505-32-8

Usage

Chemical Properties

colourless viscous liquid

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C20H40O/c1-7-20(6,21)16-10-15-19(5)14-9-13-18(4)12-8-11-17(2)3/h7,17-19,21H,1,8-16H2,2-6H3

Synthetic route

3,7,11,15-tetramethyl-1-hexadecyne-3-ol (29171-23-1) → dihydroisophytol (20685-73-8, 85761-30-4) + isophytol (505-32-8)

Conditions	Yield
With hydrogen; silica gel In ethanol at 69.9℃; under 3750.3 Torr;	A 99.4% B 0.6%
With hydrogen; silica gel In ethanol at 29.9℃; under 3750.3 Torr;	A 48% B 52%
With hydrogen; Ni(C17H35COO)2; triethylaluminum In toluene at 40℃; Kinetics; Object of study: selectivity;
With quinoline; hydrogen; Lindlar catalyst with MnCl2 doping salt In n-heptane at 25℃; under 735 - 738 Torr; Product distribution; without doping salt;
With hydrogen; ShPAK-0.5 modified by Zn(OAc)2 + NH3 In isopropyl alcohol at 50℃; under 735.508 - 1471.02 Torr; for 5h;

3-Bromomethyl-2-methyl-2-(4,8,12-trimethyl-tridecyl)-oxirane (135508-17-7) → isophytol (505-32-8)

Conditions	Yield
With copper(l) iodide; zinc In ethanol sonication;	94%

3-Iodomethyl-2-methyl-2-(4,8,12-trimethyl-tridecyl)-oxirane (135787-83-6) → isophytol (505-32-8)

Conditions	Yield
With copper(l) iodide; zinc In ethanol sonication;	94%

3,7,11,15-tetramethyl-1-hexadecyne-3-ol (29171-23-1) → isophytol (505-32-8)

Conditions	Yield
With 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol; hydrogen; Pd/ZnO/sintered metal fibers (SMF) catalyst at 80℃; under 3000.3 Torr; for 4.5h; Product distribution / selectivity;	93.7%
With hydrogen; 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol at 80℃; under 1500.15 Torr; for 4h; Product distribution / selectivity; Autoclave;	89.6%
With methanol; palladium on activated charcoal; hydrogen

Vinyl bromide (593-60-2) + 6,10,14-Trimethyl-2-pentadecanon (502-69-2) → isophytol (505-32-8)

Conditions	Yield
Stage #1: Vinyl bromide With magnesium In tetrahydrofuran Metallation; Stage #2: 6,10,14-Trimethyl-2-pentadecanon In tetrahydrofuran at 0 - 20℃; for 14h; Grignard reaction;	90%

6,10,14-Trimethyl-2-pentadecanon (502-69-2) + vinylmagnesium chloride (3536-96-7) → isophytol (505-32-8)

Conditions	Yield
In tetrahydrofuran Grignard reaction;	85%
In tert-butyl methyl ether at 0 - 5℃; for 2h;	85%
at 0 - 5℃; for 2h; Inert atmosphere;	42.6 g

C21H42O4S → isophytol (505-32-8)

Conditions	Yield
With naphthalen-1-yl-lithium In tetrahydrofuran at -25℃; for 0.166667h;	84%

6,10,14-Trimethyl-2-pentadecanon (502-69-2) + vinyl magnesium bromide (1826-67-1) → isophytol (505-32-8)

Conditions	Yield
In tetrahydrofuran 1.) r.t. 2.) reflux 2 h;	80%

[3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol (107438-44-8) → neophytadiene (504-96-1, 508181-25-7) + isophytol (505-32-8) + 3,7,11,15-tetramethyl-2-hexadecen-1-ol (7541-49-3)

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

6,10,14-Trimethyl-2-pentadecanon (502-69-2) + allylmagnesium bromide (2622-05-1) → isophytol (505-32-8)

5-benzenesulfonyl-3,7,11,15-tetramethyl-hexadec-1-en-3-ol (60012-66-0) → isophytol (505-32-8)

Conditions	Yield
With sodium amalgam In methanol

Toluene-4-sulfonic acid (R)-1-(1-hydroxy-1-methyl-allyl)-4,8,12-trimethyl-tridecyl ester → isophytol (505-32-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

methanol (67-56-1) + 3,7,11,15-tetramethyl-1-hexadecyne-3-ol (29171-23-1) + hydrogen + palladium + calcium carbonate → isophytol (505-32-8)

