Cuminaldehyde
4-(1-Methylethyl)benzaldehyde
Cuminal
Cumaldehyde
- 122-03-2 checkY
- CHEBI:28671 checkY
- ChEMBL161577 checkY
- 21106431 checkY
- 204-516-9
- CU7000000
- O0893NC35F checkY
- 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
- CC(C)c1ccc(C=O)cc1
- Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine
- Flammability 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
- Instability (yellow): no hazard code
- Special hazards (white): no code
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 ]- ^ 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. S2CID 42611668.
- ^ 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.