101373-01-7

Basic information

• Product Name: 4,6,10-Hexadecatrien-1-ol, (E,E,Z)-
• Synonyms: (E,E,Z)-4,6,10-hexadecatriene-1-ol;4,6,10-Hexadecatrien-1-ol,(E,E,Z)
• CAS NO: 101373-01-7
• Molecular Formula: C16H28O
• Molecular Weight: 236.398
• Mol File: 101373-01-7.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: 4,6,10-Hexadecatrien-1-ol, (E,E,Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6,10-Hexadecatrien-1-ol, (E,E,Z)-(101373-01-7)
• EPA Substance Registry System: 4,6,10-Hexadecatrien-1-ol, (E,E,Z)-(101373-01-7)

Safety Data

• Hazardous Substances Data: 101373-01-7(Hazardous Substances Data)

Usage

General Description

4,6,10-Hexadecatrien-1-ol, (E,E,Z)-, also known as Squalene monohydroperoxide, is a chemical compound that is widely used in cosmetics due to its properties that enhance skin moisture retention and elasticity. Its chemical formula is C16H28O and it is characterized by a double bond configuration with (E,E,Z) stereoisomers. It is typically found in shark liver oil, as well as other plant and fish oils. In skincare products, it is often used as an antioxidant and for its potential anti-carcinogenic properties. However, it should be used with caution as in some cases, it has been known to cause skin irritations.

Synthetic route

(6E,10Z)-hexadecadiene-4-yn-1-ol → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
With ammonium hydroxide; lithium Concentration;	83%

(4E,10Z)-hexadeca-4,10-dien-6-yn-1-ol → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
With lithium aluminium tetrahydride; diethylene glycol dimethyl ether In tetrahydrofuran at 117 - 121℃; for 24h; Inert atmosphere; stereoselective reaction;	74%

(Z)-4-decen-1-ol (57074-37-0) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 2.1: triphenylphosphine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 2.2: 20 °C / Cooling; Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 4.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 2: triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 3: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere; Cooling 4: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 5: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

(Z)-4-decenal (30390-50-2, 65405-70-1, 21662-09-9) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Cooling; Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 3.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere; Cooling 3: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 4: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

(Z)-1,1-dibromoundeca-1,5-diene → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere; Cooling 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 3: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

5-bromo-trans-4-pentenal → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 3 h / 0 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 3: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

(Z)-undec-5-en-1-yne → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 2: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

(E)-5-bromopent-4-en-1-ol → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 2: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

hexyltriphenylphosphonium bromide (4762-26-9) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: water; hydrogenchloride / dichloromethane / 5 h / 20 °C 2.2: 11 h / -78 - 20 °C 3.1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 4.1: triphenylphosphine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 4.2: 20 °C / Cooling; Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 6.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: water; hydrogenchloride / dichloromethane / 5 h / 20 °C 2.2: 11 h / -78 - 20 °C 3.1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 4.1: triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere; Cooling 6.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 7.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

hexylidenetriphenylphosphoran (16666-79-8, 19493-12-0) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: water; hydrogenchloride / dichloromethane / 5 h / 20 °C 1.2: 11 h / -78 - 20 °C 2.1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 3.2: 20 °C / Cooling; Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 5.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1.1: water; hydrogenchloride / dichloromethane / 5 h / 20 °C 1.2: 11 h / -78 - 20 °C 2.1: pyridinium chlorochromate; silica gel / dichloromethane / 5 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere; Cooling 5.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diethylamine / 12 h / Inert atmosphere 6.1: lithium aluminium tetrahydride; diethylene glycol dimethyl ether / tetrahydrofuran / 24 h / 117 - 121 °C / Inert atmosphere View Scheme

(6E,10Z)-1-tetrahydropyran-2-yloxy-hexadecadiene-4-yne → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 20 °C 2: lithium; ammonium hydroxide View Scheme

pent-1-yn-5-ol (5390-04-5) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 0 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diisopropylamine / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 3.1: iron(III)-acetylacetonate; 1-methyl-pyrrolidin-2-one / tetrahydrofuran / -20 - -15 °C / Inert atmosphere 3.2: 8 h / -15 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / methanol / 20 °C 5.1: lithium; ammonium hydroxide View Scheme