Conditions	Yield
Hydrogenation;

2,2-Ethylenedioxy-6,10,14-trimethylpentadecane (58475-03-9) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / 5 percent aq. H2SO4 / acetone / 10 h / 20 °C 2: 85 percent / tetrahydrofuran View Scheme

6,10,14-Trimethyl-5-pentadecen-2-one (3689-69-8) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd/C 2: 85 percent / tetrahydrofuran View Scheme

2,2-Ethylenedioxy-6,10,14-trimethyl-5-pentadecene → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / H2 / 5 percent Pd/C / ethyl acetate / 5 h / 20 °C 2: 85 percent / 5 percent aq. H2SO4 / acetone / 10 h / 20 °C 3: 85 percent / tetrahydrofuran View Scheme

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 2.1: Mg / tetrahydrofuran 2.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: H2 / Pd-C View Scheme
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / isopropyl alcohol / 3 h / 100 °C 2: 2 h / 0 - 5 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 2: tert-butyl methyl ether / 2 h / 0 - 5 °C View Scheme

trans,trans,trans-1,5,9-trimethyl-1,5,9-cyclododecatriene (21064-19-7) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: O3; O2 / cyclohexane; methanol / 5 °C 1.2: 53 percent / H2 / Pd/CaCO3/PbO 2.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 2.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 3.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 4.1: Mg / tetrahydrofuran 4.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme

4,8-Dimethyl-1,12-dioxotrideca-4E,8E-diene (63525-04-2) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: t-BuOK / tetrahydrofuran / 2.5 h / -40 - 25 °C 1.2: 57 percent / tetrahydrofuran / 2 h / -78 - 25 °C 2.1: 0.6 g / H2 / 10 percent Pd/C / ethanol / 72 h / 20 °C 3.1: Mg / tetrahydrofuran 3.2: 90 percent / tetrahydrofuran / 14 h / 0 - 20 °C View Scheme

(4R)-hydroxyisophytol → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: LiAlH4 / diethyl ether View Scheme

3,7,11-trimethyldodecyl alcohol (6750-34-1) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 2: 70 percent / benzene / 10 h / Heating 3: 60 percent / KOH / methanol; H2O / 4 h / Heating 4: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme
Multi-step reaction with 4 steps 1: PBr3, Py 2: dimethylformamide 3: nBuLi / tetrahydrofuran 4: Na-Hg / methanol View Scheme

trans geranyl acetone (3796-70-1) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: 1) NaH / tetrahydrofuran / 1.) r. t., 6 h 3.) 50-55 deg C, 4 h 2: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 3: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 4: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 5: 70 percent / benzene / 10 h / Heating 6: 60 percent / KOH / methanol; H2O / 4 h / Heating 7: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 6 h / 0 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethanol / 24 h / 20 °C / 1520.1 Torr 3: tert-butyl methyl ether / 2 h / 0 - 5 °C View Scheme

ethyl 3,7,11-trimethyldodecanoate (52948-69-3) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 2: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 3: 70 percent / benzene / 10 h / Heating 4: 60 percent / KOH / methanol; H2O / 4 h / Heating 5: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme

ethyl 2-acetyl-5,9,13-trimethyltetradecanoate (65703-80-2, 66289-93-8) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / KOH / methanol; H2O / 4 h / Heating 2: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme

(2Z,6E)-ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate (20085-71-6) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating 6: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme

1-mesyloxy-3,7,11-trimethyldodecane (76337-15-0) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / benzene / 10 h / Heating 2: 60 percent / KOH / methanol; H2O / 4 h / Heating 3: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme

2-<2-(phenylthio)ethyl>prop-2-en-1-ol (72445-15-9) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 8 steps 1: Hg(OAc)2 / 24 h / Heating 2: xylene / 3 h / 140 °C 3: 62 percent / tetrahydrofuran / 2 h / Heating 4: 79 percent / t-BuOOH, V2O5 5: n-BuLi / tetrahydrofuran / 1 h / -78 °C 6: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 7: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme

(3-Vinyloxymethyl-but-3-enylsulfanyl)-benzene (78791-55-6) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: xylene / 3 h / 140 °C 2: 62 percent / tetrahydrofuran / 2 h / Heating 3: 79 percent / t-BuOOH, V2O5 4: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 6: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme

4-Methylene-6-phenylsulfanyl-hexanal (78791-56-7) → isophytol (505-32-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 62 percent / tetrahydrofuran / 2 h / Heating 2: 79 percent / t-BuOOH, V2O5 3: n-BuLi / tetrahydrofuran / 1 h / -78 °C 4: PdCl2, CuCl, O2 / dimethylformamide; H2O / 12 h / Ambient temperature 5: 1.) DBU, CH2Cl2, reflux, 1 hr 2.) Pd/C, H2, EtOH View Scheme

titanium montmorillonite + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
In octane	100%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → vitamin E (59-02-9)

Conditions	Yield
With hydroxylated magnesium fluoride In 1,2-propylene cyclic carbonate; n-heptane at 100℃; for 3h;	99.9%
With nanoscopic partly hydroxylated AlF3-50 In n-heptane; propylene carbonate at 100℃; for 1h; Friedel-Crafts alkylation;	99.9%
With 2,6-di-tert-butyl-pyridine; trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide In n-heptane Heating;	97%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In tetrachloromethane	99.1%
With hydrogenchloride; sodium dithionite; Zinc chloride In toluene	99.8%
With hydrogenchloride; zinc dibromide; zinc	98.6%

2-methylpropyl acetate (110-19-0) + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In water; toluene	99.6%
With hydrogenchloride; Zinc chloride In water; toluene	98.6%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + Diethyl carbonate (105-58-8) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; sodium chloride; Zinc chloride In water; toluene	99.2%
With hydrogen bromide; zinc dibromide In water	99.1%
With hydrogenchloride; Zinc chloride In water; toluene	98.9%

isophytol (505-32-8) → (7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide (943232-38-0)

Conditions	Yield
With pyridine; phosphorus tribromide In hexane at -10 - -7℃; for 3h;	99%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + butanone (78-93-3) → Tocopherol (59-02-9)

Conditions	Yield
With sodium hydroxide; sodium chloride; scandium tris(trifluoromethanesulfonate) In ethyl acetate; toluene	99%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + butan-1-ol (71-36-3) → Tocopherol (59-02-9)

Conditions	Yield
With hydrogenchloride; Zinc chloride In hexane; water; toluene	98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	98.1%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	95.9%
With hydrogenchloride; Zinc chloride In hexane; water; toluene	95.9%

scandium fluorosulfonate + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
With sodium chloride In ethyl acetate; toluene	98%

isophytol (505-32-8) + 2,3,5-trimethyl-1,4-hydroquinone diacetate (7479-28-9) → vitamin E (59-02-9)

Conditions	Yield
Stage #1: isophytol; 2,3,5-trimethyl-1,4-hydroquinone diacetate With C8H15N2(1+)*Br(1-)*ZnBr2 In Petroleum ether at 70℃; for 6h; Stage #2: With acetic anhydride at 120℃; for 3h; Reagent/catalyst; Temperature;	98%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → vitamin E (59-02-9) + 2-phytyl-3,5,6-trimethylhydroquinone (85353-80-6)

Conditions	Yield
indium (III) iodide In Ethylene carbonate; n-heptane at 140 - 145℃; for 2h; Product distribution / selectivity; Heating / reflux;	A 97.3% B 0.25%
indium(III) chloride In pentan-3-one at 140 - 145℃; for 5h; Product distribution / selectivity; Heating / reflux;	A 95.1% B 0.37%
indium(III) chloride In Ethylene carbonate; n-heptane at 140 - 145℃; for 2 - 5h; Product distribution / selectivity; Heating / reflux;	A 94.8% B 0%

isophytol (505-32-8) → 6,10,14-Trimethyl-2-pentadecanon (502-69-2)

Conditions	Yield
With dichromic acid; acetic acid In acetone at 50℃; for 14h; Reagent/catalyst; Temperature;	97%
With sodium periodate; acetic acid In acetone at 80℃; for 8h; Reagent/catalyst; Temperature;	95%

isophytol (505-32-8) + 2,3,5-trimethyl-1,4-hydroquinone diacetate (7479-28-9) → vitamin E acetate (58-95-7, 7695-91-2, 18920-61-1, 52225-20-4, 54165-54-7, 66900-46-7, 79200-45-6, 79200-46-7, 79200-47-8, 79434-84-7, 79434-85-8, 79434-86-9, 79434-87-0, 79434-88-1, 104154-81-6)

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride In water; ethyl acetate at 60℃; for 6h; Temperature; Reagent/catalyst; Time;	94.94%
With acetic anhydride; acetic acid at 70℃; for 3h; Reagent/catalyst; Temperature;

