Cuminaldehyde

The simplest araliphatic aldehyde, benzaldehyde and its 4-isopropyl homologue, cuminaldehyde, are used to a limited extent as fragrance and flavor materials. However, both compounds are used in large quantity for the production of the corresponding cinnamic and dihydrocinnamic aldehydes. 

Cumin Cuminum cyminum L. Cuminaldehyde (20-40), p-mentha- l,4-dien-7-al (20-45), p-mentha-l,3-dien-7-al (4-12)... 

The determination of aldehydes and ketones is of importance in the analysis of those essential oils characterised especially by aldehydic or ketoruc principles, e g.,the citral contained in lemon and lemongrass oils, citronellal in citronella Oil and some eucalyptus oils, benzaldehyde in bitter almond oil, salicylaldehyde in meadow-sweet oil, anisaldehyde in aniseed and fennel oils, cuminaldehyde m cumin oil, cinnamaldehyde in cinnamon oil, carvone in caraway oil, pulegone in pennyroyal oil and methyl nonyl ketone in rue oil The determination of the aldehydes and ketones presents, however, difficulties and the above methods are moderately exact in only a few cases, especially when the content of aldehydes or ketones is considerable The bisulphite method is applicable particularly to the determination of cinnamaldehyde and benzaldehyde in cinnamon oil and bitter almond oil, and, up to a certain pomt, to that of citral in lemongrass Oil. The sulphite method gives good results in the same cases and for the determination of carvone and pulegone... 

The carbonyl number method gives moderately exact results for the determinations of benzaldehyde in bitter almond oil, of cuminaldehyde in cumin oil and of methyl nonyl ketone in rue oil. The method devised by Hanus gives, according to this author, good results for the amount of cinnamaldehyde in cinnamon oil. 

Valeraldehyde, caproaldehyde, benzaldehyde 2 (or) 3-methoxybezaldehyde, coniferaldehyde, cuminaldehyde, geranial. 

The essential oil content of cumin seed ranges from 2.3 to 5.0%. Cumin fruits have a distinctive bitter flavour and a strong, warm aroma due to their abundant essential oil content. Of this, 40-65% is cuminaldehyde (4-isopropylbenzaldehyde), the major constituent and important aroma compound, and also the bitterness compound reported in cumin (Hirasa and Takemasa, 1998). The odour is best described as penetrating, irritating, fatty, overpowering, curry-like, heavy, spicy, warm and persistent, even after drying out (Farrell, 1985.) The characteristic flavour of cumin is probably due to dihydrocuminaldehyde and monoterpenes (Weiss, 2002). 

In the essential oil, apart from cuminaldehyde, perilla aldehyde (4-(l-methyl-ethenyl)-l-cyclohexene-l-carboxaldehyde), cumin alcohol or 4-isopropylbenzyl alcohol, a-pinene and /3-pinene (21%), dipentene, p-cymene, /3-phellandrene and limonene (Fig. 11.1) have been reported by Baser et al. (1992). 

The composition of Indian cumin oil, which contains less cuminaldehyde, is ... 

Cumin oil is usually obtained by steam distillation of the milled spice hydrodiffusion gives a higher yield and, more recently, supercritical gaseous extraction is claimed to give oil closer to the aroma and taste of the spice (Eikani et al., 1999). The yields of cumin seed oil with steam distillation are 2.3-3.6%, with liquid carbon dioxide it is 4.5% and with ethanol it is 12%. The major components are cuminaldehyde, cuminyl alcohol, p-mentha and 1.3-dien-7-al, the minimum perceptible levels being at 0.2 ppm. Naik et al. (1989) reported that liquid C02 extraction was quicker than steam distillation for the quantitative extraction of cumin oil without loss of active flavour components, at 58 bar and 20°C. 

Behera et al. (2004) concluded that the optimum conditions for the conventional roasting method were 125°C for 10 min and, in the microwave processing method, the best conditions were 730 W for 10min. The yields and physico-chemical properties of the volatile oils were similar in both cases. Changes were observed in the optical rotation values, which indicated differences in the chemical compositions. GC and GC-MS analysis of optimized condition samples showed that microwave-heated samples could better retain the characteristic flavour compounds of cumin (i.e. total aldehydes) than conventionally roasted samples (Table 11.5). Earlier GC reports showed cuminaldehyde as the only major aldehyde present in Indian cumin oil, but this study revealed the... 

The volatile oil of cumin, which is a mixture of about 32 components, principally cuminaldehyde (40.7%), terpinene (16.7%) and p-cymene (14.5%), inhibits Curvularia lunata and F. moniliforme by 100%, while the acetone extract is 85% effective in inhibiting the mycelial growth of A. ochraceus, A. flavus and P. citrinum (Singh et al., 2006). 

Among the 60 constituents of the cumin oil identified by GC, GC-MS and olfactometry as essential volatiles, cuminaldehyde (36%), /3-pinene (19.3%), p-cymene (18.4%) and y-terpinene (15.3%) are the principal components showing high antimicrobial activity against the mould A. niger, the Gram-positive bacteria, Bacillus subtilis and S. epidermidis, as well as the yeasts, Saccharomyces cerevisiae and Candida albicans (Jirovetz et al., 2005). 

Tyrosinase inhibitors prevent browning in foodbecause they inhibit the oxidation caused by the enzyme tyrosinase. Cuminaldehyde is identified as a potent mushroom tyrosinase monophenol monooxygenase inhibitor from cumin seeds, ft inhibits the oxidation of L-3,4-dihydroxyphenylalanine (l-DOPA) by mushroom tyrosinase with an ID50 of 7.7g/ml (0.05 mM). Its oxidized analogue, cumic acid (p-isopropylbenzoic acid), also inhibits this oxidation with an 1D50 of 43g/ml (0.26mM). These two inhibitors affect mushroom tyrosinase activity in different ways (Kubo and Kinst-Hori, 1998). 

Assay Not less than 45.0% and not more than 54.0% of aldehydes, calculated as cuminaldehyde (C H O). 

FEMA No. 2341 Cuminal Cuminaldehyde p-Cuminic Aldehyde p-Isopropylbenzaldehyde... 

Cumin Cuminum cyminum Cuminaldehyde (49), p-mentha-1,4-dien-7-al (50) 95,100... 

Cuminaldehyde Carum carvi, Cuminum cyminum (fruit, OD-R (curry) (TYR)... 

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