765-17-3

Basic information

• Product Name: bombykol
• Synonyms: bombykol;(E,Z)-10,12-Hexadecadienyl acetate;(10E,12Z)-Hexadecadien-1-ol
• CAS NO: 765-17-3
• Molecular Formula: C₁₆H₃₀O
• Molecular Weight: 238.41
• Product Categories: insect pheromone
• Mol File: 765-17-3.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 298.3°C at 760 mmHg
• Flash Point: 133.5°C
• Appearance: /
• Density: 0.859g/cm³
• Vapor Pressure: 0.000129mmHg at 25°C
• Refractive Index: 1.473
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: bombykol(CAS DataBase Reference)
• NIST Chemistry Reference: bombykol(765-17-3)
• EPA Substance Registry System: bombykol(765-17-3)

Safety Data

• Hazardous Substances Data: 765-17-3(Hazardous Substances Data)

Usage

Uses

Bombykol can be used in engineered or chemical process and biological study of quantitative analysis of pheromone-binding protein specificity.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 1527, 1983 DOI: 10.1016/S0040-4039(00)81700-1

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

1-Tetrahydropyranyloxyhexadec-(E)10,(Z)12-diene (74502-09-3) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 70℃; for 4h;	97.7%

(4Z,6E)-16-(tert-butyldimethylsilyl)oxy-4,6-hexadecadiene (220083-29-4) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; Substitution;	93%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 4h;

(E)-10-hexadecen-12-yn-1-ol (765-21-9) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With water; silver; copper; zinc In methanol at 60 - 70℃; for 6.5h;	90%
With quinoline; hydrogen; Lindlar's catalyst
With hydrogen; Lindlar's catalyst In methanol

(Z)-1-pentenyl bromide (31849-75-9) + (E)-(11-hydroxy-1-undecenyl)boronic acid (87096-18-2) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium ethanolate In ethanol; benzene for 2.5h; Heating;	82%

(Z)-(1-pentenyl)-diisopropyloxyborane (110897-15-9) + (E)-11-hydroxy-1-undecenyl iodide (87096-20-6) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With potassium hydroxide; PdL4	82%

C6H12ClMgO(1-)*Cl(1-)*Mg(2+) + 1-iodo, (E,Z)4,6-decadiene (94742-73-1) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With copper(I) bromide In tetrahydrofuran at 10℃; for 0.5h;	76%

(bromo-8 octyloxy-1)-1, ethoxy-1 ethane (56904-95-1) + acetoxy-1 octadiene-2,4 (E,Z) (56904-76-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + (10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5)

Conditions	Yield
With magnesium In tetrahydrofuran; diethyl ether at -30℃; for 1.5h;	A 75% B 20%

chloro-8 trimethylsilyl oxy-1 octane (72621-48-8) + acetoxy-1 octadiene-2,4 (E,Z) (56904-76-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + (10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5)

Conditions	Yield
With magnesium In tetrahydrofuran; diethyl ether at -30℃; for 1.5h;	A 75% B 20%

(10E,12Z)-Hexadeca-1,10,12-triene (270074-60-7) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Stage #1: (10E,12Z)-Hexadeca-1,10,12-triene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 2h; Addition; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 25℃; for 2h; Oxidation;	67%

(E)-11-hydroxy-1-undecenyl iodide (87096-20-6) + (Z)-1-pentenyldisiamylborane (87096-19-3) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium ethanolate In ethanol; benzene for 2.5h; Heating;	50%

(E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran (72858-83-4) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
(i) disiamylborane, (ii) NaOH, H2O2; Multistep reaction;
Multi-step reaction with 2 steps 1: pTsOH*H2O / methanol / Heating 2: 90 percent / H2O / Zn/Cu/Ag / methanol / 6.5 h / 60 - 70 °C View Scheme

(10E,12Z)-hexadeca-10,12-dienoic acid (1002-80-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

(10E,12Z)-10,12-Hexadecadiensaeure-methylester (63024-91-9) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride

hexadec-10t-en-12-ynoic acid ethyl ester (764-70-5) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
(i) H2, Lindlar catalyst, quinoline, (ii) LiAlH4; Multistep reaction;

(E)-1-trimethylsiloxy-10-hexadecen-12-yne (51760-74-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
(i) bis-(1,2-dimethyl-propyl)-borane, THF, (ii) iPrCO2H, (iii) LiAlH4; Multistep reaction;
Yield given. Multistep reaction;

