2 Methyl Undecanal Synthesis Essay

2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil.[2] This compound smells herbaceous, orange, and ambergris-like.[3] At high dilution it has a flavor similar to honey and nuts.[2] It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol.[4] It is used as a fragrance component in soaps, detergents, and perfumes.


The first synthesis of 2-methylundecanal was recorded by Georges Darzens in 1904 from methyl nonyl ketone and ethyl chloroacetate.[5] This method of synthesis can be used to produce a variety of aldehydes and became known as the Darzens reaction and is still used today. 2-Methylundecanal is synthesized in industry by two main routes. The first route, like Darzens, involves converting methyl nonyl ketone to its glycidate by allowing it to react with alkyl chloroacetate. The glycidate then undergoes saponification followed by decarboxylation.[6]

CH3(CH2)8C(O)CH3 + ClCH2CO2CH3 → CH3(CH2)8CH(CH3)OCH(CO2R) + HCl

The second method for the synthesis of 2-methylundecanal begins with the conversion of undecanal to 2-methyleneundecanal by allowing it to react with formaldehyde in the presence of base. The 2-methyleneundecanal is then hydrogenated to give 2-methylundecanal. The required undecanal is generated from 1-decene by hydroformylation. The resulting solution is over 50% 2-methyleneundecanal. The double bond of this compound is hydrogenated and the resulting 2-methylundecanal is separated from the by-products using fractional distillation.[6]

CH3(CH2)7CH2=CH2 + H2 + CO → CH3(CH2)10CHO
CH3(CH2)10CHO + HCHO → CH3(CH2)8C(CH2)CHO + H2O
CH3(CH2)8C(CH2)CHO + H2 → CH3(CH2)8CH(CH3)CHO


2-Methylundecanal contains one asymmetric carbon atom.

The enantiomers can be synthesized with high enantiomeric purity using the SAMP/RAMP hydrazone method. This process involves starting with simple achiral aldehydes and converting them to their SAMP hydrazones then obtaining the corresponding chiral hydrazones using RAMP as a chiral auxiliary. The chiral hydrazones are then metalated with lithium diisopropylamide (LDA) and alkylated with a slight excess of dimethyl sulfate. Testing of the enantiomers by a professional perfumer indicated only a slight difference in odor quality and intensity.[7]


2-Methylundecanal is used widely as a fragrance element in soaps and detergents as well as in the perfume industry to give conifer notes, fir in particular, but is also used in fantasy compositions.[6] This aldehyde was one of the first synthetics to be used in a prestigious perfume, namely Chanel No. 5.[8]


External links[edit]

Further reading[edit]

