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FEMA 3377, also known as 2-trans-6-cis-Nonadienal, is an unsaturated aldehyde with a distinct green cucumber odor. It is primarily responsible for the characteristic smell of cucumbers and can be obtained from natural hexenol or through steam distillation of fresh cucumbers. The organoleptic character of FEMA 3377 is attributed almost entirely to olfactory sensations, making it a valuable compound in various applications.

557-48-2

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557-48-2 Usage

Uses

Used in Flavor and Fragrance Industry:
FEMA 3377 is used as a flavoring agent for imparting a cucumber-like aroma to food products and beverages. Its natural and refreshing scent makes it a popular choice for creating cucumber-flavored products.
Used in Perfumery:
FEMA 3377 is used as a fragrance ingredient in perfumes and colognes to add a fresh, green, and cucumber-like note to the scent profile. Its unique aroma can enhance the overall appeal of fragrances and create a more natural and invigorating scent experience.
Used in Cosmetics and Personal Care Products:
FEMA 3377 is used as a scent component in cosmetics and personal care products, such as soaps, lotions, and shampoos, to provide a refreshing and cucumber-like fragrance. Its natural aroma can make these products more appealing and enjoyable to use.
Used in Environmental Applications:
FEMA 3377 is used in the detection and monitoring of drinking water contaminants, as it is a common natural contaminant found in water sources. Its distinct cucumber smell can serve as an indicator of water quality and potential contamination issues.

Preparation

From natural hexenol

Safety Profile

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

Check Digit Verification of cas no

The CAS Registry Mumber 557-48-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 7 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 557-48:
(5*5)+(4*5)+(3*7)+(2*4)+(1*8)=82
82 % 10 = 2
So 557-48-2 is a valid CAS Registry Number.
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+

557-48-2 Well-known Company Product Price

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  • TCI America

  • (N0836)  trans,cis-2,6-Nonadienal  >95.0%(GC)

  • 557-48-2

  • 1g

  • 250.00CNY

  • Detail
  • TCI America

  • (N0836)  trans,cis-2,6-Nonadienal  >95.0%(GC)

  • 557-48-2

  • 5g

  • 840.00CNY

  • Detail
  • Alfa Aesar

  • (A18356)  trans-2,cis-6-Nonadienal, 90+% (major isomer), remainder mainly trans,trans-isomer   

  • 557-48-2

  • 1g

  • 253.0CNY

  • Detail
  • Alfa Aesar

  • (A18356)  trans-2,cis-6-Nonadienal, 90+% (major isomer), remainder mainly trans,trans-isomer   

  • 557-48-2

  • 5g

  • 801.0CNY

  • Detail
  • Alfa Aesar

  • (A18356)  trans-2,cis-6-Nonadienal, 90+% (major isomer), remainder mainly trans,trans-isomer   

  • 557-48-2

  • 25g

  • 3740.0CNY

  • Detail
  • Sigma-Aldrich

  • (05549)  trans-2,cis-6-Nonadienal  analytical standard

  • 557-48-2

  • 05549-100MG

  • 585.00CNY

  • Detail

557-48-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (2E,6Z)-nona-2,6-dienal

1.2 Other means of identification

Product number -
Other names 2-trans-6-cis-nonadienal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:557-48-2 SDS

557-48-2Synthetic route

nona-2(Z),6(Z)-dienal diethyl acetal
67674-37-7

nona-2(Z),6(Z)-dienal diethyl acetal

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

(3Z,6Z)-1,1-dimethoxynona-3,6-diene

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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)-2,6-nonadien-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
With manganese(IV) oxide In pentane67%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 4h;52%
With chromium(III) oxide; sulfuric acid
(Z)-4-heptenal
6728-31-0

(Z)-4-heptenal

(triphenylphosphoranylidene)acetaldehyde
2136-75-6

(triphenylphosphoranylidene)acetaldehyde

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

nona-2c,6c-dien-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid
2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine
26939-18-4

