10378-01-5

Usage

Uses

Used in Pheromone Production:
CIS-9-HEXADECENOL is used as a component in the production of pheromones, specifically for the female sex pheromone of the sugarcane borer, Diatraea flavipennella. As an antennally inactive component, it plays a crucial role in the chemical communication and mating behavior of these insects.
Used in Chemical Synthesis:
CIS-9-HEXADECENOL can be utilized as a starting material or intermediate in the synthesis of various chemical compounds, particularly those with similar structures or functional groups. Its unique double bond and hydroxyl group make it a valuable building block for creating new molecules with specific properties and applications.
Used in Fragrance Industry:
Due to its distinct chemical structure, CIS-9-HEXADECENOL can be employed in the fragrance industry as a component in the creation of various scent profiles. Its ability to contribute to the overall aroma of a fragrance makes it a valuable asset in the development of new and unique scents.
Used in Research and Development:
CIS-9-HEXADECENOL can be used in research and development for studying the properties and behavior of compounds with similar structures. Understanding its interactions with other molecules and its reactivity can lead to the discovery of new applications and advancements in various fields, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h7-8,17H,2-6,9-16H2,1H3/b8-7-

Synthetic route

cis-9-hexadecenoic acid (373-49-9) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;	98%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 24h;	97%
Multi-step reaction with 2 steps 1: 0.19 g / conc. H2SO4 / 6 h / Heating 2: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

9-hexadecyn-1-ol (88109-73-3) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With hydrogen; ethylendiamine poisoned P-2 Ni In ethanol	97%
With hydrogen; Ni-P2	88%
With bis(cyclopentadienyl)titanium dichloride; di-iso-butylmagnesium; ammonium chloride 1.) Et2O, 20 deg C, 30 min, 2.) H2O; Yield given. Multistep reaction;

(Z)-9-hexadecenoic acid methyl ester (1120-25-8) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 5h;	96%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;	92%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Ambient temperature;	0.14 g
With lithium aluminium tetrahydride In diethyl ether for 2h; Reflux;	2.3 g

9-tetradecyn-1-ol (60037-69-6) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With hydrogen; P2Ni	86%

(Z)-hexadec-9-en-1-yl acetate (34010-20-3) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 5h;	82%
With sodium hydroxide In methanol

(Z)-tert-butyl(hexadec-9-en-1-yloxy)dimethylsilane → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 3h;	82%

heptanal (111-71-7) + (9-hydroxynonyl)(triphenyl)phosphonium bromide (73945-70-7) → trans-hexadec-9-en-1-ol (64437-47-4) + palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(Z)-16-(1-Ethoxy-ethoxy)-hexadec-7-ene → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water at 20℃; for 15h; Yield given;

2-[((Z)-Hexadec-9-enyl)oxy]-tetrahydro-pyran (99159-88-3) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 3h; Heating; Yield given;
With toluene-4-sulfonic acid In methanol at 20℃; for 16h;

(Z)-4-undecene-1-ol (21676-07-3) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 2: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 3: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 82 percent / PBr3, pyridine / diethyl ether / 1) rt, overnight, 2) reflux, 2 h 2: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 3: p-toluenesulphonic acid / methanol / 3 h / Heating View Scheme

(Z)-4-undecenal (68820-32-6) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme

(Z)-4-undecenyl bromide (109523-23-1) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 2: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 2: p-toluenesulphonic acid / methanol / 3 h / Heating View Scheme

1,1-dimethoxy-8-tosyloxy-(4Z)-octene (82861-01-6) → palmitoleyl alcohol (10378-01-5)

Conditions

Yield

Multi-step reaction with 6 steps 1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h 2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme

1,1-dimethoxy-(4Z)-undecene (104187-94-2) → palmitoleyl alcohol (10378-01-5)

Conditions

Yield

Multi-step reaction with 5 steps 1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme

methyl aleuritate → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 3.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme

methyl ester of azelaic acid aldehyde (1931-63-1) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 2: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / toluene / 4 h / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 2 h / Reflux View Scheme

triphenylheptylphosphonium bromide (13423-48-8) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C View Scheme

(+)-threo-9,10,16-trihydroxyhexadecanoic acid → palmitoleyl alcohol (10378-01-5)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation 2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 4.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme

8-Bromo-1-octene (2695-48-9) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 View Scheme

1-octynyllithium (21433-45-4) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 View Scheme

hexadec-1-en-9-yne (197901-27-2) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 88 percent / H2 / Ni-P2 View Scheme

10,11-dibromo-undecanoic acid (6308-96-9) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme

10-undecenoic acid (112-38-9) + aqueous KOH-solution → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 7 steps 1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme

9-undecynoic acid (22202-65-9) + hydrogen → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme

9-undecynoic acid methyl ester (18937-76-3) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme

(Z)-0-undecenoic acid methyl ester (54299-07-9) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / O3 / CH2Cl2 / -78 °C 2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 3: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 1.2: 16 h / Reflux 2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme

1,8-Octanediol (629-41-4) + primary-secondary glycol C8H18O2 → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 75 percent / 48percent HBr / Heating 2: 99 percent / p-toluenesulfonic acid 3: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 4: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 5: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme

8-bromooctanol (50816-19-8) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / p-toluenesulfonic acid 2: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 3: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 4: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 2.2: 16 h / Reflux 3.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 4.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme

1-tetrahydropyranyloxy-n-9-hexadecyn (25258-24-6) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 2: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme

palmitoleyl alcohol (10378-01-5) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	98%
With pyridinium chlorochromate In dichloromethane for 1.5h; Ambient temperature;	94%
With pyridinium chlorochromate	94%

palmitoleyl alcohol (10378-01-5) → (Z)-hexadec-9-enyl bromide (132538-05-7)

Conditions	Yield
With bromine; triphenylphosphine In benzene at 20℃; for 3h;	97%
With carbon tetrabromide; triphenylphosphine In dichloromethane for 16h; Ambient temperature;	94%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 16h;	94%

palmitoleyl alcohol (10378-01-5) → (Z)-16-iodohexadec-7-ene

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In toluene at 20℃; for 3h;	89%

palmitoleyl alcohol (10378-01-5) + acetic anhydride (108-24-7) → (Z)-hexadec-9-en-1-yl acetate (34010-20-3)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	85%
With pyridine for 24h; Ambient temperature;	68%
With pyridine for 25h; Ambient temperature;	0.1 g
In pyridine at 20℃; for 24h;	1.4 g

cholesteryl p-toluenesulfonate (1182-65-6, 3381-56-4) + palmitoleyl alcohol (10378-01-5) → cholesteryl cis-9'-hexadecenyl ether (74996-37-5)

Conditions	Yield
at 110℃; for 2.5h;	54.1%

palmitoleyl alcohol (10378-01-5) + methanesulfonyl chloride (124-63-0) → palmitoleyl methanesulfonate (93135-85-4)

Conditions	Yield
With pyridine
With pyridine at 0 - 20℃; for 24h;

methanol (67-56-1) + palmitoleyl alcohol (10378-01-5) → 10-Methoxy-hexadecan-1-ol + 9-Methoxy-hexadecan-1-ol

Conditions	Yield
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction;

palmitoleyl alcohol (10378-01-5) → tert-butyl [4-hydroxy-3-(10(Z)-heptadecenyl)]phenyl carbonate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C View Scheme

palmitoleyl alcohol (10378-01-5) → tert-butyl [2-bromo-3-hydroxy-4-(10(Z)-heptadecenyl)]phenyl carbonate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C View Scheme

palmitoleyl alcohol (10378-01-5) → (3S,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-8aH-benzo[1,4]dioxine-2,6-dione (903522-41-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C 4.1: 93 percent / ZnBr; CH3NO2 / 20 °C 5.1: 55 percent / PhIOTMS(OTf); TMSOTf / CH2Cl2 / 0.25 h / 0 °C View Scheme

palmitoleyl alcohol (10378-01-5) → 2-(2-bromo-6-heptadec-10-enyl-3-hydroxy-phenoxy)-N-methoxy-N-methyl-propionamide (903522-40-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C 4.1: 93 percent / ZnBr; CH3NO2 / 20 °C View Scheme

palmitoleyl alcohol (10378-01-5) → 2,2-Dimethyl-propionic acid 2-bromo-4-((Z)-heptadec-10-enyl)-3-[(S)-1-(methoxy-methyl-carbamoyl)-ethoxy]-phenyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C View Scheme

palmitoleyl alcohol (10378-01-5) → 2-(10(Z)-heptadecenyl)-1,4-hydroquinone

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 90 percent / HCl / dioxane / 1.25 h / 80 °C View Scheme

Upstream product

• 1120-25-8 (Z)-9-hexadecenoic acid methyl ester 
• 60037-69-6 9-tetradecyn-1-ol 
• 373-49-9 cis-9-hexadecenoic acid 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 68820-32-6 (Z)-4-undecenal 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 2695-48-9 8-Bromo-1-octene 
• 55362-80-6 9-bromononan-1-ol 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 1619-68-7 16-hydroxy-9-hexadecenoic acid 
• 64437-47-4 trans-hexadec-9-en-1-ol 
• 6949-98-0 9,10,16-trihydroxyhexadecanoic acid 
• 17643-36-6 9-decyn-1-ol 
• 629-41-4 1,8-Octanediol 

Downstream Products

• 93135-85-4 palmitoleyl methanesulfonate 
• 903522-40-7 2-(2-bromo-6-heptadec-10-enyl-3-hydroxy-phenoxy)-N-methoxy-N-methyl-propionamide 
• 373-49-9 cis-9-hexadecenoic acid 
• 40426-22-0 ( Z )-hexadec-9-enoyl chloride 
• 56219-04-6 (Z)-9-hexadecenal 

Relevant academic research and scientific papers

SYNTHESIS OF HEXADEC-9Z-ENAL - ONE OF THE COMPONENTS OF THE SEX PHEROMONE OF Heliothis armigera

Hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera - has been obtained by a three-stage synthesis from 9-acetoxynonanal and n-heptyltriphenylphosphonium bromide followed by reduction and oxidation.

Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

INSECT PHEROMONES AND THEIR ANALOGUES. XVI. PRACTICAL SYNTHESIS OF HEXADEC-9Z-ENAL - A COMPONENT OF THE SEX PHEROMONE OF THE COTTON BOLLWORM Heliothis armigera

A synthesis of hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera (Huebner) - based on cyclooctene (I) is proposed.Through a solution of 22 g of (I), 250 ml of cyclohexane, and 40 ml of MeOH is passed (at 5 deg C) 0.2 M O3/O2, the solution is decanted off, and the precipitated ozonide is dissolved in 200 ml of MeOH and is reduced with 19 g of NaBH4 (40 deg C) with the isolation, after the usual working up, of 23.4 g of octane-1,8-diol (II).From 0.5 mole of (II) and 0.6 mole of 45percent HBr 8-bromooctan-1-ol (III) is obtained and this is converted into 1-(2-(THPL)oxy)-8-bromooctane (IV).The condensation of (IV) with oct-1-yne (Ar, LiNH2, HMPTA, 10 deg C, 1 h, and then 55 deg C, 10 h) leads to 1-(2-THPL-oxy)hexadec-9-yne (V) the hydrolysis of which (MeOH, H2O, p-TsOH, 20 deg C for 20 h) yields hexadec-9-yn-ol (VI).The reduction of (VI) (Et2O, iso-BuMgBr, Cp2TiCl2, 0 deg C, 15 min, then 20 deg C, 1 h) yields hexadec-9Z-en-1-ol (VII).The oxidation of (VII) (PyHCrO3+ Cl-, CH2Cl2, 20 deg C, 2 h) gives hexadec-9Z-enal (VIII).Characteristics of the compounds (yield (percent), nD20(25): (II) - 80, mp 61-62 deg C; (III) - 75, 1.4807; (IV) - 99, -; (V) - 52, 1,4650; (VI) - 85, 1.4657; (VII) - 99, 1.4650; (VIII) - 98, 1.4600.Characteristics of the IR and PMR spectra of compounds (V-VII) are given.

Use of enyne compounds in the synthesis of insect pheromones

A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.

A hydroxylamine probe for profiling: S-acylated fatty acids on proteins

Reversible S-palmitoylation is a key regulatory mechanism of protein function and localization. There is increasing evidence that S-acylation is not restricted to palmitate but it includes shorter, longer, and unsaturated fatty acids. However, the diversity of this protein modification has not been fully explored. Herein, we report a chemical probe that combined with MS-based analysis allows the rapid detection and quantification of fatty acids linked to proteins. We have used this approach to profile the S-acylome and to show that the oncogene N-Ras is heterogeneously acylated with palmitate and palmitoleate. Studies on protein distribution in membrane subdomains with semisynthetic proteins revealed that unsaturated N-Ras presents an increased tendency toward clustering and higher insertion kinetic rate constants.

Stereo- and chemoselective character of supported CEO2 catalysts for continuous-flow three-phase alkyne hydrogenation

TiO2-, Al2O3-, and ZrO2- supported CeO2 catalysts with different Ce loadings were prepared by wet impregnation of the carriers with an acidified solution of cerium ammonium nitrate. The calcined catalysts were characterized by bulk and surface-sensitive techniques, which included microcalorimetry, and evaluated in the three-phase hydrogenation of alkynes under continuous-flow conditions at variable temperature (293-413 K) and pressure (1-90 bar). A number of acetylenic compounds, which contain terminal or internal triple bonds, conjugated unsaturations, and additional functionalities, were systematically assessed. The results revealed the full stereo- and chemoselective character of the ceria catalysts, which outperform the well-known Lindlar catalyst, and open promising perspectives for the revolutionary use of a cost-effective oxide for the production of olefinic compounds in the vitamin and fine chemical industries.

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

Bacteria of the Roseobacter group (Rhodobacteraceae) are important members of many marine ecosystems. Similar to other Gram-negative bacteria many roseobacters produce N-acylhomoserine lactones (AHLs) for communication by quorum sensing systems. AHLs regulate different traits like cell differentiation or antibiotic production. Related N-acylalanine methyl esters (NAMEs) have been reported as well, but so far only from Roseovarius tolerans EL-164. While screening various roseobacters isolated from macroalgae we encountered four strains, Roseovarius sp. D12_1.68, Loktanella sp. F13, F14 and D3 that produced new derivatives and analogs of NAMEs, namely N-acyl-2-aminobutyric acid methyl esters (NABME), N-acylglycine methyl esters (NAGME), N-acylvaline methyl esters (NAVME), as well as for the first time a methyl-branched NAME, N-(13-methyltetradecanoyl)alanine methyl ester. These compounds were detected by GC–MS analysis, and structural proposals were derived from the mass spectra and by derivatization. Verification of compound structures was performed by synthesis. NABMEs, NAVMEs and NAGMEs are produced in low amounts only, making mass spectrometry the method of choice for their detection. The analysis of both EI and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a yet unknown function as signalling compounds in the ecology of these bacteria, although their singular occurrence is in strong contrast to the common occurrence of AHLs. Obviously the structural motif is not restricted to Roseovarius spp. and occurs also in other genera.

Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities

Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.

Simple syntheses of (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate from aleuritic acid

Insect sex pheromones are used for monitoring and management of crop pests. Four compounds (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate reported as components of some important agricultural insect pests have been synthesized from theo-aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) involving simplified Wittig reactions with improved yield.

General synthesis for chiral 4-alkyl-4-hydroxycyclohexenones

Some selective transformations of resorcinol-derived cyclohexadienone are reported. Efforts led to a structure reported to display anticancer properties. On the basis of the results, the structures for natural products reported to contain a 4,6-dihydroxy-4-alkyl-cyclohexenone nucleus are corrected.