  • Burdock, George A., Fenorali, Giovanni. Fenorali’s Handbook of Flavor Ingredients, 5th ed.; CRC Press: Boca Raton, 2004. ISBN 0-8493-3034-3
  • Ullmann’s Encyclopedia of Industrial Chemistry 7th Ed: Fragrances and Flavors, John Wiley & Sons Inc, Hoboken 2009. doi:10.1002/14356007.a11_141
  • CRC Handbook of Chemistry and Physics. 89th ed. [Online] 2008-2009.
  • Darzens, Georges; Comptes Rendus Hebdomadaires des séances de l’Académie des Sciences. 1904, 139, 1214-1217.
  • Dieter Enders; Hubert Dyker, Synthesis and Properties of Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal. Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule. 1990, 1107–1110, http://www3.interscience.wiley.com/journal/112355592/abstract?CRETRY=1&SRETRY=0. doi:10.1002/jlac.1990199001200.
  • Ramsden, E. N. A-Level Chemistry. 4th ed. Nelson Thornes: UK, 2000.
(R)-2-Methylundecanal (above) and (S)-2-Methylundecanal (below)
  1. ^"2-Methylundecanal - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 12 October 2011. 
  2. ^ abFenorali, Giovanni (2004). Fenorali’s Handbook of Flavor Ingredients (5th ed.). Boca Raton: CRC Press. 
  3. ^Molecule of the Month: Chanel No 5 and 2-methylundecanal
  4. ^CRC Handbook of Chemistry and Physics (89th ed.). CRC Press. 2008–2009. 
  5. ^Darzens, Georges (1904). Comptes Rendus Hebdomadaires des séances de l'Académie des Sciences. 
  6. ^ abcUllmann's Encyclopedia of Industrial Chemistry (7th ed.). Hoboken: John Wiley & Sons Inc. 2009. 
  7. ^Dyker, Hubert (1990). Synthesis and Properties of Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal. 
  8. ^Ramsden, E.N. (2000). A-Level Chemistry (4th ed.). UK: Nelson Thornes. 
2-methyl undecanal (aldehyde C-12 mna)
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      5AG07528 2-Aldehyde C-12 MNA 10% in DPG
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      502732 Aldehyde C-12 MNA
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 98.00 to 100.00 % 
Food Chemicals Codex Listed: Yes
Specific Gravity: 0.82200 to 0.83000 @  25.00 °C.
Pounds per Gallon - (est).: 6.840 to  6.906
Specific Gravity: 0.82300 to 0.83100 @  20.00 °C.
Pounds per Gallon - est.: 6.856 to 6.923
Refractive Index: 1.43000 to 1.43600 @  20.00 °C.
Boiling Point: 171.00 °C. @ 760.00 mm Hg
Boiling Point: 233.00 °C. @ 760.00 mm Hg
Acid Value: 2.00 max. KOH/g
Vapor Pressure: 1.428000 mm/Hg @ 25.00 °C. (est)
Vapor Density: >1 ( Air = 1 )
Flash Point: 200.00 °F. TCC ( 93.33 °C. )
logP (o/w): 4.834 (est)
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light. store under nitrogen.
Storage: store under nitrogen.
Soluble in:
 dipropylene glycol
 fixed oils
 paraffin oil
 water, 5.372 mg/L @ 25 °C (est)
Insoluble in:
 deodorant spray
 detergent powder
 hair spray
 household product
 non-discoloring in most media
 talcum powder
Odor Type: aldehydic
Odor Strength: high ,
recommend smelling in a 1.00 % solution or less
 fresh  amber  aldehydic  mossy  citrus  tuberose  metallic  waxy  coumarinic  
Odor Description:
at 1.00 % in dipropylene glycol. 
fresh amber aldehydic moss citrus tuberose metallic waxy coumarinic
Luebke, William tgsc, (1984)
 gassy  metallic  waxy  coumarinic  citrus  
Odor Description:
Gassy, diffusive, metallic, waxy, with coumarin and citrus nuances
Mosciano, Gerard P&F 19, No. 2, 55, (1994)
 waxy  fatty  metallic  citrus  
Taste Description:
at 2.00 ppm.  
Waxy, fatty, metallic, with citrus nuances
Mosciano, Gerard P&F 19, No. 2, 55, (1994)
Substantivity: 308 hour(s) at 100.00 %
Associate Allied Chemicals
Aldehyde C-12 MNA
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Aldehyde C12 MNA
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Aldehyde C-12 MNA
Happening at Berje
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Aldehyde C-12 Mna
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Aldehyde C 12 MNA Pure
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Aldehyde C-12 MNA
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Diffusions Aromatiques
ECSA Chemicals
Aldehyde C 12 MNA
Company Profile
Ernesto Ventós
Ernesto Ventós
Aldehyde MNA
Odor: A classical and powerful aldehyde with citrus, fresh, ozonic and slightly ambery tones
Use: A long-lasting fresh and clean note that brings bloom and brightness to virtually all fragrance types.
Aldehyde C 12 MNA Pure
Odor: Aldehydic, Dry, Amber, Warm
Use: This product is a classic in the family of fatty aldehydes. It is widely used in all types of perfumery but blends particularly well with floral, woody, amber and tobacco accords. Good fabric substantivity.
