(E,E,E,E)-Squalene supplier

Name
Squalene
EINECS 203-826-1
CAS No. 111-02-4
Article Data69
CAS DataBase
Density 0.858
Solubility <0.1 g/100 mL at 19 ºC
Melting Point -75 ºC
Formula C30H50
Boiling Point 285 ºC (25 mmHg)
Molecular Weight 410.727
Flash Point 254.1°C
Transport Information
Appearance Clear, slightly yellow liquid with a faint odor.
Safety Moderately toxic by intravenous route. Slightly toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,6,10,14,18,22-Tetracosahexaene,2,6,10,15,19,23-hexamethyl-, (all-E)- (8CI); (E,E,E,E)-Squalene;2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene; Nikko Squalane EX;Spinacen; Spinacene; Squalen; Squalene; Super Squalene; all-trans-Squalene;trans-Squalene
PSA 0.00000
LogP 10.60500

Synthetic route

: C36H54O2S

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium triethylborohydride In tetrahydrofuran at -78 - 20℃; for 50h;	88.7%

: 106-28-5
Farnesol

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

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

C: 66633-32-7
(E)-3,7,11-trimethyldodeca-1,6,10-triene

Conditions

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 2h; Solvent; Inert atmosphere; Reflux; regioselective reaction;	A 9% B 8% C 78%

...Expand

: 1299297-72-5
[(6E,10E,14E,18E)-13-(1-ethoxyethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-12-yl]sulfonylbenzene

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride In tetrahydrofuran; 1,4-dioxane at 20 - 70℃; for 10h; Inert atmosphere;	77%

: 14050-42-1, 54910-48-4, 54910-49-5, 54910-50-8, 55058-26-9, 55058-27-0, 132199-42-9, 138809-21-9, 147731-51-9, 7200-26-2
2,3-Oxidosqualene

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate at -78℃;	70%
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate In toluene at -78℃; for 12h;	70%

: 106-28-5
Farnesol

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
Stage #1: Farnesol With tert.-butyl lithium In tetrahydrofuran; n-heptane at -78 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 10h; Inert atmosphere; Reflux;	67%
Multi-step reaction with 2 steps 1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C 2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C View Scheme
Multi-step reaction with 2 steps 1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C 2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 / 0.5 h / -40 °C 2: lithium bromide / CH2Cl2; tetrahydrofuran / 1 h / 0 °C 3: 1) lithium biphenylide, barium iodide / 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h View Scheme
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 / 0.5 h / -40 °C 2: lithium chloride / CH2Cl2; tetrahydrofuran / 1 h / 0 °C 3: 1) lithium biphenylide, barium iodide / 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h View Scheme

: C22H25NO5S

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; for 16h; Wurtz type coupling reaction; Inert atmosphere; stereoselective reaction;	60%

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 86342-81-6
(6E,14E)-2,6,10,11,15,19-Hexamethyl-10,11-divinyl-icosa-2,6,14,18-tetraene

C: 86342-79-2
(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions

Conditions	Yield
With chlorotris(triphenylphosphine)cobalt(I) In benzene for 0.5h; Ambient temperature;	A 55% B 12% C 22%
With chlorotris(triphenylphosphine)cobalt(I) In benzene for 3h; Ambient temperature;	A 55% B 12% C 22%

...Expand

: 106-28-5
Farnesol

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 66633-32-7
(E)-3,7,11-trimethyldodeca-1,6,10-triene

Conditions

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 6h; Inert atmosphere; Reflux;	A 23% B 42%
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 4h; Time; Inert atmosphere; Reflux;	A 36% B 24%

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

: 3,12-dibromo-10-ethyl-2,6-dimethyl-dodeca-6,10-dien-2-ol

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 3-((3E,7E,11E,15E)-7-Ethyl-3,12,16,20-tetramethyl-henicosa-3,7,11,15,19-pentaenyl)-2,2-dimethyl-oxirane

