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mandarine undecenal
Mandarine undecenal is an aldehydic flavor and fragrance compound valued for its waxy, citrus-mandarin aroma in perfuming and flavoring applications.
General Material Description
Mandarine undecenal, also known as 9-undecenal or aldehyde supra (Firmenich), is an aliphatic unsaturated aldehyde with the molecular formula C11H20O. It typically appears as a colorless to pale liquid and exhibits a distinctive odor profile combining aldehydic, waxy, and clean citrus notes reminiscent of mandarin orange peel. This compound is chemically categorized as an unsaturated primary aldehyde with a chain length of eleven carbons and a double bond in the ninth position. It is sourced synthetically and widely utilized in the flavor and fragrance industry. Further chemical structure and identifiers are documented in public resources such as PubChem. Its sensory qualities make it important as a flavor and scent ingredient derived either through synthesis or biotechnological processes.
Occurrence, Applicability & Potential Uses
Mandarine undecenal is not commonly found naturally but is produced synthetically for use in various flavor and fragrance applications. It imparts fresh, citrusy, and aldehydic notes, making it valuable as a mandarin or citrus rind aroma replacement and is also used to simulate notes found in clary sage, jasmine, neroli, and orris oils. Under the FEMA (US) standard, it is assigned the number 3094 and is recognized as safe for flavor use within regulated limits. Additionally, IFRA (Global) allows its use in perfuming agents with a maximum concentration of 1.0% in fragrance concentrates. Its applications include fine fragrances, shampoos, soaps, detergents, and household products, where it enhances aromas with a waxy and aldehydic character while providing substantial odor longevity.
Physico-Chemical Properties Summary
Mandarine undecenal is a colorless liquid with a molecular weight of approximately 168.28 g/mol. It has a boiling point near 239 to 240°C at atmospheric pressure (760 mm Hg), indicating moderate volatility suitable for fragrance evaporation. Its specific gravity ranges between 0.843 and 0.852 at 20 to 25°C, showing it is slightly less dense than water. The refractive index lies from 1.441 to 1.447 at 20–25°C, reflecting its optical properties in formulation. The estimated log P value of 4.1 suggests significant hydrophobicity with good solubility in alcohols and limited solubility in water (~22 mg/L). The compound exhibits a relatively high flash point (approximately 212°F or 100°C), indicating stability under standard handling conditions. Its aldehydic nature contributes to its strong odor and substantivity, with odor persistence measured at over 700 hours in pure form. Shelf life extends to at least 12 months when stored properly, and it maintains stability in various product bases such as detergents and fine fragrances.
FAQ
What is mandarine undecenal and what are its main characteristics?
Mandarine undecenal is a synthetic unsaturated aliphatic aldehyde with the chemical formula C11H20O. It is notable for its waxy, aldehydic, and citrus mandarin odor that resembles fresh laundered cloth and clean citrus peel. The compound is primarily used as a flavor and fragrance ingredient to impart fresh mandarin and citrus notes with an aldehydic sharpness. Its synonyms include 9-undecenal and aldehyde supra, and it typically appears as a clear liquid with moderate volatility and high odor substantivity.
How is mandarine undecenal used and where can it be found in products?
Mandarine undecenal is employed in fine fragrances, perfumes, shampoos, soaps, detergents, and household products to provide fresh, waxy citrus aromas. It acts as a replacement for natural oils such as clary sage, neroli, and orris, contributing aldehydic and mandarin notes. Usage levels are controlled under regulatory frameworks to ensure safety and product stability, with acclaimed efficacy in enhancing top notes within fragrance compositions.
What regulations and safety assessments apply to mandarine undecenal?
Mandarine undecenal is listed under FEMA (US) number 3094 and recognized as Generally Recognized As Safe (GRAS) for flavor use at specified levels. The IFRA (Global) Code of Practice allows its use in fragrance concentrates up to 1.0%. Toxicological data show a relatively low oral toxicity with an LD50 in rats around 5010 mg/kg. No significant GHS hazard classifications or precautionary statements apply. Regulatory assessments, including EFSA opinions and RIFM safety reviews, support its controlled use in flavors and fragrances.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| 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): | HMDB37807 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | mandarine undecenal |
| Trivial Name | 9-Undecenal |
| Short Description | aldehyde supra (Firmenich) |
| Formula | C11 H20 O |
| CAS Number | 143-14-6 |
| FEMA Number | 3094 |
| Flavis Number | 5.036 |
| ECHA Number | 205-586-3 |
| FDA UNII | 879S4Y7K6F |
| Nikkaji Number | J193.640I |
| COE Number | 123 |
| xLogP3-AA | 3.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 329 9-undecenal |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 143-14-6 ; 9-UNDECENAL |
| Synonyms |
|
Suppliers
| Azelis UK | BOC Sciences |
| Ernesto Ventós | Firmenich |
| Penta International | Perfumery Laboratory |
| Reincke & Fichtner | Vigon International |
| Penta International Corporation | Ernesto Ventós S.A. |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.27960205078 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.015 to 7.065 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.048 to 7.098 |
| Refractive Index | 1.443 to 1.447 @ 20 °C |
| Refractive Index | 1.441 to 1.445 @ 25 °C |
| Boiling Point | 239 to 240°C @ 760 mm Hg |
| Acid Value | 5 max KOH/g |
| Vapor Pressure | 0.033 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 4.107 est |
| Shelf life | 12 months (or longer if stored properly.) |
| Solubility | |
| alcohol | Yes |
| water, 22.27 mg/L @ 25 °C (est) | Yes |
| Stability | |
| APC: traces - 0.5% | Unspecified |
| candle: traces - 0.5% | Unspecified |
| detergent: traces - 0.5% | Unspecified |
| fine fragrances: Top note | Unspecified |
| shampoo: | Unspecified |
| shower gel: | Unspecified |
| soap: traces - 0.5% | Unspecified |
| softener: traces - 0.5% | Unspecified |
Organoleptic Properties
| Odor Type: Aldehydic | |
| aldehydic, waxy, clean, cloth laundered cloth, ozone, green, mandarin, citrus, metallic | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | 746 hour(s) at 100.00 % |
| Luebke, William tgsc, (2021) | At 1.00 % in dipropylene glycol. aldehydic waxy clean laundered cloth ozone green mandarin citrus metallic |
| Flavor Type: Waxy | |
| waxy, citrus rind, costus, aldehydic, oily, clean, greasy, creamy | |
| Luebke, William tgsc, (2021) | Waxy citrus rind costus aldehydic oily clean greasy creamy |
Potential Uses
| Applications | |
| Odor purposes | Aldehydic , Citrus , Clary sage oil replacer , Jasmin , Mandarin , Neroli , Orris |
| Other purposes | Waxy |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 5010 mg/kg Luebke, William tgsc, (2021) | |
| Dermal Toxicity: | |
| Not determined | |
| 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 mandarine undecenal usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.97 (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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 4.60000 | |
| beverages(nonalcoholic): | - | 4.80000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 4.20000 | |
| fruit ices: | - | 4.20000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 4.50000 | |
| 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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):143-14-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6431148 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| undec-9-enal |
| Chemidplus:0000143146 |