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; diisopropylamine / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 2.1: iron(III)-acetylacetonate; 1-methyl-pyrrolidin-2-one / tetrahydrofuran / -20 - -15 °C / Inert atmosphere 2.2: 8 h / -15 - 20 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 20 °C 4.1: lithium; ammonium hydroxide View Scheme

trans-7-chloro-1-tetrahydropyran-2-yloxy-6-hepten-4-yne → (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: iron(III)-acetylacetonate; 1-methyl-pyrrolidin-2-one / tetrahydrofuran / -20 - -15 °C / Inert atmosphere 1.2: 8 h / -15 - 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / methanol / 20 °C 3.1: lithium; ammonium hydroxide View Scheme

(4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol (101373-01-7) + acetic anhydride (108-24-7) → (4E,6E,10Z)-4,6,10-hexadecatrienyl acetate (101372-99-0)

Conditions	Yield
With pyridine at 20℃; Concentration; Inert atmosphere;	97%

Upstream product

• 7785-26-4 (-)-α-pinene 
• 473-62-1 (1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one 
• 14575-93-0 isopinocamphone 
• 144054-76-2 6-<(tetrahydropyranyl)oxy>-2E-hexanetriphenylphosphonium bromide 
• 144054-75-1 (Z)-4-decenyltriphenylphosphonium bromide 
• 30390-50-2 (Z)-4-decenal 
• 142143-84-8 1-<(tetrahydropyranyl)oxy>-(4E,10Z)-hexadecatriene 
• 7785-70-8 (+)-α-pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 276253-82-8 tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate 
• 329710-76-1 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate 
• 138175-23-2 (1R,2R,5R)-2,6,6-Trimethyl-3-[(E)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 101372-99-0 (4E,6E,10Z)-4,6,10-hexadecatrienyl acetate 
• 139650-81-0 (4E,6Z,10Z)-4,6,10-hexadecatrienyl acetate 

Relevant articles and documents

Synthesis of (4: E,6 Z,10 Z)-hexadeca-4,6,10-trien-1-ol and (4 E,6 E,10 Z)-hexadeca-4,6,10-trien-1-ol, the pheromone components of cocoa pod borer moth Conopomorpha cramerella

A concise and efficient synthesis of the pheromone components of the cocoa pod borer moth, namely (4E,6Z,10Z)-hexadeca-4,6,10-trien-1-ol and (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol, starting from commercially available materials, was reported. The overall yield was 30.4% and 27.4%, respectively. The stereoselective formation of (E,Z)- or (E,E)-conjugated double bond relied on Sonogashira coupling with (E)-5-bromopent-4-en-1-ol prepared from (E)-5-bromopent-4-enal and the stereoselective hydrogenation of the enyne, while the 10Z-double bond was formed by Wittig reaction from 4-hydroxybutanal and n-hexyltriphenylphosphonium bromide.

Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one

Seven novel palladium complexes of the type [Pd(HL)Cl2] and [Pd(L)Cl] containing chiral pinane ligands (HL = 3-[(2-aminoethyl)imino]-pinane-2-ol; 3,3′-(ethylenediimino)bis-pinane-2-ol; cis-3-(2-aminoethylamino)-pinane-2-ol; cis-3,3′(ethylenediamino)bis-pinane-2-ol; trans-3,3′(ethylenediamino)bis-pinane-2-ol; 3-[2-(2-hydroxybenzylamino)ethylamino]-pinane-2-ol; L = 3-[2-(3,5-di-tert-butyl-2-hydroxybenzylidene)aminoethylimino]pinane-2-ol) were synthesized in good yields from the direct reaction of chiral nitrogen ligands with Li2PdCl4 in MeOH. These synthesized complexes were characterized by means of elemental analysis, FT-IR, multidimensional and multinuclear NMR spectroscopic methods.

Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water

Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals.