PHYTOL supplier | CasNO.150-86-7

Name
PHYTOL
EINECS 205-776-6
CAS No. 150-86-7
Article Data16
CAS DataBase
Density 0.845 g/cm₃
Solubility
Melting Point <25 °C
Formula C₂₀H₄₀O
Boiling Point 335.5 °C at 760 mmHg
Molecular Weight 296.537
Flash Point 157.5 °C
Transport Information
Appearance
Safety 37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Hexadecen-1-ol,3,7,11,15-tetramethyl-, [R-[R*,R*-(E)]]-;Phytol (6CI,8CI);(7R,11R,2E)-Phytol;(E)-Phytol;(E,R,R)-Phytol;trans-Phytol;
PSA 20.23000
LogP 6.36410

Synthetic route

: 7437-61-8
2-methyl-3,4-epoxy-1-butene

: 130627-55-3
(3R,7R)-3,7,11-Trimethyldodecylmagnesium-bromid

: 150-86-7
phytol

Conditions

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -20 - 0℃; for 24h;	95%

: 66432-63-1
(2E,7R,11R)-Phytyl-(2'-tetrahydropyranyl)aether

: 150-86-7
phytol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 55℃; for 1.5h;	94%

: 92116-50-2
(E)-(7R,11R)-1-(1'-ethoxy)ethoxy-3,7,11,15-tetramethyl-2-hexadecene

: 150-86-7
phytol

Conditions

Conditions	Yield
With hydrogenchloride; ammonium chloride In tetrahydrofuran at 0 - 20℃; for 3h;	68%

: 679841-68-0
2',4'-dimethylpent-3'-yl (7R,11R)-3,7,11,15-tetramethyl-5-methanesulfonyloxyhexadec-2-enoate

: 150-86-7
phytol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Heating;	67%

: 13853-16-2
(2E,7R,11R)-3,7,11,15-tetramethyl-hexadec-2-enoic acid methyl ester

: 150-86-7
phytol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether at 0℃;

: 101541-51-9
(2Z,7R,11R)-3,7,11,15-tetramethyl-hexadec-2-enoic acid ethyl ester

: 150-86-7
phytol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride

chlorophyll: chlorophyll

: 150-86-7
phytol

Conditions

Conditions	Yield
With lithium hydroxide
With tetramethyl ammoniumhydroxide

: 50-00-0
formaldehyd

: 75-24-1
trimethylaluminum

: 179991-80-1
6,10,14-Trimethyl-pentadec-1-yne

A: (2E,7S,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol

B: 150-86-7
phytol

Conditions

Conditions	Yield
Stage #1: trimethylaluminum; 6,10,14-Trimethyl-pentadec-1-yne With zirconocene dichloride In 1,2-dichloro-ethane Stage #2: With n-butyllithium In tetrahydrofuran Stage #3: formaldehyd In tetrahydrofuran Further stages.;

...Expand

: 105470-79-9
(3R,7R,5E)-3,7,11-trimethyldodecan-1-al

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 2: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 3: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 541-47-9
3-Methylbutenoic acid

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 81 percent / DMAP; DCC / CH2Cl2 / 3 h / 20 °C 2.1: (i-Pr)2NLi / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 99 percent / hexane; tetrahydrofuran / 1 h / -78 - 20 °C 3.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 4.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 5.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 54307-74-3, 15466-88-3
(R)-5-methyl-cyclohex-2-enone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 74 percent / Et2AlI / hexane; CH2Cl2 / 0.5 h / 0 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C 3.1: Li / tetrahydrofuran / 26 h 3.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 3.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 4.1: Li / tetrahydrofuran 4.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 4.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 5.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 6.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 7.1: 54 percent / pyridine / CH2Cl2 / 4 h 8.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 9.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 10.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 11.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 12.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 13.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 74 percent / Et2AlI / hexane; CH2Cl2 / 0.5 h / 0 °C
2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C
2.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C
3.1: Li / tetrahydrofuran / 26 h
3.2: CuI / tetrahydrofuran / 0.33 h / -20 °C
3.3: 169 mg / tetrahydrofuran / 1 h / -20 °C
4.1: Li / tetrahydrofuran
4.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
4.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
5.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
6.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
7.1: 54 percent / pyridine / CH2Cl2 / 4 h
8.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
9.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
10.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
11.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
12.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
13.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 73311-67-8
1-(2',4'-dimethylpent-3'-yloxy)-3-methyl-1-trimethylsilyloxybuta-1,3-diene

