557-48-2

Basic information

• Product Name: FEMA 3377
• Synonyms: TIMTEC-BB SBB006611;T2 C6 NONADIENAL;TRANS-2,CIS-6-NONADIENAL;TRANS-2,CIS-6-NONADIEN-1-AL;(2E,6Z)-2,6-Nonadienal;(2E,6Z)-Nonadienal;(E)-2,(Z)-6-nonadienal;(E,Z)-2,6-nonadienal
• CAS NO: 557-48-2
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.21
• EINECS: 209-178-6
• Mol File: 557-48-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 94-95 °C18 mm Hg(lit.)
• Flash Point: 181 °F
• Appearance: /
• Density: 0.86 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.28mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)
• Sensitive: Air Sensitive
• CAS DataBase Reference: FEMA 3377(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3377(557-48-2)
• EPA Substance Registry System: FEMA 3377(557-48-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 2
• RTECS: RA5391800
• TSCA: Yes
• Hazardous Substances Data: 557-48-2(Hazardous Substances Data)

Usage

Description

2-trans-6-cis-Nonadienal has an odor reminiscent of green cucumber. The organoleptic character is attributed almost entirely to olfactory sensations. It may be obtained from natural hexenol; from steam distillation of fresh cucumber.

Chemical Properties

Different sources of media describe the Chemical Properties of 557-48-2 differently. You can refer to the following data:
1. Nona-2-trans-6-cis-dienal has an odor reminiscent of green cucumber. The organoleptic character of this compound is attributed almost entirely to olfactory sensations. May be obtained from the steam distillation of fresh cucumber.
2. clear colorless to pale yellow liquid

Occurrence

Reported as naturally occurring in violet leaves and flowers, in cucumber, sweet and sour cherry, guava, peas, tomato, potato, bell pepper, wheat bread, rye bread, milk, milk powder, fish and fish oil, roast chicken, guinea hen, beef, beer, coffee, tea, oats, mango, kelp, prickly pear, malt, dried bonito, endive, oysters, clam and mate.

Uses

trans-2,cis-6-Nonadienal is an unsaturated aldehyde that is responsible for the cucumber smell of Synura petersenii, a freshwater colonial flagellate. trans-2,cis-6-Nonadienal is also a common natural and drinking water contaminant.

Preparation

From natural hexenol

Definition

ChEBI: An enal that is (2E,6Z)-nona-2,6-diene substituted by an oxo group at position 1.

Taste threshold values

Taste characteristics at 10 ppm: green, melon, cucumber-like with an aldehydic nuance

General Description

Unialgal cultures of various Synurophycean species for the occurrence of trans-2,cis-6-nonadienal have been investigated.

Safety Profile

Low toxicity by ingestion and skin contact. A moderate skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C9H14O/c1-2-3-4-5-6-7-8-9-10/h3-4,7-9H,2,5-6H2,1H3/b4-3-,8-7+

Synthetic route

nona-2(Z),6(Z)-dienal diethyl acetal (67674-37-7) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Stage #1: nona-2(Z),6(Z)-dienal diethyl acetal In water at 3 - 8℃; for 0.166667h; Stage #2: With hydrogenchloride In water at 3 - 25℃; for 2h;	93.2%
With sulfuric acid In acetone at 70℃; for 1h;	25%
With sulfuric acid
With hydrogenchloride In hexane; water at 20℃; for 0.5h; Solvent;	52.56 g

(3Z,6Z)-1,1-dimethoxynona-3,6-diene → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With hydrogenchloride In water; acetone for 3h;	80%

(2E,6Z)-2,6-nonadien-1-ol (5820-89-3, 7786-44-9, 28069-72-9) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With manganese(IV) oxide In pentane	67%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 4h;	52%
With chromium(III) oxide; sulfuric acid

(Z)-4-heptenal (6728-31-0) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
In 1,4-dioxane at 0 - 20℃; for 16h; Solvent;	38%
In benzene Wittig reaction; Heating;

nona-2c,6c-dien-1-ol (186906-31-0) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid

2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine (26939-18-4) + (Z)-4-heptenal (6728-31-0) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multistep reaction;

methyl colnelenate (52077-22-2) → 2E,6Z-nonadienal (557-48-2) + methyl ester of azelaic acid aldehyde (1931-63-1)

Conditions	Yield
With hydrogenchloride In methanol for 18h; Ambient temperature;

