2-Hexadecen-1-ol,3,7,11,15-tetramethyl- supplier

Name
3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-OL
EINECS 310-127-6
CAS No. 7541-49-3
Article Data11
CAS DataBase
Density 0.845 g/cm³
Solubility
Melting Point
Formula C₂₀H₄₀O
Boiling Point 335.5 °C at 760 mmHg
Molecular Weight 296.537
Flash Point 157.5 °C
Transport Information
Appearance clear colourless to yellow liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3,7,11,15-Tetramethyl-2-hexadecene-1-ol;Phytol;3,7,11,15-tetramethyl-hexadec-2-en-1-ol;
PSA 20.23000
LogP 6.36410

Synthetic route

: 505-32-8
isophytol

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Stage #1: isophytol With phosphorus tribromide In n-heptane at -10 - 0℃; for 1h; Stage #2: With sodium hydroxide In water at 50 - 60℃; for 2h; pH=6 - 7;	89%
Multi-step reaction with 3 steps 1: hydrogenchloride; tetramethlyammonium chloride / water / 10 - 20 °C / Large scale 2: tetramethlyammonium chloride / acetonitrile / 50 - 60 °C / Large scale 3: sodium hydroxide; water / 40 - 50 °C / Large scale View Scheme

: 502-69-2
6,10,14-Trimethyl-2-pentadecanon

: C7H13ClMgO2

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Stage #1: 6,10,14-Trimethyl-2-pentadecanon; C7H13ClMgO2 In tert-butyl methyl ether at 0℃; for 6h; Inert atmosphere; Stage #2: With pyridinium p-toluenesulfonate In ethanol; water for 2h; Reflux;	84%

: 107438-44-8
[3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol

A: 504-96-1, 508181-25-7
neophytadiene

B: 505-32-8
isophytol

C: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
With methyltrioxorhenium(VII); triphenylphosphine In toluene for 3h; Reflux;	A 7.4% B n/a C n/a

...Expand

: 505-32-8
isophytol

A: 21980-71-2
neophytadiene

B: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
With acetic anhydride at 96 - 97℃; dann Verseifen mit methylalkoholischer Kalilauge;

: 505-32-8
isophytol

: 108-24-7
acetic anhydride

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
at 96 - 97℃; nachfolgende Verseifung mit methylalkoholischer Kalilauge;

: 5492-31-9
3,7,11,15-tetramethyl-hexadec-2-enoic acid ethyl ester

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

: 10236-11-0
ethyl-5,9-dimethyldec-2-anoate

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: (i) NaH, THF, (ii) Al-Hg, aq. THF 2: (i) NaH, DMF, (ii) /BRN= 1722657/ 3: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 4: (i) NaH, THF, (ii) Al-Hg, aq. THF 5: (i) NaH, THF, (ii) /BRN= 1724987/ 6: LiAlH4 / diethyl ether View Scheme

: 928-68-7
6-methylheptan-2-one

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: (i) NaH, THF, (ii) /BRN= 635835/ 2: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 3: (i) NaH, THF, (ii) Al-Hg, aq. THF 4: (i) NaH, DMF, (ii) /BRN= 1722657/ 5: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 6: (i) NaH, THF, (ii) Al-Hg, aq. THF 7: (i) NaH, THF, (ii) /BRN= 1724987/ 8: LiAlH4 / diethyl ether View Scheme

: 2,6-Dimethyl-6,8-nonadien-9-carbonsaeureethylester

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 2: (i) NaH, THF, (ii) Al-Hg, aq. THF 3: (i) NaH, DMF, (ii) /BRN= 1722657/ 4: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 5: (i) NaH, THF, (ii) Al-Hg, aq. THF 6: (i) NaH, THF, (ii) /BRN= 1724987/ 7: LiAlH4 / diethyl ether View Scheme

: 2,6,10-Trimethyl-trideca-10,12-dien-13-carbonsaeureethylester

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 2: (i) NaH, THF, (ii) Al-Hg, aq. THF 3: (i) NaH, THF, (ii) /BRN= 1724987/ 4: LiAlH4 / diethyl ether View Scheme