[8-(1-ethoxy-ethoxy)-octyl]-magnesium bromide + acetoxy-1 octadiene-2,4 (E,Z) (56904-76-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
(i) CuI, THF, (ii) /BRN= 3931985/, (iii) (acid hydrolysis); Multistep reaction;

pentynyl bromide (14752-60-4) + (E)-11-hydroxy-1-undecenyl iodide (87096-20-6) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With bis-(1,2-dimethylpropyl)borane; tetrakis(triphenylphosphine) palladium(0) Yield given. Multistep reaction;

undec-10-yn-1-ol (2774-84-7) + (Z)-1-pentenyl bromide (31849-75-9) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

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

(Z)-(6R,7R)-16-(Tetrahydro-pyran-2-yloxy)-6-trimethylsilanyl-hexadec-4-en-7-ol (116513-87-2, 123877-34-9) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With oxonium; sodium hydride Yield given. Multistep reaction;
With pyridinium p-toluenesulfonate In ethanol r.t., overnight, 50 deg C, 2 h;

(4Z,6E)-16-(2-Ethoxy-ethoxy)-hexadeca-4,6-diene → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water at 0℃; for 3h; Yield given;

2-[((10E,12Z)-Hexadeca-10,12-dienyl)oxy]-tetrahydro-pyran (74502-09-3, 74502-10-6, 123474-78-2) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With methanol; toluene-4-sulfonic acid In water at 60℃;

(10E,12Z)-hexadeca-10,12-dienal (63024-98-6) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
With lithium aluminium tetrahydride; sulfuric acid 1.) Et2O, 0 deg C, 1 h, 2.) Et2O, 0 deg C, 1 h; Yield given. Multistep reaction;

n-butyl(triphenyl)phosphonium bromide (1779-51-7) + trans-12-Hydroxy-2-dodecen-1-al (74016-78-7) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + (10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5)

Conditions	Yield
With potassium tert-butylate 1.) THF, -30 deg C, 45 min, 2.) THF, -20 deg C, 3.5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

methanol (67-56-1) + (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran (72858-83-4) + acetic acid (64-19-7) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Stage #1: (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran With dimethylsulfide borane complex; cyclohexene In tetrahydrofuran at 20℃; Hydrogenation; Stage #2: acetic acid at 0℃; Acetylation; Stage #3: methanol With toluene-4-sulfonic acid In pentane Reduction;

1-Pentyne (627-19-0) + chromium hexacarbonyl → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: trans-Pd(PPh3)2Cl2; CuI; i-Pr2NH / tetrahydrofuran / 1.5 h / 5 - 10 °C 2: pTsOH*H2O / methanol / Heating 3: 90 percent / H2O / Zn/Cu/Ag / methanol / 6.5 h / 60 - 70 °C View Scheme

(E)-tetrahydro-2-<(11-iodo-10-undecenyl)oxy>-2H-pyran (107148-56-1) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: trans-Pd(PPh3)2Cl2; CuI; i-Pr2NH / tetrahydrofuran / 1.5 h / 5 - 10 °C 2: pTsOH*H2O / methanol / Heating 3: 90 percent / H2O / Zn/Cu/Ag / methanol / 6.5 h / 60 - 70 °C View Scheme

10-(tert-butyldimethylsilanyloxy)decanal (139670-36-3) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: 83 percent / NaH / tetrahydrofuran / 1 h / 20 °C 2: 679 mg / DIBAL-H / CH2Cl2; hexane / 0.5 h / -78 °C 3: 67 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C 4: 88 percent / Ph3P / CH2Cl2 / 0 °C 5: 85 percent / Bu3SnH / Pd(PPh3P)4 / benzene / 1 h / 20 °C 6: 84 percent / NiCl2(dppp) / diethyl ether; tetrahydrofuran / 20 °C 7: 93 percent / Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme

(E)-12-(tert-butyldimethylsilyl)oxy-2-dodecen-1-al (288612-24-8) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / Ph3P / CH2Cl2 / 0 °C 2: 85 percent / Bu3SnH / Pd(PPh3P)4 / benzene / 1 h / 20 °C 3: 84 percent / NiCl2(dppp) / diethyl ether; tetrahydrofuran / 20 °C 4: 93 percent / Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme

(1Z,3E)-1-bromo-13-(tert-butyldimethylsilyl)oxy-1,3-tridecadiene (288612-26-0) → (10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / NiCl2(dppp) / diethyl ether; tetrahydrofuran / 20 °C 2: 93 percent / Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) → (10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5)

