cis-4-Decenal

Base Information

• Chemical Name: cis-4-Decenal
• CAS No.: 21662-09-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• European Community (EC) Number: 244-514-5
• UNII: 5R675PGU7K
• DSSTox Substance ID: DTXSID5041514
• Nikkaji Number: J225.408E
• Wikidata: Q27162280
• Metabolomics Workbench ID: 3542
• Mol file: 21662-09-9.mol

Synonyms:cis-4-Decenal;21662-09-9;(Z)-4-Decenal;(Z)-dec-4-enal;(4Z)-4-Decenal;cis-4-Decen-1-al;4Z-Decenal;(Z)-4-Decen-1-al;4-cis-Decenal;4-DECENAL, (Z)-;5R675PGU7K;4-Decenal, (4Z)-;DTXSID5041514;(4z)-dec-4-enal;4-DECENAL, CIS-;UNII-5R675PGU7K;SCHEMBL1255463;DTXCID3021514;(Z)-4-DECENAL [FCC];CHEBI:90056;CWRKZMLUDFBPAO-SREVYHEPSA-N;WAA66209;Tox21_300829;LMFA06000147;MFCD00007024;AKOS037621276;cis-4-Decenal, technical grade, 80%;NCGC00248186-01;NCGC00254733-01;cis-4-Decenal, >=93%, stabilized, FG;CAS-21662-09-9;J-014217;Q27162280

Chemical Property of cis-4-Decenal

Chemical Property:

• Appearance/Colour: colorless to slightly yellow liquid
• Vapor Pressure: 0.00383mmHg at 25°C
• Melting Point: -16°C (estimate)
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: 78-80 °C10 mm Hg
• Flash Point: 181 °F
• PSA: 17.07000
• Density: 0.847 g/mL at 25 °C
• LogP: 3.10200
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Not miscible in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 105

Purity/Quality:

99%, ^*data from raw suppliers

cis-4-Decenal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion and skin contact. A skin irritant.
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCCC=O
• Isomeric SMILES: CCCCC/C=C\CCC=O
• Uses: cis-4-Decenal is suitable for use as standard compound to investigate the release of odorants in hydrocolloid model systems containing original or regio-selectively carboxylated cellulose at different pH values using static headspace gas chromatographic (SHS-GC) analysis. It may be used as standard for the standardization of 9-decenal by gas-chromatography. It may be used in the preparation of cis-4-decenol. It has been identified as one of the volatile biological marker for grey mold (Botrytis cinerea) infections in strawberry.

Technology Process of cis-4-Decenal

There total 12 articles about cis-4-Decenal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,1-dimethoxy-4Z-decene (68133-80-2) → (Z)-4-decenal (30390-50-2,65405-70-1,21662-09-9)

Guidance literature:

With hydrogenchloride; In acetone; for 4h; Ambient temperature;

Reference yield: 89.0%

(Z)-4-decen-1-ol (57074-37-0) → (Z)-4-decenal (30390-50-2,65405-70-1,21662-09-9)

Guidance literature:

(Z)-4-decen-1-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201300739

Reference yield:

trans,trans-2,4-decadienal (25152-84-5,65909-91-3) → (2E,4Z)-2,4-decadienal (25152-83-4,65909-91-3) + (Z)-4-decenal (30390-50-2,65405-70-1,21662-09-9) + benzaldehyde (100-52-7) + hexanal (66-25-1)

Guidance literature:

With L-lysine; at 125 ℃; for 0.333333h; Closed vial;

DOI:10.1021/jf104091p

upstream raw materials:

(Z)-4-decen-1-ol

1,1-dimethoxy-4Z-decene

1,1-dimethoxy-8-tosyloxy-(4Z)-octene

(Z)-4-decenoic acid ethyl ester

Downstream raw materials:

(Z)-dec-4-enoic acid

Refernces

• 1、 Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li. "A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant". supporting information. p. 2262 - 2267. Retrieved 2019/04/17.
• 2、 Huang, Fei,Zhang, Yushun,Yao, Yun,Yang, Wanqiu,Tao, Yunhai. "Synthesis of (4: E,6 Z,10 Z)-hexadeca-4,6,10-trien-1-ol and (4 E,6 E,10 Z)-hexadeca-4,6,10-trien-1-ol, the pheromone components of cocoa pod borer moth Conopomorpha cramerella". . p. 35575 - 35580. Retrieved 2017/07/28.