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → vitamin E (59-02-9) + (all-rac)-3,4-dehydro-α-tocopherol (3808-26-2, 125276-57-5)

Conditions	Yield
indium(III) chloride In n-heptane at 147℃; under 2550.26 Torr; for 3.1h; Product distribution / selectivity;	A 93.7% B n/a

isophytol (505-32-8) + 4-acetoxy-2,3,5-trimethylphenol (36592-62-8) → vitamin E (59-02-9) + (E,Z)-(all-rac)-3-phytyl-2,5,6-trimethylhydroquinone-1-acetate (728894-66-4) + vitamin E acetate (58-95-7, 7695-91-2, 18920-61-1, 52225-20-4, 54165-54-7, 66900-46-7, 79200-45-6, 79200-46-7, 79200-47-8, 79434-84-7, 79434-85-8, 79434-86-9, 79434-87-0, 79434-88-1, 104154-81-6)

Conditions	Yield
hafnium tetrakis(trifluoromethanesulfonate) In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.66667h; Product distribution / selectivity; Heating / reflux;	A 1.4% B 0.2% C 93.3%
scandium tris(trifluoromethanesulfonate) In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333 - 1.66667h; Product distribution / selectivity; Heating / reflux;	A 0.5% B 0% C 90.7%
silver trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333 - 1.66667h; Product distribution / selectivity; Heating / reflux;	A 0.3% B 0% C 87%

scandium bentonite + isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → Tocopherol (59-02-9)

Conditions	Yield
In hexane; toluene	93%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → vitamin E (59-02-9) + neophytadiene (21980-71-2)

Conditions	Yield
With hydroxylated magnesium fluoride In 1,2-propylene cyclic carbonate; n-heptane at 100℃; for 1h;	A 92.6% B n/a

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → (+/-)-α-tocopherol (10191-41-0)

Conditions	Yield
methanetrisulfonic acid In Ethylene carbonate; n-heptane; water at 50 - 140℃; for 1 - 1.66667h;	92.4%
methanetrisulfonic acid In 1,2-propylene cyclic carbonate; n-heptane; water at 50 - 140℃; for 1h;	91.2%
SnTf(51)-MCM-41 In hexane at 100℃; for 1h;

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) → vitamin E (59-02-9) + 2,3,4,6,7-Pentamethyl-2-(4,8,12-trimethyl-tridecyl)-2,3-dihydro-benzofuran-5-ol

Conditions	Yield
With Nafion NR 50 In various solvent(s) at 100 - 140℃; under 760 Torr; for 1h;	A 92.3% B n/a
With Nafion NR 50 In various solvent(s) at 100 - 140℃; under 760 Torr; for 1h; Product distribution; var. strong solid acids as catalysts; var. solv.;	A 92.3% B n/a
With manganese(II) sulfate; monmorillonite K In benzene for 1.16667h; Heating; Title compound not separated from byproducts;	A 89% B n/a
With scandium tris(trifluoromethanesulfonate) In xylene for 3h; Product distribution; Heating; var. solvents and rare earth metal(III) triflate;
With europium(III) trifluoroacetate In xylene for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

isophytol (505-32-8) + 4-acetoxy-2,3,5-trimethylphenol (36592-62-8) → vitamin E (59-02-9) + vitamin E acetate (58-95-7, 7695-91-2, 18920-61-1, 52225-20-4, 54165-54-7, 66900-46-7, 79200-45-6, 79200-46-7, 79200-47-8, 79434-84-7, 79434-85-8, 79434-86-9, 79434-87-0, 79434-88-1, 104154-81-6)

Conditions	Yield
gallium(III) triflate In Ethylene carbonate; n-heptane at 80 - 140℃; for 1.08333h; Product distribution / selectivity; Heating / reflux;	A 2.1% B 92.2%
bismuth(lll) trifluoromethanesulfonate In Ethylene carbonate; n-heptane at 120 - 145℃; Product distribution / selectivity; Heating / reflux;	A 6.9% B 78.5%

isophytol (505-32-8) → RRR-α-tocopheryl acetate (58-95-7)

Conditions	Yield
	92%

isophytol (505-32-8) → Tocopherol (59-02-9)

Conditions	Yield
In toluene	91%
	88.7%

isophytol (505-32-8) + boric acid (11113-50-1) → RRR-α-tocopheryl acetate (58-95-7)

Conditions	Yield
With hydrogenchloride; sulfuric acid; oxalic acid; acetic anhydride In tetralin; n-heptane	89%

isophytol (505-32-8) + Trimethylhydroquinone (700-13-0) + acetic anhydride (108-24-7) → vitamin E acetate (58-95-7, 7695-91-2, 18920-61-1, 52225-20-4, 54165-54-7, 66900-46-7, 79200-45-6, 79200-46-7, 79200-47-8, 79434-84-7, 79434-85-8, 79434-86-9, 79434-87-0, 79434-88-1, 104154-81-6)

Conditions	Yield
Stage #1: Trimethylhydroquinone With sulfuric acid; toluene-4-sulfonic acid In ethyl acetate at 10℃; for 0.5h; Stage #2: isophytol With magnesium sulfate In ethyl acetate at 25 - 55℃; for 7h; Stage #3: acetic anhydride Further stages;	89%

isophytol (505-32-8) → 3,7,11,15-tetramethyl-2-hexadecen-1-ol (7541-49-3)

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

Upstream product

• 29171-23-1 3,7,11,15-tetramethyl-hexadec-1-yn-3-ol 
• 29171-23-1 3,7,11,15-tetramethyl-1-hexadecyne-3-ol 
• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 2622-05-1 allylmagnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 593-60-2 Vinyl bromide 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 21064-19-7 trans,trans,trans-1,5,9-trimethyl-1,5,9-cyclododecatriene 
• 72445-08-0 ((E)-7,11-Dimethyl-3-methylene-dodeca-6,10-dienylsulfanyl)-benzene 
• 76936-19-1 (1,5-Dimethyl-4-hexenylidene)-triphenylphosphorane 
• 78791-61-4 ((E)-7,11-Dimethyl-3-methylene-dodeca-6,10-diene-1-sulfonyl)-benzene 
• 78791-62-5 (E)-4-Benzenesulfonyl-10,14-dimethyl-6-methylene-pentadeca-9,13-dien-2-one 
• 18794-84-8 (E)-β-farnesene 
• 3625-46-5 3,7,11-trimethyl-dodec-1-en-3-ol 

Downstream Products

• 10191-41-0 (+/-)-α-tocopherol 
• 185672-33-7 (S)-2,3,4,6,7-Pentamethyl-2-((4S,8S)-4,8,12-trimethyl-tridecyl)-2,3-dihydro-benzofuran-5-ol 
• 81818-54-4 2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone 
• 21980-71-2 neophytadiene 
• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 59-02-9 vitamin E 
• 74515-24-5 3,5,6-trimethyl-2-phytylhydroquinone 
• 85314-70-1 3,5,6-trimethyl-2-phytyl-1,4-benzoquinone 
• 61016-72-6 1-methyl ether of 2,3-dimethoxy-5-methyl-6-phthylylhydroquinone 
• 61016-72-6 1-methyl ether of 2,3-dimethoxy-5-methyl-6-phthylylhydroquinone 
• 85460-71-5 1-thio-α-tocopherol 
• 101836-32-2 2,3,6-Trimethyl-4-((E)-3,7,11,15-tetramethyl-hexadec-1-enylsulfanyl)-phenol 
• 261929-91-3 E_.Z, RS, RS, RS-phytyl-trimethyl-hydroxy-benzenethiol 
• 101836-33-3 4,5,7,8-Tetramethyl-4-(4,8,12-trimethyl-tridecyl)-thiochroman-6-ol 

Relevant academic research and scientific papers

A LINEAR DITERPENE DIOL FROM LEMNA MINOR

Four known isoprenoids were isolated from Lemna minor besides a novel diterpene which was attributed the structure (4R)-4-hydroxyisophytol by spectroscopic studies and chemical correlation.Key Word Index - Lemna minor; Lemnaceae; isoprenoids; 4-hydroxyisophytol.

Method for efficiently preparing enol through selective hydrogenation of alkynol

The invention provides a method for efficiently preparing enol through selective hydrogenation of alkynol. A conventional tank reactor and a micro-channel reactor are combined for use, and the micro-channel reactor can be used for quickly preparing an enol product after immobilizing a rare earth metal doped catalyst, so that the reaction time is shortened, and the production efficiency is improved. And a phosphine compound is added as a side reaction inhibitor to improve the selectivity.