C9H15O(1-)*Br(1-)*Mg(2+) → (2E,6Z)-2,6-nonadien-1-ol (5820-89-3, 7786-44-9, 28069-72-9) + 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With benzaldehyde In diethyl ether for 5h; Yield given. Yields of byproduct given;
With benzaldehyde In diethyl ether for 5h; Product distribution;

(3Z,6Z)-1,1-dimethoxynona-3,6-diene → 2E,6Z-nonadienal (557-48-2) + (3Z,6Z)-nona-3,6-dienal (21944-83-2)

Conditions	Yield
With water; hydrogen cation In acetone Yield given;

S-[3-[1-oxonon-(Z)-6-enyl]]-glutathione → 2E,6Z-nonadienal (557-48-2) + GLUTATHIONE (70-18-8)

Conditions	Yield
With phosphate buffer at 25℃; pH=7.2; Kinetics; Decomposition;

nona-2(Z),6(Z)-dienal diethyl acetal (67674-37-7) + sulfuric acid (7664-93-9) → 2E,6Z-nonadienal (557-48-2)

nona-2c,6c-dien-1-ol (186906-31-0) + sulfuric acid (7664-93-9) + chromium (VI)-oxide → 2E,6Z-nonadienal (557-48-2)

3-(N-Methylanilino)-2-propenal (14189-82-3) + hex-3c-enyl magnesium chloride → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With tetrahydrofuran; diethyl ether; benzene

((1E,5Z)-2-Octa-1,5-dienyl)-[1,3]dioxolane → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran

(Z)-4-heptenal (6728-31-0) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene / tetrahydrofuran / Heating 2: aq. HCl / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 2: 70 percent / LAH, EtOH / diethyl ether 3: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

(Z)-4-hepten-1-ol (6191-71-5) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / NACAA / CH2Cl2; pyridine / 0.33 h / 20 °C 2: benzene / Heating View Scheme
Multi-step reaction with 4 steps 1: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 2: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 3: 70 percent / LAH, EtOH / diethyl ether 4: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme
Multi-step reaction with 2 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 1 h / 20 °C 2: 1,4-dioxane / 16 h / 0 - 20 °C View Scheme

(Z)-2-(hept-4-en-1-yloxy)tetrahydro-2H-pyran (530086-82-9) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / conc. H2SO4 / acetone; H2O / 20 °C 2: 65 percent / NACAA / CH2Cl2; pyridine / 0.33 h / 20 °C 3: benzene / Heating View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / methanol / 15 h / 20 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 1 h / 20 °C 3: 1,4-dioxane / 16 h / 0 - 20 °C View Scheme

1-bromo-pent-2-yne (16400-32-1) → 2E,6Z-nonadienal (557-48-2)

Conditions

Yield

Multi-step reaction with 8 steps 1: 60 percent / benzene / 12 h / Heating 2: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 3: 76 percent / LAH, EtOH / diethyl ether 4: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 5: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 6: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 7: 70 percent / LAH, EtOH / diethyl ether 8: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

hept-4-yn-1-ol (42397-24-0) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 2: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 3: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 4: 70 percent / LAH, EtOH / diethyl ether 5: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

pent-2-yn-1-ol (6261-22-9) → 2E,6Z-nonadienal (557-48-2)

Conditions

Yield

Multi-step reaction with 9 steps 1: 77 percent / PBr3, pyridine / diethyl ether / Ambient temperature 2: 60 percent / benzene / 12 h / Heating 3: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 4: 76 percent / LAH, EtOH / diethyl ether 5: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 6: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 7: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 8: 70 percent / LAH, EtOH / diethyl ether 9: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

ethyl 2-carbethoxy-hept-4-yn-1-oate (98442-18-3) → 2E,6Z-nonadienal (557-48-2)

Conditions

Yield

Multi-step reaction with 7 steps 1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 5: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 6: 70 percent / LAH, EtOH / diethyl ether 7: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

ethyl hept-4-yn-1-oate (98442-19-4) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 4: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 5: 70 percent / LAH, EtOH / diethyl ether 6: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

ethyl nona-2E,6Z-dienoate (98442-20-7) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / LAH, EtOH / diethyl ether 2: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

nona-2,6-diynal-diethylacetal (106380-28-3) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / H2 / 5percent Pd-BaSO4 / ethyl acetate / 3 h 2: 25 percent / H2SO4 / acetone / 1 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: palladium/calcium carbonate; ethyl acetate / Hydrogenation 2: aqueous sulfuric acid View Scheme

octa-1,5-diyne (764-74-9) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent 2: 64 percent / H2 / 5percent Pd-BaSO4 / ethyl acetate / 3 h 3: 25 percent / H2SO4 / acetone / 1 h / 70 °C View Scheme

