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150-86-7 Usage

Description

Phytol is a diterpene alcohol obtained from the degradation of chlorophyll and has been used in the synthesis of Vitamins E and K. During the digestion process of ruminants, phytol is liberated from chlorophyll and converted to phytanic acid to be stored in fats. While humans cannot derive phytol from chlorophyll, free phytol, obtained from the consumption of ruminant adipose tissue and dairy products, is readily absorbed in the small intestine and converted to phytanic acid. Phytanic acid accumulates to toxic levels in a number of metabolic disorders, and the conversion of phytol to phytanic acid has been shown to be regulated via the activation of peroxisome proliferator-activated receptor α (PPARα). Phytol and its metabolites have also been reported to activate retinoid X receptors (RXRs; Kis range from 2.3-67.2 μM) and to promote the activity of PPAR/RXR heterodimers. Phytol also demonstrates sedative and anxiolytic effects through interaction with the GABAA receptor, and it has been explored as an antischistosomal agent in a mouse model of schistosomiasis.

Chemical Properties

Different sources of media describe the Chemical Properties of 150-86-7 differently. You can refer to the following data:
1. Colorless to yellow liquid
2. Colorless to yellow viscous liquid; faint floral aroma.

Occurrence

Reported found in Herniaria incana lam oil Greece (2.60%) and Witch hazel leaf oil (9.79%).

Uses

Different sources of media describe the Uses of 150-86-7 differently. You can refer to the following data:
1. trans-Phytol is a reagent that is used in the preparation of α-tocopherol analogs as mitochondrial antioxidants.
2. Preparation of vitamins E and K1.

Definition

ChEBI: A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15.

Aroma threshold values

Low strength odor, floral type.

Safety Profile

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

Check Digit Verification of cas no

The CAS Registry Mumber 150-86-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 0 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 150-86:
(5*1)+(4*5)+(3*0)+(2*8)+(1*6)=47
47 % 10 = 7
So 150-86-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19+/m0/s1

150-86-7 Well-known Company Product Price

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  • TCI America

  • (P0411)  Phytol  >90.0%(GC)

  • 150-86-7

  • 25g

  • 1,180.00CNY

  • Detail

150-86-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name phytol

1.2 Other means of identification

Product number -
Other names PHYTOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:150-86-7 SDS

150-86-7Synthetic route

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

2-methyl-3,4-epoxy-1-butene

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

(3R,7R)-3,7,11-Trimethyldodecylmagnesium-bromid

phytol
150-86-7

phytol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at -20 - 0℃; for 24h;95%
(2E,7R,11R)-Phytyl-(2'-tetrahydropyranyl)aether
66432-63-1

(2E,7R,11R)-Phytyl-(2'-tetrahydropyranyl)aether

phytol
150-86-7

phytol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In ethanol at 55℃; for 1.5h;94%
(E)-(7R,11R)-1-(1'-ethoxy)ethoxy-3,7,11,15-tetramethyl-2-hexadecene
92116-50-2

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride In tetrahydrofuran at 0 - 20℃; for 3h;68%
2',4'-dimethylpent-3'-yl (7R,11R)-3,7,11,15-tetramethyl-5-methanesulfonyloxyhexadec-2-enoate
679841-68-0

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether Heating;67%
(2E,7R,11R)-3,7,11,15-tetramethyl-hexadec-2-enoic acid methyl ester
13853-16-2

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether at 0℃;
(2Z,7R,11R)-3,7,11,15-tetramethyl-hexadec-2-enoic acid ethyl ester
101541-51-9

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; aluminium trichloride
chlorophyll

chlorophyll

phytol
150-86-7

phytol

Conditions
ConditionsYield
With lithium hydroxide
With tetramethyl ammoniumhydroxide
formaldehyd
50-00-0

formaldehyd

trimethylaluminum
75-24-1

trimethylaluminum

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

6,10,14-Trimethyl-pentadec-1-yne

A

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

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

B

phytol
150-86-7

phytol

Conditions
ConditionsYield
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.;
(3R,7R,5E)-3,7,11-trimethyldodecan-1-al
105470-79-9

(3R,7R,5E)-3,7,11-trimethyldodecan-1-al

phytol
150-86-7

phytol

Conditions
ConditionsYield
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
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

phytol
150-86-7

phytol

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

(R)-5-methyl-cyclohex-2-enone

phytol
150-86-7

phytol

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

1-(2',4'-dimethylpent-3'-yloxy)-3-methyl-1-trimethylsilyloxybuta-1,3-diene

phytol
150-86-7

phytol

Conditions
ConditionsYield
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
1-bromo-5-methylpentane
626-88-0