Conditions	Yield
With iodine In Petroleum ether Irradiation;

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) → (10E,12Z)-hexadeca-10,12-dienal (63024-98-6)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane
With pyridine; chromium(VI) oxide; hydrogenchloride
With dipyridinium dichromate In dichloromethane for 1h; Ambient temperature; Yield given;
With dipyridinium dichromate In dichloromethane Oxidation;

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + acetic anhydride (108-24-7) → (Z,Z)-10,12-hexadecadien-1-ol acetate (73829-33-1) + (10E,12Z)-hexadeca-10,12-dien-1-yl acetate (63025-06-9)

Conditions	Yield
In pyridine Title compound not separated from byproducts;

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + acetic anhydride (108-24-7) → (10E,12Z)-hexadeca-10,12-dien-1-yl acetate (63025-06-9)

Conditions	Yield
In pyridine
With pyridine

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + 4-(4-nitrophenylazo)benzoyl chloride (22286-74-4) → 4-(4-nitro-phenylazo)-benzoic acid hexadeca-10t,12c-dienyl ester (1260-98-6)

Conditions	Yield
With pyridine

(10E,12Z)-hexadeca-10,12-dien-1-ol (765-17-3) + acetyl chloride (75-36-5) → (10E,12Z)-hexadeca-10,12-dien-1-yl acetate (63025-06-9)

Conditions	Yield
In pyridine; diethyl ether at 20℃; Acetylation;

Upstream product

• 72858-83-4 (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran 
• 1002-80-8 (10E,12Z)-hexadeca-10,12-dienoic acid 
• 765-21-9 (E)-10-hexadecen-12-yn-1-ol 
• 63024-91-9 (10E,12Z)-10,12-Hexadecadiensaeure-methylester 
• 764-70-5 hexadec-10t-en-12-ynoic acid ethyl ester 
• 51760-74-8 (E)-1-trimethylsiloxy-10-hexadecen-12-yne 
• 56904-76-8 acetoxy-1 octadiene-2,4 (E,Z) 
• 14752-60-4 pentynyl bromide 
• 87096-20-6 (E)-11-hydroxy-1-undecenyl iodide 
• 2774-84-7 undec-10-yn-1-ol 
• 31849-75-9 (Z)-1-pentenyl bromide 
• 87096-18-2 (E)-(11-hydroxy-1-undecenyl)boronic acid 
• 94742-73-1 1-iodo, (E,Z)4,6-decadiene 
• 56904-95-1 (bromo-8 octyloxy-1)-1, ethoxy-1 ethane 

Downstream Products

• 63024-98-6 (10E,12Z)-hexadeca-10,12-dienal 
• 73829-33-1 (Z,Z)-10,12-hexadecadien-1-ol acetate 
• 63025-06-9 (10E,12Z)-hexadeca-10,12-dien-1-yl acetate 
• 1260-98-6 4-(4-nitro-phenylazo)-benzoic acid hexadeca-10t,12c-dienyl ester 
• 1109-83-7 Hexadecadien-(10t,12t)-yl-⁽¹⁾-4'-nitro-azobenzol-carbonsaeure-⁽⁴⁾-ester 

Relevant articles and documents

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).

A facile preparation of geometrically pure alkenyl, alkynyl, and aryl conjugated Z-alkenes: Stereospecific synthesis of bombykol

Ni- and Pd-catalyzed cross coupling reactions of 2-alkenyl, 2-alkynyl, and 2-aryl substituted (1Z)-1-bromoalkene with alkyl Grignard reagents gave 1-alkyl substituted (1Z,3E)-diene, (1Z)-en-3-yne, and (1Z)-2-arylethene, each in good yield. When (trimethylsilyl)-methylmagnesium chloride was used as the Grignard reagent, conjugated Z-allylsilane was produced. Bombykol, (10E, 12Z)-10,12-hexadecadien-1-ol, a sex pheromone of female moss, Bombyx mori, was synthesized stereospecifically. 2000 Elsevier Science Ltd.

Stereospecific synthesis of (E,Z)- and (Z,Z)-hexadeca-10,12-dienal. Sex pheromone components of Diaphania hyalinata

Isomeric (E,Z)- and (Z,Z)-hexadeca-10,12-dienal were prepared, stereospecifically, in 51% and 43% overall yields from dec-1-yne.