2277-19-2

Basic information

• Product Name: CIS-6-NONENAL
• Synonyms: (6Z)-6-Nonenal;(z)-6-nonena;(Z)-6-Nonenal;(Z)-non-6-enal;6-cis-Nonenal;6-Nonenal, (Z)-;6-Nonenal, cis-;FEMA 3580
• CAS NO: 2277-19-2
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• EINECS: 218-900-9
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 2277-19-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: -28°C (estimate)
• Boiling Point: 87 °C19 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.841 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.449mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible or difficult to mix in water. Soluble in alcohol.
• Sensitive: Air Sensitive
• BRN: 2323664
• CAS DataBase Reference: CIS-6-NONENAL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-6-NONENAL(2277-19-2)
• EPA Substance Registry System: CIS-6-NONENAL(2277-19-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: RA8509200
• TSCA: Yes
• Hazardous Substances Data: 2277-19-2(Hazardous Substances Data)

Usage

Description

CIS-6-NONENAL, also known as cis-6-nonenal, is a clear colorless to pale yellow liquid with a citrus, melon odor. It is synthesized by catalytic hydrogenation of 6-nonynal diethyl acetal followed by hydrolysis. CIS-6-NONENAL has a strong aroma with a detection threshold value of 0.005 ppb and is characterized by its green cucumber and melon taste with a waxy vegetative nuance at 25 ppm.

Uses

Used in Flavor Industry:
CIS-6-NONENAL is used as a flavor component for its characteristic citrus, melon odor and taste, which is reminiscent of green cucumber and melon with a waxy vegetative nuance. It is particularly useful in the creation of artificial flavors for the food and beverage industry, where it can enhance the taste and aroma of various products.
Used in Fragrance Industry:
CIS-6-NONENAL is used as a fragrance ingredient for its pleasant and distinct citrus, melon scent. It can be incorporated into perfumes, colognes, and other personal care products to provide a fresh and invigorating aroma.
Used in the Food Industry:
CIS-6-NONENAL is used as an additive in the food industry to impart a natural, fruity flavor to various products, such as fruit juices, candies, and desserts. Its ability to mimic the taste and aroma of muskmelon fruit makes it a valuable ingredient in the development of new and innovative food products.
Used in the Agricultural Industry:
CIS-6-NONENAL can be used in the agricultural industry to enhance the flavor and aroma of certain crops, such as cucumber and muskmelon. By increasing the natural occurrence of this compound in these fruits, farmers can potentially improve the taste and marketability of their produce.

Preparation

By catalytic hydrogenation of 6-nonynal diethyl acetal followed by hydrolysis

Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. Flammable liquid when exposed to heat, sparks, or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h3-4,9H,2,5-8H2,1H3/b4-3-

Upstream product

• 80634-88-4 (Z)-2-(oct-5-en-1-yl)-1,3-dioxolane 
• 118794-69-7 6-[(tert-butyldimethylsilyl)oxy]hexanal 
• 103202-59-1 6-(tert-butyldimethylsilyl)oxyhexan-1-ol 
• 31502-19-9 (Z)-6-nonenol 
• 629-11-8 1,6-hexanediol 
• 1136196-28-5 C₁₅H₃₂OSi 

Downstream Products

• 81980-06-5 Z-7-decen-2-ol 
• 76123-38-1 cis-2-E-propenylcyclohexanol 
• 139606-58-9 (Z)-1-phenylnon-6-en-1-ol 
• 81980-06-5 7-decen-2-ol 
• 1072-21-5 hexanedial 
• 123-38-6 propionaldehyde 
• 2277-20-5 (E)-non-6-enal 
• 1276111-32-0 (S,Z)-2-phenylnon-6-en-1-ol 
• 139585-14-1 ((Z)-1,1-Dimethoxy-non-6-enyl)-benzene 

Relevant articles and documents

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant

A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)?H Alkylation of Alkenes

The terminal-selective, remote C(sp3)?H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)?C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.

Design, synthesis, and biological evaluation of N-Alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection

We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENV) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENV in BHK cells of 6.5 μM, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure-activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 μM) against DENV infection, while maintaining low cytotoxicity (CC50 > 500 μM, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 α 4%).