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HomeProduct name listcyclamen aldehyde

cyclamen aldehyde

Synonym(s):Cyclamen aldehyde

  • CAS NO.:103-95-7
  • Empirical Formula: C13H18O
  • Molecular Weight: 190.28
  • MDL number: MFCD00024160
  • EINECS: 203-161-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
cyclamen aldehyde Structural

What is cyclamen aldehyde?

Description

2-Methyl-3-(p-isopropylphenyl) propionaldehyde has a strong, flowery odor. May be prepared by condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.

Chemical properties

The commercially available racemate is a colorless to yellowish liquid with an intense floral odor reminiscent of Cyclamen europaeum (cyclamen, sowbread).
Production. Two main processes are used for the industrial synthesis of cyclamen aldehyde:
1) Alkaline condensation of 4-isopropylbenzaldehyde and propanal results, via the aldol, in the formation of 2-methyl-3-(4-isopropylphenyl)-2-propenal. The unsaturated aldehyde is hydrogenated selectively to the saturated aldehyde in the presence of potassium acetate and a suitable catalyst, such as palladium–alumina:
2) Friedel–Crafts reaction of isopropylbenzene and 2-methylpropenal diacetate (methacrolein diacetate) in the presence of titanium tetrachloride/boron trifluoride etherate gives cyclamen aldehyde enolacetate, which is hydrolyzed to aldehyde:
Uses. Cyclamen aldehyde is an important component for obtaining special blossomnotes in perfume compositions, particularly the cyclamen type. Because of its fresh, floral aspect, it is also used as the top note in many other blossomfragrances.

Chemical properties

2-Methyl-3-(p-isopropylphenyl)-propionaldehyde has a strong, flowery odor

Occurrence

Reported found in nutmeg and starfruit.

The Uses of cyclamen aldehyde

Cyclamal, is an ingredient in perfume. It can also be used in the synthesis of Cyclamen Alcohol (C987655).

The Uses of cyclamen aldehyde

Cyclamen Aldehyde is a very powerful, floral, green note used in many perfumery applications to blend into fresh, floral, green or ozonic/marine accords. It is an ingredient with growing use and importance in helping to build replacement accords for materials disappearing from the Perfumers’ palette. Cyclamen has good overall stability except in extremes of pH. It has good tenacity and substantivity and represents very good value for money in new creations.

Definition

ChEBI: Xi-3-(4-Isopropylphenyl)-2-methylpropanal is a monoterpenoid.

Preparation

By condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst

Safety Profile

Moderately toxic by ingestion. A human skin irritant. See also ALDEHYDES. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Cyclamen aldehyde is synthesized from Cuminaldehyde plus Ropionaldehyde by condensation followed by selective hydrogenation and finally dehydrogenation of the Cyclamen alcohol to aldehyde.

Properties of cyclamen aldehyde

Boiling point: 270 °C(lit.)
Density  0.95 g/mL at 25 °C(lit.)
vapor pressure  0.3Pa at 20℃
refractive index  n20/D 1.505(lit.)
FEMA  2743 | 2-METHYL-3-(P-ISOPROPYLPHENYL)PROPIONALDEHYDE
Flash point: 228 °F
storage temp.  Inert atmosphere,Room Temperature
solubility  Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
form  Oil
color  Colourless liquid.
Odor Powerful floral-green with a characteristic cucumber-melon note used in floral types.
Water Solubility  66mg/L at 20℃
JECFA Number 1465
Stability: Hygroscopic
CAS DataBase Reference 103-95-7(CAS DataBase Reference)
EPA Substance Registry System Benzenepropanal, .alpha.-methyl-4-(1-methylethyl)- (103-95-7)

Safety information for cyclamen aldehyde

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
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.

Computed Descriptors for cyclamen aldehyde

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