Indukern F&F
Kao Corporation
Odor: Powerful dry amber like
Lluch Essence
M&U International
Aldehyde C-12 MNA
Odor: floreal,fresh (orange), amber note
Flavor: waxy, fatty, metallic, citrus nuances
Nagar Haveli Perfumes & Aromatics
2 - Methyl Undecanal (aldehyde C-12 mna)
Odor: Fresh amber aldehydic moss citrus tuberose metallic waxy coumarinic
Pell Wall Perfumes
Aldehyde C12 MNA
Odor: fresh, amber, aldehydic, moss, sweaty-musk, citrus, tuberose, metallic, waxy, coumarinic
Use: Arctander writes enthusiastically about it, including: “This aldehyde is probably one of the most preferred perfumery aldehydes with respect to �aldehydic topnote’. It blends very well with Galbanum, the Hexenyl family or the Methyl phenyl carbinyl esters, the Methyl-ionones or with Oakmoss. � It lends excellent notes to a �Tabac’ base and blends well with Vetiver for such purpose. In Mimosa it will supply part of the peculiar dry notes, and in Ambre fragrances it is an almost inevitable component. Interesting effects are achieved with Ginger oil and Clary Sage.”
Penta International
Perfumer Supply House
Aldehyde C12 MNA (2-Methyl Undecanal)
Odor: Amber, mossy, citrus, tuberose, coumarin somewhat metallic with waxy undertones
2-Aldehyde C-12 MNA 10% in DPG
2-Aldehyde C-12 MNA
Odor: fresh amber citrus moss tuberose fresh orange amber diffusive conifer dry-fruity Honey Nut
Use: Blends-well-with - +Clary Sage Fixer For This Aldehyde +Olibanum Fixer For This Aldehyde +Labdanum Fixer For This Aldehyde +Oakmoss Fixer For This Aldehyde +Musks Fixer For This Aldehyde
Prasad Organics
Aldehyde C12 MNA
Reincke & Fichtner
Santa Cruz Biotechnology
For experimental / research use only.
SRS Aromatics
Odor: Fresh, Citrus, Metallic, Waxy
Aldehyde C12 MNA
Odor: very intensive, relatively good tenacity, aldehydic with nuances reminiscent of ambergris and incense
Flavor: dry fruit taste with honey-nut note
Aldehyde C-12 MNA
Odor: Amber/ Ambery, Dry, Herbal/ Herbaceous
The Good Scents Company
2-methyl undecanal (aldehyde C-12 mna)
Odor: fresh amber aldehydic moss citrus tuberose metallic waxy coumarinic
The John D. Walsh Company
Aldehyde C-12 MNA
The Lermond Company
Aldehyde C-12 MNA
The Perfumers Apprentice
Aldehyde C-12 MNA
Odor: Powerful and diffusive dry ambre like
Aldehyde C-12 M.N.A.
Vigon International
Aldehyde C-12 MNA
Odor: Very intensive, relatively good tenacity, aldehydic with nuances reminiscent of ambergris and incense
Preferred SDS: View
European information :
Most important hazard(s):
N - Dangerous for the environment.
R 52/53 - Harmful to qauatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Skin irritation (Category 2), H315
Skin sensitisation (Category 1), H317
Eye irritation (Category 2A), H319
Chronic aquatic toxicity (Category 3), H412
GHS Label elements, including precautionary statements
Signal word Warning
Hazard statement(s)
H315 - Causes skin irritation
H317 - May cause an allergic skin reaction
H319 - Causes serious eye irritation
H330 - Fatal if inhaled
H412 - Harmful to aquatic life with long lasting effects
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P272 - Contaminated work clothing should not be allowed out of the workplace.
P273 - Avoid release to the environment.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P333 + P313 - IF SKIN irritation or rash occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P501 - Dispose of contents/container in accordance with local/regional/national/international regulations.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50  > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 485, 1973.

Dermal Toxicity:
skin-rabbit LD50 > 10000 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 485, 1973.

Inhalation Toxicity:
Not determined
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for 2-methyl undecanal (aldehyde C-12 mna) usage levels up to:
  2.0000 % in the fragrance concentrate.
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 ppmaverage maximum ppm
baked goods: -1.30000
beverages(nonalcoholic): -0.31000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -0.20000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.11000
fruit ices: -0.11000
gelatins / puddings: 0.500002.50000
granulated sugar: --
gravies: --
hard candy: -0.94000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -0.33000
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: --

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