(Z)-3-Hexen-1-ol (928-96-1) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: PBr3 / Umsetzen der Magnesiumverbindung des nicht naeher beschriebenen 1-Brom-cis-hexens-(3) mit Acrolein 2: ueber nicht rein erhaltenes 1-Brom-nonadien-(2t.6c) und Nonadien-(2t.6c)-yl-benzoat 3: Cr2O3-H2SO4 View Scheme

nona-1,6c-dien-3-ol (66972-01-8) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: ueber nicht rein erhaltenes 1-Brom-nonadien-(2t.6c) und Nonadien-(2t.6c)-yl-benzoat 2: Cr2O3-H2SO4 View Scheme

nona-2,6-diyn-1-ol (102369-60-8) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/calcium carbonate; ethyl acetate / Hydrogenation 2: chromium (VI)-oxide; aqueous sulfuric acid View Scheme

2-hex-3-enyl-4,4,6-trimethyl-[1,3]oxazinane (36872-14-7) → 2E,6Z-nonadienal (557-48-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. oxalic acid View Scheme

2E,6Z-nonadienal (557-48-2) + tris-iso-propylsilyl acetylene (89343-06-6) → C20H36OSi (1198837-43-2)

Conditions	Yield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; [Rh(OAc)(C2H4)2]2 In methanol at 40℃; for 24h; optical yield given as %ee; enantioselective reaction;	93%

2E,6Z-nonadienal (557-48-2) → (2E,6Z)-nona-2,6-dienoic acid (23605-13-2)

Conditions	Yield
With silver(l) oxide	91%
With sodium hydroxide; silver nitrate In water at 25℃; for 1h;	91%

2E,6Z-nonadienal (557-48-2) + vinylmagnesium chloride (3536-96-7) → (4E, 8Z)-undeca-1,4,8-trien-3-ol

Conditions	Yield
In tetrahydrofuran at 0 - 25℃;	90%

2E,6Z-nonadienal (557-48-2) + (carbobenzyloxymethylene)triphenylphosphorane (15097-38-8) → C18H22O2

Conditions	Yield
In toluene at 90℃; for 10h; Wittig Olefination; Inert atmosphere;	89%

2E,6Z-nonadienal (557-48-2) + (+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C5H4OCHCH2) (354574-99-5, 354144-91-5, 354574-93-9) → (+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H9O(CHO)(Z-3-hexyl))

Conditions	Yield
diethylaluminium chloride In dichloromethane reaction of molybdenum compd. with aldehyde deriv. in CH2Cl2 at 0°C for 45 min in presence of 1.1 equiv. of aluminium compd.; NMR;	87%

m-chloroperoxybenzoic acid (64741-01-1) + 2E,6Z-nonadienal (557-48-2) → (2E)-cis-6,7-epoxy-2-nonenal

Conditions	Yield
With sodium thiosulfate	85%

2E,6Z-nonadienal (557-48-2) → (E)-(6R,7S)-6,7-epoxy-2-nonenal

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 25℃; for 3h;	85%

2E,6Z-nonadienal (557-48-2) → (E2)-cis-6,7-epoxy-2-nonenal

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at -5 - 0℃; for 13h; Inert atmosphere;	82.6%

2E,6Z-nonadienal (557-48-2) + C12H11ClO4 → (4S,4aS,5R,10bS)-ethyl 9-chloro-5-((Z)-hex-3-enyl)-4-hydroxy-4,4a,5,10b-tetrahydropyrano[3,4-c]chromene-2-carboxylate

Conditions	Yield
Stage #1: 2E,6Z-nonadienal With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 4-methoxybenzoic acid In chlorobenzene at -5℃; for 0.5h; Stage #2: C12H11ClO4 In chlorobenzene at -5℃; for 18h; enantioselective reaction;	82%

2E,6Z-nonadienal (557-48-2) + N-nitromethylphtalimide (65004-95-7) → (3R)-3-(hex-3-enyl)-4-nitro-4-phthalimidobutanal (1311321-81-9)

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In chloroform at 4℃; for 24h; Michael reaction; optical yield given as %ee; enantioselective reaction;	78%

