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111-02-4

Basic Information
CAS No.: 111-02-4
Name: Squalene
Article Data: 69
Molecular Structure:
Molecular Structure of 111-02-4 (Squalene)
Formula: C30H50
Molecular Weight: 410.727
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
EINECS: 203-826-1
Density: 0.858
Melting Point: -75 ºC
Boiling Point: 285 ºC (25 mmHg)
Flash Point: 254.1°C
Solubility: <0.1 g/100 mL at 19 ºC
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.
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
ConditionsYield
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
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 2h; Solvent; Inert atmosphere; Reflux; regioselective reaction;A 9%
B 8%
C 78%
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
ConditionsYield
With (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride In tetrahydrofuran; 1,4-dioxane at 20 - 70℃; for 10h; Inert atmosphere;77%
Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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
ConditionsYield
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%
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
ConditionsYield
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%

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
ConditionsYield
With copper(l) iodide; lithium pyrrolidideA 15%
B 33%
C 10%
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
ConditionsYield
With lithium; ethylamine; tert-butyl alcohol In tetrahydrofuran at 0℃; for 2.5h;31%
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Chemistry

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 .
 

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.

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.


 

Consensus Reports

Reported in EPA TSCA Inventory.

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

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.