Cuminaldehyde

Cuminaldehyde
Names
Preferred IUPAC name 4-Isopropylbenzaldehyde
Systematic IUPAC name 4-(1-Methylethyl)benzenecarbaldehyde
Other names p-Isopropylbenzaldehyde
4-(1-Methylethyl)benzaldehyde
Cuminal
Cumaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.107
EC Number
  • 204-516-9
KEGG
PubChem CID
RTECS number
  • CU7000000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 checkYKey: WTWBUQJHJGUZCY-UHFFFAOYSA-N checkY
  • InChI=1/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3Key: WTWBUQJHJGUZCY-UHFFFAOYAP
SMILES
  • CC(C)c1ccc(C=O)cc1
Properties
Chemical formula C10H12O
Molar mass 148.205 g·mol−1
Appearance Colorless oil
Density 0.978 g/cm3
Boiling point 235.5 °C (455.9 °F; 508.6 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H317
Precautionary statements P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501
NFPA 704 (fire diamond) NFPA 704 four-colored diamond 1 2
Flash point 93 °C (199 °F; 366 K)
Related compounds
Related compounds Benzaldehyde
Cumene
Cuminol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Cuminaldehyde (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. 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, which, if aggregated, forms insoluble fibrils in pathological conditions characterized by Lewy bodies, such as Parkinson's disease, dementia with Lewy bodies and multiple system atrophy.

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. ^ a b Merck Index, 11th Edition, 2623
  2. ^ Morshedi D; Aliakbari F; Tayaranian-Marvian, Fassihi; Pan-Montojo, Pérez-Sánchez (Sep 2015). "Cuminaldehyde as the Major Component of Cuminum cyminum, a Natural Aldehyde with Inhibitory Effect on Alpha-Synuclein Fibrillation and Cytotoxicity". Journal of Food Science. 80 (10): H2336–H2345. doi:10.1111/1750-3841.13016. PMID 26351865.
  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. S2CID 42611668.
  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. S2CID 10804119.