: 253686-88-3
(E)-3,7,11,15-tetramethylhexadec-2-en-1-ol

A: 504-96-1, 508181-25-7
neophytadiene

B: 505-32-8
isophytol

C: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: vanadium trisacetylacetonate; tert.-butylhydroperoxide / hexane; decane / Inert atmosphere; Reflux 2: triphenylphosphine; methyltrioxorhenium(VII) / toluene / 3 h / Reflux View Scheme

...Expand

: 24034-73-9
Geranylgeraniol

A: 504-96-1, 508181-25-7
neophytadiene

B: 505-32-8
isophytol

C: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: vanadium trisacetylacetonate; tert.-butylhydroperoxide / toluene / Reflux; Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol / 4 h / 40 °C 3: triphenylphosphine; methyltrioxorhenium(VII) / toluene / 3 h / Reflux View Scheme

...Expand

: 500996-28-1
geranylgeraniol-2,3-epoxide

A: 504-96-1, 508181-25-7
neophytadiene

B: 505-32-8
isophytol

C: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5%-palladium/activated carbon; hydrogen / ethanol / 4 h / 40 °C 2: triphenylphosphine; methyltrioxorhenium(VII) / toluene / 3 h / Reflux View Scheme

...Expand

: 1117-52-8
6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 2.1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2.2: 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 2.1: tert-butyl methyl ether / 2 h / 0 - 5 °C 3.1: phosphorus tribromide / n-heptane / 1 h / -10 - 0 °C 3.2: 2 h / 50 - 60 °C / pH 6 - 7 View Scheme

: 5631-96-9
2-(2-chloroethoxy)-tetrahydro-2H-pyrane

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / tert-butyl methyl ether / 5 h / 50 - 60 °C / Inert atmosphere 2.1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2.2: 2 h / Reflux View Scheme

: 3796-70-1
trans geranyl acetone

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 3.1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 3.2: 2 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 3.1: tert-butyl methyl ether / 2 h / 0 - 5 °C 4.1: phosphorus tribromide / n-heptane / 1 h / -10 - 0 °C 4.2: 2 h / 50 - 60 °C / pH 6 - 7 View Scheme

: 76337-16-1
3,7,11,15-tetramethylhexadec-2-en-1-yl acetate

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
With methanol; potassium carbonate Reflux; Large scale;
With methanol; sodium carbonate for 12h; Reagent/catalyst; Reflux;	108 g

: 65592-98-5
1-chloro-3,7,11,15-tetramethylhexadec-2-ene

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetramethlyammonium chloride / acetonitrile / 50 - 60 °C / Large scale 2: sodium hydroxide; water / 40 - 50 °C / Large scale View Scheme

: (E/Z)-(all-rac)-phytyl formiate

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
With water; sodium hydroxide at 40 - 50℃; Large scale;

: 76524-59-9
1-bromo-3,7,11,15-tetramethylhexadec-2-ene

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide / N,N-dimethyl-formamide / 50 - 60 °C / Large scale 2: potassium carbonate; methanol / Reflux; Large scale View Scheme

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

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

Conditions

Conditions	Yield
With hydrogen; sodium hydrogencarbonate; platinum(IV) oxide In tetrahydrofuran under 760.051 Torr; for 20h;	100%
With hydrogen; platinum(IV) oxide In tetrahydrofuran under 760.051 Torr; for 20h;	100%
With hydrogen In ethanol at 20℃; for 104h; Reagent/catalyst; Pressure; Time;	100%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 107438-44-8
[3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	99%
With PW12O40(3-)*polymer; dihydrogen peroxide at 20℃; for 7h;	96%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 76524-59-9
1-bromo-3,7,11,15-tetramethylhexadec-2-ene

Conditions

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane	91%
With phosphorus tribromide In diethyl ether at 0 - 20℃;	86%
With phosphorus tribromide In hexane at 0℃; for 0.166667h; Inert atmosphere;