2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine

(Z)-4-heptenal
6728-31-0

(Z)-4-heptenal

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
Multistep reaction;
methyl colnelenate
52077-22-2

methyl colnelenate

A

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

B

methyl ester of azelaic acid aldehyde
1931-63-1

methyl ester of azelaic acid aldehyde

Conditions
ConditionsYield
With hydrogenchloride In methanol for 18h; Ambient temperature;
C9H15O(1-)*Br(1-)*Mg(2+)

C9H15O(1-)*Br(1-)*Mg(2+)

A

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

(2E,6Z)-2,6-nonadien-1-ol

B

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

(3Z,6Z)-1,1-dimethoxynona-3,6-diene

A

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

B

(3Z,6Z)-nona-3,6-dienal
21944-83-2

(3Z,6Z)-nona-3,6-dienal

Conditions
ConditionsYield
With water; hydrogen cation In acetone Yield given;
S-[3-[1-oxonon-(Z)-6-enyl]]-glutathione

S-[3-[1-oxonon-(Z)-6-enyl]]-glutathione

A

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

B

GLUTATHIONE
70-18-8

GLUTATHIONE

Conditions
ConditionsYield
With phosphate buffer at 25℃; pH=7.2; Kinetics; Decomposition;
nona-2(Z),6(Z)-dienal diethyl acetal
67674-37-7

nona-2(Z),6(Z)-dienal diethyl acetal

sulfuric acid
7664-93-9

sulfuric acid

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

nona-2c,6c-dien-1-ol
186906-31-0

nona-2c,6c-dien-1-ol

sulfuric acid
7664-93-9

sulfuric acid

chromium (VI)-oxide

chromium (VI)-oxide

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

3-(N-Methylanilino)-2-propenal
14189-82-3

3-(N-Methylanilino)-2-propenal

hex-3c-enyl magnesium chloride

hex-3c-enyl magnesium chloride

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
With tetrahydrofuran; diethyl ether; benzene
((1E,5Z)-2-Octa-1,5-dienyl)-[1,3]dioxolane

((1E,5Z)-2-Octa-1,5-dienyl)-[1,3]dioxolane

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran
(Z)-4-heptenal
6728-31-0

(Z)-4-heptenal

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

(Z)-4-hepten-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

(Z)-2-(hept-4-en-1-yloxy)tetrahydro-2H-pyran

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

1-bromo-pent-2-yne

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

hept-4-yn-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

pent-2-yn-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

ethyl 2-carbethoxy-hept-4-yn-1-oate

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

ethyl hept-4-yn-1-oate

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

ethyl nona-2E,6Z-dienoate

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

nona-2,6-diynal-diethylacetal

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

octa-1,5-diyne

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

(Z)-3-Hexen-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

nona-1,6c-dien-3-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

nona-2,6-diyn-1-ol

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
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

2-hex-3-enyl-4,4,6-trimethyl-[1,3]oxazinane

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. oxalic acid
View Scheme
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

C20H36OSi
1198837-43-2

C20H36OSi

Conditions
ConditionsYield
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-nonadienal

(2E,6Z)-nona-2,6-dienoic acid
23605-13-2

(2E,6Z)-nona-2,6-dienoic acid

Conditions
ConditionsYield
With silver(l) oxide91%
With sodium hydroxide; silver nitrate In water at 25℃; for 1h;91%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

(4E, 8Z)-undeca-1,4,8-trien-3-ol

(4E, 8Z)-undeca-1,4,8-trien-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃;90%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(carbobenzyloxymethylene)triphenylphosphorane
15097-38-8

(carbobenzyloxymethylene)triphenylphosphorane

C18H22O2

C18H22O2

Conditions
ConditionsYield
In toluene at 90℃; for 10h; Wittig Olefination; Inert atmosphere;89%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C5H4OCHCH2)
354574-99-5, 354144-91-5, 354574-93-9

(+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C5H4OCHCH2)

(+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H9O(CHO)(Z-3-hexyl))

(+/-)-[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H9O(CHO)(Z-3-hexyl))

Conditions
ConditionsYield
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

m-chloroperoxybenzoic acid

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(2E)-cis-6,7-epoxy-2-nonenal

(2E)-cis-6,7-epoxy-2-nonenal

Conditions
ConditionsYield
With sodium thiosulfate85%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(E)-(6R,7S)-6,7-epoxy-2-nonenal

(E)-(6R,7S)-6,7-epoxy-2-nonenal

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 25℃; for 3h;85%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(E2)-cis-6,7-epoxy-2-nonenal

(E2)-cis-6,7-epoxy-2-nonenal

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at -5 - 0℃; for 13h; Inert atmosphere;82.6%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

C12H11ClO4

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

(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
ConditionsYield
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

2E,6Z-nonadienal

N-nitromethylphtalimide
65004-95-7

N-nitromethylphtalimide

(3R)-3-(hex-3-enyl)-4-nitro-4-phthalimidobutanal
1311321-81-9

(3R)-3-(hex-3-enyl)-4-nitro-4-phthalimidobutanal

Conditions
ConditionsYield
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

2E,6Z-nonadienal

methyl phenylphosphonium bromide

methyl phenylphosphonium bromide

(3E,7Z)-deca-1,3,7-triene

(3E,7Z)-deca-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 12h; Inert atmosphere;76%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

methyl (E)-4-((((benzyloxy)carbonyl)amino)oxy)but-2-enoate

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

benzyl (3R,4S,5S)-4-formyl-3-((Z)-hex-3-en-1-yl)-5-(2-methoxy-2-oxoethyl)-1,2-oxazinane-2-carboxylate

Conditions
ConditionsYield
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

2E,6Z-nonadienal

2-(prop-2-yn-1-yl)propanedinitrile
130575-28-9

2-(prop-2-yn-1-yl)propanedinitrile

(S,Z)-3-formyl-2-(hex-3-enyl)-4-methylcyclopent-3-ene-1,1-dicarbonitrile
1219359-60-0

(S,Z)-3-formyl-2-(hex-3-enyl)-4-methylcyclopent-3-ene-1,1-dicarbonitrile

Conditions
ConditionsYield
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,6Z-nonadienal

(2E)-cis-6,7-epoxy-2-nonenal

(2E)-cis-6,7-epoxy-2-nonenal

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 15h;65%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(+/-)-E-dicarbonyl(hydridotrispyrazolylborate)(3-propenyl-η-4,5,6-pyranyl)molybdenum

(+/-)-E-dicarbonyl(hydridotrispyrazolylborate)(3-propenyl-η-4,5,6-pyranyl)molybdenum

[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H8O(CHO)(Me)(Z-3-hexyl))

[hydridotris(1-pyrazolyl)borato]Mo(carbonyl)2(C9H8O(CHO)(Me)(Z-3-hexyl))

Conditions
ConditionsYield
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

formaldehyd

2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(2E,6Z)-4-methylenenona-2,6-dienal

(2E,6Z)-4-methylenenona-2,6-dienal

Conditions
ConditionsYield
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

2E,6Z-nonadienal

tert-butyl 3-oxooctanoate
66720-07-8

tert-butyl 3-oxooctanoate

(5R)-2-butyl-5-(3Z-hexenyl)-cyclohex-2-en-1-one
1079832-56-6

(5R)-2-butyl-5-(3Z-hexenyl)-cyclohex-2-en-1-one

Conditions
ConditionsYield
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

2E,6Z-nonadienal

α-bromoacetophenone
70-11-1

α-bromoacetophenone

4E,8Z-1-phenyl-(3,7-decadien)-1-one

4E,8Z-1-phenyl-(3,7-decadien)-1-one

Conditions
ConditionsYield
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

2E,6Z-nonadienal

phenylboronic acid
98-80-6

phenylboronic acid

(2E,4E)-7-phenylnona-2,4-dienal

(2E,4E)-7-phenylnona-2,4-dienal

B

C15H18O

C15H18O

Conditions
ConditionsYield
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

2E,6Z-nonadienal

recorcinol
108-46-3

recorcinol

C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene

C-trans-2, cis-6-octa-1,5-dien-1-ylcalix[4]resorcinarene

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 0℃; for 13h; Reflux;50%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

