Cuminaldehyde

From Wikipedia, the free encyclopedia

Cuminaldehyde^[1]

IUPAC name 4-(1-Methylethyl)benzaldehyde
Other names Cuminaldehyde p-Isopropylbenzaldehyde 4-Isopropylbenzaldehyde Cuminal Cumaldehyde
Identifiers
CAS number	122-03-2^Y
ChemSpider	21106431^Y
UNII	O0893NC35F^Y
KEGG	C06577^Y
ChEMBL	CHEMBL161577^Y
RTECS number	CU7000000
Jmol-3D images	Image 1
SMILES CC(C)c1ccc(C=O)cc1
InChI InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3^Y Key: WTWBUQJHJGUZCY-UHFFFAOYSA-N^Y InChI=1/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 Key: WTWBUQJHJGUZCY-UHFFFAOYAP
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
Solubility in water	Insoluble
Hazards
R-phrases	R22
S-phrases	S36/37
NFPA 704	2 1 0
Flash point	93 °C; 199 °F; 366 K
Related compounds
Related compounds	Benzaldehyde Cumene Cuminol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

↑ 1.0 1.1 Merck Index, 11th Edition, 2623
↑ 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.
↑ 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.

Cuminaldehyde

References

See also