: 64-18-6
formic acid

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: (E/Z)-(all-rac)-phytyl formiate

Conditions

Conditions	Yield
at 60℃; for 2.5h;	90%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: methyl (132R)-propyl-pyropheophorbide a

: 132-propyl-pyropheophytin a

Conditions

Conditions	Yield
With 1,3-dichlorotetrabutyldistannoxane In toluene for 3h; Reflux; Inert atmosphere;	89%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 108-24-7
acetic anhydride

: 76337-16-1
3,7,11,15-tetramethylhexadec-2-en-1-yl acetate

Conditions

Conditions	Yield
With pyridine In hexane at 21 - 22℃; for 16 - 18h;	83%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: phytol phosphate

Conditions

Conditions	Yield
With pyruvate kinase; phosphoenolpyruvic acid; undecaprenol kinase; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride at 37℃; for 24h; pH=8; Kinetics; Enzymatic reaction;	82%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 93-97-0
benzoic acid anhydride

: 844467-81-8
(E/Z)-(all-rac)-phytyl benzoate

Conditions

Conditions	Yield
With dmap In hexane at 23 - 24℃; for 20h;	76%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: C20H39I

Conditions

Conditions	Yield
With iodine; triphenylphosphine In diethyl ether at 20℃; for 4h;	70%

: 868540-55-0
2,3-dimethyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-hydroquinone

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 868602-40-8
Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-5-yl]-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With zinc(II) chloride	66%

: 868540-58-3
3,5-dimethyl-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-hydroquinone

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-hydroxy-2,5,7-trimethyl-2-(4,8,12-trimethyl-tridecyl)-3,4,4a,8a-tetrahydro-2H-chromen-8-yl]-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With zinc(II) chloride	63%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: 695179-28-3
2-cyanoethoxy-2-thiono-1,3,2-oxathiaphospholane

: C20H41O3PS*C9H16N2*H3N

Conditions

Conditions	Yield
Stage #1: 3,7,11,15-tetramethyl-2-hexadecen-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-cyanoethoxy-2-thiono-1,3,2-oxathiaphospholane In acetonitrile at 20℃; for 0.5h; Stage #2: With ammonium hydroxide In 1,4-dioxane; water at 20℃; for 48h;	62.2%

...Expand

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 502-69-2
6,10,14-Trimethyl-2-pentadecanon

Conditions

Conditions	Yield
With ozone In carbon dioxide at 20 - 140℃; under 45754.6 - 186769 Torr; for 0.458333h; Autoclave;	58%
With chloroethane beim Ozonisieren und Behandeln des entstandenen Ozonids mit Zinkstaub und Eisessig;
With chromium(VI) oxide; acetic acid unter Zusatz von Kaliumdisulfat;

: 616-91-1
N-acetylcystein

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: N-acetyl-S-phytyl-L-cysteine

Conditions

Conditions	Yield
sulfuric acid at 120℃;	48%

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

A: 120467-03-0
3,7,11,15-tetramethylhexadec-2-enal

B: 107438-44-8
[3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; chromium(VI) oxide In dichloromethane for 5h; Ambient temperature;	A 10% B 20%

: 85-44-9
phthalic anhydride

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 21980-71-2
neophytadiene

: 85-44-9
phthalic anhydride

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 142571-14-0
phthalic acid monophytyl ester

Conditions

Conditions	Yield
With benzene

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 14237-73-1
2-hexadecene, 3,7,11,15-tetramethyl-,[R-[R*,R*-(E)]]-

Conditions

Conditions	Yield
With diethyl ether; ammonia; sodium

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 21980-71-2
neophytadiene

Conditions

Conditions	Yield
With phthalic anhydride; benzene

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 638-36-8
phytane

Conditions

Conditions	Yield
With diethyl ether; hydrogen; platinum
durch elektrolytische Reduktion;

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 532426-78-1
(2E)-3,7,11,15-tetramethyl-2-hexadecene

