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(Z)-6-nonenal
(Z)-6-nonenal is a naturally occurring aldehyde known for its strong melon and green cucumber scent, used in flavors and fragrances.
General Material Description
(Z)-6-nonenal is an unsaturated aliphatic aldehyde characterized by the molecular formula C9H16O. It presents as a colorless to pale liquid with a notably potent melon-like odor, reminiscent of green cucumber and fresh melons. This compound is also known by several synonyms including cis-6-nonenal and (6Z)-6-nonenal. Its aroma profile is distinguished by a fresh, green, and mildly waxy character, often described as evocative of cantaloupe and honeydew. (Z)-6-nonenal is primarily obtained through natural extraction from plant sources or via synthetic routes intended to replicate its natural scent. It is extensively used in flavor and fragrance industries for enhancing fruit and green notes in various consumer products.
Occurrence, Applicability & Potential Uses
(Z)-6-nonenal naturally occurs in various fruits such as cantaloupe, cucumber, melons, pepino fruit, and red raspberry. It contributes significantly to the characteristic fresh and green aromas of these foods. Due to its distinctive odor, it finds application as a flavoring and fragrance agent, particularly in formulations aiming to impart melon and cucumber-like notes. Its use is recognized and considered safe within guidelines established by FEMA (US) and IFRA (Global), with recommended concentration limits to ensure consumer safety. Typical applications include incorporation into fruit flavors, fragrances, and perfuming agents designed for personal care products. The compound's presence is also valued for its ability to add natural freshness and complexity to tropical and green fruit blends.
Physico-Chemical Properties Summary
(Z)-6-nonenal has a molecular weight of approximately 140.22 g/mol and a chemical formula C9H16O. It exhibits a moderately high logP value of 3.113 (estimated), indicating moderate lipophilicity which affects its solubility and volatility. At 25 °C, its specific gravity ranges between 0.842 and 0.852, reflecting typical density for such aldehydes. The refractive index varies from 1.436 to 1.446 at 20 °C. The compound shows limited vapor pressure (0.449 mmHg at 25 °C), contributing to its substantivity in odor applications. It is soluble in alcohol and moderately soluble in water at about 204.9 mg/L (estimated). The flash point is 150 °C (converted from 150 °F), indicating reasonable stability under typical handling conditions. Proper storage under nitrogen atmosphere extends its shelf life beyond 12 months, ensuring preservation of its olfactory characteristics for commercial use.
FAQ
What is (Z)-6-nonenal and what are its main sensory characteristics?
(Z)-6-nonenal is an unsaturated aldehyde known for its distinctive fresh, green, and melon-like aroma. It is predominantly described as having a very strong melon scent, reminiscent of cantaloupe and cucumber, with additional waxy and vegetative notes. This compound plays a key role in imparting natural fruitiness and freshness in flavor and fragrance formulations.
In which natural sources is (Z)-6-nonenal found, and what are its typical applications?
(Z)-6-nonenal occurs naturally in several fruits including cantaloupe, cucumber, melons, pepino fruit, and red raspberry. Its strong green and melon odor profile makes it valuable in the flavor industry for enhancing fruit and vegetable notes. It is also used in perfumery as a fragrance ingredient to provide fresh, natural green and fruity scent characteristics in personal care products.
How is (Z)-6-nonenal regulated and what safety considerations are associated with its use?
