The aroma of rice ... and tiger

Brahmachary, R. L.; Poddar-Sarkar, Mousumi; Dutta, J.

doi:10.1038/344026b0

Cited by 29 publications

(37 citation statements)

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“…Since its first identification in cooked rice, 2-acetyl-1-pyrroline (6) has also been isolated from entirely different sources, e.g. Pandan leaves (Pandanus amaryllifolius Roxb) (Buttery et al, 1983b), cooked beef (Gasser and Grosch, 1988), and even the urine of tigers, which is used for territorial and sexual connotations (Brahmachary and Sarkar, 1990). Since the aroma character of a dilute solution of 2-acetyl-1-pyrroline (6) shows great resemblance to that of cooked rice (Buttery et al, 1982), this compound has been used as a flavorant to impart a scented rice flavor to foods (Buttery et al, 1985).…”

Section: Introductionmentioning

confidence: 99%

Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

Kimpe

Keppens

1996

J. Agric. Food Chem.

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A new synthetic pathway toward the Maillard flavor compounds 6-acyl-1,2,3,4-tetrahydropyridines and 2-acetyl-1-pyrroline is presented. The reaction sequence involves deprotonation of a vicinal diimine and subsequent alkylation with an N,N-diprotected ω-bromoalkylamine, followed by deprotection and intramolecular transimination of the functionalized intermediate. Acidic workup affords the above-mentioned heterocycles, which are principal flavor constituents of bread and cooked rice, respectively. In addition, the synthesis of the more stable diethyl acetal of 2-acetyl-1-pyrroline is described.

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Section: Introductionmentioning

confidence: 99%

Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

Kimpe

Keppens

1996

J. Agric. Food Chem.

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“…2-Phenylethylamine (Brahmachary and Dutta 1979) and 2-acetylpyrroline (Brahmachary 1996) were identified as two of the compounds responsible for the characteristic odor of the animal's urine. This odor was less persistent in the absence of the lipid fraction of the fluid (Brahmachary et al 1990). The lipid material consists of a complex mixture of, inter alia, long-chain free and esterified saturated and unsaturated fatty acids and alcohols with carbon chains of 14 to 22 carbon atoms (Poddar-Sarkar 1996).…”

Section: Introductionmentioning

confidence: 99%

Chemical Characterization of Territorial Marking Fluid of Male Bengal Tiger, Panthera tigris

Burger

Viviers

Bekker³

et al. 2008

J Chem Ecol

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The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the volatile constituents of the fluid. Using gas chromatography and gas chromatography-mass spectrometry, 98 volatile compounds and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic acids, γ-and δ-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure (R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The γ-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C8 to C16 saturated (R)-γ-lactones and (S)-δ-lactones were present in high enantiomeric purities.The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses ranging from 16 to 69 kDa, inter alia, the carboxylesteraselike urinary protein known as cauxin, previously identified in the urine of the domestic cat and other felid species, were identified in the urine fraction of the marking fluid.

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“…The smell of cooked Basmati rice (grown in parts of India) is uncannily similar to that emanating from tiger's urine and has been attributed to 2-acetyl pyrroline [118]. While a stretch of imagination suggests that the tiger is likely to be using this to mark his territory, it is not clear why basmati rice should have this chemical.…”

Section: Discussionmentioning

confidence: 97%

Biodiversity and Chemodiversity: Future Perspectives in Bioprospecting

Ramesha¹,

Gertsch²,

Ravikanth³

et al. 2011

CDT

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Biological diversity and its constituent chemical diversity have served as one of the richest sources of bioprospecting leading to the discovery of some of the most important bioactive molecules for mankind. Despite this excellent record, in the recent past, however, bioprospecting of biological resources has met with little success; there has been a perceptible decline in the discovery of novel bioactive compounds. Several arguments have been proposed to explain the current poor success in bioprospecting. Among them, it has been argued that to bioprospect more biodiversity may not necessarily be productive, considering that chemical and functional diversity might not scale with biological diversity. In this paper, we offer a critique on the current perception of biodiversity and chemodiversity and ask to what extent it is relevant in the context of bioprospecting. First, using simple models, we analyze the relation among biodiversity, chemodiversity and functional redundancies in chemical plans of plants and argue that the biological space for exploration might still be wide open. Second, in the context of future bioprospecting, we argue that brute-force high throughput screening approaches alone are insufficient and cost ineffective in realizing bioprospecting success. Therefore, intelligent or non-random approaches to bioprospecting need to be adopted. We review here few examples of such approaches and show how these could be further developed and used in the future to accelerate the pace of discovery.

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The aroma of rice ... and tiger

Cited by 29 publications

References 0 publications

Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

Chemical Characterization of Territorial Marking Fluid of Male Bengal Tiger, Panthera tigris

Biodiversity and Chemodiversity: Future Perspectives in Bioprospecting

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