10378-01-5

Basic information

• Product Name: CIS-9-HEXADECENOL
• Synonyms: DELTA 9 PALMITOLEYL ALCOHOL;DELTA 9 TRANS-PALMITELAIDYL ALCOHOL;CIS-9-HEXADECENOL;PALMITOLEYL ALCOHOL;PALMITOYL ALCOHOL;(9Z)-9-Hexadecen-1-ol;(z)-9-hexadecen-1-o;9-hexadecenol, Z
• CAS NO: 10378-01-5
• Molecular Formula: C₁₆H₃₂O
• Molecular Weight: 240.42
• EINECS: 233-831-4
• Mol File: 10378-01-5.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 340 °C at 760 mmHg
• Flash Point: 115.4 °C
• Appearance: /
• Density: 0.847 g/cm³
• Vapor Pressure: 5.88E-06mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: −20°C
• PKA: 15.20±0.10(Predicted)
• CAS DataBase Reference: CIS-9-HEXADECENOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-9-HEXADECENOL(10378-01-5)
• EPA Substance Registry System: CIS-9-HEXADECENOL(10378-01-5)

Safety Data

• Hazardous Substances Data: 10378-01-5(Hazardous Substances Data)

Usage

Uses

Palmitoleyl Alcohol is an antennally inactive component of the female sex pheromone of sugarcane borer Diatraea flavipennella.

Definition

ChEBI: A member of the class of hexadecen-1-ols that is hexadecanol containing a double bond located at position 9 (the Z-geoisomer).

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 
• 109523-23-1 (Z)-4-undecenyl bromide 
• 6308-96-9 10,11-dibromo-undecanoic acid 
• 112-38-9 10-undecenoic acid 
• 22202-65-9 9-undecynoic acid 
• 18937-76-3 9-undecynoic acid methyl ester 
• 54299-07-9 (Z)-0-undecenoic acid methyl ester 
• 693-80-1 oleyl acetate 
• 143-28-2 oleoyl alcohol 
• 629-41-4 1,8-Octanediol 
• 369657-02-3 cis-10-heptadecenoic acid methyl ester 
• 114157-22-1 9-(tert-butyl-dimethyl-silanyloxy)-1-nonanal 
• 157730-99-9 9-(tert-butyldimethylsilanyloxy)-1-nonanol 

Downstream Products

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

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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.

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.