Cuminaldehyde
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Names | |||
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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)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.004.107 | ||
EC Number |
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KEGG | |||
PubChem CID
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RTECS number |
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UNII | |||
CompTox Dashboard (EPA)
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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: | |||
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Warning | |||
H302, H317 | |||
P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 93 °C (199 °F; 366 K) | ||
Related compounds | |||
Related compounds
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Benzaldehyde Cumene Cuminol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ a b Merck Index, 11th Edition, 2623
- ^ 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.
- ^ 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.
- ^ 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.