1-bromo-5-methylpentane

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

2,4-dimethylpent-3-yl 3-methylbut-2-enoate

phytol
150-86-7

phytol

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

(5R)-2-(1'-hydroxyethyl)-5-methylcyclohex-2-enone

phytol
150-86-7

phytol

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

(5R)-2-(1'-methoxycarbonyloxyethyl)-5-methylcyclohex-2-enone

phytol
150-86-7

phytol

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

(3R,7R,5E)-3,7,11-trimethyldodec-5-en-1-al

phytol
150-86-7

phytol

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

(3R,7R,5E)-3,7,11-trimethyldodec-5-enonitrile

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / Et3N / CH2Cl2 / 1 h / 0 °C
2: 67 percent / LiAlH4 / diethyl ether / Heating
View Scheme
(3R,5S,2'R)-3-dimethyl(phenyl)silyl-5-methyl-2-(6'-methylhept-2'-yl)-1-trimethysilyloxylcyclohexene
679841-63-5

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

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

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

phytol
150-86-7

phytol

Conditions
ConditionsYield
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
racemic Hexahydrofarnesylmagnesium bromid
42933-01-7

racemic Hexahydrofarnesylmagnesium bromid

phytol
150-86-7

phytol

Conditions
ConditionsYield
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
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
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%
phytol
150-86-7

phytol

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

(3R,7R,11R)-3,7,11,15-tetramethyl-1-hexadecanol (dihydrophytol)

Conditions
ConditionsYield
With hydrogen; <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) In methanol under 77572.2 Torr; for 24h;100%
Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

phytol
150-86-7

phytol

C29H50O3

C29H50O3

Conditions
ConditionsYield
With potassium methanolate at 110℃; for 18.0833h; Inert atmosphere;99.5%
phytol
150-86-7

phytol

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

3,7,11,15-tetramethyl-hexadecanol

Conditions
ConditionsYield
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 ethanol82.3%
With hydrogen; nickel In ethanol for 5h; Hydrogenation;
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
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
phytol
150-86-7

phytol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

trans-palmitoylphytol

trans-palmitoylphytol

Conditions
ConditionsYield
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;
pivaloyl chloride
3282-30-2

pivaloyl chloride

phytol
150-86-7

phytol

1-O-pivaloylphytol
127951-52-4

1-O-pivaloylphytol

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;96%
With pyridine; dmap at 30 - 35℃; for 14h;
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

aqueous 3N-K2 CO3

aqueous 3N-K2 CO3

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

water
7732-18-5

water

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
silica gel In diethyl ether; dichloromethane95%
acetyl chloride
75-36-5

acetyl chloride

phytol
150-86-7

phytol

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

(R,R,E)-phytyl acetate

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;95%
With pyridine; dmap at 30 - 35℃; for 14h;
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
Stage #1: phytol With ozone
Stage #2: With potassium tribromide; sodium hydroxide
94%
With potassium tribromide; ozone; sodium hydroxide94%
undecanoyl chloride
17746-05-3

undecanoyl chloride

phytol
150-86-7

phytol

phytyl dodecanoate

phytyl dodecanoate

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;94%
m-anisoyl chloride
1711-05-3

m-anisoyl chloride

phytol
150-86-7

phytol

1-O-(m-anisoyl)phytol

1-O-(m-anisoyl)phytol

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;93%
With pyridine; dmap at 30 - 35℃; for 14h;
benzoyl chloride
98-88-4

benzoyl chloride

phytol
150-86-7

phytol

1-O-benzoylphytol

1-O-benzoylphytol

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;92%
3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

phytol
150-86-7

phytol

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

1-O-(3,4,5-trimethoxybenzoyl)phytol

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;92%
With pyridine; dmap at 30 - 35℃; for 14h;
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

1,1-dichloroethane
75-34-3

1,1-dichloroethane

Diethyl tartrate
408332-88-7

Diethyl tartrate

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sodium hydroxide In CHCl3 -benzene; diethyl ether; dichloromethane91.3%
N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
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%
phytol
150-86-7

phytol

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

3,7,11,15-tetramethylhexadecan-1-ol

Conditions
ConditionsYield
With hydrogen; nickel In ethanol at 20℃; under 760.051 Torr; for 6h;88%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

phytol
150-86-7

phytol

1-O-cinnamoylphytol

1-O-cinnamoylphytol

Conditions
ConditionsYield
With pyridine; dmap at 30 - 35℃; for 14h;88%
With pyridine; dmap at 30 - 35℃; for 14h;
phytol
150-86-7

phytol

phytyl bromide
4444-13-7

phytyl bromide

Conditions
ConditionsYield
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
Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With acetic acid at 138℃; Johnson-Claisen Rearrangement;86%
6-Chloro-pyridin-3-ylamine
5350-93-6

