Cinnamic acid, «- 7-LACTONE

Hydrolysis. The lactone is easily hydroly2ed by alkaUes to the corresponding salts of coumarinic acid or o-hydroxy-i j -cinnamic acid [495-79 ]. Coumarinic acid salts are odorless. Coumarinic acid and salts revert to coumarin upon acidification with inorganic acids. Alkaline fusion of coumarin yields salts of sahcyhc and acetic acids. 

Simple phenolic compounds include (1) the phenylpropanoids, trans-cinnamic acid, p-coumaric acid and their derivatives (2) the phenylpropanoid lactones called coumarins (Fig. 3.4) and (3) benzoic acid derivatives in which two carbons have been cleaved from the three carbon side chain (Fig. 3.2). More complex molecules are elaborated by additions to these basic carbon skeletons. For example, the addition of quinic acid to caffeic acid produces chlorogenic acid, which accumulates in cut lettuce and contributes to tissue browning (Fig. 3.5). 

The jalapin-like chloroform-soluble material from the dried tubers of I. batatas was subjected to successive column chromatography over silica gel and HPLC to yield batatosides J-L (55-57) with the oligosaccharide core based on operculinic acid E. The lactonization site was placed at C-2 of the first rhamnose unit. Cinnamic acid was present as the esterifying residue at the C-2 position of the third rhamnose unit. These resin glycosides also contain esterifying residues composed of n-dodecanoic or (25)-methylbutyric acids at the C-2 or C-3 positions on the second rhamnose unit of the oligosaccharide core as well as n-decanoic or n-dodecanoic acids at C-4 on the third rhamnose (40). 

As reported for all pentasaccharides from sweet potato (64, 86), pure compounds 232 and 233 were also submitted to sapoiufication yielding simonic acid B (87). The liberated fatty acids were identified as isobutyric, (25)-methyIbutanoic, -decanoic, -dodecanoic, and cinnamic acids. The site of lactonization by the aglycone in the macrocyclic unit was placed at C-2 of the second saccharide. The position of the ester linkage on the macrocyclic unit was C-2 of the terminal rhamnose. The acylations were identified as follows for the macrocyclic unit at C-2 of the third saccharide (n-dodecanoic acid), and at C-3 and C-4 of the branched... 

Several biogenetic schemes have been suggested to account for the origin of biphenyl and biphenyl ether lactonic alkaloids (52, 62, 83, 84). The proposals differ in the mode of biogenesis of the phenylquinolizidine moiety. Steps common to all the proposals are the reduction of oxo group in the phenylquinolizidone (130) followed by esterification with of / -coumaric acid (C6 C3) unit derived from phenylalanine via cinnamic acid. 

Cinnamic acid, a-(/9-HYDROXYSTYRYL)-, y-LACTONE, 43, 3 Cinnamyl bromide, 44, 32 Condensation, of aldehydes and ketones with esters to give (S-hydroxy-esters, 44, 58... 

This lactone derives from the shikimic acid-cinnamic acid pathway, via oxidative dimerization of coniferyl alcohol. Whereas the presence of yatein itself was not detected in the plants producing steganes, presteganes A and B were isolated in Steganotaenia araliaceae and constitute therefore viable biogenetic precursors [82,83]. 

The nature of the nonbasic portion of aphelandrine was determined in two different ways KMn04 oxidation of 181, followed by CH2N2 treatment afforded two esters methyl 4-methoxybenzoate (182) and dimethyl 4-meth-oxyisophthalate (183) (Scheme 33). Both compounds answer the question of the substitution pattern of the cinnamic acid units of aphelandrine. The mode of connection of the two cinnamic acid residues can be deduced from products of the hydrolysis of 180, which forms lactone 184. The structure of... 