Conditions

Conditions	Yield
With hydrogen iodide Reduktion des entstandenen Jodids mit Zinkstaub;

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 220904-31-4
3,7,11,15-tetramethyl-2-hexadecen-1-oic acid

Conditions

Conditions	Yield
With potassium hydrogensulfate; chromic acid; acetic acid

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 3,7,11,15-tetramethyl-hexadec-2-en-1-ol; sodium-compound

Conditions

Conditions	Yield
With diethyl ether; sodium

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

: 141-46-8
Glycolaldehyde

Conditions

Conditions	Yield
With chloroethane durch Ozonisiation; Zersetzung des entstandenen Ozonids mit Zinkstaub in Aether+Eisessig+wenig Wasser;
With acetic acid ester durch Ozonisiation; Hydrierung des Ozonids in Gegenwart von Palladium-Calciumcarbonat;

: 7541-49-3
3,7,11,15-tetramethyl-2-hexadecen-1-ol

3,5-Dimethyl-4-hydroxy-thiophenol: 43132-86-1
3,5-Dimethyl-4-hydroxy-thiophenol

: 108-24-7
acetic anhydride

6-Acetoxy-2,5,7-trimethyl-2-(4,8,12-trimethyl-tridecyl)-thiochroman: 6-Acetoxy-2,5,7-trimethyl-2-(4,8,12-trimethyl-tridecyl)-thiochroman

Conditions

Conditions	Yield
With pyridine; formic acid

...Expand

2-Hexadecen-1-ol,3,7,11,15-tetramethyl- Specification

The 2-Hexadecen-1-ol,3,7,11,15-tetramethyl- with CAS registry number of 7541-49-3 is also called Phytol and 3,7,11,15-Tetramethyl-2-hexadecene-1-ol. It is clear colourless to yellow liquid, which is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. Its IUPAC name is called (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol. Its EINECS registry number is 205-776-6.

Physical properties about this chemical are: (1) ACD/LogP: 8.66; (2) # of Rule of 5 Violations: 1; (3) ACD/LogD (pH 5.5): 8.66; (4) ACD/LogD (pH 7.4): 8.66; (5) ACD/BCF (pH 5.5): 1000000; (6) ACD/BCF (pH 7.4): 1000000; (7) ACD/KOC (pH 5.5): 1228911.13; (8) ACD/KOC (pH 7.4): 1228911.13; (9) #H bond acceptors: 1; (10) #H bond donors: 1; (11) #Freely Rotating Bonds: 14; (12) Polar Surface Area: 9.23 Å²; (13) Index of Refraction: 1.459; (14) Molar Refractivity: 96.01 cm³; (15) Molar Volume: 350.7 cm³; (16) Polarizability: 38.06×10^-24 cm³; (17) Surface Tension: 29.8 dyne/cm; (18) Density: 0.845 g/cm³; (19) Flash Point: 157.5 °C; (20) Enthalpy of Vaporization: 67.03 kJ/mol; (21) Boiling Point: 335.5 °C at 760 mmHg; (22) Vapour Pressure: 8.32E-06 mmHg at 25°C.

Uses of 2-Hexadecen-1-ol,3,7,11,15-tetramethyl-: (1) it is used in the fragrance industry and used in cosmetics, shampoos, toilet soaps, household cleaners, and detergents. (2) it is used to produce other chemicals. For example, it is used to produce 1-bromo-3,7,11,15-tetramethyl-hexadec-2-ene.

The reaction occurs with reagent CBr₄, PPh₃ and solvent CH₂Cl₂. The yield is 91%.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: OCC=C(CCCC(CCCC(C)CCCC(C)C)C)C;
(2) 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;
(3) InChIKey: BOTWFXYSPFMFNR-UHFFFAOYAU;
(4) Std. InChI: InChI=1S/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;
(5) Std. InChIKey: BOTWFXYSPFMFNR-UHFFFAOYSA-N

Product Name

3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-OL

Synthetic route

2-Hexadecen-1-ol,3,7,11,15-tetramethyl- Specification

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