Structural Studies of Curcuminoids. I. The Crystal Structure of Curcumin.

Tønnesen, Hanne; Karlsen, Jan; Mostad, Arvid; Samuelsson, Bertil; Enzell, Curt R.; Berg, Jan-Eric

doi:10.3891/acta.chem.scand.36b-0475

Cited by 145 publications

(97 citation statements)

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“…It is a member of the linear diarylheptanoid class of natural products in which two oxy-substituted aryl moieties are linked together through a seven-carbon chain [2]. Its crystal structure was the subject of several papers which are agreed that the enol-form is the major tautomer of curcumin [3][4][5]. This picture was also supported by both spectral and theoretical studies [6][7][8][9][10].…”

Section: Introductionsupporting

confidence: 52%

Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

et al. 2013

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Section: Introductionsupporting

confidence: 52%

Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

et al. 2013

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“…Some studies on curcumin are based on the ionic structure where the keto-enol equilibrium ( Fig. 1) is present or when it is fully in keto form [7][8][9] with the resulting properties depending on the latter. The strong chelating ability of diketones has been widely investigated towards a great number of metal ions; therefore, curcumin could be of great importance in the chelating treatment of metal intoxication and overload [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of some Ternary Metal Complexes of Curcumin with 1,10-phenanthroline and their Anticancer Applications

et al. 2014

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Some ternary complexes of curcumin have been synthesized by the reaction of M(II) nitrate with curcumin as primary ligand and 1,10-phenanthroline (phen) as supporting ligand in water/ethanol solution under a nitrogen atmosphere. The composition of the complexes has been characterized by elemental analysis, molar conductivity, thermogravimetric analysis, IR, UV-vis spectroscopy. The results reveal that curcumin ligand coordinates with M(II) in bidentate mode after deprotonation. The supporting ligand (phen) uses its two N atoms in coordination with metal ions in bidentate mode. The general formula of the complexes is [M(Cur)(phen)]NO 3 (M = Ni(II), Co(II), Cu(II) and Z(II)). The results of antibacterial activity indicated that the complexes have good antibacterial ability for the testing bacterium than that of curcumin. Furthermore, the [M(Cur)(phen)]NO 3 complexes were evaluated for its in vitro anticancer activity against hepatocellular carcinoma.

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“…This is most frequently the enol form in which the hydrogen-bonded ring is virtually planar with the two C---O bonds necessarily cis (T~nnesen, Karlsen & Mostad, 1982;TCnnesen, Karlsen, Mostad, Pedersen, Rasmussen & Lawesson, 1983;Etter, Jahn & Urbanczyk-Lipkowska, 1987;Baxter, Blake, Heath & Stephenson, 1990 (Gyepes, Glowiak, Toma & Sold~inov~i, 1984) the ring containing the 1,3-diketone fragment is twisted severely as a result of the ring strain in the [3]ferrocenophane skeleton, so that enolization is again prevented. However, in the acyclic diketone 2-ethyl-1,3-diphenyl-l,3-propanedione, (PhCO)2CHC2H5 (MuUica, Karban & Grossie, 1987), the solid-state structure again indicates a complete lack of enolization associated with a markedly non-planar O==C~C---C==O fragment, although 1,3-diphenyl-1,3-propanedione itself is wholly in the enol form in both crystalline modifications (Jones, 1976a;Etter, Jahn & Urbanczyk-Lipkowska, 1987).…”

Section: Commentmentioning

confidence: 99%

4-(Ferrocenylmethyl)-2,2,6,6-tetramethyl-3,5-heptanedione, a non-enolized 1,3-diketone

Ferguson¹,

Glidewell²,

Zakaria³

1994

Acta Crystallogr C

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Program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1991). Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993 AbstractThe analysis of the title compound, (r/5-cyclopentadien -shows that it exists in the solid state in the diketo form; there is no evidence at all for any keto-enol tautomeric contribution to the ground-state structure. CommentBoth in solution and in the vapour phase (Lowrey, George, D'Antonio & Karle, 1971), 1,3-diketones R'COCH2COR" generally exist as equilibrium mixtures of keto and enol tautomers where the enol tautomer contains a six-membered hydrogen-bonded ring.In the solid state, however, only a single form is generally observed. This is most frequently the enol form in which the hydrogen-bonded ring is virtually planar with the two C---O bonds necessarily cis (T~nnesen, Karlsen & Mostad, 1982;TCnnesen, Karlsen, Mostad, Pedersen, Rasmussen & Lawesson, 1983;Etter, Jahn & Urbanczyk-Lipkowska, 1987;Baxter, Blake, Heath & Stephenson, 1990 (Gyepes, Glowiak, Toma & Sold~inov~i, 1984) the ring containing the 1,3-diketone fragment is twisted severely as a result of the ring strain in the [3]ferrocenophane skeleton, so that enolization is again prevented. However, in the acyclic diketone 2-ethyl-1,3-diphenyl-l,3-propanedione, (PhCO)2CHC2H5 (MuUica, Karban & Grossie, 1987), the solid-state structure again indicates a complete lack of enolization associated with a markedly non-planar O==C~C---C==O fragment, although 1,3-diphenyl-1,3-propanedione itself is wholly in the enol form in both crystalline modifications (Jones, 1976a;Etter, Jahn & Urbanczyk-Lipkowska, 1987). In a study of the 1-ferrocenyldiketone [(CsHs)Fe-{(CsH4)COCH2COCH3}], it was found (Bell, Crayston, Glidewell, Mazid & Hursthouse, 1992) that in chloroform solution the enol:keto ratio was ca 17:1, but in the solid state both XSC CP-MAS (cross-polarization magic angle spinning) NMR and X-ray diffraction revealed only the enol form, 1-ferrocenyl-3-hydroxybut-2-en-l-one. In contrast, the 4-ferrocenylmethyl derivative [(CsHs)Fe{(CsHn)CH2CH(COCMe3)2}] (I) exhibits an enol:keto ratio in chloroform solution of 1:3 (Zakaria, Morrison, McAndrew, Bell & Glidewell, 1994), suggesting that, like (PhCO)2CHC2Hs, it might exist in the solid state solely in the diketo form. Here we report a single-crystal X-ray study of this compound which confirms that in the solid state it is indeed a non-enolizedCompound (I) crystallizes in the triclinic system (space group Pi) with one molecule in the asymmetric unit. The structure comprises isolated molecules with no short intermolecular contacts. In the --CH2CH(COCMe3)2 substituent, the C2---C3 and C2--C5 bond lengths (Table 2, Fig. 1) are typical of those in unenolized 1,3-diketones (range 1.507-1.537 ,~; Gyepes, Glowiak, Toma & Sold~inov~i, 1984;Gyepes, Glowiak & Toma, 1986;Mullica, Karban & Grossie, 1987), whereas in enolized 1,3-diketones the corresponding C---C distances lie in the range 1.34-1.43/~ (Bell, Crayston, Glidewell, Mazid & Hursthouse, 1992).The C3---O1 and C5----O2 distance...

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Structural Studies of Curcuminoids. I. The Crystal Structure of Curcumin.

Cited by 145 publications

References 0 publications

Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

Synthesis and Characterization of some Ternary Metal Complexes of Curcumin with 1,10-phenanthroline and their Anticancer Applications

4-(Ferrocenylmethyl)-2,2,6,6-tetramethyl-3,5-heptanedione, a non-enolized 1,3-diketone

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