2E,6Z-nonadienal (557-48-2) + methyl phenylphosphonium bromide → (3E,7Z)-deca-1,3,7-triene

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 12h; Inert atmosphere;	76%

2E,6Z-nonadienal (557-48-2) + methyl (E)-4-((((benzyloxy)carbonyl)amino)oxy)but-2-enoate → benzyl (3R,4S,5S)-4-formyl-3-((Z)-hex-3-en-1-yl)-5-(2-methoxy-2-oxoethyl)-1,2-oxazinane-2-carboxylate

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; p-N,N-dimethylaminobenzoic acid In chloroform at 20℃; for 24h; Sealed tube; stereoselective reaction;	67%

2E,6Z-nonadienal (557-48-2) + 2-(prop-2-yn-1-yl)propanedinitrile (130575-28-9) → (S,Z)-3-formyl-2-(hex-3-enyl)-4-methylcyclopent-3-ene-1,1-dicarbonitrile (1219359-60-0)

Conditions	Yield
With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; copper(I) trifluoromethanesolfonate toluene complex; triphenylphosphine; benzoic acid In toluene at 4℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	66%

2E,6Z-nonadienal (557-48-2) → (2E)-cis-6,7-epoxy-2-nonenal

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 15h;	65%

2E,6Z-nonadienal (557-48-2) + (+/-)-E-dicarbonyl(hydridotrispyrazolylborate)(3-propenyl-η-4,5,6-pyranyl)molybdenum → [hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H8O(CHO)(Me)(Z-3-hexyl))

Conditions	Yield
diethylaluminium chloride In dichloromethane reaction of molybdenum compd. with acroleine deriv. in CH2Cl2 in presence of 1.1 equiv. of aluminium compd. at 0°C for 10-45 min;	64%

formaldehyd (50-00-0) + 2E,6Z-nonadienal (557-48-2) → (2E,6Z)-4-methylenenona-2,6-dienal

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid In chloroform; 2,2,2-trifluoroethanol; water at 0℃; for 55h; Aldol Condensation; regioselective reaction;	63%

2E,6Z-nonadienal (557-48-2) + tert-butyl 3-oxooctanoate (66720-07-8) → (5R)-2-butyl-5-(3Z-hexenyl)-cyclohex-2-en-1-one (1079832-56-6)

Conditions	Yield
Stage #1: 2E,6Z-nonadienal; tert-butyl 3-oxooctanoate With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine at 25℃; for 16h; Inert atmosphere; neat (no solvent); Stage #2: With toluene-4-sulfonic acid In toluene at 80℃; for 23h; Inert atmosphere; optical yield given as %ee;	55%

2E,6Z-nonadienal (557-48-2) + α-bromoacetophenone (70-11-1) → 4E,8Z-1-phenyl-(3,7-decadien)-1-one

Conditions	Yield
Stage #1: 2E,6Z-nonadienal; α-bromoacetophenone With N-ethyl-N,N-diisopropylamine; triphenylphosphine In dichloromethane Inert atmosphere; Reflux; Stage #2: With trichlorosilane In dichloromethane at -78℃; for 2h; Inert atmosphere;	54%

2E,6Z-nonadienal (557-48-2) + phenylboronic acid (98-80-6) → (2E,4E)-7-phenylnona-2,4-dienal + C15H18O

Conditions	Yield
With [Pd(OTs)2(MeCN)2]; (S)-4-(tert-butyl)-2-(5-(trifluoromethyl)pyridine-2-yl)-4,5-dihydrooxazole; oxygen In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 24h; Heck Reaction; Molecular sieve; regioselective reaction;	A 51% B n/a

2E,6Z-nonadienal (557-48-2) + recorcinol (108-46-3) → C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene

Conditions	Yield
With hydrogenchloride In ethanol; water at 0℃; for 13h; Reflux;	50%

2E,6Z-nonadienal (557-48-2) + [(1-Ethoxycyclopropyl)oxy]trimethylsilane (27374-25-0) → (E,Z)-5,9-dodecadien-4-olide (1286701-21-0)

Conditions	Yield
Stage #1: [(1-Ethoxycyclopropyl)oxy]trimethylsilane With titanium tetrachloride at 20℃; Stage #2: With titanium(IV) tert-butoxide Stage #3: 2E,6Z-nonadienal Homo-Reformatsky reaction;	36%