[(1-Ethoxycyclopropyl)oxy]trimethylsilane
27374-25-0

[(1-Ethoxycyclopropyl)oxy]trimethylsilane

(E,Z)-5,9-dodecadien-4-olide
1286701-21-0

(E,Z)-5,9-dodecadien-4-olide

Conditions
ConditionsYield
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

2E,6Z-nonadienal

7-hydroxy-heptyl-triphenyl-phosphonium bromide
76771-95-4

7-hydroxy-heptyl-triphenyl-phosphonium bromide

(7Z,9E,13Z)-Hexadeca-7,9,13-trien-1-ol

(7Z,9E,13Z)-Hexadeca-7,9,13-trien-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran20%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

(8-methoxycarbonyloctyl)triphenylphosphonium bromide
67878-16-4

(8-methoxycarbonyloctyl)triphenylphosphonium bromide

methyl 9Z,11E,15Z-octadecatrienoate
265108-57-4

methyl 9Z,11E,15Z-octadecatrienoate

Conditions
ConditionsYield
With water; potassium carbonate In 1,4-dioxane at 95℃; Wittig reaction;14%
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

nona-2,6-dienoic acid
1005483-30-6

nona-2,6-dienoic acid

Conditions
ConditionsYield
With sodium hydroxide; silver nitrate
2E,6Z-nonadienal
557-48-2

2E,6Z-nonadienal

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

(2E,6Z)-2,6-nonadien-1-ol

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol

557-48-2Relevant articles and documents

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

Woodcock, Steven R.,Salvatore, Sonia R.,Freeman, Bruce A.,Schopfer, Francisco J.

supporting information, (2021/09/13)

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 A 5-ALKEN-1-YNE COMPOUND, (6Z)-1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND, (2E,6Z)-2,6-NONADIENAL AND (2E)-CIS-6,7-EPOXY-2-NONENAL, AND 1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND

-

Paragraph 0175-0179, (2020/02/27)

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y-Z-CR1═CR2—(CH2)2—C≡CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y-Z-CR1═CR2—(CH2)2-X1 (1) and (ii) an alkyne compound of the following formula (2): X2=C≡C—Si(R3)(R4)(R5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR1═CR2—(CH2)2—C≡C—Si(R3)(R4)(R5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

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

-

Paragraph 0080-0085, (2020/03/09)

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 (E2,Z6)-2,6-NONADIENAL

-

Paragraph 0061-0066, (2020/03/09)

The object of the present invention is to provide an industrial and economical process for preparing (E2,Z6)-2,6-nonadienal of the following formula (4): The present invention provides a process for preparing (E2,Z6)-2,6-nonadienal (4), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1): to oxidation with a sulfoxide compound of the following formula (2): [in-line-formulae]CH3(R′)S═O??(2)[/in-line-formulae]in which R1 represents a monovalent hydrocarbon group having from 1 to 12 carbon atoms,in the presence of a sulfur trioxide complex and an amine compound of the following formula (3): [in-line-formulae]N(R2)(R3)(R4)??(3)[/in-line-formulae]in which R2, R3, and R4 each independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms, or R3 and R4 may be bonded to each other to form a divalent hydrocarbon group having from 3 to 12 carbon atoms, R3-R4,to form the aforesaid (E2,Z6)-2,6-nonadienal (4).

