B

(-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol
162250-46-6

(-)-(3E,6E,10S)-3,7,11-trimethyldodeca-1,3,6-triene-10,11-diol

C

(-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol
162250-47-7

(-)-(3E,6S,7S,10S)-3,7,11-trimethyldodeca-1,3-diene-6,7,10,11-triol

D

(-)-(3S,4S,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

(-)-(3S,4S,6E)-3,7,11-trimethyldodeca-1,6,10-triene-3,4-diol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene

6,7-epoxy-3,7,11-trimethyldodeca-1,3,10-triene

B

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene
153580-68-8

10,11-epoxy-3,7,11-trimethyldodeca-1,3E,6E-triene

C

3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene

3,4-epoxy-3,7,11-trimethyldodeca-1,6E,10-triene

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In dichloromethane for 1h;A 5%
B 7%
C 9%
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

Conditions
ConditionsYield
With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide In dichloromethane for 2h;6%
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

acetic anhydride
108-24-7

acetic anhydride

[(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] acetate
40266-29-3

[(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] acetate

Conditions
ConditionsYield
With manganese triacetate In acetic acid for 1.5h; Heating;4%
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol
17909-91-0

2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

A

2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol
17909-91-0

2,6,10-trimethyldodeca-2,6,9,11-tetraen-1-ol

B

3,7,11-trimethyldodeca-1,3,6,10-tetraen-8-ol

3,7,11-trimethyldodeca-1,3,6,10-tetraen-8-ol

Conditions
ConditionsYield
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

(E,E)-alpha-farnesene

(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene
3899-18-1

(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene

Conditions
ConditionsYield
(i) (irradiation), (ii) Na, EtOH; Multistep reaction;
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

(3Z,6E)-α-farnesene
26560-14-5

(3Z,6E)-α-farnesene

Conditions
ConditionsYield
In benzene Irradiation;
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

3,7,11-trimethyldodeca-1,3(E),5(E),10-tetraen-7-ol
67832-25-1, 340013-36-7

3,7,11-trimethyldodeca-1,3(E),5(E),10-tetraen-7-ol

Conditions
ConditionsYield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

(E)-3,11-dimethyl-7-methylene-dodeca-1,3,10-trien-6-ol
30220-29-2

(E)-3,11-dimethyl-7-methylene-dodeca-1,3,10-trien-6-ol

Conditions
ConditionsYield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

3,7-dimethyl-11-methylenedodeca-1,3,6-trien-10-ol
30220-28-1

3,7-dimethyl-11-methylenedodeca-1,3,6-trien-10-ol

Conditions
ConditionsYield
(i) eosine, O2, EtOH, (ii) NaBH4, (iii) H2O; Multistep reaction;
(E,E)-alpha-farnesene
502-61-4

(E,E)-alpha-farnesene

3,7,11-trimethyldodeca-1,3,6,9-tetraen-11-ol
30220-27-0

3,7,11-trimethyldodeca-1,3,6,9-tetraen-11-ol

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

502-61-4Relevant articles and documents

PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL

-

Page/Page column 36, (2022/01/05)

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

Faraldos, Juan A.,Gonzalez, Veronica,Senske, Michael,Allemann, Rudolf K.

supporting information; experimental part, p. 6920 - 6923 (2011/11/04)

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

Huang,Williams,Roessner,Scott

, p. 9701 - 9704 (2007/10/03)

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.

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