Characteristics of Vanillin and Coumarin

Hitchens, R.M.

doi:10.1021/ie50268a012

Cited by 3 publications

(2 citation statements)

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“…Pyrene is significantly less soluble than coumarin, , and although specific solubility data are not available for 7OHC, our calculations of the free energy of solvation of each of these species suggest that it has an even higher affinity for water than coumarin. This trend is not surprising, given the apolar nature of the PAH, pyrene, compared to coumarin, which contains a polar ester group, and finally 7OHC, which also contains an extra hydroxyl group compared to coumarin and is thus able to form hydrogen bonds with water.…”

Section: Discussionmentioning

confidence: 75%

“…This differing chemical morphology is attributed to the difference in solubility of pyrene, compared to that of coumarin and 7OHC, and is in line with previous results demonstrating the nonuniform distribution and self-association of apolar species at the ice surface and the observation of liquid regions or channels at the ice surface. [6][7][8][9]11,22 Pyrene is significantly less soluble than coumarin, 37,38 and although specific solubility data are not available for 7OHC, our calculations of the free energy of solvation of each of these species suggest that it has an even higher affinity for water than coumarin. This trend is not surprising, given the apolar nature of the PAH, pyrene, compared to coumarin, which contains a polar ester group, and finally 7OHC, which also contains an extra hydroxyl group compared to coumarin and is thus able to form hydrogen bonds with water.…”

Section: ■ Discussionmentioning

confidence: 78%

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Chemical Morphology Controls Reactivity of OH Radicals at the Air–Ice Interface

et al. 2021

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At the air−ice interface, some aromatic compounds such as benzene and anthracene are surprisingly unreactive toward OH. This may be a consequence of the poor solvation of these compounds at the interface, resulting in clustering there. We test this hypothesis by comparing the reaction of OH with pyrene, a 4ring polyaromatic hydrocarbon (PAH), to reactions of OH with the more water-soluble compounds coumarin and 7-hydroxycoumarin (7OHC). We observe that OH reacts readily with coumarin and 7OHC at both liquid and frozen air−water interfaces. Pyrene, a much less soluble compound, reacts with OH at the liquid surface but not at the air−ice interface. We report evidence of pyrene aggregation at the ice surface based on its broadened and redshifted emission spectrum alongside fluorescence mapping of anthracene, a closely related 3-ring PAH, which shows bunching at the ice surface. By contrast, fluorescence mapping shows that coumarin is fairly homogeneously distributed at the air−ice interface. Together, these results suggest that the limited reactivity of some compounds toward OH at the ice surface may be a consequence of their propensity to self-aggregate, demonstrating that chemical morphology can play an important role in reactions at the ice surface.

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Section: Discussionmentioning

confidence: 75%

Section: ■ Discussionmentioning

confidence: 78%

Chemical Morphology Controls Reactivity of OH Radicals at the Air–Ice Interface

et al. 2021

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Coumarin

Boisde¹,

Meuly²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Coumarin is an important aroma chemical widely used in the perfumery, soap, and cosmetic industries for its characteristic herbaceous odor and as a valuable odor fixative. It also has several other unrelated industrial uses. It occurs naturally in many plants and was first extracted from Tonka beans in 1820. Coumarin is a crystalline solid. The commercial product is manufactured synthetically and the usual preparation methods start from o ‐cresol, phenol, and most currently from salicylaldehyde. The perfume‐grade product is highly purified and purification methods are given as well as the manufacturers' specifications. Production figures and commercial prices in the United States are listed since the 1940s. Health and safety data are reported. Since 1954, the use of coumarin in foods has been banned in the United States by the FDA. The carcinogenicity of coumarin has been debated. Recent studies have led IARC to classify coumarin as a Group 3 chemical indicating insufficient evidence of carcinogenicity in humans. In addition to its use in the fragrance industry and as an industrial odorant or odor masking agent, coumarin is also an electroplating adjuvant. Coumarin and some of its derivatives are used as fluorescent brighteners and as pharmaceuticals in anticoagulant therapy. Several of the most important coumarin derivatives are described including 3,4‐dihydrocoumarin, 3‐ and 6‐methyl coumarins, 4‐hydroxycoumarin, umbelliferone, dicoumarol, and warfarin.

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