2E,6Z-nonadienal (557-48-2) + 7-hydroxy-heptyl-triphenyl-phosphonium bromide (76771-95-4) → (7Z,9E,13Z)-Hexadeca-7,9,13-trien-1-ol

Conditions	Yield
With n-butyllithium In tetrahydrofuran	20%

2E,6Z-nonadienal (557-48-2) + (8-methoxycarbonyloctyl)triphenylphosphonium bromide (67878-16-4) → methyl 9Z,11E,15Z-octadecatrienoate (265108-57-4)

Conditions	Yield
With water; potassium carbonate In 1,4-dioxane at 95℃; Wittig reaction;	14%

2E,6Z-nonadienal (557-48-2) → nona-2,6-dienoic acid (1005483-30-6)

Conditions	Yield
With sodium hydroxide; silver nitrate

2E,6Z-nonadienal (557-48-2) → (2E,6Z)-2,6-nonadien-1-ol (5820-89-3, 7786-44-9, 28069-72-9)

Conditions	Yield
With aluminum isopropoxide; isopropyl alcohol

Upstream product

• 26939-18-4 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine 
• 6728-31-0 (Z)-4-heptenal 
• 98442-18-3 ethyl 2-carbethoxy-hept-4-yn-1-oate 
• 98442-19-4 ethyl hept-4-yn-1-oate 
• 98442-20-7 ethyl nona-2E,6Z-dienoate 
• 53046-97-2 (Z,Z)-1-hydroxynona-3,6-diene 
• 21676-01-7 (Z)-3-hexenyl chloride 
• 41301-84-2 (5Z)-5-octen-1-yne 
• 10417-94-4 all cis-5,8,11,14,17-eicosapentaenoic acid 
• 1638153-00-0 (3Z,6Z)-9,9-dimethoxy-nona-3,6-dien-1-yl 4-methylbenzenesulfonate 
• 696-86-6 cis,cis,cis-1,4,7-cyclononatriene 
• 1638152-99-4 (3Z,6Z)-9,9-dimethoxynona-3,6-dien-1-ol 
• 36872-14-7 2-hex-3-enyl-4,4,6-trimethyl-[1,3]oxazinane 
• 102369-60-8 nona-2,6-diyn-1-ol 

Downstream Products

• 100950-21-8 nonadien-(2t.6c)-al-⁽¹⁾-(4-nitro-phenylhydrazone) 
• 1277184-85-6 (3R,4aS,9S,9aR)-3-((Z)-hex-3-enyl)-7-nitro-9-phenyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile 
• 1260396-04-0 (3R,6Z)-3-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]-6-nonen-1-ol 

Relevant articles and documents

Synthesis of 9- and 12-nitro conjugated linoleic acid: Regiospecific isomers of naturally occurring conjugated nitrodienes

Conjugated diene-containing fatty acids (rumenic and rumelenic acids) are major substrates for nitration under physiological conditions. Their nitrated products are present in human urine. These nitrodiene-containing lipid electrophiles contain a strongly electron-withdrawing pair of conjugated double bonds amenable to nucleophilic attack in biological milieu, which affords them pluripotent signaling capabilities. We report synthetic methods to obtain useful quantities of three main biological nitrated fatty acids (9- and 12-nitro-conjugated linoleic acids and 9-nitro-conjugated linolenic acid) in six or seven steps from commercially available starting materials, for biological evaluation of these naturally occurring biomolecules.

PROCESS FOR PREPARING (E2)-CIS-6,7-EPOXY-2-NONENAL

The object of the present invention is to provide an industrial and economical process for preparing (E2)-cis-6,7-epoxy-2-nonenal of the following formula (3):The present invention provides a process for preparing (E2)-cis-6,7-epoxy-2-nonenal (3), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1) to oxidation:to form (E2,Z6)-2,6-nonadienal of the following formula (2); andepoxidizing the resulting (E2,Z6)-2,6-nonadienal to form the aforesaid (E2)-cis-6,7-epoxy-2-nonenal (3).

PROCESS FOR PREPARING (2E,6Z)-2,6-NONADIENAL AND A PROCESS FOR PREPARING (2E)-CIS-6,7-EPOXY-2-NONENAL

Provided herein are convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. For instance, provided herein is a process for preparing (2E,6Z)-2,6-nonadienal, including at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar3P═CH(CH2)2CH═CHCH(OR1)(OR2) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysis to form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal.