1002-94-4

Usage

Uses

Used in Flavoring Industry:
(10Z,12E)-10,12-Hexadecadien-1-ol is used as a flavoring agent for its unique taste and aroma, enhancing the sensory experience of food and beverages.
Used in Fragrance Industry:
(10Z,12E)-10,12-Hexadecadien-1-ol is utilized as a fragrance ingredient, contributing to the creation of various scents in perfumes and other scented products.
Used in Insect Attractant Pheromone Industry:
(10Z,12E)-10,12-Hexadecadien-1-ol serves as an attractant pheromone for insects, playing a crucial role in pest control and monitoring efforts in agriculture and environmental management.
Used in Perfume Production:
(10Z,12E)-10,12-Hexadecadien-1-ol is used as a key component in the formulation of perfumes, adding depth and complexity to the overall scent profile.
Used in Soap Making:
(10Z,12E)-10,12-Hexadecadien-1-ol is incorporated into soap formulations to provide a pleasant scent and enhance the product's appeal to consumers.
Used in Disinfectant Production:
(10Z,12E)-10,12-Hexadecadien-1-ol is employed in the manufacturing of disinfectants, leveraging its properties to contribute to the overall effectiveness of these cleaning and sanitizing products.

InChI:InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h4-7,17H,2-3,8-16H2,1H3/b5-4-,7-6+

Synthetic route

(E)-pent-1-en-1-yl-1,3,2-benzodioxaborole (37494-02-3) + (Z)-11-hydroxy-1-undecenyl bromide (87096-21-7) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium ethanolate In ethanol; benzene for 2.5h; Heating;	77%

ω-(Ethoxycarbonyl)nonanal (692-87-5) + <(E)-hex-2-enyl>triphenylphosphonium bromide (88517-93-5) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
(i) NaOEt, EtOH, (ii) LiAlH4; Multistep reaction;

ω-(Ethoxycarbonyl)nonanal (692-87-5) + <(E)-hex-2-enyl>triphenylphosphonium bromide (88517-93-5) → (10Z,12E)-hexadecadien-1-ol (1002-94-4) + (10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5)

Conditions	Yield
(i) NaOEt, EtOH, (ii) LiAlH4; Multistep reaction;

hexadec-12t-en-10-yn-1-ol (765-23-1) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
With quinoline; hydrogen; Lindlar's catalyst

hexadeca-10c,12t-dienoic acid methyl ester (929-66-8) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

1-Pentyne (627-19-0) + (Z)-11-hydroxy-1-undecenyl bromide (87096-21-7) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
With benzo[1,3,2]dioxaborole; tetrakis(triphenylphosphine) palladium(0) Yield given. Multistep reaction;

(E)-(11-hydroxy-1-undecenyl)boronic acid (87096-18-2) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Br2; 2.) NaOEt / 1.) CHCl3, CCl4, -10 to 0 deg C, 1 h; 2.) CHCl3, CCl4, ethanol, 30 min 2: 77 percent / Pd(PPh3)4/NaOEt / benzene; ethanol / 2.5 h / Heating View Scheme

undec-10-yn-1-ol (2774-84-7) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) 1,3,2-benzodioxaborole, then hydrolysis; 2) bromine 2: NaOMe 3: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme

10-Undecen-1-ol (112-43-6) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / -10 - 0 °C 2: NaOMe 3: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme

Methyl 10-undecenoate (111-81-9) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiAlH4 2: Br2 / -10 - 0 °C 3: NaOMe 4: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme

10,11-Dibromo-1-undecanol (24724-18-3) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOMe 2: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme

2-(9-bromononyloxy)tetrahydropyran (55695-90-4) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaNH2, liq. NH3, (ii) aq. H2SO4, MeOH 2: H2, quinoline / Lindlar catalyst View Scheme

(E)-1-bromo-2-hexene (73881-10-4) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme
Multi-step reaction with 2 steps 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme

ethyl 10-undecenenoate (692-86-4) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) O3, CH2Cl2, (ii) (reduction) 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme
Multi-step reaction with 2 steps 1: (i) O3, CH2Cl2, (ii) (reduction) 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme

(E)-hept-3-ene-1-yne (764-58-9) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaNH2, liq. NH3, (ii) aq. H2SO4, MeOH 2: H2, quinoline / Lindlar catalyst View Scheme

Hexadeca-10c,12t-dien-1-saeure (96752-09-9) → (10Z,12E)-hexadecadien-1-ol (1002-94-4)

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

(10Z,12E)-hexadecadien-1-ol (1002-94-4) + 4-(4-nitrophenylazo)benzoyl chloride (22286-74-4) → Hexadecadien-(10c,12t)-yl-(1)-4'-nitro-azobenzol-carbonsaeure-(4)-ester (864-40-4)

Conditions	Yield
With pyridine

Upstream product

• 692-87-5 ω-(Ethoxycarbonyl)nonanal 
• 88517-93-5 <(E)-hex-2-enyl>triphenylphosphonium bromide 
• 765-23-1 hexadec-12t-en-10-yn-1-ol 
• 929-66-8 hexadeca-10c,12t-dienoic acid methyl ester 
• 627-19-0 1-Pentyne 
• 87096-21-7 (Z)-11-hydroxy-1-undecenyl bromide 
• 37494-02-3 (E)-pent-1-en-1-yl-1,3,2-benzodioxaborole 
• 87096-18-2 (E)-(11-hydroxy-1-undecenyl)boronic acid 
• 2774-84-7 undec-10-yn-1-ol 
• 112-43-6 10-Undecen-1-ol 
• 111-81-9 Methyl 10-undecenoate 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 73881-10-4 (E)-1-bromo-2-hexene 
• 692-86-4 ethyl 10-undecenenoate 

Downstream Products

• 864-40-4 Hexadecadien-(10c,12t)-yl-⁽¹⁾-4'-nitro-azobenzol-carbonsaeure-⁽⁴⁾-ester 

Relevant academic research and scientific papers

NEW STEREOSPECIFIC SYNTHESES OF PHEROMONE BOMBYKOL AND ITS THREE GEOMETRICAL ISOMERS

We describe stereospecific syntheses of pheromone, bombykol and the three geometrical isomers by means of the palladium-catalyzed cross-coupling between an appropriate alkenylborane and an alkenyl halide in the presence of a base.

NEW STEREOSPECIFIC SYNTHESES OF PHEROMONE BOMBYKOL AND ITS THREE GEOMETRICAL ISOMERS

New stereospecific syntheses of the pheromone bombykol and its three geometrical isomers are achieved by palladium-catalyzed cross-coupling reaction between an appropriate alkenylborane and an alkenyl halide in the presence of a base.

Bidirectional, organocatalytic synthesis of lepidopteran sex pheromones

Shuffling of two simple building blocks and a regioselective transfer hydrogenation allow for the rapid synthesis of a small collection of lepidopteran sex pheromones, e.g., 8E,10Z-tetradeca-8,10-dienal 5c, from the horse chestnut leafminer (Cameraria ohridella).

Synthesis of (E,E)-10,12-hexadecadienal and (Z)-11-octadecenal

Two economically important insect pheromones, viz. (E,E)-10,12-hexadecadien-1-al (1) and (Z)-11-octadecenal (2) of cotton pests have been synthesised from cheap and readily available materials utilising in situ alkylation of dianion of 4-pentyn-1-ol obtainable easily by lithium amide induced opening of tetrahydrofurfuryl chloride in liquid ammonia.