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 2: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 3: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 626-88-0
1-bromo-5-methylpentane

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: Li / tetrahydrofuran 1.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 1.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 2.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 3.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 4.1: 54 percent / pyridine / CH2Cl2 / 4 h 5.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 6.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 7.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 8.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 9.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 10.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 10 steps
1.1: Li / tetrahydrofuran
1.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
1.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
2.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
3.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
4.1: 54 percent / pyridine / CH2Cl2 / 4 h
5.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
6.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
7.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
8.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
9.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
10.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-33-9
(3R,5S,1'Z)-2-ethylidene-3-dimethyl(phenyl)silyl-5-methylcyclohexanone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: Li / tetrahydrofuran 1.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 1.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 2.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 3.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 4.1: 54 percent / pyridine / CH2Cl2 / 4 h 5.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 6.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 7.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 8.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 9.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 10.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

: 73311-65-6
2,4-dimethylpent-3-yl 3-methylbut-2-enoate

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: (i-Pr)2NLi / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 99 percent / hexane; tetrahydrofuran / 1 h / -78 - 20 °C 2.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 3.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 679841-37-3
(5R)-2-(1'-hydroxyethyl)-5-methylcyclohex-2-enone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 1.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Li / tetrahydrofuran / 26 h 2.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 2.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 3.1: Li / tetrahydrofuran 3.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 6.1: 54 percent / pyridine / CH2Cl2 / 4 h 7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 12.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 12 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - 0 °C
1.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 - 20 °C
2.1: Li / tetrahydrofuran / 26 h
2.2: CuI / tetrahydrofuran / 0.33 h / -20 °C
2.3: 169 mg / tetrahydrofuran / 1 h / -20 °C
3.1: Li / tetrahydrofuran
3.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
5.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
6.1: 54 percent / pyridine / CH2Cl2 / 4 h
7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
12.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-58-8
(5R)-2-(1'-methoxycarbonyloxyethyl)-5-methylcyclohex-2-enone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: Li / tetrahydrofuran / 26 h 1.2: CuI / tetrahydrofuran / 0.33 h / -20 °C 1.3: 169 mg / tetrahydrofuran / 1 h / -20 °C 2.1: Li / tetrahydrofuran 2.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 5.1: 54 percent / pyridine / CH2Cl2 / 4 h 6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 11.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 11 steps
1.1: Li / tetrahydrofuran / 26 h
1.2: CuI / tetrahydrofuran / 0.33 h / -20 °C
1.3: 169 mg / tetrahydrofuran / 1 h / -20 °C
2.1: Li / tetrahydrofuran
2.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
4.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
5.1: 54 percent / pyridine / CH2Cl2 / 4 h
6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
11.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-66-8
(3R,7R,5E)-3,7,11-trimethyldodec-5-en-1-al

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 2: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 3: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 679841-42-0
(3R,7R,5E)-3,7,11-trimethyldodec-5-enonitrile

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 2: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 3: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 4: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 5: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 679841-36-2
(2R,3R,5S)-2-(1'-hydroxyethyl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 92 percent / N,N-4-dimethylaminopyridine; pyridine / CH2Cl2 / 12 h / 0 °C 2.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C 3.1: Li / tetrahydrofuran 3.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 6.1: 54 percent / pyridine / CH2Cl2 / 4 h 7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 12.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 92 percent / N,N-4-dimethylaminopyridine; pyridine / CH2Cl2 / 12 h / 0 °C
2.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C
3.1: Li / tetrahydrofuran
3.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
3.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
4.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
5.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
6.1: 54 percent / pyridine / CH2Cl2 / 4 h
7.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
8.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
9.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
10.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
11.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
12.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-55-5
(2R,3R,5S)-2-(1'-acetoxyethyl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C 2.1: Li / tetrahydrofuran 2.2: CuBrMe2S / tetrahydrofuran / 0.5 h / -20 °C 2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 66 percent / NH2OHHCl; pyridine / ethanol / Heating 5.1: 54 percent / pyridine / CH2Cl2 / 4 h 6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 11.1: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 98 percent / DBU / dimethylformamide / 5 h / 100 °C
2.1: Li / tetrahydrofuran
2.2: CuBr*Me2S / tetrahydrofuran / 0.5 h / -20 °C
2.3: 670 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
3.1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
4.1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
5.1: 54 percent / pyridine / CH2Cl2 / 4 h
6.1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
7.1: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
8.1: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
9.1: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
10.1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
11.1: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-40-8
(2R,3R,5S,2'R)-2-(6'-methylhept-2'-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 2: 54 percent / pyridine / CH2Cl2 / 4 h 3: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 4: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 5: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 6: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 7: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 8: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 8 steps
1: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
2: 54 percent / pyridine / CH2Cl2 / 4 h
3: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
4: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
5: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
6: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
7: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
8: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-64-6
(2R,3R,5S,2'R)-3-dimethyl(phenyl)silyl-5-methyl-2-(6'-methylhept-2'-yl)cyclohexanone oxime

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 54 percent / pyridine / CH2Cl2 / 4 h 2: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 3: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 4: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 5: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 6: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 7: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 679841-43-1
2',4'-dimethylpent-3'-yl-(7R,11R)-3,7,11,15-tetramethyl-5-hydroxyhexadec-2-enoate

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 2: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 679841-63-5
(3R,5S,2'R)-3-dimethyl(phenyl)silyl-5-methyl-2-(6'-methylhept-2'-yl)-1-trimethysilyloxylcyclohexene

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C 2: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating 3: 54 percent / pyridine / CH2Cl2 / 4 h 4: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 5: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 6: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 7: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 8: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 9: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

Yield

Multi-step reaction with 9 steps
1: 96 percent / aq. HCl / tetrahydrofuran / 12 h / 20 °C
2: 66 percent / NH2OH*HCl; pyridine / ethanol / Heating
3: 54 percent / pyridine / CH2Cl2 / 4 h
4: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C
5: 59 percent / DIBAl / hexane / 2.5 h / 20 °C
6: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C
7: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C
8: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
9: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme

: 679841-41-9
(E)-(2R,3R,5S,2'R)-2-(6'-methylhept-2'-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone oxime acetate

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / Me3SiOTf / CH2Cl2 / 4 h / 0 °C 2: 59 percent / DIBAl / hexane / 2.5 h / 20 °C 3: 98 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 67 percent / TiCl4 / CH2Cl2 / 1 h / -78 °C 5: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C 6: 67 percent / LiAlH4 / diethyl ether / Heating View Scheme

: 24529-80-4
(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl3 / 0.5 h 3: dimethylformamide / 3 h / 80 °C 4: 72 percent / Mg / Li2CuCl4 / tetrahydrofuran / 10 min, -78 deg C then 2 h, 0 deg C then 15 h, r.t. 5: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 5 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl3 / 0.5 h 3: dimethylformamide / 3 h / 80 °C 4: 57 percent Chromat. / Mg / CuI / tetrahydrofuran 5: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 4 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl3 / 0.5 h 3: 48 percent Chromat. / Mg / CuCl / tetrahydrofuran 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 4 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl3 / 0.5 h 3: 33.7 percent / Li2CuCl4 / tetrahydrofuran / 2 h / 0 °C 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme

: 53170-97-1
(E)-4-chloro-3-methyl-2-buten-1-ol

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: POCl3 / 0.5 h 2: dimethylformamide / 3 h / 80 °C 3: 72 percent / Mg / Li2CuCl4 / tetrahydrofuran / 10 min, -78 deg C then 2 h, 0 deg C then 15 h, r.t. 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 4 steps 1: POCl3 / 0.5 h 2: dimethylformamide / 3 h / 80 °C 3: 57 percent Chromat. / Mg / CuI / tetrahydrofuran 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1: POCl3 / 0.5 h 2: 48 percent Chromat. / Mg / CuCl / tetrahydrofuran 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1: POCl3 / 0.5 h 2: 33.7 percent / Li2CuCl4 / tetrahydrofuran / 2 h / 0 °C 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme

: 42933-01-7
racemic Hexahydrofarnesylmagnesium bromid

: 150-86-7
phytol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent Chromat. / Li2CuCl4 / tetrahydrofuran 2: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C View Scheme

: 150-86-7
phytol

: 189302-44-1
(3RS,7R,11R)-3,7,11,15-tetramethylhexadecan-1-ol

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol for 72h;	100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 72h;	100%
With platinum(IV) oxide; hydrogen In tetrahydrofuran at 20℃; under 750.075 Torr; for 4h;	96%

: 150-86-7
phytol

: 18654-63-2
(3R,7R,11R)-3,7,11,15-tetramethyl-1-hexadecanol (dihydrophytol)

Conditions

Conditions	Yield
With hydrogen; <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) In methanol under 77572.2 Torr; for 24h;	100%

: 122-60-1
Phenyl glycidyl ether

: 150-86-7
phytol

: C29H50O3

Conditions

Conditions	Yield
With potassium methanolate at 110℃; for 18.0833h; Inert atmosphere;	99.5%

: 150-86-7
phytol

: 645-72-7
3,7,11,15-tetramethyl-hexadecanol

Conditions

Conditions	Yield
With hydrogen In ethanol; water at 20℃; for 72h;	99%
With platinum(IV) oxide hydrate; hydrogen; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	90%
With hydrogen In ethanol	82.3%
With hydrogen; nickel In ethanol for 5h; Hydrogenation;

: 150-86-7
phytol

: 14237-72-0
((2R,3R)-3-methyl-3-((4R,8R)-4,8,12-trimethyltridecyl)-oxiran-2-yl)methanol

Conditions

Conditions	Yield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In nonane; dichloromethane at -20℃; for 3h; Sharpless epoxidation; Molecular sieve; Inert atmosphere;	96%
With titanium(IV) isopropylate; Dimethyl D-tartrate; Trimethylacetic acid In dichloromethane at -20℃;	85%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane

: 150-86-7
phytol

: 112-67-4
n-hexadecanoyl chloride

: trans-palmitoylphytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	96%
With triethylamine In hexane at 80℃; for 2h;	85%
With pyridine; dmap at 30 - 35℃; for 14h;

: 3282-30-2
pivaloyl chloride

: 150-86-7
phytol

: 127951-52-4
1-O-pivaloylphytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	96%
With pyridine; dmap at 30 - 35℃; for 14h;

: 546-68-9
titanium(IV) isopropylate

aqueous 3N-K2 CO3: aqueous 3N-K2 CO3

: 110-05-4
di-tert-butyl peroxide

: 220038-45-9
DIPT

: 7732-18-5
water

: 150-86-7
phytol

: (2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol

Conditions

Conditions	Yield
silica gel In diethyl ether; dichloromethane	95%

...Expand

: 75-36-5
acetyl chloride

: 150-86-7
phytol

: 10236-16-5
(R,R,E)-phytyl acetate

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	95%
With pyridine; dmap at 30 - 35℃; for 14h;

: 150-86-7
phytol

: (5R,9R)-5,9,13-trimethyltetradecanoic acid

Conditions

Conditions	Yield
Stage #1: phytol With ozone Stage #2: With potassium tribromide; sodium hydroxide	94%
With potassium tribromide; ozone; sodium hydroxide	94%

: 17746-05-3
undecanoyl chloride

: 150-86-7
phytol

: phytyl dodecanoate

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	94%

: 1711-05-3
m-anisoyl chloride

: 150-86-7
phytol

: 1-O-(m-anisoyl)phytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	93%
With pyridine; dmap at 30 - 35℃; for 14h;

: 98-88-4
benzoyl chloride

: 150-86-7
phytol

: 1-O-benzoylphytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	92%

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 150-86-7
phytol

: 127951-49-9
1-O-(3,4,5-trimethoxybenzoyl)phytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	92%
With pyridine; dmap at 30 - 35℃; for 14h;

: 546-68-9
titanium(IV) isopropylate

: 75-34-3
1,1-dichloroethane

: 408332-88-7
Diethyl tartrate

: 150-86-7
phytol

: (2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydroxide In CHCl3 -benzene; diethyl ether; dichloromethane	91.3%

...Expand

: 103-69-5
N-ethyl-N-phenylamine

: 150-86-7
phytol

: N-ethyl-N-(3,7,11,15-tetramethylhexadecyl)aniline

Conditions

Conditions	Yield
With formic acid; C28H28Cl2O3PRuS In toluene at 150℃; for 16h; Inert atmosphere; chemoselective reaction;	90%
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron In ethanol at 50℃; for 20h; Inert atmosphere; Schlenk technique; Irradiation;	65%

: 150-86-7
phytol

: 1257631-81-4
3,7,11,15-tetramethylhexadecan-1-ol

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol at 20℃; under 760.051 Torr; for 6h;	88%

: 102-92-1
cinnamoyl chloride

: 150-86-7
phytol

: 1-O-cinnamoylphytol

Conditions

Conditions	Yield
With pyridine; dmap at 30 - 35℃; for 14h;	88%
With pyridine; dmap at 30 - 35℃; for 14h;

: 150-86-7
phytol

: 4444-13-7
phytyl bromide

Conditions

Conditions	Yield
With pyridine; phosphorus tribromide In benzene at 4 - 35℃; for 3.5h;	86%
With phosphorus tribromide In benzene at 4 - 35℃; for 4.5h;	86%
With phosphorus tribromide In pyridine

