21662-09-9

Basic information

• Product Name: CIS-4-DECENAL
• Synonyms: (4Z)-4-Decenal;(Z)-4-Decen-1-al;(z)-4-decena;(Z)-4-Decenal;4-cis-Decenal;4-Decenal, (Z)-;4Z-decenal;FEMA 3264
• CAS NO: 21662-09-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 244-514-5
• Product Categories: Alphabetical Listings;C-D;Flavors and Fragrances;Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 21662-09-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: -16°C (estimate)
• Boiling Point: 78-80 °C10 mm Hg(lit.)
• Flash Point: 181 °F
• Appearance: colorless to slightly yellow liquid
• Density: 0.847 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00383mmHg at 25°C
• Refractive Index: n20/D 1.443(lit.)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Not miscible in water.
• Stability: Light Sensitive
• BRN: 2323646
• CAS DataBase Reference: CIS-4-DECENAL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-4-DECENAL(21662-09-9)
• EPA Substance Registry System: CIS-4-DECENAL(21662-09-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3334
• WGK Germany: 2
• RTECS: HE2071400
• TSCA: Yes
• Hazardous Substances Data: 21662-09-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to very faint yellow liquid

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.

General Description

cis-4-Decenal has been identified as one of the volatile biological marker for grey mold (Botrytis cinerea) infections in strawberry.

Safety Profile

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

InChI:InChI=1/C10H18O/c1-2-3-4-5-6-7-8-9-10-11/h4-7,11H,2-3,8-10H2,1H3/b5-4+,7-6+

Upstream product

• 16666-79-8 hexylidenetriphenylphosphoran 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 25152-84-5 trans,trans-2,4-decadienal 
• 69222-06-6 4-decyne-1-ol 
• 66-25-1 hexanal 
• 7367-84-2 (Z)-4-decenoic acid ethyl ester 
• 82861-01-6 1,1-dimethoxy-8-tosyloxy-(4Z)-octene 
• 68133-80-2 1,1-dimethoxy-4Z-decene 
• 57074-37-0 (Z)-4-decen-1-ol 

Downstream Products

• 854001-04-0 (Z)-1-Phenyl-dec-4-en-1-ol 
• 57074-37-0 (Z)-4-decen-1-ol 
• 101373-01-7 (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol 

Relevant articles and documents

Total synthesis of (8S,11R,12R)- and (8R,11R,12R)-topsentolide B 2 diastereomers and assignment of the absolute configuration

An improved total synthesis of (8S,11R,12R)- and (8R,11R,12R)-topsentolide B2 diastereomers has been completed in eight steps with overall yields of 10.2% and 10.4%, respectively. The key steps involve a regioselective asymmetric dihydroxylation, diastereoselective Roush allylation, and ring closing metathesis. The stereochemistry of natural topsentolide B2 has been determined to be (8S,11R,12R) by comparison of the specific rotation.

A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2

A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

Synthesis of epoxyisoprostanes: Effects in reducing secretion of pro-inflammatory cytokines IL-6 and IL-12

Anti-inflammatory: The efficient and general synthetic route to the elusive epoxyisoprostanoid phospholipids PECPC and PEIPC, along with the isoprostanoids EC and EI, relies on a number of stereo- and chemoselective steps, including a C-H insertion for the rapid construction of the cyclopentanone ring. The synthesized compounds display unprecedented biological activity in reducing the secretion of pro-inflammatory cytokines. Copyright