Cuminaldehyde

Cuminaldehyde[1]
Names
IUPAC name
4-(1-Methylethyl)benzaldehyde
Other names
Cuminaldehyde
p-Isopropylbenzaldehyde
4-Isopropylbenzaldehyde
Cuminal
Cumaldehyde
Identifiers
122-03-2 Yes
ChEBI CHEBI:28671 Yes
ChEMBL ChEMBL161577 Yes
ChemSpider 21106431 Yes
Jmol-3D images Image
KEGG C06577 Yes
RTECS number CU7000000
UNII O0893NC35F Yes
Properties
Molecular formula
 C10H12O
Molar mass 148.20 g·mol−1
Appearance Colorless oil
Density 0.978 g/cm3
Boiling point 235.5 °C (455.9 °F; 508.6 K)
Insoluble
Hazards
R-phrases R22
S-phrases S36/37
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
2
1
Flash point 93 °C (199 °F; 366 K)
Related compounds
Related compounds
 Benzaldehyde
Cumene
Cuminol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Cuminaldehyde, or 4-isopropylbenzaldehyde, is a natural organic compound with the molecular formula C10H12O. It is a benzaldehyde with an isopropyl group substituted in the 4-position.

Cuminaldehyde is a constituent of the essential oils of eucalyptus, myrrh, cassia, cumin and others.[1] It has a pleasant smell and contributes to the aroma of these oils. It is used commercially in perfumes and other cosmetics.

It has been shown that cuminaldehyde, as a small molecule, inhibits the fibrillation of alpha-synuclein,[2] which, if aggregated, forms insoluble fibrils in pathological conditions characterized by Lewy bodies, such as Parkinson's disease, dementia with Lewy bodies[3] and multiple system atrophy.[4]

Cuminaldehyde can be prepared synthetically by the reduction of 4-isopropylbenzoyl chloride or by the formylation of cumene.

The thiosemicarbazone of cuminaldehyde has antiviral properties.

References

  1. ↑ 1.0 1.1 Merck Index, 11th Edition, 2623
  2. ↑ Morshedi D, Aliakbari F, (Spring 2012). "The Inhibitory Effects of Cuminaldehyde on Amyloid Fibrillation and Cytotoxicity of Alpha-synuclein". modares journal of medical sciences: pathobiology 15 (1): 45–60.
  3. ↑ Arima K, Uéda K, Sunohara N, Hirai S, Izumiyama Y, Tonozuka-Uehara H, Kawai M (October 1998). "Immunoelectron-microscopic demonstration of NACP/alpha-synuclein-epitopes on the filamentous component of Lewy bodies in Parkinson's disease and in dementia with Lewy bodies". Brain Res. 808 (1): 93–100. doi:10.1016/S0006-8993(98)00734-3. PMID 9795161.
  4. ↑ Arima K, Uéda K, Sunohara N, Arakawa K, Hirai S, Nakamura M, Tonozuka-Uehara H, Kawai M (November 1998). "NACP/alpha-synuclein immunoreactivity in fibrillary components of neuronal and oligodendroglial cytoplasmic inclusions in the pontine nuclei in multiple system atrophy". Acta Neuropathol. 96 (5): 439–44. doi:10.1007/s004010050917. PMID 9829806.

See also