Cuminaldehyde

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Cuminaldehyde[1]
Cuminaldehyde.png
Cuminal-3d-balls.png
Names
Preferred IUPAC name
4-Isopropylbenzaldehyde
Systematic IUPAC name
4-(1-Methylethyl)benzenecarbaldehyde
Other names
p-Isopropylbenzaldehyde
4-(1-Methylethyl)benzaldehyde
Cuminal
Cumaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.107 Edit this at Wikidata
EC Number
  • 204-516-9
KEGG
RTECS number
  • CU7000000
UNII
  • InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 checkY
    Key: WTWBUQJHJGUZCY-UHFFFAOYSA-N checkY
  • InChI=1/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
    Key: WTWBUQJHJGUZCY-UHFFFAOYAP
  • CC(C)c1ccc(C=O)cc1
Properties
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)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H317
P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501
NFPA 704 (fire 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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[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.[medical citation needed]

References[edit]

  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.
  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.