C: C32H54O2

Conditions

Conditions	Yield
With copper(l) iodide; lithium pyrrolidide	A 15% B 33% C 10%

...Expand

: 130673-53-9
4-{Phenyl-[(3E,7E)-4,8,12-trimethyl-1-((1E,5E)-2,6,10-trimethyl-undeca-1,5,9-trienyl)-trideca-3,7,11-trienyl]-phosphinoyl}-morpholine

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With lithium; ethylamine; tert-butyl alcohol In tetrahydrofuran at 0℃; for 2.5h;	31%

: 24163-93-7, 24163-94-8, 28290-41-7, 56881-57-3, 6874-67-5
farnesyl bromide

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With diethyl ether; lithium

: 4128-17-0
(2E,6E)-farnesyl acetate

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 56782-22-0
(6E,10Z,14Z,18E)-squalene

C: 86342-80-5
(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

D: 86342-79-2
(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions

Conditions	Yield
With [2,2]bipyridinyl; copper; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 115h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 4128-17-0
(2E,6E)-farnesyl acetate

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 86342-80-5
(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

C: 86342-79-2
(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

D: (5E,9Z,13Z,17E)-2,5,9,14,18,21-Hexamethyl-docosa-2,5,9,13,17,20-hexaene

Conditions

Conditions	Yield
With zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; methanol for 2.5h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

: 6784-45-8, 67023-85-2, 72132-86-6, 67023-84-1
(2E,6E)-farnesyl chloride

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With lithium biphenylide; barium(II) iodide 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h; Yield given. Multistep reaction;

: 85611-33-2
(E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 24566-13-0
squalene

C: 56782-22-0
(6E,10Z,14Z,18E)-squalene

D: 86342-79-2
(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions

Conditions	Yield
With [2,2]bipyridinyl; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 72h; Heating; Yield given. Further byproducts given. Yields of byproduct given;
With [2,2]bipyridinyl; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 72h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 6784-45-8, 67023-85-2, 72132-86-6, 67023-84-1
(2E,6E)-farnesyl chloride

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 86342-79-2
(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions

Conditions	Yield
With lithium biphenylide; barium(II) iodide In tetrahydrofuran at -78℃; for 1h; Yield given. Yields of byproduct given;
With lithium biphenylide; barium(II) iodide In tetrahydrofuran at -78℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: Farnesyl diphosphate

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With PP1; Tween-80 Kinetics; Mechanism; buffer (KF, MgCl2, DTT, NADHP);

: Presqualene diphosphate

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With (ammonium analogue); inhib. phosphonophosphate 8 Kinetics; Mechanism;

: 1-((6E,10E,14E,18E)-2,6,10,14,18,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-sulfonyl)-4-methyl-benzene

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 24566-13-0
squalene

Conditions

Conditions	Yield
With lithium triethylborohydride; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 0℃; Yield given. Yields of byproduct given;

: 106-28-5
Farnesol

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: (6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-5-thiol

C: (6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-thiol

D: (6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-9-thiol

Conditions

Conditions	Yield
With iron sulfide; hydrogen sulfide In water at 100℃; under 1500.1 Torr; for 144h; Yield given;

...Expand

: 99548-50-2
3,6-dichloro-octane-2,7-dione

homogeranyl lithium: homogeranyl lithium

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With diethyl ether at -70℃; Behandeln des Reaktionsprodukts mit methanol.Kalilauge, dann mit Natriumjodid und Natriumacetat in Essigsaeure und Propionsaeure bei -20grad bis +20grad; dann mit Zinn(II)-chlorid in Aether und Pyridin und mit Phosphoroxychlorid;

P,P,P,P',P',P'-hexaphenyl-butane-1,4-diyldiphosphonium dibromide: P,P,P,P',P',P'-hexaphenyl-butane-1,4-diyldiphosphonium dibromide

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With tetrahydrofuran; n-butyllithium; diethyl ether Erwaermen des Reaktionsprodukts mit 6,10-Dimethyl-undeca-5t,9-dien-2-on;

Botryococcus braunii: Botryococcus braunii

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 42719-34-6
(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene

C: 88361-07-3, 127483-82-3, 127483-86-7
(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

D: showacene

Conditions

Conditions	Yield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;

...Expand

Botryococcus braunii: Botryococcus braunii

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 42719-34-6
(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene

C: 88361-07-3, 127483-82-3, 127483-86-7
(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

D: darwinene

Conditions

Conditions	Yield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;

...Expand

Botryococcus braunii: Botryococcus braunii

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 88361-07-3, 127483-82-3, 127483-86-7
(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

C: showacene

D: darwinene

Conditions

Conditions	Yield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;

...Expand

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

A: (6E,10E,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

B: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

C: Squalene

Conditions

Conditions	Yield
With manganese; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 20℃;

...Expand

: 6138-90-5
trans-geranyl bromide

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

A: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B: 35162-77-7
digeranyl

C: 38235-83-5
2,6,10,15,19-pentamethyleicosa-(6E,10E,14E)-2,6,10,14,18-pentaene

Conditions

Conditions	Yield
With pyrrolidine; copper(l) iodide; n-butyllithium In diethyl ether at -38℃; for 1h;	A n/a B 20 mg C 28 mg

...Expand

: 24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7
farnesyl bromide

: 870-63-3
prenyl bromide

A: 2,6,10,15-tetramethylhexadeca-(6E,10E)-2,6,10,14-tetraene

B: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With pyrrolidine; copper(l) iodide; n-butyllithium In diethyl ether at -38℃; for 1h;

...Expand

: 106-24-1
Geraniol

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C 2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C View Scheme

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 111-01-3
2,6,10,15,19,23-hexamethyltetracosane

Conditions

Conditions	Yield
With hydrogen In ethanol at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Temperature; Solvent; chemoselective reaction;	99.6%
With hydrogen; nickel
With palladium 10% on activated carbon; hydrogen In ethanol at 100℃; under 3750.38 Torr; for 1h; Autoclave;

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 654052-53-6
2,3,22,23-Dioxidosqualene

Conditions

Conditions	Yield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With N-Bromosuccinimide; water In tetrahydrofuran for 3h; Stage #2: With potassium carbonate In methanol for 2h; Further stages.;	90%
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid or NBS; Multistep reaction;
Multi-step reaction with 2 steps 1: 22 percent / dimethyldioxirane 2: 60 percent / methyl(trifluoromethyl)dioxirane View Scheme

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 10008-64-7
(rac)-hexaepoxysqualene

Conditions

Conditions	Yield
With polyoxotungstate PW4O24[methyltri((C8-C10)alkyl)ammonium]3 In water at 20℃; for 12h; pH=7.0; Green chemistry;	89%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 77-76-9
2,2-dimethoxy-propane

: 642093-28-5
(3R)-2,3-isopropylidenedioxy-2,3-dihydrosqualene

Conditions

Conditions	Yield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With potassium osmate(VI); methanesulfonamide; potassium hexacyanoferrate(III); chiral monocinchona derivative C70H63N5O3; potassium carbonate In water; tert-butyl alcohol at 0℃; for 20h; Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid at 23℃; for 1h; Further stages.;	88%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 56882-09-8
(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-al

Conditions

Conditions	Yield
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 10h;	86%
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With 3-chloro-benzenecarboperoxoic acid In dichloromethane Epoxidation; Stage #2: With periodic acid Oxidation;
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; Stage #2: With periodic acid In diethyl ether	3.1 g

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 57434-13-6
2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol

Conditions

Conditions	Yield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 1.33333h; Stage #2: With dihydrogen peroxide In tetrahydrofuran for 0.5h; Further stages.;	67%
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With borane-THF; 2-methyl-but-2-ene In tetrahydrofuran at 0 - 4℃; for 77h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 12h;	51%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 14050-42-1, 54910-48-4, 54910-49-5, 54910-50-8, 55058-26-9, 55058-27-0, 132199-42-9, 138809-21-9, 147731-51-9, 7200-26-2
2,3-Oxidosqualene