The simple coumarin nucleus (Fig 7.3), which is derived by lactone formation of an ortho-hydroxy-czs cinnamic acid, is a common metabolite in higher plants and is often found in glycosidic form. Coumarins are common in Api-aceae, in certain genera of Fabaceae (e.g. Dipteryx odorata, Melilotus officinalis), Poaceae (e.g. Anthoxanthum odoratum) and Rubiaceae (e.g. Galium odoratum). However, proliferation of coumarins to the status of major chemical markers occurs in only a few cases, most notably, but not exclusively, in the Api-aceae (subfamily Apioideae) and in the Rutaceae (Gray and Waterman, 1978 Murray et al., 1982). In these cases, the coumarin nucleus has almost invariably been embellished by the addition of a prenyl unit leading to furocoumarin (Fig 7.3) and pyranocoumarin structures. 

Cardui benedicti herba Cnici herba Blessed thistle Cnicus beiiedictus L. Asteraceae DAC 86. GAB 90, MD Sesquiterpene lactons (-0.25%), (germacran type) cnicin, salonitenolid and artemisiifoliii lit of the drug, 800-1800 Essential oil (0.03%-0.1%) citral, cilronellal cinnamic acid, acetylene derivatives Pig. 8... 

Beilstein Handbook Reference) AI3-00753 Benzo-a-pyrone BRN 0383644 Caswell No. 259C CCRIS 181 Cinnamic acid, o-hydroxy-, 8-lKtone ois-o-Coumaric acid anhydride Coumarin cis-o-Coumarinic acid lactone Coumarinic anhydride Coumarinic lactone Cumarin EINECS 202-086-7 EPA Pesticide Chemical Code 127301 HSDB 1623 o-Hydroxycinnamic lactone 0-Hydroxyzimtsaure-lacton Kumarin NCI C07103 NSC 8774 Rattex Tonka bean camphor. Used in pharmaceuticals as a flavorant. Crystals mpo 71" bp = 301.7 d O = 0.936 Xm = 273, 311 nm (e = 11200, 6710, MeOH) moderately soluble in H2O, EtOH, more soluble in EtzO, CHCI3, C5H5N. Alfa Aesar Rhodia Inc. Rhodia Organique Fine Ltd. 

Basic catalysts other than alkali acetates have been employed in the Perkin reaction thus salicylaldehyde condenses with acetic anhydride in the presence of triethylamine to yield coumarin (the lactone of the cis form of o-hydroxy-cinnamic acid) together with some of the acetyl derivative of the trans form (o-acetoxycoiimaric acid) ... 

Coumarins are lactones with the basic structure of 1,2-benzopyrone. Biosynthetically, they are mainly originated from shikimic acid padiway, with the intermediate of cinnamic acid. By the addition of a furan ring, the furanocoumarins are resulted, which are represented by psoralen (linear) and angelicin (angular) [10]. 

Cinnamic acid, 2,4-diisopropyl-, ethyl ester. See Ethyl diisopropylcinnamate Cinnamic acid-1,5-dimethyl-1-vinyl-4-hexenyl ester Cinnamic acid-1,5-dimethyl-1-vinyl-4-hexen-1-yl ester. See Linalyl cinnamate Cinnamic acid, o-hydroxy-, 5-lactone. See Coumarin... 

Synonyms 1-Benzopyran-2-one 2H-1-Benzopyran-2-one 2H-1-Benzopyran, 2-oxo- Benzopyrone 1,2-Benzopyrone Benzo-a-pyrone Chromen-2-one Cinnamic acid, o-hydroxy-, 5-lactone Coumaric acid cis-o-Coumaric acid lactone cis-o-Coumarinic acid lactone Coumarinic anhydride Cumarin o-Hydroxycinnamic acid lactone o-Hydroxycinnamic acid 5-lactone o-Hydroxycinnamic lactone 2-Oxo-1,2-benzopyran 2-Propenoic acid, 3-(2-hydroxyphenyl)-5-lactone Tonka bean camphor... 

Hydroxide ions open the lactone ring of coumarin forming the dianion 6 of (Z)-(2-hydroxy)cinnamic acid (coumarinic acid), which recyclizes to coumarin on addition of acid. On methylation with dimethyl sulfate, the dianion 6 is transformed to the (Z)-methoxy ester 8 however, on prolonged reaction with base it isomerizes to the ( )-dianion 7 ... 

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