6-Chloro-pyridin-3-ylamine

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With potassium hydrogensulfate; iron(II) bromide In toluene at 120℃; for 24h;86%
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane for 24h; Reflux;85%
With pyridine; chromium(VI) oxide In dichloromethane75%
With pyridinium chlorochromate In dichloromethane for 6h; Reflux;74%
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
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;
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; 4-methylmorpholine N-oxide In chloroform at -10 - 20℃;83%
phytol
150-86-7

phytol

methyl iodide
74-88-4

methyl iodide

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

(2E,7R,11R)-Phytyl-methylaether

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;82%
8-amino quinoline
578-66-5

8-amino quinoline

phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With potassium hydrogensulfate; iron(II) bromide In toluene at 120℃; for 24h;81%
phytol
150-86-7

phytol

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

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

Conditions
ConditionsYield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;81%
Trimethylhydroquinone
700-13-0

Trimethylhydroquinone

phytol
150-86-7

phytol

(2RS,4R,8R)-α-tocopherol
186537-56-4

(2RS,4R,8R)-α-tocopherol

Conditions
ConditionsYield
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

150-86-7Related news

Cholinesterase inhibitory activity and structure elucidation of a new PHYTOL (cas 150-86-7) derivative and a new cinnamic acid ester from Pycnanthus angolensis09/30/2019

The leaves of Pycnanthus angolensis (Welw.) Warb., Myristicaceae, are used as memory enhancer and anti-ageing in Nigerian ethnomedicine. This study aimed at evaluating the cholinesterase inhibitory property as well as isolates the bioactive compounds from the plant. The acetylcholinesterase and ...detailed

PHYTOL (cas 150-86-7) as an anticarcinogenic and antitumoral agent: An in vivo study in swiss mice with DMBA‐Induced breast cancer09/29/2019

Phytol (PHY) (3,7,11,15‐tetramethylhexadec‐2‐en‐1‐ol) exhibits various pharmacological properties including toxicity and cytotoxicity, and exerts antitumor activity. Owing to the urgent need of new pharmaceutical formulations for breast cancer therapy, this study aimed at the evaluation of ...detailed

Comparison of the photodegradation rates of chlorophyll chlorin ring and PHYTOL (cas 150-86-7) side chain in phytodetritus: is the phytyldiol versus PHYTOL (cas 150-86-7) ratio (CPPI) a new biogeochemical index?09/28/2019

Rates of photodegradation of chlorophylls in their entirety and of chlorophyll phytyl chains, and time evolution of the Chlorophyll Phytyl side-Chain Photodegradation Index (CPPI) under visible light exposure were determined and compared in laboratory experiments. Killed phytoplanktonic cells of...detailed

150-86-7Relevant articles and documents

van Rysselberghe et al.

, p. 809 (1947)

New 29-nor-cycloartanes with a 3,4-seco- and a novel 2,3-seco-structure from the leaves of Sinocalycanthus chinensis

Kashiwada, Yoshiki,Nishimura, Kazuya,Kurimoto, Shin-Ichiro,Takaishi, Yoshihisa

experimental part, p. 2790 - 2796 (2011/06/19)

Eight new triterpenoids, including sinocalycanchinensins A-E (1-5) with a 3,4-seco-29-nor-cycloartane skeleton, sinocalycanchinensin F (6) possessing a novel 2,3-seco-29-nor-cycloartane skeleton, and 29-nor-cycloartanes, sinocalycanchinensins G and H (7 and 8), have been isolated from the leaves of Sinocalycanthus chinensis. Their structures were elucidated on the basis of spectroscopic examinations. The cytotoxicities of the isolated new triterpenes against a panel of human cancer cell lines, including multi-drug resistant (MDR) cancer cell lines, were also evaluated. Compound 5 demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine, although all the compounds showed moderate or no cytotoxicities.

A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K.

Huo,Negishi

, p. 3253 - 3256 (2007/10/03)

[reaction: see text]. A convenient and asymmetric protocol for the synthesis of chiral oligoisoprenoids is described. Typically, a C14 vitamin E side chain 5 was synthesized in 47% yield over four steps. Isomeric purity of 5 was upgraded to >99% R at C-2 and 97% R at C-6 by the statistical formation of stereoisomeric p-phenylenebisurethanes and their diastereomeric separation. In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.

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