Process for preparing (2e,6z)-2,6-nonadienal and a process for preparing (2e)-cis-6,7-epoxy-2-nonenal

-

Paragraph 0119-0121-0131, (2019/12/25)

The object of the invention is to provide convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. The present invention provides a process for preparing (2E,6Z)-2,6-nonadienal, comprising at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar3P=CH(CH2)2CH=CHCH(OR)(OR) 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 hydrolysisto 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.

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

-

, (2019/12/24)

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.

Synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii

-

Paragraph 0052; 0053; 0054; 0055; 0056; 0057; 0058; 0059, (2019/05/08)

The invention relates to a synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii, which belongs to the field of pharmaceutical synthesis. The synthesis method comprises the following steps: taking 1, 4-butanediol as a raw material, singly protecting diol with DHP (dihexylphthalate) and then oxidizing TEMPO (tetramethylpiperidine oxide) into 4-((tetrahydro-2H-pyran-2-base) oxy) butyraldehyde; performing a Wittig reaction, so as to obtain (Z)-2-(hepta-4- alkene-1-base-oxy) tetrahydro-2H-pyran; removing the protection of the DHP and oxidizing TEMPO, so as to obtain (Z)-4-heptenal; performing a Wittig reaction, so as to obtain (2E, 6Z)-nona-2, 6-heptadienal; finally, performing epoxidation, so as to obtain the aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenalof the Aromia bungii. The total yield is 6.5%. In the synthesis method, the 1, 4-butanediol with low cost is taken as the starting raw material; the synthesis method has the advantages of being simple in operation and mild in conditions, therefore, the synthesis method is suitable for large-scale preparation.

One-Step Bioconversion of Fatty Acids into C8-C9 Volatile Aroma Compounds by a Multifunctional Lipoxygenase Cloned from Pyropia haitanensis

Zhu, Zhu-Jun,Chen, Hai-Min,Chen, Juan-Juan,Yang, Rui,Yan, Xiao-Jun

, p. 1233 - 1241 (2018/02/19)

The multifunctional lipoxygenase PhLOX cloned from Pyropia haitanensis was expressed in Escherichia coli with 24.4 mg·L-1 yield. PhLOX could catalyze the one-step bioconversion of C18-C22 fatty acids into C8-C9 volatile organic compounds (VOCs), displaying higher catalytic efficiency for eicosenoic and docosenoic acids than for octadecenoic acids. C20:5 was the most suitable substrate among the tested fatty acids. The C8-C9 VOCs were generated in good yields from fatty acids, e.g., 2E-nonenal from C20:4, and 2E,6Z-nonadienal from C20:5. Hydrolyzed oils were also tested as substrates. The reactions mainly generated 2E,4E-pentadienal, 2E-octenal, and 2E,4E-octadienal from hydrolyzed sunflower seed oil, corn oil, and fish oil, respectively. PhLOX showed good stability after storage at 4 °C for 2 weeks and broad tolerance to pH and temperature. These desirable properties of PhLOX make it a promising novel biocatalyst for the industrial production of volatile aroma compounds.

A nine carbon homologating system for skip-conjugated polyenes

Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.

, p. 34 - 42 (2014/07/08)

Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids.

Easy access to aroma active unsaturated γ-lactones by addition of modified titanium homoenolate to aldehydes

Frerot, Eric,Bagnoud, Alain

experimental part, p. 4057 - 4061 (2011/10/31)

The homo-Reformatsky reaction, in which a metal homoenolate of an ester is added to an aldehyde, was adapted to produce γ-lactones from unsaturated, enolizable aldehydes. By use of titanium homoenolate, 11 different γ-lactones were synthesized in one step with moderate to good yields from readily available aldehydes. In particular, this procedure allowed the rapid preparation of a series of C12 unsaturated γ-lactones differing in the position and configuration of the double bond. These reference compounds will be used to identify previously unknown lactones in butter oil. The chromatographic, spectral, and sensory descriptions of the synthesized lactones are provided.

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