: 78-39-7
Triethyl orthoacetate

: 150-86-7
phytol

: ethyl 3,7,11,15-tetramethyl-3-vinylhexadecanoate

Conditions

Conditions	Yield
With acetic acid at 138℃; Johnson-Claisen Rearrangement;	86%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 150-86-7
phytol

: N-(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl-5-amino-2-chloropyridine

Conditions

Conditions	Yield
With potassium hydrogensulfate; iron(II) bromide In toluene at 120℃; for 24h;	86%

: 150-86-7
phytol

: 13754-69-3
(2’E,7’R,11‘R)-3,7,11,15-tetramethylhexadec-2-enal

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 24h; Reflux;	85%
With pyridine; chromium(VI) oxide In dichloromethane	75%
With pyridinium chlorochromate In dichloromethane for 6h; Reflux;	74%

: 150-86-7
phytol

: (3-methyl-3-((4R,8R)-4,8,12-trimethyltridecyl)oxiran-2-yl)methanol

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.75h;	85%
With methyl hexanoate; CpLIP2 Y179F (ipase/acyltransferase) from Candida parapsilosis; dihydrogen peroxide In aq. phosphate buffer; water at 20℃; pH=6.5; Enzymatic reaction;	55%
With dihydrogen peroxide; methyltrioxorhenium(VII) In aq. phosphate buffer at 20℃; for 3h; pH=2.0;

: 150-86-7
phytol

: 2-chloro-3,7,11,15-tetramethylhexadecan-1,3-diol

Conditions

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; 4-methylmorpholine N-oxide In chloroform at -10 - 20℃;	83%

: 150-86-7
phytol

: 74-88-4
methyl iodide

: 66432-64-2
(2E,7R,11R)-Phytyl-methylaether

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;	82%

: 578-66-5
8-amino quinoline

: 150-86-7
phytol

: N-(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl-8-quinolinamine

Conditions

Conditions	Yield
With potassium hydrogensulfate; iron(II) bromide In toluene at 120℃; for 24h;	81%

: 150-86-7
phytol

: 3,7,11,15-tetramethylhexadecane-1,3-diol

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	81%

: 700-13-0
Trimethylhydroquinone

: 150-86-7
phytol

: 186537-56-4
(2RS,4R,8R)-α-tocopherol

Conditions

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In toluene at 110℃; for 0.5h; Friedel-Crafts Alkylation; Microwave irradiation; Green chemistry;	77%
With hydrogenchloride; diethyl ether
With ethanol; phosphorus pentoxide

PHYTOL Chemical Properties

Phytol is a precursor for vitamins E and K1. It is an extremely common terpenoid, found in all plants esterified to Chlorophyll to confer lipid solubility.It has some synonyms like E)-3,7,11,15-Tetramethyl-2-hexadedcen-1-ol;(E)-phytol;2,6,10,14-Tetramethylhexadec-14-en-16-ol;2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, [R-[R*,R*-(E)]]-;3,7,11,15-tetramethyl-,(r-(r*,r*-(e)))-2-hexadecen-1-o;3,7,11,15-tetramethyl-,[R-(R*,R*-(E))]-2-Hexadedcen-1-ol,and so on.

Molecular Formula: C₂₀H₄₀O
Molecular Weight: 296.53
EINECS: 205-776-6
boiling point: 202-204 °C (10 mmHg)
Density: 0.85
Refractive index: 1.461-1.469
Merck: 7390

PHYTOL Uses

Phytol is commonly used as the basic raw materialsFor the production of vitamin K1, vitamin E.

PHYTOL Toxicity Data With Reference

1.	skn-rbt 500 mg/24H MOD	FCTOD7 Food and Chemical Toxicology. 20 (1982),811.
2.	orl-rat LD₅₀:>5 g/kg	FCTOD7 Food and Chemical Toxicology. 20 (1982),811.
3.	skn-rbt LD₅₀:>5 g/kg	FCTOD7 Food and Chemical Toxicology. 20 (1982),811.

RTECS: TJ3490000

PHYTOL Consensus Reports

Reported in EPA TSCA Inventory.

PHYTOL Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 37/39-26

Product Name

PHYTOL

Synthetic route

PHYTOL Chemical Properties

PHYTOL Uses

PHYTOL Toxicity Data With Reference

PHYTOL Consensus Reports

PHYTOL Safety Profile

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