Method for preparing allyl alcohol compound by reduction of propargyl alcohol compound

A hydrazide compound is used as a reducing agent, an organic amine is used as an auxiliary, and the propargyl alcohol compound is selectively reduced to obtain an allyl alcohol compound under the presence of a solvent and a certain temperature. The method does not need Pd catalyst which is expensive, and the reducing agent and auxiliary agent are cheap and easily available, easy to separate, free of residue in the product, simple in reaction operation process, mild in reaction condition, high in target product selectivity and the like.

An Efficient Alternative to the Total Synthesis of Isophytol

An improved and alternative method for the total synthesis of isophytol from citral via using pseudoionone intermediate was developed and described in this manuscript. This alternative commercially viable approach involves six steps and it represents an alternative method commercially viable over existing published synthetic methods in the literature. This goal was achieved by developing and optimizing an efficient and high yield procedure for the synthesis of a key intermediate i.e. 6,10,14-trimethylpentadectrimethylpentadec-5-en-2-one, by reacting 2-methoxypro-pene with a tertiary alcohol (3,7,11-trimethyldodec-1-ene-3-ol). Isophytol was provided in 58-60% overall yield from citral with >99% purity, evaluated by TLC, GC, and NMR.

SELECTIVE HYDROGENATION OF ALKYNOLS TO ALKENOLS IN THE PRESENCE OF A PHOSPHORUS COMPOUND

The present invention relates to a process of hydrogenating an aIkynoI selectively to an alkenol by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive which is an organic phosphorus compound bearing either a phosphine or a phosphine oxide group and with the proviso that if the additive bears a phosphino group that the additive bears two or more phosphino groups.

Synthesis method and method for synthesizing plant alcohol, isoplant alcohol and geranyl geraniol by using intermediate farnesylacetone (by machine translation)

The invention relates to a synthesis method of intermediate farnesyl acetone and a method for synthesizing vitamin E, vitamin K1, vitamin K2 side chain isovegetable alcohol, plant alcohol and geranyl geraniol by using farnesyl acetone, and concretely relates to hydrogenation of 5 - farnesyl -2 - acetone and farnesyl acetone through three Grignard reaction to obtain plant ketone. The farnesyl acetone reacts with the vinyl chloride Grignard reagent to obtain geranyl linalool, the aromatic leaf-based geraniol is rearranged under acid catalysis, or farnesyl acetone is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain geraniol. The plant alcohol is reacted with the vinyl chloride Grignard reagent to obtain the plant alcohol, and the plant alcohol is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain the plant alcohol. The method has the advantages of cheap and easily available starting materials, short synthetic process steps, low product cost and the like. (by machine translation)

Preparation method for high-purity tocopherol succinate salt

The invention relates to the field of organic synthesis, specifically to a preparation method for tocopherol succinate salt. The preparation method for the tocopherol succinate salt provided by the invention comprises the following steps: hydrogenating dl-alpha-tocopherol in the presence of a precious metal catalyst, subjecting a hydrogenated product and succinic anhydride to an esterification reaction in the presence of alkali so as to prepare a tocopherol succinate intermediate; and subjecting the tocopherol succinate intermediate to salt-forming. The preparation method for the tocopherol succinate salt provided by the invention can effectively improve the purity of a target product, can effectively reduce the content of a single impurity, and can prepare a calcium salt product with a purity capable of reaching 99.9% or above.

HYDROGENATION PROCESS

The present invention relates to a process of reacting specific compounds, which are defined below with hydrogen in the presence of a structured catalyst based on sintered metal fibers (SMF) coated by a ZnO layer with Pd-nanoparticles, to reactions of these specific compounds with hydrogen in the presence of said catalyst and an organic base as well as to vitamins, carotinoids, perfume ingredients, and/or food or feed ingredients prepared by using this reaction.

NOVEL SELECTIVE HYDROGENATION CATALYST COMPRISING PALLADIUM ON POROUS SILICA GLASS AND THE USE THEREOF

The present invention is directed to a catalyst comprising palladium on a porous Silica glass as carrier, as well as to the use of such catalyst for the selective hydrogenation of alkines to alkenes.

HYDROGENATION PROCESS

The present invention relates to a process of reacting specific compounds, which are defined below with hydrogen in the presence of a structured catalyst based on sintered metal fibers (SMF) coated by a ZnO layer with Pd-nanoparticles, to reactions of these specific compounds with hydrogen in the presence of said catalyst and an organic base as well as to vitamins, carotinoids, perfume ingredients, and/or food or feed ingredients prepared by using this reaction.