Conditions

Conditions	Yield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With N-Bromosuccinimide; water In tetrahydrofuran for 0.75h; Stage #2: With methanol; potassium carbonate for 0.333333h;	62%
With 3,3-dimethyldioxirane	22%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;	14%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 63976-65-8
(3R)-(6E,10E,14E,18E)-2,3-dihydroxy-2,3-dihydrosqualene

Conditions

Conditions	Yield
With potassium osmate(VI); methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; butan-1-ol at 0℃; for 19h; ligand: 1,4-bisnaphthopyridazine Monomethiodide Salt;	62%
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In tert-butyl alcohol at 0℃; for 48h; optical yield given as %ee; enantioselective reaction;	12%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A: (6E,10E,14E,18E)-3,22-Dichloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,23-hexaene

B: (6E,10E,14E,18E)-3-Chloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,22-hexaene

Conditions

Conditions	Yield
With N-chloro-succinimide; selenenyl bromide In dichloromethane at 20℃; for 8h;	A 18% B 55%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 65746-05-6
squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)

Conditions

Conditions	Yield
With N-Bromosuccinimide; water In tetrahydrofuran at 20℃; for 1h;	51%
With N-Bromosuccinimide; water In tetrahydrofuran for 1h; Ambient temperature;	35%
With N-Bromosuccinimide In tetrahydrofuran; water 1.) 0 deg C, 30 min; 2.) RT, 1 h;	35%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 2-[5''''-(1-hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-eicosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions

Conditions	Yield
With sodium periodate; ruthenium(IV) oxide In water; ethyl acetate; acetonitrile for 0.5h;	50%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions

Conditions	Yield
With sodium periodate; ruthenium(IV) oxide In ethanol; water; acetonitrile at 0℃; for 0.5h;	50%
With sodium periodate; ruthenium tetroxide
With sodium periodate; ruthenium tetroxide

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: C21H16BF2N3O2S

A: C23H20BF2N3O2S

B: C28H28BF2N3O2S

C: C47H58BF2N3O2S

D: C33H36BF2N3O2S

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In dichloromethane at 40℃; for 1h; Cross Metathesis; regioselective reaction;	A 45% B 6.3% C 20.3% D 8.5%

...Expand

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: (3R)-2,3,22,23-tetrahydroxy-2,3,22,23-tetrahydrosqualene

Conditions

Conditions	Yield
With potassium osmate(VI); methanesulfonamide; potassium hexacyanoferrate(III); chiral monocinchona derivative C70H63N5O3; potassium carbonate In methanol; water; tert-butyl alcohol at 0℃; for 3h;	40%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A: 65746-05-6
squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)

B: 110390-75-5
squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran; water 1.) 30 min, 0 deg C; 2.) 1 h, RT;	A n/a B 30%
With N-Bromosuccinimide; water In tetrahydrofuran for 1h; Ambient temperature;	A n/a B 30%
With N-Bromosuccinimide; water In tetrahydrofuran at 0℃; for 1.5h;

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 1-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,9,13,17-tetramethyl-octadeca-4,8,12,16-tetraen-1-ol

: (4E,8E)-(R)-1-[(2S,5R,2'S,5'R)-5'-(1-Hydroxy-1-methyl-ethyl)-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl]-5,9,13-trimethyl-tetradeca-4,8,12-trien-1-ol

: (E)-(S)-2-[(2S,5S,2'S,5'R,2''R,5''S)-5''-(1-Hydroxy-1-methyl-ethyl)-2',2''-dimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl]-6,10-dimethyl-undeca-5,9-dien-2-ol

: 2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions

Conditions	Yield
With sodium periodate; ruthenium(IV) oxide In ethanol; water; acetonitrile at 0℃; for 0.0666667h;	A 5% B 4.5% C 4.3% D 28%

...Expand

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 110390-75-5
squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran at 0℃;	27%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one In 1,2-dimethoxyethane; dichloromethane; water Ambient temperature;
With N-Bromosuccinimide; water In tetrahydrofuran