(Z)-6-nonenal is regulated by bodies such as FEMA (US) and IFRA (Global), which provide guidelines for its safe use in flavor and fragrance applications. It has been assessed for safety with recommended maximum usage levels, typically up to 1.0% in fragrance concentrates. The compound requires handling precautions to avoid skin and eye irritation and potential respiratory effects. Safety data sheets recommend storage in well-ventilated areas and use of protective clothing to minimize exposure.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Google Books | Start search |
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| HMDB (The Human Metabolome Database): | HMDB30958 |
| FooDB: | FDB002937 |
| Export Tariff Code: | 2912.19.9000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | (Z)-6-nonenal |
| Trivial Name | cis-6-Nonenal |
| Short Description | cis-6-nonenal |
| Formula | C9 H16 O |
| CAS Number | 2277-19-2 |
| FEMA Number | 3580 |
| Flavis Number | 5.059 |
| ECHA Number | 218-900-9 |
| FDA UNII | D8027Y6086 |
| Nikkaji Number | J59.357E |
| Beilstein Number | 2323664 |
| MDL | MFCD00014683 |
| COE Number | 661 |
| xLogP3-AA | 2.30 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 325 cis-6-nonenal |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 2277-19-2 ; CIS-6-NONENAL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 140.2257232666 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.006 to 7.089 |
| Refractive Index | 1.436 to 1.446 @ 20 °C |
| Acid Value | 5 max KOH/g |
| Vapor Pressure | 0.449 mmHg @ 25 °C |
| Flash Point TCC Value | 65.56 °C TCC |
| logP (o/w) | 3.113 est |
| Shelf life | 12 months (or longer if stored properly.) |
| Storage notes | Store under nitrogen. |
| Solubility | |
| alcohol | Yes |
| water, 204.9 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Melon | |
| green, cucumber, melon, cantaloupe, honeydew, waxy, vegetable, orris, violet leaf, woody | |
| Odor strength | very high , recommend smelling in a 1.00 % solution or less |
| Substantivity | > 252 hour(s) at 100.00 % |
| Luebke, William tgsc, (2003) | At 1.00 % in dipropylene glycol. green cucumber melon cantaloupe honeydew waxy vegetable orris violet leaf |
| Mosciano, Gerard P&F 20, No. 1, 31, (1995) | Green cucumber and melon with a woody orris-type nuance |
| Flavor Type: Green | |
| green, cucumber, melon, waxy, oily, watermelon, vegetable, violet leaf | |
| General comment | Green cucumber melon waxy oily watermelon vegetable violet leaf |
| Mosciano, Gerard P&F 20, No. 1, 31, (1995) | At 25.00 ppm. Green cucumber and melon with a waxy vegetative nuance |
| Useful in melon flavors, especially cantaloupe, watermelon, cucumber, and tropical fruits. Can add fresh cut, crisp apple notes. | Fresh, green, watermelon, melon and hints of vegetables |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Crabapple , Apple green apple , Banana , Blueberry , Cilantro , Citrus , Coconut tropical coconut , Country meadow , Cucumber , Dill weed , Dillenia , Fresh outdoors , Gooseberry , Green , Hugonia , Kiwi , Kiwi blossom , Lychee , Mango flower , Melon , Mimosa , Ocean sea , Pansy , Reseda , Stephanotis , Violet |
| Flavoring purposes | Chocolate cacao , Cilantro , Dill weed , Fruit tropical fruit , Jackfruit , Tropical |
| Other purposes | Blossom tropical blossom , Fantasy blends , Natural |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 36 - Wear suitable protective clothing. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| Skin irritation (Category 2), H315 Eye irritation (Category 2A), H319 Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |  |
| Signal word | Warning |
| Hazard statement(s) | |
| H315 - Causes skin irritation H319 - Causes serious eye irritation H335 - May cause respiratory irritation | |
| Precautionary statement(s) | |
| P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P264 - Wash skin thouroughly after handling. P271 - Use only outdoors or in a well-ventilated area. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P302 + P352 - IF ON SKIN: wash with plenty of soap and water. P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P312 - Call a POISON CENTER or doctor/physician if you feel unwell. P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention. P337 + P313 - IF eye irritation persists: Get medical advice/attention. P362 - Take off contaminated clothing and wash before reuse. P403 + P233 - Store in a well-ventilated place. Keep container tightly closed. P405 - Store locked up. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Oral/Parenteral Toxicity: | |
| oral-mouse LD50 > 5000 mg/kg (Moreno, 1978b) oral-mouse LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 20, Pg. 777, 1982. | |
| Dermal Toxicity: | |
| skin-guinea pig LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 20, Pg. 777, 1982. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for (Z)-6-nonenal usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.70 (μg/capita/day) | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.00000 | |
| beverages(nonalcoholic): | - | 0.20000 | |
| beverages(alcoholic): | - | 0.10000 | |
| breakfast cereal: | - | 0.10000 | |
| cheese: | - | - | |
| chewing gum: | - | 1.00000 | |
| condiments / relishes: | - | 0.10000 | |
| confectionery froastings: | - | 1.50000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.30000 | |
| fruit ices: | - | 0.30000 | |
| gelatins / puddings: | - | 0.50000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 6 (FGE.06): Straight-and branched-chain aliphatic unsatured primary alcohols, aldehydes, carboxylic acids, and esters from chemical groups 1 and 4 View page or View pdf |
| Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to Flavouring Group Evaluation 5: Esters of 23 branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and 24 branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 View page or View pdf |
| Flavouring Group Evaluation 6, Revision 1 (FGE.06Rev1) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 5, Revision 1 (FGE.05Rev1):Esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 5, Revision 2 (FGE.05Rev2): Branched- and straight-chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols from chemical groups 1, 2, 3 and 5 View page or View pdf |
| Safety and efficacy of non-conjugated and accumulated unsaturated straight-chain and branched-chain, aliphatic primary alcohols, aldehydes, acids, acetals and esters belonging to chemical group 4 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):2277-19-2 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5362720 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| (Z)-non-6-enal |
| Chemidplus:0002277192 |
| RTECS:RA8509200 for cas# 2277-19-2 |