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 67858-78-0
(4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal

Conditions

Conditions	Yield
With MMPP In tetrahydrofuran; water at 25℃; for 48h;	26%
Multi-step reaction with 2 steps 1: MCPBA / CH2Cl2 / 0 °C 2: HIO4 / diethyl ether / 25 °C View Scheme

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

: 62399-03-5
(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaenedioic acid

Conditions

Conditions	Yield
soil bacterium;	26%

: 111-02-4
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A: (2E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,23-hexaene-1,22-diol

B: 97232-74-1
(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-1,6,10,14,18,22-hexaen-3-ol

C: 79370-71-1
(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene-1-ol

D: 79370-70-0
(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,22-hexaene-1,24-diol

Conditions

Conditions	Yield
Multistep reaction;	A 9% B 26% C 20% D 6%

...Expand

(E,E,E,E)-Squalene Chemical Properties

IUPAC Name: (6Z,10E,14Z,18E)-2,6,10,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4)
Synonyms : Trans-squalene ; (all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
Molecular Structure:
Molecular Formula: C₃₀H₅₀
Molecular Weight : 410.72
CAS Registry Number : 111-02-4
EINECS : 203-826-1
Product Categories: Biochemistry;Terpenes;Terpenes (Others)
Mol File: 111-02-4.mol
Surface Tension: 29.2 dyne/cm
Density: 0.848 g/cm³
Flash Point: 254.1 °C
Melting point -75 ºC
Enthalpy of Vaporization: 65.81 kJ/mol
Boiling Point: 429.3 °C at 760 mmHg
Vapour Pressure: 3.56E-07 mmHg at 25°C
Refractive index: 1.4945-1.4965
Water solubility: <0.1 g/100 mL at 19 ºC
refractive index : n20/D 1.494(lit.)
storage temp: 2-8°C
Water Solubility: <0.1 g/100 mL at 19 ºC
Appearance: Trans-squalene (111-02-4) is clear colourless to faint yellow oil .

(E,E,E,E)-Squalene Uses

Trans-squalene (111-02-4) is used for nutrition medicine,mainly for oral treatment of high-, low blood pressure, anemia, diabetes, liver cirrhosis, cancer, constipation, cavities; topical treatment of tonsillitis, wheezing, bronchitis, influenza, tuberculosis, rhinitis, gastric ulcer, duodenal ulcer, gall bladder stone , rheumatism and neuralgia.

(E,E,E,E)-Squalene Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	1800mg/kg (1800mg/kg)		Japanese Journal of Cancer Research. Vol. 76, Pg. 1021, 1985.
mouse	LD50	oral	5gm/kg (5000mg/kg)		Japanese Journal of Cancer Research. Vol. 76, Pg. 1021, 1985.

(E,E,E,E)-Squalene Consensus Reports

Reported in EPA TSCA Inventory.

(E,E,E,E)-Squalene Safety Profile

Safety Statements 24/25
24/25: Trans-squalene (111-02-4) used, avoid contact with skin and eyes
WGK Germany 2
RTECS XB6010000
F 8-10-23
HS Code 29012980

(E,E,E,E)-Squalene Specification

Chemical Properties: clear colourless to faint yellow oil
General Description Clear, slightly yellow liquid with a faint odor.
Air & Water Reactions : May become discolored on exposure to air. Insoluble in water.
Reactivity Profile: (all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene is incompatible with strong oxidizing agents. .
Health Hazard : ACUTE/CHRONIC HAZARDS: When heated to decomposition (all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene emits toxic fumes of carbon monoxide and carbon dioxide.
Fire Hazard : (all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene is probably combustible.

Product Name

Squalene

Synthetic route

(E,E,E,E)-Squalene Chemical Properties

(E,E,E,E)-Squalene Uses

(E,E,E,E)-Squalene Toxicity Data With Reference

(E,E,E,E)-Squalene Consensus Reports

(E,E,E,E)-Squalene Safety Profile

(E,E,E,E)-Squalene Specification

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